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Results: 108 Rentals

  • Cute and Cozy 2 Bedroom
    From $162 per night (USD)

    VRBO

    Cute and Cozy 2 Bedroom

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Enjoy Classic decor in a spacious two bedroom one bathroom. Large eat-in kitchen and laundry in the basement! Tony's gro ...

    From $162 per night (USD)

    VRBO

    Details
  • The NICEST place in Evanston for Families 1500Main
    From $292 per night (USD)

    VRBO

    The NICEST place in Evanston for Families 1500Main

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    No Additional Cleaning Fee! --- Fully Furnished 2-story, 2 bedroom attached Townhouse/Duplex with a new King bed in th ...

    From $292 per night (USD)

    VRBO

    Details
  • Retro Apartment in Andersonville
    From $177 per night (USD)

    VRBO

    Retro Apartment in Andersonville

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Escape to a colorful paradise in one of Andersonville's best-kept vintage buildings. Located on the ground floor, full o ...

    From $177 per night (USD)

    VRBO

    Details
  • The Greenleaf House—Whole House
    From $505 per night (USD)

    Expedia

    The Greenleaf House—Whole House

    Bedrooms:
    3
    Bathrooms:
    9
    Sleeps:
    12

    The Greenleaf House, built in 1915, is our 3600ft² home with 6 bedrooms, 2.5 baths, & an open floor plan—perfect for gat ...

    From $505 per night (USD)

    Expedia

    Details
  • Bright & Spacious Brick 2-Flat Great for families!
    From $305 per night (USD)

    VRBO

    Bright & Spacious Brick 2-Flat Great for families!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    As you step into our thoughtfully designed apartment, you'll immediately feel the warm and inviting atmosphere. The spac ...

    From $305 per night (USD)

    VRBO

    Details
  • Comfortable place in Evanston!  Close to Northwestern and Loyola University.
    Click For Pricing

    Expedia

    Comfortable place in Evanston! Close to Northwestern and Loyola University.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Located on the southwest side of Evanston in a quiet neighborhood, this beautiful bi-level townhome with 2 bedrooms and ...

    Click For Pricing

    Expedia

    Details
  • Oakton St. Inn, Evanston near Northwestern, Loyola and Chicago
    From $341 per night (USD)

    VRBO

    Oakton St. Inn, Evanston near Northwestern, Loyola and Chicago

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Experience Oakton St. Inn - Your Chic and Spacious Retreat Welcome to the top floor of Oakton St. Inn, where sunlight ...

    From $341 per night (USD)

    VRBO

    Details
  • Soft Suede and Warm Bricks at a Stylish Rogers Park Home
    From $272 per night (USD)

    Expedia

    Soft Suede and Warm Bricks at a Stylish Rogers Park Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Meet NEW and CHARM with exposed brick,dim LED lighting,rainfall shower with bluetooth wiring, In-unit washer/dryer, open ...

    From $272 per night (USD)

    Expedia

    Details
  • Walking distance to restaurants, shops and Lake Michigan,
    From $291 per night (USD)

    VRBO

    Walking distance to restaurants, shops and Lake Michigan,

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    8

    Residence on the Avenue. A Spacious 1700 sq.ft. condo in a stunning blonde brick/limestone 1928 building on a tree lined ...

    From $291 per night (USD)

    VRBO

    Details
  • Walking distance to restaurants, shops and Lake Michigan,
    From $246 per night (USD)

    Expedia

    Walking distance to restaurants, shops and Lake Michigan,

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Residence on the Avenue. A Spacious Vintage condo in a stunning 1928 Art Deco building on a tree lined avenue. We are a ...

    From $246 per night (USD)

    Expedia

    Details
  • ✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨
    From $353 per night (USD)

    VRBO

    ✨Chic|Luxurious|2BR|Trendy|Evanston Next To Beach✨

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Our apartment is located right next to the beach and a very nice path to take long walks where you can enjoy the views o ...

    From $353 per night (USD)

    VRBO

    Details
  • Soft Palate & Warm Bricks At A Rogers Park Home
    From $341 per night (USD)

    Expedia

    Soft Palate & Warm Bricks At A Rogers Park Home

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Meet NEW and CHARM with exposed brick,dim LED lighting,rainfall shower with bluetooth wiring, In-unit washer/dryer, open ...

