Cook Area Rentals
From $377 per night (USD)VRBO
Modern Apt | Billiards, 1 Private Patio,1 Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Summary: Stunning 3 bedroom modern garden unit apartment with 1 Gated Parking Space, Pool Table (Also a dining table), P ...
From $377 per night (USD)VRBO
From $264 per night (USD)Expedia
The Vibe Headquarters
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Come and enjoy your stay here at The Vibe Headquarters, where you’re sure to find peace. This condo is located in Washin ...
From $264 per night (USD)Expedia
From $244 per night (USD)VRBO
Wrigleyville Suites Room 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Wrigleyville Suites are great for couples, solo adventurers, and business travelers. Experience the comfortable and casu ...
From $244 per night (USD)VRBO
From $149 per night (USD)Expedia
Cozy Midway Home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to your perfect home away from home! Our charming 2 bedroom, 1 bathroom house offers everything you need for a c ...
From $149 per night (USD)Expedia
From $278 per night (USD)VRBO
Spacious, cozy 3 bedroom house with a perfect location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stay at our centrally-located home, perfect for families! Enjoy the convenience of being close to parks, restaurants, gr ...
From $278 per night (USD)VRBO
From $321 per night (USD)Expedia
House in the Park
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
Bring the whole family to this great place with lots of room across the street for fun fishing, golfing, bike track, val ...
From $321 per night (USD)Expedia
From $287 per night (USD)VRBO
Cozy 4-bedroom house in adorable Evanston with WiFi, AC
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Located in Evanston, enjoy what this 4-bedroom house has to offer. With 4 queen beds, our property provides ample space ...
From $287 per night (USD)VRBO
From $329 per night (USD)VRBO
2 x Superior 2 Doubles at Millennium Knickerbocker Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $329 per night (USD)VRBO
From $961 per night (USD)VRBO
3 x Millennium Suite King at Millennium Knickerbocker Chicago
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $961 per night (USD)VRBO
From $659 per night (USD)VRBO
4 x Superior 2 Doubles at Millennium Knickerbocker Chicago
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $659 per night (USD)VRBO
From $198 per night (USD)VRBO
Central Chicago Retreat with Modern Comforts! Minutes to Oak Street Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $198 per night (USD)VRBO
From $495 per night (USD)VRBO
3 x Superior 2 Doubles at Millennium Knickerbocker Chicago
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $495 per night (USD)VRBO
From $320 per night (USD)VRBO
Millennium Suite King at Millennium Knickerbocker Chicago, Near Oak Street Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $320 per night (USD)VRBO
From $264 per night (USD)VRBO
Luxury Stay in Chicago's Iconic District! Near Chicago Tribune Tower
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $264 per night (USD)VRBO
From $790 per night (USD)VRBO
Best Place to Unwind! 4 Convenient Units, Near Oak Street Beach
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $790 per night (USD)VRBO
From $1153 per night (USD)VRBO
Prime Location for Exploring Chicago's Best Attractions! 3 Relaxing Units
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $1153 per night (USD)VRBO
From $168 per night (USD)VRBO
Historic Elegance in the Heart of Chicago! Near 360 Chicago Observation Deck
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $168 per night (USD)VRBO
From $1538 per night (USD)VRBO
Ideal Spot for Exploring Chicago's Cultural Gems! 4 Relaxing Units
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $1538 per night (USD)VRBO
From $769 per night (USD)VRBO
Short Distance From The Well Known Sites! 2 Comfortable Units
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $769 per night (USD)VRBO
From $396 per night (USD)VRBO
Enjoy a Hassle-Free and Comfortable Stay! 2 Relaxing Units near Oak Street Beach
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $396 per night (USD)VRBO
From $385 per night (USD)VRBO
Experience Soothing Moments & Luxury! Minutes to Oak Street Beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $385 per night (USD)VRBO
From $221 per night (USD)VRBO
Studio Suite King at Millennium Knickerbocker Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $221 per night (USD)VRBO
From $641 per night (USD)VRBO
2 x Millennium Suite King at Millennium Knickerbocker Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $641 per night (USD)VRBO
From $154 per night (USD)VRBO
Superior King at Millennium Knickerbocker Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $154 per night (USD)VRBO
From $1281 per night (USD)VRBO
4 x Millennium Suite King at Millennium Knickerbocker Chicago
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $1281 per night (USD)VRBO
From $140 per night (USD)VRBO
Standard King at Millennium Knickerbocker Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $140 per night (USD)VRBO
From $184 per night (USD)VRBO
Elegant Urban Oasis in Downtown Chicago! Near Museum of Contemporary Art
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $184 per night (USD)VRBO
From $166 per night (USD)VRBO
Superior 2 Doubles at Millennium Knickerbocker Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $166 per night (USD)VRBO
From $134 per night (USD)VRBO
Cozy Garden Unit 1st flr with private entrance and Turo vehicle available.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a peaceful stay at this 1-bedroom apartment in Hickory Hills. This serene and quaint property offers everything yo ...
