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  • Trendy West Loop 2BR w\/ Lounge & Pool, nr Union Park, by Blueground
    Click For Pricing

    VRBO

    Trendy West Loop 2BR w\/ Lounge & Pool, nr Union Park, by Blueground

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Show up and start living from day one in Chicago with this stylish two bedroom Blueground apartment. You’ll love coming ...

    Click For Pricing

    VRBO

    Details
  • Deluxe Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground
    From $167 per night (USD)

    Expedia

    Deluxe Edgewater 1BR w\/ Gym, Deck & Lounge, nr L, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Show up and start living from day one in Chicago with this cozy one bedroom Blueground apartment. You’ll love coming hom ...

    From $167 per night (USD)

    Expedia

    Details
  • Lovely Uptown 1BR w\/ Gym w\/ Boxing Ring, close to Beach, by Blueground
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    VRBO

    Lovely Uptown 1BR w\/ Gym w\/ Boxing Ring, close to Beach, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated Uptown furnished one bedroom ap ...

    Click For Pricing

    VRBO

    Details
  • Stellar West Loop 2BR w\/ Rooftop & Gym, close to L, by Blueground
    Click For Pricing

    Expedia

    Stellar West Loop 2BR w\/ Rooftop & Gym, close to L, by Blueground

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Show up and start living from day one in Chicago with this lovely two bedroom Blueground apartment. You’ll love coming h ...

    Click For Pricing

    Expedia

    Details
  • Sonder The Burnham | One-Bedroom Apartment
    From $94 per night (USD)

    VRBO

    Sonder The Burnham | One-Bedroom Apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Burnham is anything but a traditional red brick building. Step inside for modern upgrades with stainless steel appli ...

    From $94 per night (USD)

    VRBO

    Details
  • 5-minute walk to the largest old school arcade in America! Family friendly.
    From $432 per night (USD)

    Expedia

    5-minute walk to the largest old school arcade in America! Family friendly.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Bring the whole family to this great place with lots of room for fun. We are located 10 miles from Downtown Chicago. Ple ...

    From $432 per night (USD)

    Expedia

    Details
  • 2BR Modern South Loop Suite With Views & Gym
    From $482 per night (USD)

    VRBO

    2BR Modern South Loop Suite With Views & Gym

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Summary: Nestled in the heart of Chicago's vibrant cityscape, we offer a luxurious urban haven that embodies modern livi ...

    From $482 per night (USD)

    VRBO

    Details
  • Splendid Corner 3BR in the Loop | City Views
    From $474 per night (USD)

    VRBO

    Splendid Corner 3BR in the Loop | City Views

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Summary: Stylish 1,300+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fa ...

    From $474 per night (USD)

    VRBO

    Details
  • Family union get together
    From $342 per night (USD)

    VRBO

    Family union get together

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    8

    Enjoy a peaceful and relaxing stay with your loved ones at this cozy suburban lodging. The two interconnected units prov ...

    From $342 per night (USD)

    VRBO

    Details
  • Quite Peaceful Glenview escapes.
    From $155 per night (USD)

    VRBO

    Quite Peaceful Glenview escapes.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    Enjoy a secure, cozy, and peaceful stay in Northbrook. Whether you're stopping over for a few hours between flights, vis ...

    From $155 per night (USD)

    VRBO

    Details
  • Gorgeous South Loop 2BR w\/ Jacuzzi & Rooftop, nr Colleges, by Blueground
    From $187 per night (USD)

    VRBO

    Gorgeous South Loop 2BR w\/ Jacuzzi & Rooftop, nr Colleges, by Blueground

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Discover the best of Chicago, with this two bedroom apartment in South Loop. with balcony views over the city. It’ll be ...

    From $187 per night (USD)

    VRBO

    Details
  • Wheeling Rental
    From $400 per night (USD)

    VRBO

    Wheeling Rental

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    1450 SF renovated unit is 23 minutes away from O’hare Airport & 35 min to downtown Chicago! This property has 3 bedrooms ...

    From $400 per night (USD)

    VRBO

    Details
  • Arlington Heights Rental
    From $491 per night (USD)

    VRBO

    Arlington Heights Rental

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    2000 SF renovated unit is 20 minutes away from O’Hare Airport & 35 min to downtown Chicago! This property has 4 bedrooms ...