    From $341 per night (USD)

    Expedia

    Details
  • Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach
    From $239 per night (USD)

    VRBO

    Luxury Loyola 3 Bedroom, 2 Bath, Near Subway and Beach

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This is a beautifully remodeled, modern, spacious, and luxuriously furnished 3 bedroom, 2 bath private city apartment. ...

    From $239 per night (USD)

    VRBO

    Details
  • Exquisite Rogers Park 1bd\/1bath Apt. Near Evanston
    From $183 per night (USD)

    Expedia

    Exquisite Rogers Park 1bd\/1bath Apt. Near Evanston

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Recently remodeled 1 bedroom, 1 bath, plus sleeper sofa and kitchen with modern finishes on the top floor of a nice owne ...

    From $183 per night (USD)

    Expedia

    Details
  • Large 12 room house steps to Park, Shopping and Restaurants, 10 minutes to beach
    Click For Pricing

    VRBO

    Large 12 room house steps to Park, Shopping and Restaurants, 10 minutes to beach

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    Large Jumbo Georgian two story brick house centrally located on the North side of Chicago in a quiet neighborhood with t ...

    Click For Pricing

    VRBO

    Details
  • Chicago Riverhouse with private fenced in oasis
    From $266 per night (USD)

    Expedia

    Chicago Riverhouse with private fenced in oasis

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the ...

    From $266 per night (USD)

    Expedia

    Details
  • The entire FLAT.  Stay Like You Own! Central AIR. TWO FULL BATHROOMS. Unique.
    From $346 per night (USD)

    VRBO

    The entire FLAT. Stay Like You Own! Central AIR. TWO FULL BATHROOMS. Unique.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Designer urban feel - completely rehabbed - reclaimed wood beams - full walk in glass master shower with an exposed bric ...

    From $346 per night (USD)

    VRBO

    Details
  • 100 Yr. Old Chicago Brick Craftsman with yard, Near Beach and Loyola!
    From $264 per night (USD)

    Expedia

    100 Yr. Old Chicago Brick Craftsman with yard, Near Beach and Loyola!

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    8

    Welcome to this thoughtfully preserved 110 year old, original Chicago brick home, just 3 blocks from the Lake Michigan s ...

    From $264 per night (USD)

    Expedia

    Details
  • Stylish, Bright Garden-Level Apt w\/ Fireplace
    Click For Pricing

    VRBO

    Stylish, Bright Garden-Level Apt w\/ Fireplace

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Modern comfort meets laid-back digs at this serene 1-bedroom, 1-bathroom Chicago vacation rental. This well-appointed ap ...

    Click For Pricing

    VRBO

    Details
  • Lovely 3 Bedroom Apartment with ample street parking
    From $120 per night (USD)

    VRBO

    Lovely 3 Bedroom Apartment with ample street parking

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    5

    Your family will be close to everything when you stay at this centrally-located place near Evanston lakes. Work from Ho ...

    From $120 per night (USD)

    VRBO

    Details
  • Retro-Chic Urban Oasis
    From $128 per night (USD)

    VRBO

    Retro-Chic Urban Oasis

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Entire top floor apartment with private entrance in a charming two-story building. Two bedrooms and 2 queen beds can hos ...

    From $128 per night (USD)

    VRBO

    Details
  • Cute, Cozy, Elegant Budlong Woods
    From $132 per night (USD)

    Expedia

    Cute, Cozy, Elegant Budlong Woods

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Book with us and enjoy classic charm and elegant décor located in the Budlong woods neighborhood. Experience a great nig ...

    From $132 per night (USD)

    Expedia

    Details
  • Comfy Garden Suite in Andersonville
    From $166 per night (USD)

    VRBO

    Comfy Garden Suite in Andersonville

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    A comfortable garden unit in a well cared for 3-flat, in a wonderful and safe neighborhood. Easy access to the lake fro ...

    From $166 per night (USD)

    VRBO

    Details
  • Great Evanston Home- great for traveling families! Parking Included
    From $292 per night (USD)

    Expedia

    Great Evanston Home- great for traveling families! Parking Included

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    This home has 3 bedrooms, 4 beds, and can accommodate up to 8 guests comfortably. There is 1 king bed, 1 queen bed and 2 ...

    From $292 per night (USD)

    Expedia

    Details
  • Chicago Charm! Free Parking w\/In-unit Laundry
    From $172 per night (USD)

    VRBO

    Chicago Charm! Free Parking w\/In-unit Laundry

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Couples, business trips, friends, small families…Welcome! Located in quiet West Ridge, this is a garden/basement unit w ...