From $134 per night (USD)VRBO
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)VRBO
From $296 per night (USD)VRBO
4-bedroom townhome in Frank Lloyd Wright District-FREE PARKING, Patio, Yard
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
After a long day of enjoying all that Chicago (our place is just a short walk to the green line which gets you in the he ...
From $296 per night (USD)VRBO
From $281 per night (USD)Expedia
Cozy apartment near zoo, DePaul, Oz Park and much more!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Beautiful brownstone in the heart of Lincoln Park. 5 minute walk to Lincoln Park zoo, lakefront, variety of restaurants/ ...
From $281 per night (USD)Expedia
From $204 per night (USD)VRBO
Charming 4-bedroom apartment in delightful Chicago with central heat\/AC, WiFi.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Discover this marvelous 4-bedroom gem in Chicago. Step into this cool apartment and be greeted by a pleasant ambiance th ...
From $204 per night (USD)VRBO
From $224 per night (USD)Expedia
Gold Coast\/Downtown Hideaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
New Listing! Freshly renovated Gold Coast hideaway provides the perfect escape from the nearby shopping and restaurant a ...
From $224 per night (USD)Expedia
From $876 per night (USD)VRBO
Chic and Spacious Bi-level 3BD in Bucktown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This one-of-a-kind condo in Bucktown is ready to host! The property features a hidden staircase leading down to the in-l ...
From $876 per night (USD)VRBO
From $202 per night (USD)Expedia
Cozy & Colorful garden unit in Logan Square
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Escape to our private 3 bedroom garden condo in trendy Logan Square. This urban retreat offers a cozy living space with ...
From $202 per night (USD)Expedia
From $102 per night (USD)VRBO
Lovely 2BR Gem w\/ Outdoor Oasis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover your perfect urban retreat in the heart of Chicago's trendy Logan Square/Avondale neighborhood. This beautiful ...
From $102 per night (USD)VRBO
From $248 per night (USD)Expedia
Charming 3-bedroom apartment with AC, WiFi in phenomenal Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Unwind in Chicago at this lovely apartment. With 3 bedrooms, including 1 queen bed, 1 child bed, and 1 full bed, this wo ...
From $248 per night (USD)Expedia
From $185 per night (USD)VRBO
The Landmark; a comfy suite near McCormick Place
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to the landmark. A cozy well appointed studio space in the heart of the historic Calumet/Giles Prairie district ...
From $185 per night (USD)VRBO
From $293 per night (USD)Expedia
Charming 3 bedrooms Apartment at the Medical District
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Come enjoy this beautiful updated unit in the heart of the Medical District/ Tri-Taylor. The apartment is conveniently l ...
From $293 per night (USD)Expedia
From $451 per night (USD)VRBO
Marvelous 3-bedroom town-home in Chicago.\n
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Marvelous 3-bedroom town-home in Chicago. Over 2100 sqft of space including 3 bedrooms, & 2.5 bathrooms. Located in a qu ...