    From $491 per night (USD)

    VRBO

    Details
  • Luxury Retreat with Home Theater
    From $529 per night (USD)

    Expedia

    Luxury Retreat with Home Theater

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    18

    Summary: Welcome to our opulent 5-bedroom sanctuary, where luxury meets entertainment in the heart of the city! Nestled ...

    From $529 per night (USD)

    Expedia

    Details
  • Chic 4-Bedroom Haven: Designer's Dream Home
    From $275 per night (USD)

    VRBO

    Chic 4-Bedroom Haven: Designer's Dream Home

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Summary: Welcome to our Chic 4-Bedroom Haven in the heart of Ukrainian Village, Chicago! This meticulously curated home ...

    From $275 per night (USD)

    VRBO

    Details
  • Ideal South Loop 2BR w\/ Pool, Gym & Rooftop, nr L, by Blueground
    From $162 per night (USD)

    Expedia

    Ideal South Loop 2BR w\/ Pool, Gym & Rooftop, nr L, by Blueground

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

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

    From $162 per night (USD)

    Expedia

    Details
  • Northbrook Rental
    From $478 per night (USD)

    VRBO

    Northbrook Rental

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    1850 SF renovated unit is 22 minutes away from O’hare Airport & 25 min to downtown Chicago! This property has 3 bedrooms ...

    From $478 per night (USD)

    VRBO

    Details
  • \My Quaint Little Escape\
    From $180 per night (USD)

    VRBO

    \"My Quaint Little Escape\"

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    My home was built in 1956 but it is very cozy. The oversized furniture will have you wanting to take a nap during the da ...

    From $180 per night (USD)

    VRBO

    Details
  • Chicago Rental - W 64th St
    From $226 per night (USD)

    VRBO

    Chicago Rental - W 64th St

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    2200 SF renovated unit in the suburbs of Chicago, and only 30 minutes south of Downtown Chicago! This property has 5 bed ...

    From $226 per night (USD)

    VRBO

    Details
  • Spacious, Clean and Steps from Wrigley Field!
    From $180 per night (USD)

    Expedia

    Spacious, Clean and Steps from Wrigley Field!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Enjoy this beautiful space, just minutes away from the very best Chicago has to offer! This condo is walking distance fr ...

    From $180 per night (USD)

    Expedia

    Details
  • South Shore Home Near Lake for long-term stays, corporate travelers, and nurses
    From $163 per night (USD)

    VRBO

    South Shore Home Near Lake for long-term stays, corporate travelers, and nurses

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    Welcome to our charming brick home in the picturesque South Shore community of Chicago! This fully furnished property of ...

    From $163 per night (USD)

    VRBO

    Details
  • Chicago Rental - W Berwyn Ave\n
    From $226 per night (USD)

    VRBO

    Chicago Rental - W Berwyn Ave\n

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    10

    1800 SF renovated unit in the North suburbs, and only 20 minutes to Downtown Chicago! This property has 4 bedrooms, & 2 ...

    From $226 per night (USD)

    VRBO

    Details
  • Route 66 Apt \/ 5min to HOSP & Metra train \/ 15min to MDW
    From $241 per night (USD)

    VRBO

    Route 66 Apt \/ 5min to HOSP & Metra train \/ 15min to MDW

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    The whole group will enjoy easy access to everything from this centrally located place. Stay includes: *Fast Wifi *50' ...

    From $241 per night (USD)

    VRBO

    Details
  • Chicago  Rental - Narragansett
    From $226 per night (USD)

    VRBO

    Chicago Rental - Narragansett

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    2000 SF renovated unit is 7 minutes away from Midway Air and 20 minutes from downtown! This property has 4 bedrooms, & 2 ...

    From $226 per night (USD)

    VRBO

    Details
  • Chicago style apt\/Near Hosp\/ORD\/MDW\/DT
    From $109 per night (USD)

    VRBO

    Chicago style apt\/Near Hosp\/ORD\/MDW\/DT

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Your family will be close to everything at this centrally-located place. Stay includes: *Free Street Parking *Free Wifi ...

    From $109 per night (USD)

    VRBO

    Details
  • Cozy retreat in a prime location
    From $267 per night (USD)

    VRBO

    Cozy retreat in a prime location

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy a clean and comfortable stay with a luxurious king bed and a private backyard. Located in a peaceful neighborhood, ...