    From $172 per night (USD)

    VRBO

    Details
  • Evanston-Sunny Stylish Studio apartment w hardwood floors, fenced yard & parking
    From $93 per night (USD)

    Expedia

    Evanston-Sunny Stylish Studio apartment w hardwood floors, fenced yard & parking

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Gorgeous vintage modern studio apartment surrounded by single-family homes on a quiet tree-lined residential block in Ev ...

    From $93 per night (USD)

    Expedia

    Details
  • Modern|Aesthetic|2BR|Evanston|Next to Beach
    From $368 per night (USD)

    VRBO

    Modern|Aesthetic|2BR|Evanston|Next to Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Our apartment is located right next to the beach and a very nice path to take long walks where you can enjoy the views o ...

    From $368 per night (USD)

    VRBO

    Details
  • Cute new Garden unit located between Andersonville and Lincoln Square , Chicago.
    From $246 per night (USD)

    VRBO

    Cute new Garden unit located between Andersonville and Lincoln Square , Chicago.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Large and quiet 1 bedroom 1 bathroom Garden unit located in a typical Chicago 2 flat building type. We are exactly betw ...

    From $246 per night (USD)

    VRBO

    Details
  • Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.
    From $178 per night (USD)

    VRBO

    Rogers Park Cozy 1 bd, 1 bath unit. Gated parking.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Kick back and relax in this cozy, calm and stylish 1 bedroom, 1 bath unit with a spacious kitchen, a dedicated work spac ...

    From $178 per night (USD)

    VRBO

    Details
  • Cozy 2BR\/1BA Garden Apartment Near Lincoln Square
    From $158 per night (USD)

    Expedia

    Cozy 2BR\/1BA Garden Apartment Near Lincoln Square

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Experience top quality in a spacious garden-level apartment during your next visit to Chicago. This garden (basement) le ...

    From $158 per night (USD)

    Expedia

    Details
  • Urban Chicago Escape ~ 1 Mi to Local Beaches!
    From $182 per night (USD)

    VRBO

    Urban Chicago Escape ~ 1 Mi to Local Beaches!

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Indulge in the city life when you stay at this 2-bedroom, 1-bathroom vacation rental! This condo is the perfect place to ...

    From $182 per night (USD)

    VRBO

    Details
  • Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.
    From $146 per night (USD)

    Expedia

    Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Licensed by the City of Chicago: Studio 1: 2209375 Immaculately clean, quiet studio, housed in a brick coach house off ...

    From $146 per night (USD)

    Expedia

    Details
  • Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.
    From $146 per night (USD)

    VRBO

    Peaceful Oasis in Top Chicago Neighborhood. Low Traffic, Pristine Cleanliness.

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Licensed by the City of Chicago: Studio 1: 2209375 Immaculately clean, quiet studio, housed in a brick coach house off ...

    From $146 per night (USD)

    VRBO

    Details
  • City Sanctuary Private
    From $294 per night (USD)

    Expedia

    City Sanctuary Private

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Welcome to our beautifully renovated 1937 print shop turned stunning 1 bedroom, 2 bathroom home located in Chicago's cha ...

    From $294 per night (USD)

    Expedia

    Details
  • The Holiday Lake House - 2br 2bth - 50 steps from the beach!
    From $273 per night (USD)

    VRBO

    The Holiday Lake House - 2br 2bth - 50 steps from the beach!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    If you enjoy the holidays, this is the place to be! This amazing property is perfect at any time of the year; however, ...

    From $273 per night (USD)

    VRBO

    Details
  • 3 BR \/ 2 BTH unit steps to the beach and close to Loyola
    From $285 per night (USD)

    Expedia

    3 BR \/ 2 BTH unit steps to the beach and close to Loyola

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Amazing lake views from 2 outdoor spaces! This spacious 3 bedroom, 2 bath unit has a front balcony with plenty of seati ...

    From $285 per night (USD)

    Expedia

    Details
  • Entire 2-flat Available- Rent both apartments!
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    VRBO

    Entire 2-flat Available- Rent both apartments!

    Bedrooms:
    3
    Bathrooms:
    6
    Sleeps:
    12

    Rent the entire building! I've combined both apartments of my two flat into one listing for large groups of families or ...