From $451 per night (USD)VRBO
From $141 per night (USD)VRBO
3-BR\/ 1.5 BATH 1st Flr Skokie Apt 2-Car driveway Parking Near Evanston\/Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Nestled in Skokie, this apartment offers convenience! Just 1-2 miles away from Old Orchard Mall, Jewel Osco, multiple re ...
From $141 per night (USD)VRBO
From $384 per night (USD)VRBO
Stylish Retreat: 4 Bedroom | Downtown Chicago
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Summary: Welcome to our stylish Tudor-style retreat! Spanning this charming 3-room apartment features 4 beds, basic amen ...
From $384 per night (USD)VRBO
From $292 per night (USD)Expedia
Modern 4BR in Hyde Park, Walk to University
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Located in the Hyde Park neighborhood on the south side of Chicago, the area is home to the University of Chicago and va ...
From $292 per night (USD)Expedia
From $269 per night (USD)VRBO
Penthouse Condo in Chicago featuring Zero Gravity Massage Chair
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to the Penthouse Loft in Chicago. As avid travelers and frequent VRBO users, we've infused our home with inspira ...
From $269 per night (USD)VRBO
From $334 per night (USD)Expedia
Remodeled w Game Room Mins to Chicago - Unit 2
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Experience modern comfort and fun at our newly remodeled and beautifully decorated home in Berwyn, IL! Designed with you ...
From $334 per night (USD)Expedia
From $333 per night (USD)VRBO
Berwyn 15 min > Downtown Game Room Grill - Unit 1
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to your perfect getaway in Berwyn, IL! This newly remodeled and beautifully decorated home offers a blend of mod ...
From $333 per night (USD)VRBO
From $161 per night (USD)VRBO
Stylish 2BR Urban Retreat in River West
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Welcome to our contemporary 2-bedroom, 1-bathroom condo in lively River West. Ideal for business and leisure, t ...
From $161 per night (USD)VRBO
From $108 per night (USD)VRBO
Gorgeous 3-bedroom apartment in Jefferson Park, Chicago
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Welcome to this charming apartment in Chicago. This tranquil retreat offers a perfect escape for guests seeking a serene ...
From $108 per night (USD)VRBO
From $222 per night (USD)Expedia
Charming 2-bedroom apartment in hip Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unwind in Chicago at this delightful apartment. With 2 bedrooms, including a king bed and a queen bed, this property is ...
From $222 per night (USD)Expedia
From $616 per night (USD)VRBO
1\/2 mile to NU, 5min walk to Lake, Swim Spa pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 9
Welcome to one of the most distinctive homes in Evanston's historic neighborhood, where charm meets modern comfort. Thi ...
From $616 per night (USD)VRBO
From $341 per night (USD)VRBO
Pulaski Mahal - Spacious “Smart” Home with Game Room. Close to Hwy, train, EL.
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Early Check-Ins and Late Check-Outs are difficult to accommodate. If you need additional time, please consider booking a ...
From $341 per night (USD)VRBO
From $484 per night (USD)VRBO
Spacious 5BR\/6BA Gorgeous Home in Fabulous Northshore Chicago location!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 10
Make yourself at home in this 5 bedroom/6+bath Glenview retreat. This brilliant house offers a phenomenal stay for guest ...
From $484 per night (USD)VRBO
From $722 per night (USD)Expedia
6BR Chicago Gem: Prime, Safe, Family-Friendly Hub
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 12
Experience Chicago in an unmatched setting: two apartments beautifully united into a grand 6-bedroom, 2-bathroom home in ...
From $722 per night (USD)Expedia
From $230 per night (USD)VRBO
Luxury 1-bedroom with WiFi, AC in charming Franklin Park
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Unwind in Franklin Park at this lovely house. This terrific property offers a cozy bedroom, perfect for a relaxing retre ...