    From $267 per night (USD)

    VRBO

    Details
  • Cozy Well Maintained Bronzeville 2 Bed 1 bath Condo! 5 min to U of C
    From $136 per night (USD)

    VRBO

    Cozy Well Maintained Bronzeville 2 Bed 1 bath Condo! 5 min to U of C

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Quiet & Cozy Condo in Bronzeville. Updated with all new stainless steel appliances, this is the perfect getaway. This pr ...

    From $136 per night (USD)

    VRBO

    Details
  • Burbank King bed Free Wi-Fi
    From $474 per night (USD)

    Expedia

    Burbank King bed Free Wi-Fi

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Welcome to our brand new remodeled 4 bedroom 2 bathroom house located in Burbank, IL. This stunning home boasts modern f ...

    From $474 per night (USD)

    Expedia

    Details
  • Modern 3-Bedroom Condo with Artistic Flair in Historic Bronzeville
    From $223 per night (USD)

    VRBO

    Modern 3-Bedroom Condo with Artistic Flair in Historic Bronzeville

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our spacious and stylish 3-bedroom, 3-bath condo located in the vibrant, historic Bronzeville community of Ch ...

    From $223 per night (USD)

    VRBO

    Details
  • The Grand Kimball Lodge, Logan Square, Sleeps 14
    From $683 per night (USD)

    Expedia

    The Grand Kimball Lodge, Logan Square, Sleeps 14

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    14

    The Grand Kimball Lodge is filled with enormous windows, a large, open concept layout, and Wes Anderson inspired decor. ...

    From $683 per night (USD)

    Expedia

    Details
  • Stunning Suite 2 @ Hotel Nemo Downtown
    From $118 per night (USD)

    VRBO

    Stunning Suite 2 @ Hotel Nemo Downtown

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Summary: Hotel Nemo is a boutique, corporate guest house stylishly designed for those who want to stay just around the c ...

    From $118 per night (USD)

    VRBO

    Details
  • 420 zen environment surrounded by boho chic decor~Luv Happii House.
    From $283 per night (USD)

    Expedia

    420 zen environment surrounded by boho chic decor~Luv Happii House.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Charming, vintage style canna friendly bed & breakfast. Perfect for a weekend getaway, business trip, work from home alt ...

    From $283 per night (USD)

    Expedia

    Details
  • Experience the Best Sites in Chicago & Rest Easy at the End of the Day by AllSet Turnover
    From $193 per night (USD)

    VRBO

    Experience the Best Sites in Chicago & Rest Easy at the End of the Day by AllSet Turnover

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Bright and open top floor apartment within easy walking distance to many of the best sites in Chicago: Wrigley Field, La ...

    From $193 per night (USD)

    VRBO

    Details
  • 2-Bed 2-Bath Apt | close to UC w\/ Free Parking
    From $175 per night (USD)

    Expedia

    2-Bed 2-Bath Apt | close to UC w\/ Free Parking

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Welcome to the UC Commons, your Near West Side apartment just steps away from the United Center! Located minutes from Do ...

    From $175 per night (USD)

    Expedia

    Details
  • Logan Square Monthly Apartment\n
    From $113 per night (USD)

    VRBO

    Logan Square Monthly Apartment\n

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The apartment features one private bedroom. In addition, there's an open-concept sleeping area, which allows for flexibi ...

    From $113 per night (USD)

    VRBO

    Details
  •  Trendy 2 bdrm near McCormick Place & Wintrust Arena
    Click For Pricing

    Expedia

    Trendy 2 bdrm near McCormick Place & Wintrust Arena

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Come enjoy Chicago via our cozy apartment in the quiet yet friendly Historical Bronzeville community. We are nestled bet ...

    Click For Pricing

    Expedia

    Details
  • The Grand Kimball Lodge, Logan Square, Sleeps 20
    From $1046 per night (USD)

    VRBO

    The Grand Kimball Lodge, Logan Square, Sleeps 20

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    20

    The Grand Kimball Lodge is an award winning property filled with enormous windows, a large, open concept layout, and Wes ...

    From $1046 per night (USD)

    VRBO

    Details
  • Orland Park Rental -Huntington Ct
    From $428 per night (USD)

    VRBO

    Orland Park Rental -Huntington Ct

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Ranch home, with 1 car garage and driveway. The home features a spacious master bedroom, which also contains a desk for ...