    Click For Pricing

    VRBO

    Details
  • Urban FAB 2
    Click For Pricing

    Expedia

    Urban FAB 2

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Fabulous apartment set in Evanston. Freshly updated 2 bedrooms and 1 full bathroom. Kitchen features maple cabinetry, qu ...

    Click For Pricing

    Expedia

    Details
  • Northside FAMLYNEST - Lincoln Sq - 4BR\/1.5BA\/2P - Rare find
    From $296 per night (USD)

    VRBO

    Northside FAMLYNEST - Lincoln Sq - 4BR\/1.5BA\/2P - Rare find

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    <p>A short distance from kayaking, birdwatching, and more, this family-friendly vacation home lets you experience it all ...

    From $296 per night (USD)

    VRBO

    Details
  • Large Apartment great for families! Close to everything w Free Parking
    From $285 per night (USD)

    Expedia

    Large Apartment great for families! Close to everything w Free Parking

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy everything Evanston has to offer in this beautiful and clean 2 bedroom apartment. One bedroom has a king bed and t ...

    From $285 per night (USD)

    Expedia

    Details
  • VintageLoversEscape|Homey|Stylish1BR|CloseToBeach
    From $180 per night (USD)

    VRBO

    VintageLoversEscape|Homey|Stylish1BR|CloseToBeach

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Conveniently located in the heart of Chicago's most popular northernmost neighborhood. The location is perfect and minut ...

    From $180 per night (USD)

    VRBO

    Details
  • MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking
    From $441 per night (USD)

    Expedia

    MDRN Kid-Friendly Apt|Charming|Private|Sunny|Fast Wi-Fi| Parking

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Relax with the whole family or explore the city with friends at this peaceful and spacious 3-bd/1.5ba condo tucked on a ...

    From $441 per night (USD)

    Expedia

    Details
  • Roomy[2BR]Loyola Park-Near Beach
    From $268 per night (USD)

    VRBO

    Roomy[2BR]Loyola Park-Near Beach

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This beautiful apartment gives a peaceful and modern feel making it a place you'll never want to leave. The apartment is ...

    From $268 per night (USD)

    VRBO

    Details
  • Convenient Location Near Loyola\/Northwestern
    From $328 per night (USD)

    VRBO

    Convenient Location Near Loyola\/Northwestern

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Apartment unit is conveniently located next to the Jarvis Red Line, 2 stops from Loyola and 3 miles from Northwestern. T ...

    From $328 per night (USD)

    VRBO

    Details
  • Urban Forest Retreat -great for couples or solo travelers
    From $334 per night (USD)

    VRBO

    Urban Forest Retreat -great for couples or solo travelers

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    2

    Close to Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop sits between Chicago River & Fo ...

    From $334 per night (USD)

    VRBO

    Details
  • Gorgeous Mid Century 3 bed with hot tub near Lincoln Square
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    Expedia

    Gorgeous Mid Century 3 bed with hot tub near Lincoln Square

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    This three bedroom, two bath house has everything you will need for a comfortable visit to the north side of Chicago. T ...

    Click For Pricing

    Expedia

    Details
  • Modern, 2-bedroom apartment just 15 minute drive to Lake Michigan
    From $160 per night (USD)

    VRBO

    Modern, 2-bedroom apartment just 15 minute drive to Lake Michigan

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Discover the perfect urban oasis in the heart of West Ridge, Chicago. This new-construction 2-bedroom basement apartment ...

    From $160 per night (USD)

    VRBO

    Details
  • Classic Chicago 2 Flat transformed into a Parisian plant lovers paradise
    From $248 per night (USD)

    Expedia

    Classic Chicago 2 Flat transformed into a Parisian plant lovers paradise

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    La Maison Verte is a Parisian-inspired 2nd floor walk up in a traditional Chicago 2 flat with vintage charm and modern a ...

    From $248 per night (USD)

    Expedia

    Details
  • Chic|Comfy|Stylish| 2BD 2BA - Little India
    From $191 per night (USD)

    VRBO

    Chic|Comfy|Stylish| 2BD 2BA - Little India

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    A bright, spacious apartment located in the West Ridge neighborhood in Chicago. Living just over a block away puts a hug ...