From $230 per night (USD)VRBO
From $541 per night (USD)Expedia
Gorgeous 5 Bedroom Gem Sleeps 18 with Pool, Ping Pong, Pac Man, Tons of Games!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 18
Gorgeous gem within 10 miles of Downtown, Airport, Lake Michigan, and United Center! About 15 miles from Wrigley Field ...
From $541 per night (USD)Expedia
From $364 per night (USD)VRBO
Charming 3-bedroom house in brilliant Chicago with WiFi, AC, plenty of sleeping.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discover this fabulous 3-bedroom gem in Chicago. This wonderful house offers a cozy and inviting atmosphere that will ma ...
From $364 per night (USD)VRBO
From $230 per night (USD)Expedia
Spacious 4-bedroom apartment with AC and WiFi in terrific Chicago
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 14
Stay comfortably in Chicago at this 4-bedroom apartment. Marvelous and superb, this amazing property offers 4 queen beds ...
From $230 per night (USD)Expedia
From $351 per night (USD)VRBO
NEW Renovated Art Gala in Rolling Meadows
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy a stylish experience at this centrally-located home. Our 4 bedroom home is very close to Schaumburg for great food ...
From $351 per night (USD)VRBO
From $151 per night (USD)Expedia
Cozy 1-bedroom house in charming Chicago with WiFi, AC, Washer\/Dryer
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Unwind in Chicago at this lovely newly renovated home! Nestled in the heart of West Town, this amazing property offers a ...
From $151 per night (USD)Expedia
From $722 per night (USD)VRBO
Top 1 Rated 4BR Lincoln Park House - King Bed
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
🌟 This property is managed by @LuxuryLodgingSTR , visit us on the web before booking here for extra savings! 🌟 ✨ I hi ...
From $722 per night (USD)VRBO
From $884 per night (USD)Expedia
Stunning NEW 5BR, 3BA house in Chicago centrally located.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our newly listed & renovated home located in family friendly Chicago's Portage Park neighborhood. Our home is ...
From $884 per night (USD)Expedia
From $627 per night (USD)VRBO
Luxury Loft Collection 703 - Terrace - River North
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious bui ...
From $627 per night (USD)VRBO
From $540 per night (USD)Expedia
5 Star Luxury Stay Near Chicago O'hare Airport, King Beds
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Chicago O'Hare Airport is just 10 minutes away. Enjoy a stylish stay with your whole family at this luxurious 5-star pro ...
From $540 per night (USD)Expedia
From $602 per night (USD)VRBO
2-Story 4-Bedroom Condo: 3-minute walk to Wrigley Field. King Bed
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
Just one block from Wrigley Field! Includes air hockey, ping-pong, foosball, and oversized Connect 4 in the basement ga ...
From $602 per night (USD)VRBO
From $100 per night (USD)Expedia
O'Hare airport Oasis #8
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Franklin Park is waiting for you at this 2-bedroom apartment. This tranquil and beautiful property offers a cozy retreat ...
From $100 per night (USD)Expedia
From $103 per night (USD)VRBO
Franklin Park's mid-term rental oasis #1
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Your home away from home in Franklin Park with 2 bedrooms. This fantastic apartment offers a tranquil and enchanting ret ...
From $103 per night (USD)VRBO
From $180 per night (USD)Expedia
Duplex 3 Bed 2 Bat Apt Steps from Lincoln Square
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your perfect Chicago getaway! This spacious 3-bedroom, 2-bathroom multi-level apartment offers everything you ...
From $180 per night (USD)Expedia
From $695 per night (USD)VRBO
Classic Chicago Charm in a Modern Setting! 3 Comfortable Units
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
The hotel is widely regarded as a paragon of the true Chicago style. With more than 300 rooms available, the property bo ...
From $695 per night (USD)VRBO
From $335 per night (USD)VRBO
Home Away From Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our charming Chicago rental home, " A Home Away From Home"! This vacation retreat offers a serene ambiance th ...