    From $428 per night (USD)

    VRBO

    Details
  • Elk Grove Village Rental
    From $359 per night (USD)

    VRBO

    Elk Grove Village Rental

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    1900 SF unit is 5 min away from O'hare, and 12 min from downtown Schaumburg, which is like a bustling mini Chicago, incl ...

    From $359 per night (USD)

    VRBO

    Details
  • Des Plaines Rental
    From $428 per night (USD)

    VRBO

    Des Plaines Rental

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    Summary - 1400 SF renovated unit is 11 min away from O'Hare Airport! This property has 3 bedrooms, & 2 bathrooms. Master ...

    From $428 per night (USD)

    VRBO

    Details
  • Newly Revamped Home - For privacy lovers
    From $362 per night (USD)

    VRBO

    Newly Revamped Home - For privacy lovers

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    13

    Total of 8beds plus kids bunk bed when the front and back unit are combined. Please read all the description. This is a ...

    From $362 per night (USD)

    VRBO

    Details
  • Elk Grove Village Rental - Kingsbridge Rd
    From $428 per night (USD)

    VRBO

    Elk Grove Village Rental - Kingsbridge Rd

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    14

    1800 SF unit is located near O'hare Airport, Schaumburg, and Hoffman Estates, which gives easy access to plenty of bars/ ...

    From $428 per night (USD)

    VRBO

    Details
  • Lakeview Lux - Apt #2
    From $156 per night (USD)

    VRBO

    Lakeview Lux - Apt #2

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    9

    Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...

    From $156 per night (USD)

    VRBO

    Details
  • Lakeview Lux - Apt #1
    From $170 per night (USD)

    Expedia

    Lakeview Lux - Apt #1

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    8

    Enjoy a classic Chicago Greystone built in 1893 and renovated in 2023, a true mix of old charm with modern touches of ar ...

    From $170 per night (USD)

    Expedia

    Details
  • 3 bedrooms In the Windy City
    From $91 per night (USD)

    VRBO

    3 bedrooms In the Windy City

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Anything you need, we have it! Anything you need, we have it! Anything you need, we have it! Anything you need, we have ...

    From $91 per night (USD)

    VRBO

    Details
  • Charming Coach House in Chicago's Hot Wicker Park
    From $113 per night (USD)

    Expedia

    Charming Coach House in Chicago's Hot Wicker Park

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Wicker Park is known as Chicago's trendy enclave. Chicagoans and tourists alike are drawn to this hot spot neighborhood. ...

    From $113 per night (USD)

    Expedia

    Details
  • Belmont & Racine - Walk to Wrigley Field, Southport Corridor, and Belmont CTA
    From $272 per night (USD)

    VRBO

    Belmont & Racine - Walk to Wrigley Field, Southport Corridor, and Belmont CTA

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Welcome to Belmont & Racine, your getaway location in the heart of the Lakeview neighborhood of Chicago, Illinois! Short ...

    From $272 per night (USD)

    VRBO

    Details
  • Chic Chicago Abode: Steps from Magnificent Mile!
    From $93 per night (USD)

    Expedia

    Chic Chicago Abode: Steps from Magnificent Mile!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    5

    Discover the best of the Windy City with a stay at this charming 3-bedroom, 1.5-bathroom home. Immerse yourself in the v ...

    From $93 per night (USD)

    Expedia

    Details
  • Hoffman Estates Rental
    From $428 per night (USD)

    VRBO

    Hoffman Estates Rental

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    1400 SF renovated unit is 7-9 min away from interstate 90, which takes you straight to O’hare Air & downtown! This prope ...

    From $428 per night (USD)

    VRBO

    Details
  • 4 Beds, Jacuzzi, EV Parking! Walk to Wrigley Field & Brown Line!
    From $419 per night (USD)

    Expedia

    4 Beds, Jacuzzi, EV Parking! Walk to Wrigley Field & Brown Line!

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    6

    Looking for a spacious, stylish, and fully-equipped home in the heart of Chicago? Book your stay now and make this beau ...

    From $419 per night (USD)

    Expedia

    Details
  • Luxury Chicago 2 Story Condo: 10 Mins to Downtown
    From $231 per night (USD)

    VRBO

    Luxury Chicago 2 Story Condo: 10 Mins to Downtown

    Bedrooms:
    3
    Bathrooms:
    2
    Sleeps:
    6

    Experience luxury in our 2 bedroom (3 bed) duplex down, spread over 2 levels, our home offers over 1800+ sq ft of room. ...