    From $191 per night (USD)

    VRBO

    Details
  • Lovely|Cozy|Homey|2 Bed|1 Bath|
    From $193 per night (USD)

    Expedia

    Lovely|Cozy|Homey|2 Bed|1 Bath|

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    This gorgeous apartment is perfectly located only 10 minutes from O'Hare International Airport. Close to the hospital, g ...

    From $193 per night (USD)

    Expedia

    Details
  • Bright Edgewater 2BR w\/ Gym & Lounge, nr Red Line, by Blueground
    From $123 per night (USD)

    VRBO

    Bright Edgewater 2BR w\/ Gym & Lounge, nr Red Line, by Blueground

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Discover the best of Chicago, with this two bedroom apartment in Edgewater. with views over the city. It’ll be easy to s ...

    From $123 per night (USD)

    VRBO

    Details
  • First Floor Brownstone Newly Renovated
    From $87 per night (USD)

    Expedia

    First Floor Brownstone Newly Renovated

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Spacious, open air design in Rogers Park with 2 bedrooms and open kitchen dinning area. Living room and front sunroom ar ...

    From $87 per night (USD)

    Expedia

    Details
  • Chicago charm! Quiet and inviting !
    From $291 per night (USD)

    VRBO

    Chicago charm! Quiet and inviting !

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Newly remodeled , 20 min walk to the lake. 20 min drive from downtown and 25 min from airport. Second floor of two flat ...

    From $291 per night (USD)

    VRBO

    Details
  • Evanston Historic Italianate - 4 Blocks to Lake!
    From $1786 per night (USD)

    VRBO

    Evanston Historic Italianate - 4 Blocks to Lake!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Fully renovated in 2022, this Historic District, 150 year old home was designed for modern family living while preservin ...

    From $1786 per night (USD)

    VRBO

    Details
  • Amazing Edgewater 2BR, nr Lake Michigan, by Blueground
    From $152 per night (USD)

    VRBO

    Amazing Edgewater 2BR, nr Lake Michigan, by Blueground

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Feel at home wherever you choose to live with Blueground. You’ll love this stylish Edgewater furnished two bedroom apart ...

    From $152 per night (USD)

    VRBO

    Details
  • Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover
    From $248 per night (USD)

    Expedia

    Centrally Located Swedish Design Andersonville 2bd by AllSet Turnover

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    This newly updated 2 bedroom, 1 bath condo has everything you need to make your Chicago stay perfect! The home was thoug ...

    From $248 per night (USD)

    Expedia

    Details
  • Elegant 3 Bedroom and 1 Bath Apartment
    From $201 per night (USD)

    VRBO

    Elegant 3 Bedroom and 1 Bath Apartment

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Experience top quality in a spacious 3 bed 1 bath apartment during your next visit to Chicago. We are located in West Ri ...

    From $201 per night (USD)

    VRBO

    Details
  • Pet-Friendly Urban Chicago Vacation Rental Condo
    From $173 per night (USD)

    Expedia

    Pet-Friendly Urban Chicago Vacation Rental Condo

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Experience the hustle and bustle of city life when you plan a trip to Chicago, Illinois, and stay at this ideally locate ...

    From $173 per night (USD)

    Expedia

    Details
  • Cozy Studio 1 bedroom apartment near the lake!
    Click For Pricing

    VRBO

    Cozy Studio 1 bedroom apartment near the lake!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Enjoy a stylish experience at this centrally-located place. 5-7 minute walk to the red & purple lines, & lakefront. Loc ...

    Click For Pricing

    VRBO

    Details
  • STYLISH-LOCAL-COMFY-SAFE \/ 5 night min. stay
    From $292 per night (USD)

    VRBO

    STYLISH-LOCAL-COMFY-SAFE \/ 5 night min. stay

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    -Please don't ask for less than 5 nights... we do not accept reservations under 5 nights ever.. Located in Chicago’s ...

    From $292 per night (USD)

    VRBO

    Details
  • Bright Garden Studio
    From $300 per night (USD)

    VRBO

    Bright Garden Studio

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Not your mothers basement—Creating an atmosphere that is both sophisticated and inviting, this open STUDIO APT provides ...

    From $300 per night (USD)

    VRBO

    Details
  • Soft Leather and Warm Bricks at a Stylish Rogers Park Home
    From $382 per night (USD)

    Expedia

    Soft Leather and Warm Bricks at a Stylish Rogers Park Home

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Meet NEW and CHARM with exposed brick, dim LED lighting,rainfall shower with bluetooth wiring, In-unit washer/dryer, ope ...