From $335 per night (USD)VRBO
From $262 per night (USD)VRBO
Updated 3 Bedroom Chicago Historic Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Ready to stay in CHARMING Chicago? Our NEWLY UPDATED masterpiece has IMPECCABLE DESIGN, 3 bedrooms, and is step ...
From $262 per night (USD)VRBO
From $178 per night (USD)Expedia
Suite 2 on Southport 4 Queen Beds
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: Check out our brand new construction Suite on Southport Ave. Centrally located in the world famous Lincoln Park ...
From $178 per night (USD)Expedia
From $203 per night (USD)VRBO
Updated Chicago Bungalow on a Beautiful and Calm Neighborhood Greenway Boulevard
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
A spacious updated bungalow at the beginning of the beautiful quite boulevard. The house is on beautiful Wrightwood Nei ...
From $203 per night (USD)VRBO
From $119 per night (USD)Expedia
Cozy 1-bedroom apartment with WiFi, AC in gorgeous Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Enjoy a peaceful stay at this delightful 1-bedroom apartment in Chicago. Unit offers everything guests need for a perfec ...
From $119 per night (USD)Expedia
From $444 per night (USD)VRBO
Tranquil King Streamwood
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
Discover the perfect blend of comfort and convenience at our charming 3-bedroom home in Streamwood, IL. Perfect for fami ...
From $444 per night (USD)VRBO
From $409 per night (USD)Expedia
Luxury King|Game Room|Fire Pit 17 miles > Downtown
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our stylish 3-bedroom home, perfect for families and groups looking to experience the charm and convenience o ...
From $409 per night (USD)Expedia
From $72 per night (USD)VRBO
Beautiful and stylish 1 bedroom apartment in the heart of Pilsen \"CASA PILSEN\"
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to Casa Pilsen!! Located in the heart of Pilsen, enjoy what this 1-bedroom apartment has to offer. This fabulous ...
From $72 per night (USD)VRBO
From $424 per night (USD)Expedia
Cozy Lemont Luxury Hideaway King Near Hwy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the Cozy Lemont Hideaway, your perfect retreat for relaxation and adventure! Nestled in the charming village ...
From $424 per night (USD)Expedia
From $136 per night (USD)VRBO
Stylish 2BR Apt in Irving Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Welcome to our charming basement unit in the heart of Irving Park! This inviting space is perfect for small families, co ...
From $136 per night (USD)VRBO
From $134 per night (USD)VRBO
Landing at Element at Veridian - 1 Bedroom in Schaumburg
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Element at Veridian unveils an exceptional portrait of living. A unique fusion of style and sophistication, our apartmen ...
From $134 per night (USD)VRBO
From $129 per night (USD)VRBO
Landing at Element at Veridian - 1 Bedroom in Schaumburg
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Element at Veridian unveils an exceptional portrait of living. A unique fusion of style and sophistication, our apartmen ...
From $129 per night (USD)VRBO
From $193 per night (USD)Expedia
Cozy 2-bedroom apartment in welcoming Chicago in the Wicker Park area
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Unwind in the stylish two-bedroom apt on Beach Street, a street in Chicago. The city is full of award-winning restaurant ...
From $193 per night (USD)Expedia
From $438 per night (USD)VRBO
Stay Inn South Shore- Pool Table, Arcade, Sleeps 10, Pet Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our stylish South Shore retreat, perfect for families and special events. This spacious 4-bedroom, 3-bathroom ...
From $438 per night (USD)VRBO
From $495 per night (USD)Expedia
The Urban Manor “Modern luxury style”
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Urban Manor in Hyde Park neighborhood, close to charming restaurants and coffee shops, exudes luxury and comfort. Th ...
From $495 per night (USD)Expedia
From $215 per night (USD)VRBO
Cozy 2-bedroom condo in Skokie
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This delightful condo in Skokie offers a cozy retreat for guests. With 2 bedrooms featuring a queen and king bed, along ...