    From $231 per night (USD)

    VRBO

    Details
  • Pearly Gates w\/ 2-Car Garage
    From $228 per night (USD)

    VRBO

    Pearly Gates w\/ 2-Car Garage

    Bedrooms:
    1
    Bathrooms:
    4
    Sleeps:
    9

    Summary: The Pearly Gates is located in the heart of Forest Park! Located just 10 miles from downtown Chicago, you can h ...

    From $228 per night (USD)

    VRBO

    Details
  • Full suburban home 30 mins from downtown Chicago!
    From $265 per night (USD)

    VRBO

    Full suburban home 30 mins from downtown Chicago!

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Bring the whole family to this great place with lots of room for fun. Full house in quiet suburb with free garage access ...

    From $265 per night (USD)

    VRBO

    Details
  • Chicago Rental - Vernon Ave
    From $193 per night (USD)

    VRBO

    Chicago Rental - Vernon Ave

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    12

    2600 SF renovated unit in the South suburbs, and only 30 minutes south of Downtown Chicago! This property has 5 bedrooms ...

    From $193 per night (USD)

    VRBO

    Details
  • Berwyn Rental
    From $334 per night (USD)

    VRBO

    Berwyn Rental

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    10

    Summary: 1800 SF renovated home is only 5 miles away from Midway airport, and approx 26 min from downtown Chicago! This ...

    From $334 per night (USD)

    VRBO

    Details
  • Great Place
    From $86 per night (USD)

    Expedia

    Great Place

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    great place, have nice stuff, yadda yadda yadda, hkhbhhbbjjbhjbvghvghcfcggfcdxgnfgfcfgxdfxfchfdxfxfdxfgdxfxdxfxfxdxddddx ...

    From $86 per night (USD)

    Expedia

    Details
  • Newly Designed 3bd In Heart of Ukrainian Village by AllSet Turnover
    From $307 per night (USD)

    VRBO

    Newly Designed 3bd In Heart of Ukrainian Village by AllSet Turnover

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Discover the charm of Ukrainian Village in my beautifully designed home just steps from award winning restaurants, cafes ...

    From $307 per night (USD)

    VRBO

    Details
  • Spacious, & Minutes from Downtown: Enjoy Your Dream 3BR\/2BA Apartment in Chicago
    From $254 per night (USD)

    Expedia

    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 $254 per night (USD)

    Expedia

    Details
  •  Cozy 5 bedrooms 2 bath near downtown loop and mcCormick Place
    From $169 per night (USD)

    VRBO

    Cozy 5 bedrooms 2 bath near downtown loop and mcCormick Place

    Bedrooms:
    2
    Bathrooms:
    6
    Sleeps:
    6

    5 bed 2 full bathroom with 2300sqft of living space. Property is located on a quiet street with long time ownership. Res ...

    From $169 per night (USD)

    VRBO

    Details
  • iKlektik House \/\/ Robin
    From $161 per night (USD)

    Expedia

    iKlektik House \/\/ Robin

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Bright, Sunny and Stylish one bedroom, full kitchen, balcony over looking the backyard in West Town. Close to Wicker Par ...

    From $161 per night (USD)

    Expedia

    Details
  • -Lovely 5 BedRoom Unit in Uptown
    From $1462 per night (USD)

    VRBO

    -Lovely 5 BedRoom Unit in Uptown

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Have fun with the whole family at this stylish place. Your family will be close to everything when you stay at this cent ...

    From $1462 per night (USD)

    VRBO

    Details
  • 5 minutes from Midway Int'l Airport Single Family Home.
    From $219 per night (USD)

    Expedia

    5 minutes from Midway Int'l Airport Single Family Home.

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    If you intend to book this house to throw a party or other disruptive events or behavior, save us the headache and DON'T ...

    From $219 per night (USD)

    Expedia

    Details
  • Upscale River North 1BR w\/ Coffee Shop & Gym, nr Lake, by Blueground
    From $164 per night (USD)

    VRBO

    Upscale River North 1BR w\/ Coffee Shop & Gym, nr Lake, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the best of Chicago, with this one bedroom apartment in River North. with views over the city. It’ll be easy to ...