    From $382 per night (USD)

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    Details
  • 2 Bed 2 Bath Condo\/Rogers Park
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    2 Bed 2 Bath Condo\/Rogers Park

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    About this space This stylish and spacious 2 Bed, 2 bath condo is perfect for long term stays. It has everything you nee ...

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  • Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover
    From $204 per night (USD)

    Expedia

    Modern Comfort 2 Bd Condo in Iconic Lincoln Square by AllSet Turnover

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Discover Chicago's charm in this newly designed 2-bedroom condo! Located a few blocks away from the heart of Lincoln Squ ...

    From $204 per night (USD)

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  • PROMO 10% WEEKLY AND 15% MONTHLY \nNear Northwestern, Beaches Parking Fenced Yard
    From $372 per night (USD)

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    PROMO 10% WEEKLY AND 15% MONTHLY \nNear Northwestern, Beaches Parking Fenced Yard

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    Discover the perfect blend of comfort and convenience in our 4-bedroom, 2.5-bathroom house near Northwestern University, ...

    From $372 per night (USD)

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  • Modern Apartment on Devon Street - Little India
    From $91 per night (USD)

    Expedia

    Modern Apartment on Devon Street - Little India

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Welcome to our apartment on historic Devon Ave, where Chicago's charm comes alive. Immerse in diverse cultures, savor gl ...

    From $91 per night (USD)

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    Details
  • Garden Unit Getaway - Close to Wrigley, Andersonville, Evanston, and more!
    From $134 per night (USD)

    VRBO

    Garden Unit Getaway - Close to Wrigley, Andersonville, Evanston, and more!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The Garden Unit Getaway is a stylish urban retreat with designer-selected furnishings that offer both comfort and sophis ...

    From $134 per night (USD)

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  • Lincolnwood Rental
    From $491 per night (USD)

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    Lincolnwood Rental

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    2000 SF renovated unit is 20 minutes away from O’hare Airport & 18 min to downtown Chicago! This property has 3 bedrooms ...

    From $491 per night (USD)

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  • Spacious, & Minutes from Downtown: Enjoy Your Dream 3BR\/2BA Apartment in Chicago
    From $263 per night (USD)

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    Spacious, & Minutes from Downtown: Enjoy Your Dream 3BR\/2BA Apartment in Chicago

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    "Your Chicago Adventure Begins Here: Modern 3BR/2BA Haven, Just 10 Minutes from Downtown! Get ready to experience the b ...

    From $263 per night (USD)

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  • Cozy North Side Chicago Studio APT for Exploring
    From $291 per night (USD)

    Expedia

    Cozy North Side Chicago Studio APT for Exploring

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Enjoy a fun and peaceful stay in Chicago's famous and vibrant North Side neighborhood. Our place is conveniently located ...

    From $291 per night (USD)

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    Details
  • Discover Northside Chicago 2BR from Modern Apartment
    From $188 per night (USD)

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    Discover Northside Chicago 2BR from Modern Apartment

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Enjoy a fun and peaceful stay in the famous and vibrant North Side neighborhood of Chicago. Our place is conveniently lo ...

    From $188 per night (USD)

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  • Stylish and Comfy Studio near Loyola Park
    From $206 per night (USD)

    Expedia

    Stylish and Comfy Studio near Loyola Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    LISTING DESCRIPTION - Welcome to your peaceful retreat near Loyola Park in Chicago! This charming studio apartment offer ...

    From $206 per night (USD)

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  • Chic and Cozy Getaway near Loyola Park
    From $181 per night (USD)

    VRBO

    Chic and Cozy Getaway near Loyola Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Listing Description Welcome to your perfect retreat near Loyola Park! This stylish studio apartment offers a comfortabl ...

    From $181 per night (USD)

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  • Duplex Retreat near Loyola Park - 2BR\/1.5BA Haven
    From $222 per night (USD)

    Expedia

    Duplex Retreat near Loyola Park - 2BR\/1.5BA Haven

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to our beautifully designed duplex 2 bedroom 1.5 bath apartment near Loyola Park! This apartment features two le ...

    From $222 per night (USD)

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    Details
  • Vintage Chicago Gem: The Rockwell Retreat\n
    From $3482 per night (USD)

    VRBO

    Vintage Chicago Gem: The Rockwell Retreat\n

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    1

    Discover your oasis in the heart of the city at our light-filled and lush apartment. Indulge in the warm and bright natu ...