From $215 per night (USD)VRBO
From $156 per night (USD)VRBO
~Exquisite 2-BR Residence| Top Notch Amenities ~
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Welcome to our Chic 2-Bedroom Haven in Ukrainian Village, Chicago! This stunning modern unit offers high-end am ...
From $156 per night (USD)VRBO
From $471 per night (USD)VRBO
1-bedroom apartment in awesome Chicago with AC, WiFi and 1FREE Garage Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Consider this apartment your home away from home while you visit Chicago. This charming space features a cozy bedroom wi ...
From $471 per night (USD)VRBO
From $354 per night (USD)Expedia
Chicago Escape w\/ Deck: Walk to Lake Michigan!
- Bedrooms:
- 1
- Bathrooms:
- 6
- Sleeps:
- 4
Experience the magic of the Windy City at this 2-bedroom, 1-bath Chicago vacation rental! This apartment unit in a large ...
From $354 per night (USD)Expedia
From $252 per night (USD)VRBO
Cozy 4-bedroom house in wonderful Matteson with AC, WiFi
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Matteson, this house is a dream. With 4 bedrooms, including 3 queen beds and 1 full bed, our welcoming and pe ...
From $252 per night (USD)VRBO
From $219 per night (USD)Expedia
2 queen beds -Boat rental opt
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to our cozy 2-bedroom apartment in the heart of Bridgeport, Chicago’s vibrant and historic neighborhood! Perfect ...
From $219 per night (USD)Expedia
From $199 per night (USD)VRBO
Central Chicago Apartment w\/ Grill: 3 Mi to Dtwn!
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Near the United Center, various museums, and top family attractions like the Shedd Aquarium and Navy Pier, this charming ...
From $199 per night (USD)VRBO
From $192 per night (USD)Expedia
Bright Chicago Apartment: Near Stadiums & Downtown
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Centrally located near top Chicago attractions, this charming vacation rental has everything you need for a memorable st ...
From $192 per night (USD)Expedia
From $334 per night (USD)VRBO
Modern 2-bedroom 2 -bath condo in wonderful Woodlawn Chicago.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the beauty of Chicago from this 2-bed, 2-bath condo. The space offers a lovely living room with a sofa that can ...
From $334 per night (USD)VRBO
From $212 per night (USD)Expedia
Chicago Apartment: 4 Mi to Lake Michigan!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Looking for a comfortable home base while exploring the city? Pack your bags and head to this welcoming 4-bedroom, 1-bat ...
From $212 per night (USD)Expedia
From $182 per night (USD)VRBO
Charming Pilsen Studio - Quick Access to Downtown Chicago!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Discover the charm of our unique studio apartment in La Vecindad, your perfect retreat in Pilsen, Chicago! This cozy stu ...
From $182 per night (USD)VRBO
From $311 per night (USD)Expedia
The Haven near Downtown, Medical District and United Center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
If you are traveling to Chicago for a special event at the united center or visiting a loved one at one of Chicago's pre ...
From $311 per night (USD)Expedia
From $205 per night (USD)VRBO
3BR House w\/ Paradise Garden Oasis and private pool in the heart of Schaumburg
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Home Away from Home in Schaumburg! Discover a truly unique retreat at our charming two-story duplex, pe ...
From $205 per night (USD)VRBO
From $164 per night (USD)Expedia
Marvelous 3-bedroom apartment with WiFi, AC 18 minutes from downtown Chicago
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
This memorable apartment is the perfect home base for your trip to Chicago. With 3 bedrooms, including 1 king bed, 1 que ...
From $164 per night (USD)Expedia
From $214 per night (USD)VRBO
Rustic Cozy Haven in West Town
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to your cozy retreat in West Town! Nestled amidst vibrant restaurants and lively bars, this charming unit offers ...
From $214 per night (USD)VRBO
From $86 per night (USD)Expedia
Basements Apartment With Free Street Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 32
Cozy basement living space, includes a full size bed, large closet, full bathroom, Tv, fridge, microwave, keurig coffee ...
From $86 per night (USD)Expedia