    From $164 per night (USD)

    VRBO

    Details
  • Maximum Comfort! w\/ Complimentary Airport Shuttle Service, Pets are Welcome!
    From $151 per night (USD)

    VRBO

    Maximum Comfort! w\/ Complimentary Airport Shuttle Service, Pets are Welcome!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...

    From $151 per night (USD)

    VRBO

    Details
  • Great Amenities Onsite! Pool, Private Parking, Free Breakfast, Close to Legoland
    From $197 per night (USD)

    VRBO

    Great Amenities Onsite! Pool, Private Parking, Free Breakfast, Close to Legoland

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Our generously sized rooms and suites are packed with thoughtful extras like comfortable bedding, ergonomic workstations ...

    From $197 per night (USD)

    VRBO

    Details
  • Best Pick! Spacious and Pet-friendly Unit, Free Airport Shuttle Service!
    From $178 per night (USD)

    VRBO

    Best Pick! Spacious and Pet-friendly Unit, Free Airport Shuttle Service!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...

    From $178 per night (USD)

    VRBO

    Details
  • Hassle-free Stay w\/ Complimentary Airport Shuttle, Pets are Welcome!
    From $152 per night (USD)

    VRBO

    Hassle-free Stay w\/ Complimentary Airport Shuttle, Pets are Welcome!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...

    From $152 per night (USD)

    VRBO

    Details
  • Stylish Streeterville 2BR w\/ Lounge & Pool, nr Riverwalk, by Blueground
    From $270 per night (USD)

    Expedia

    Stylish Streeterville 2BR w\/ Lounge & Pool, nr Riverwalk, by Blueground

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Feel at home wherever you choose to live with Blueground. You’ll love this lovely Streeterville furnished two bedroom ap ...

    From $270 per night (USD)

    Expedia

    Details
  • Great South Loop 1BR w\/ Games & Pool, nr Park & Train, by Blueground
    From $142 per night (USD)

    VRBO

    Great South Loop 1BR w\/ Games & Pool, nr Park & Train, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover the best of Chicago, with this one bedroom apartment in South Loop. . It’ll be easy to simply show up and start ...

    From $142 per night (USD)

    VRBO

    Details
  • Upscale Streeterville Jr 1BR w\/ Gym, nr Magnificent Mile, by Blueground
    From $127 per night (USD)

    Expedia

    Upscale Streeterville Jr 1BR w\/ Gym, nr Magnificent Mile, by Blueground

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Feel at home wherever you choose to live with Blueground. You’ll love this stylish Streeterville furnished one bedroom a ...

    From $127 per night (USD)

    Expedia

    Details
  • 3 Apartments 1 blk to Metra, EZPark, Grill, Safe
    From $487 per night (USD)

    VRBO

    3 Apartments 1 blk to Metra, EZPark, Grill, Safe

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    17

    Summary: Do you have a larger group you're trying to accommodate? This listing offers three modern Apartments in 1 build ...

    From $487 per night (USD)

    VRBO

    Details
  • Spacious, Good Location & Parking!
    From $536 per night (USD)

    Expedia

    Spacious, Good Location & Parking!

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    No Hidden Fees! This fully furnished rental offers a clean, bright, and spacious 2 bedroom/1 bathroom apartment locate ...

    From $536 per night (USD)

    Expedia

    Details
  • 13 Mi to Dtwn Chicago: Maywood Home w\/ Fireplace
    From $248 per night (USD)

    VRBO

    13 Mi to Dtwn Chicago: Maywood Home w\/ Fireplace

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Laptop-Friendly Workspace | 10 Mi to Airport Make yourself at home at this 3-bedroom, 2-bath vacation rental in Maywood ...

    From $248 per night (USD)

    VRBO

    Details
  • Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
    From $159 per night (USD)

    VRBO

    Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Our generously sized rooms and suites are packed with thoughtful extras like comfortable bedding, ergonomic workstations ...

    From $159 per night (USD)

    VRBO

    Details
  • Best Value, Quality Stay! Pets Allowed, Complimentary Airport Shuttle!
    From $178 per night (USD)

    VRBO

    Best Value, Quality Stay! Pets Allowed, Complimentary Airport Shuttle!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...