    From $3482 per night (USD)

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    Details
  • Gorgeous Bunglow Nestled in a Quit Neighborhood\n\n
    From $200 per night (USD)

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    Gorgeous Bunglow Nestled in a Quit Neighborhood\n\n

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Skillfully updated 3 bedroom, 2 bath, 1800 sq ft home in West Ridge, pictures speak for themselves! The home exudes exqu ...

    From $200 per night (USD)

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    Details
  • Best Winter Vacay Spot U Will Find - Beautiful & Quiet Unit Chicago - SuperHost!
    From $249 per night (USD)

    VRBO

    Best Winter Vacay Spot U Will Find - Beautiful & Quiet Unit Chicago - SuperHost!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Come and play in Chicago this winter and book yourself in our beautiful Rogers Park unit - newly rehabbed (2023) apartm ...

    From $249 per night (USD)

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  • Modern Apartment on Quiet Street in Andersonville
    From $154 per night (USD)

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    Modern Apartment on Quiet Street in Andersonville

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Remodeled, spacious private apartment in Andersonville, the coolest neighborhood in the US, according to TimeOut magazin ...

    From $154 per night (USD)

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  • EVANSTON whole building, 2 units combined sleeps 12, 5 bed 5 bath
    From $778 per night (USD)

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    EVANSTON whole building, 2 units combined sleeps 12, 5 bed 5 bath

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    12

    Discover modern luxury in this 5-bed, 5-bath 2 unit building adorned with captivating mid-century modern decor. The inte ...

    From $778 per night (USD)

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    Details
  • New apt. Spacious, with private entrance.
    From $365 per night (USD)

    VRBO

    New apt. Spacious, with private entrance.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Wonderful remodeled Basement - apartment in a nice quiet neighborhood. With shopping centers and restaurants. - big new ...

    From $365 per night (USD)

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  • Stylish Chicago Retreat: Walk to Loyola University
    From $439 per night (USD)

    VRBO

    Stylish Chicago Retreat: Walk to Loyola University

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    Take the trip of a lifetime with friends and family when you stay at this ultimate Chicago getaway! Boasting a sophistic ...

    From $439 per night (USD)

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  • 10 minutes to the lake! Family-sized Apt with  free parking.
    From $160 per night (USD)

    Expedia

    10 minutes to the lake! Family-sized Apt with free parking.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Full kitchen............................................................................................................ ...

    From $160 per night (USD)

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    Details
  • Spacious home w Chef’s Kitchen, Natural Light, Open Floor Plan, Ideal for Groups
    From $501 per night (USD)

    VRBO

    Spacious home w Chef’s Kitchen, Natural Light, Open Floor Plan, Ideal for Groups

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our Remodeled 3 Bedroom, 3-Bathroom Family Home in the Heart of East Rogers Park on the North side of Chicago ...

    From $501 per night (USD)

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  • The Lincoln Square Hideaway
    From $411 per night (USD)

    Expedia

    The Lincoln Square Hideaway

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    6

    As you walk into your private 1st floor apartment from Western Ave, you’ll be greeted by a stunning wide-open great room ...

    From $411 per night (USD)

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  • Greenhouse Inn,  Evanston Northwestern Loyola Chicago.  Kid Friendly w\/parking
    From $461 per night (USD)

    VRBO

    Greenhouse Inn, Evanston Northwestern Loyola Chicago. Kid Friendly w\/parking

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    Explore The Greenhouse Inn in Evanston! A 3-bed, 3-bath duplex for 6 guests with 2 kitchens, in-unit laundry, and parkin ...

    From $461 per night (USD)

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  • Spacious 2BR, this hidden gem combines vintage allure with urban flair!
    From $148 per night (USD)

    Expedia

    Spacious 2BR, this hidden gem combines vintage allure with urban flair!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Discover the charm of The Maestro, an amazing 2-bedroom, 1-bath apartment nestled within a stunning 1920’s era Chicago b ...

    From $148 per night (USD)

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  • Spacious 3 Bed 1 Bath Apartment in West Rogers park
    From $281 per night (USD)

    VRBO

    Spacious 3 Bed 1 Bath Apartment in West Rogers park

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    5

    Discover the hidden gems and welcoming atmosphere of Chicago’s West Ridge neighborhood when you stay at this diversely l ...