    From $178 per night (USD)

    VRBO

    Details
  • Convenience & Comfort! w\/ Airport Shuttle Service, Pet-friendly Property!
    From $152 per night (USD)

    VRBO

    Convenience & Comfort! w\/ Airport Shuttle Service, Pet-friendly Property!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...

    From $152 per night (USD)

    VRBO

    Details
  • Maximum Comfort! With Airport Shuttle Service, Pets are Welcome!
    From $178 per night (USD)

    VRBO

    Maximum Comfort! With Airport Shuttle Service, Pets are Welcome!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...

    From $178 per night (USD)

    VRBO

    Details
  • Your Home Away From Home! Pet-friendly Property, Full Kitchen, Free Shuttle!
    From $143 per night (USD)

    VRBO

    Your Home Away From Home! Pet-friendly Property, Full Kitchen, Free Shuttle!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    The hotel offers a variety of guestrooms to make visitors feel right at home complete with in-room microwaves, refrigera ...

    From $143 per night (USD)

    VRBO

    Details
  • TWO Comfortable 1BR Suites With Kitchens, Short Drive to Kohl Children's Museum!
    From $285 per night (USD)

    VRBO

    TWO Comfortable 1BR Suites With Kitchens, Short Drive to Kohl Children's Museum!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    8

    The hotel offers a variety of guestrooms to make visitors feel right at home complete with in-room microwaves, refrigera ...

    From $285 per night (USD)

    VRBO

    Details
  • Spacious Unit with Full Kitchen, Free Airport Shuttle! Near Ruby Park!
    From $119 per night (USD)

    VRBO

    Spacious Unit with Full Kitchen, Free Airport Shuttle! Near Ruby Park!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The hotel offers a variety of guestrooms to make visitors feel right at home complete with in-room microwaves, refrigera ...

    From $119 per night (USD)

    VRBO

    Details
  • THREE Convenient 1BR Suites with Kitchens, Pets Are Welcome, Airport Shuttle!
    From $429 per night (USD)

    VRBO

    THREE Convenient 1BR Suites with Kitchens, Pets Are Welcome, Airport Shuttle!

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    12

    The hotel offers a variety of guestrooms to make visitors feel right at home complete with in-room microwaves, refrigera ...

    From $429 per night (USD)

    VRBO

    Details
  • FOUR Large 1BR Suites with Full Kitchen, Free Shuttle Chicago O'Hare Airport!
    From $571 per night (USD)

    VRBO

    FOUR Large 1BR Suites with Full Kitchen, Free Shuttle Chicago O'Hare Airport!

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    16

    The hotel offers a variety of guestrooms to make visitors feel right at home complete with in-room microwaves, refrigera ...

    From $571 per night (USD)

    VRBO

    Details
  • Spacious Suites with Swimming Pool, Short Drive to West Meadows Ice Arena!
    From $232 per night (USD)

    VRBO

    Spacious Suites with Swimming Pool, Short Drive to West Meadows Ice Arena!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    Our generously sized rooms and suites are packed with thoughtful extras like comfortable bedding, ergonomic workstations ...

    From $232 per night (USD)

    VRBO

    Details
  • Memorable Vacation, Short Drive To Arlington Heights Historical Museum!
    From $464 per night (USD)

    VRBO

    Memorable Vacation, Short Drive To Arlington Heights Historical Museum!

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    12

    Our generously sized rooms and suites are packed with thoughtful extras like comfortable bedding, ergonomic workstations ...

    From $464 per night (USD)

    VRBO

    Details
  • Great Pick! With Complimentary Airport Shuttle Service, Pet-friendly
    From $152 per night (USD)

    VRBO

    Great Pick! With Complimentary Airport Shuttle Service, Pet-friendly

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...

    From $152 per night (USD)

    VRBO

    Details
  • Comfort & Convenience! Pet-friendly Property, w\/ Complimentary Airport Shuttle
    From $152 per night (USD)

    VRBO

    Comfort & Convenience! Pet-friendly Property, w\/ Complimentary Airport Shuttle

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The property offers spacious guest rooms featuring plush bedding and complimentary Wi-Fi. Dine at the on-site restaurant ...

    From $152 per night (USD)

    VRBO

    Details
  • Spacious Haven \/ 8-Min to Chicago \/ Sleeps 10
    From $294 per night (USD)

    VRBO

    Spacious Haven \/ 8-Min to Chicago \/ Sleeps 10

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Introducing Spacious Haven; your home away from home in the heart of Forest Park. With luxurious finishes and modern ame ...

    From $294 per night (USD)

    VRBO

    Details
  • New renovation-1BR-Stylish-Modern-Next to the Lake\n
    From $252 per night (USD)

    Expedia

    New renovation-1BR-Stylish-Modern-Next to the Lake\n

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    LISTING DESCRIPTION - Experience the best of Evanston in our cozy 1BR/1BA apartment near Lake Michigan. Enjoy a fully e ...

    From $252 per night (USD)

    Expedia

    Details
  • Modern Spacious New Renovation 1BR Evanston
    From $244 per night (USD)

    VRBO

    Modern Spacious New Renovation 1BR Evanston

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Listing Description Experience the best of Evanston in our cozy 1BR/1BA apartment near Lake Michigan. Enjoy a fully equ ...

    From $244 per night (USD)

    VRBO

    Details
  • Spacious 5 BR \/ King Size Beds + Private Parking!
    From $476 per night (USD)

    Expedia

    Spacious 5 BR \/ King Size Beds + Private Parking!

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    12

    Discover Chicago from our cozy home! Just .5 mile from the Green Line CTA station, explore downtown with ease. 3 minute ...

    From $476 per night (USD)

    Expedia

    Details
  • Wicker Parks, Designers Dream, on-trend 2 Bdrm
    Click For Pricing

    VRBO

    Wicker Parks, Designers Dream, on-trend 2 Bdrm

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    About this space Wicker Parks, Designers Dream is just that. As a facet of Red Robin Rentals property portfolio, you are ...

    Click For Pricing

    VRBO

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

    Expedia

    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)

    Expedia

    Details
  • Apartment in Historic Lakeview Mansion - Best Location for Vacationers!
    From $139 per night (USD)

    VRBO

    Apartment in Historic Lakeview Mansion - Best Location for Vacationers!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This 1902 home was completely renovated into 16 apartments in 2022. These brand new luxury apartments feature in unit la ...

    From $139 per night (USD)

    VRBO

    Details
  • Relaxing 2BR Apartment in Lively West Rogers Park
    From $223 per night (USD)

    Expedia

    Relaxing 2BR Apartment in Lively West Rogers Park

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Listing Description Welcome to this beautiful two-bed, one-bath apartment in the heart of West Rogers Park! Perfectly l ...

    From $223 per night (USD)

    Expedia

    Details
  • A Dream Home in Chicagoland
    From $232 per night (USD)

    VRBO

    A Dream Home in Chicagoland

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Relax with your friends and family at this peaceful home!. This 3 bedroom, 1.5 bath home is perfect for a family getaway ...

    From $232 per night (USD)

    VRBO

    Details
  • Summit Rental
    From $491 per night (USD)

    VRBO

    Summit Rental

    Bedrooms:
    2
    Bathrooms:
    5
    Sleeps:
    12

    Summary:   2340 SF renovated home is only 3 miles away from Midway airport, and approx. 16 min from downtown Chicago! Th ...

    From $491 per night (USD)

    VRBO

    Details
  • 3BD West Town Gem: Explore the Windy City in Style
    From $381 per night (USD)

    VRBO

    3BD West Town Gem: Explore the Windy City in Style

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Welcome to our stylish 3-bed, 2-bath Condo in the heart of Chicago's vibrant West Town. Designed for your comfort, it's ...

    From $381 per night (USD)

    VRBO

    Details
  • Palos Hills Rental
    From $370 per night (USD)

    VRBO

    Palos Hills Rental

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    8

    2300 SF updated home is the GEM of the South suburbs, nestled in between Midway airport and Tinley/Orland Park! Our home ...

    From $370 per night (USD)

    VRBO

    Details
  • Arlington Heights Rental
    From $491 per night (USD)

    VRBO

    Arlington Heights Rental

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    2000 SF renovated unit is 20 minutes away from O’Hare Airport & 35 min to downtown Chicago! This property has 4 bedrooms ...

    From $491 per night (USD)

    VRBO

    Details
  • Elgin Rental- Jay St\n
    From $491 per night (USD)

    VRBO

    Elgin Rental- Jay St\n

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    2100 SF renovated unit is 7-9 min away from interstate 90, which takes you straight to O'hare Air & downtown! This prope ...

    From $491 per night (USD)

    VRBO

    Details