    From $281 per night (USD)

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  • 2 bedroom Pastel Loft 1 mi from Lake Michigan!
    From $235 per night (USD)

    Expedia

    2 bedroom Pastel Loft 1 mi from Lake Michigan!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Welcome to our chic and colorful lofted apartment in the lovely neighborhood of Roger’s Park in Chicago! It's convenient ...

    From $235 per night (USD)

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  • 24\/7 Rentals
    From $199 per night (USD)

    VRBO

    24\/7 Rentals

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Experience comfort and style Since 2014, 24/7 Rentals has been offering luxury short-term apartment/loft rentals to tra ...

    From $199 per night (USD)

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  • Modern, Cozy & Chic 2 BR\/1BA Apartment in Lincoln Square\/Ravenswood, Chicago, IL
    From $205 per night (USD)

    VRBO

    Modern, Cozy & Chic 2 BR\/1BA Apartment in Lincoln Square\/Ravenswood, Chicago, IL

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to our newly renovated apartment in the heart of Lincoln Square! This modern, cozy space features 2 bedrooms w/ ...

    From $205 per night (USD)

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  • Private Coach house near Lincoln Square!
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    Private Coach house near Lincoln Square!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Lovely 625 Sq Ft detached, single-story coach house(100 years old) located in Bowmanville, nestled between Andersonville ...

    Click For Pricing

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  • Room in Town house Rogers Park
    From $132 per night (USD)

    Expedia

    Room in Town house Rogers Park

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    Welcome to our fully furnished clean and cozy room in a shared 3 bed room 1 bath townhouse in Rogers Park area. This tow ...

    From $132 per night (USD)

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    Details
  • Haus Of Hues: MDRN Bright Peaceful Private Apt
    From $389 per night (USD)

    VRBO

    Haus Of Hues: MDRN Bright Peaceful Private Apt

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Peaceful and centrally-located, this flat is the perfect place to relax with the whole family or explore the city with f ...

    From $389 per night (USD)

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  • Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!
    From $241 per night (USD)

    Expedia

    Vintage City Chic: The Artist's Haven. 5 Blocks from Lake Michigan!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to Vintage City Chic: The Artist's Haven, where timeless elegance meets artistic inspiration in a meticulously r ...

    From $241 per night (USD)

    Expedia

    Details
  • Garden 2-bedroom Unit 1 Block from the Lake and Public Transportation + Wifi
    From $188 per night (USD)

    VRBO

    Garden 2-bedroom Unit 1 Block from the Lake and Public Transportation + Wifi

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    2

    Consider this apartment your home away from home while you visit Chicago. It is RIGHT by the lake/park with free tennis ...

    From $188 per night (USD)

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  • 2BR Apartment in Andersonville Neighborhood.
    From $267 per night (USD)

    VRBO

    2BR Apartment in Andersonville Neighborhood.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    2 bedroom apartment in a prime location, 2 minutes from the center of Andersonville shopping and dining. Easy access to ...

    From $267 per night (USD)

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  • Relaxing City Haven
    From $204 per night (USD)

    VRBO

    Relaxing City Haven

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Your cozy getaway awaits in Chicago at this fabulous house. With 3 bedrooms including 2 queen beds and 1 sofa bed, this ...

    From $204 per night (USD)

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    Details
  • Cozy Andersonville Unit
    From $174 per night (USD)

    Expedia

    Cozy Andersonville Unit

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Welcome to our cozy and stylish unit in the vibrant Andersonville neighborhood of Chicago! Nestled in the heart of this ...

    From $174 per night (USD)

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    Details
  • Cozy Private & Spacious  6-bedroom Duplex with Parking in charming Evanston
    From $787 per night (USD)

    VRBO

    Cozy Private & Spacious 6-bedroom Duplex with Parking in charming Evanston

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    16

    Relax with the whole family or explore the city with friends at this peaceful and spacious 6 bedroom duplex conversion. ...

    From $787 per night (USD)

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  • Family friendly 3-bedroom apartment near parks in vibrant Chicago
    From $352 per night (USD)

    Expedia

    Family friendly 3-bedroom apartment near parks in vibrant Chicago

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Discover the beauty of Chicago from this 3-bedroom apartment. This phenomenal apartment boasts 2 queen beds and 2 twin b ...

    From $352 per night (USD)

    Expedia

    Details