Step into the enchanting world of Chicago, a haven nestled in Illinois. Renowned for its condos, the region combines breathtaking scenery with a rich tapestry of culture. With a selection of 4,373 properties, your perfect stay is just a click away.

In Chicago, condos range from rustic hideaways to luxurious sanctuaries. Prices start at $39 and can go up to $7,268. Top features often include Air conditioner, offering a unique stay.

Top Features: Air conditioner, Internet / Wifi, Kitchen or Kitchenette, TV and Laundry

Local Highlights: Millennium Park, Navy Pier, Chicago Riverwalk, Museum of Science and Industry, Chicago and Museum Campus

Unlock the secrets of Chicago by booking your condos now. Experience the diverse culture and scenery of Illinois.

Top condos in Chicago

Property view
4.1 / 5.0
Excellent(20 Ratings)
McCormick Place spacious 3br-2ba designer suite with optional parking for 10 guests
Apartment
 in Chicago
Pets allowed · Kitchen or Kitchenette · Air conditioner

Enjoy the best of Chicago in our Apartment, McCormick Place spacious 3br-2ba designer suite with optional parking for 10 guests. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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TV and multimedia, Living room, Seating area
4.8 / 5.0
Outstanding(39 Ratings)
Wrigley Oasis! Steps from the Field! - 3BD 1BA
Apartment
 in Chicago
Pets allowed · Kitchen or Kitchenette · Air conditioner

Apartment in Chicago, for $76 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Property view
3.6 / 5.0
Good(16 Ratings)
Perfect Wrigleyville Stay
Apartment
 in Chicago
Pets allowed · Kitchen or Kitchenette · Air conditioner

This Apartment in Chicago, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Living room
3.5 / 5.0
Average(12 Ratings)
Penthouse Level, Stunning Wrigley Stay
Apartment
 in Chicago
Garden · Pets allowed · Kitchen or Kitchenette

Business stays, family stays, couples stay, getaway vacation, and rental in Chicago at Penthouse Level, Stunning Wrigley Stay for $77 for your next trip.

$$$$
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Living room
4.4 / 5.0
Excellent(43 Ratings)
✪ Cozy 1 Bedroom close to Downtown Chicago ✪
Apartment
 in Chicago
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Apartment in Chicago, for $87 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Property view
4.1 / 5.0
Excellent(287 Ratings)
The Double Play, Wrigley Flats - Located Right next to Wrigley
Apartment
 in Chicago
Pets allowed · Kitchen or Kitchenette · Air conditioner

Enjoy the best of Chicago in our Apartment, The Double Play, Wrigley Flats - Located Right next to Wrigley. A stunning property with amenities including Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
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Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Lounge
4.7 / 5.0
Outstanding(6 Ratings)
Historic Oak Park Residence
Apartment
 in Oak Park
Internet / Wifi

Looking to create some memories in Chicago? Look no further than our Apartment, Historic Oak Park Residence. Enjoy top-rated amenities including Internet / Wifi, and more.

$$$$
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Aerial view
5.0 / 5.0
Outstanding(264 Ratings)
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
Apartment
 in Chicago
6 guests · 3 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This Apartment in Chicago, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Exclusive Room, Private Bathroom, Garden View (2nd Floor) | Lounge
4.7 / 5.0
Outstanding(6 Ratings)
Historic Oak Park Residence
Apartment
 in Oak Park
2 guests
Internet / Wifi

Looking to create some memories in Chicago? Look no further than our Apartment, Historic Oak Park Residence. Enjoy top-rated amenities including Internet / Wifi, and more.

$$$$
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Apartment, Private Bathroom | Terrace/patio
4.8 / 5.0
Outstanding(4 Ratings)
At Home in Oak Park
Apartment
 in Oak Park
2 guests
Internet / Wifi · Parking

Soak up the beauty of Chicago in our Apartment, At Home in Oak Park. With a range of amenities such as Internet / Wifi and Parking, you'll feel right at home.

$$$$
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Communal lounge/ TV room, Living room
4.4 / 5.0
Excellent(77 Ratings)
1549 North Maplewood Avenue
Apartment
 in Chicago
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Experience vacation in Chicago with our Apartment, 1549 North Maplewood Avenue. Enjoy amenities such as Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Interior
4.7 / 5.0
Outstanding(3 Ratings)
Historic Oak Park Apartment ~ 8 Mi to Downtown
Apartment
 in Oak Park
2 guests
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This attractive Apartment in Chicago, $274 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Condos with air conditioning in Chicago

Interior
4.7 / 5.0
Outstanding(3 Ratings)
Historic Oak Park Apartment ~ 8 Mi to Downtown
Apartment
 in Oak Park
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This inviting Apartment in Chicago can fit your needs for many types of vacations, at $274 per night.

$$$$
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Terrace/patio
No ratings yet
Chic Forest Park Home w/ Patio - 10 Mi to Chicago
Apartment
 in Forest Park
2 guests
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Business stays, family stays, couples stay, getaway vacation, and rental in Chicago at Chic Forest Park Home w/ Patio - 10 Mi to Chicago for $237 for your next trip.

$$$$
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Bed, Bedroom, City view, City view
4.5 / 5.0
Excellent(12 Ratings)
Uptown Gem
Apartment
 in Chicago
Garden · Pool · Kitchen or Kitchenette

This Apartment for $102 in Chicago, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property view
4.3 / 5.0
Excellent(13 Ratings)
Wrigleyville Friends Unit - 5bdrm
Apartment
 in Chicago
Pets allowed · Kitchen or Kitchenette · Air conditioner

Indulge in a peaceful retreat at Wrigleyville Friends Unit - 5bdrm, our elegant Apartment in Chicago. Enjoy amenities including Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
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Microwave, oven, stovetop, blender
No ratings yet
Dog-friendly Unit Near Chicago w/ Backyard!
Apartment
 in Blue Island
2 guests
Pets allowed · Kitchen or Kitchenette · Air conditioner

The best choice in Chicago for Apartment, for $473 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property view
3.4 / 5.0
Average(21 Ratings)
Wrigley Garden Unit
Apartment
 in Chicago
Garden · Pets allowed · Kitchen or Kitchenette

Experience the best of Chicago with this Apartment available for $77. This property is equipped with amenities including Air conditioner, Internet / Wifi and Pets allowed, and more.

$$$$
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Property view
4.5 / 5.0
Excellent(124 Ratings)
Perfect place to enjoy the city or just relax
Apartment
 in Chicago
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

The best choice in Chicago for Apartment, for $93 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Miscellaneous
No ratings yet
Sonder Onterie
Apartment
 in Chicago
2 guests · 3 bedrooms · 2 baths
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Indulge in a peaceful retreat at Sonder Onterie, our elegant Apartment in Chicago. Enjoy amenities including Air conditioner, Internet / Wifi and Kitchen or Kitchenette, and more.

$$$$
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BBQ facilities, Balcony/Terrace
4.7 / 5.0
Outstanding(28 Ratings)
Superior
Apartment
 in Chicago
Garden · Kitchen or Kitchenette · Air conditioner

Looking for the perfect place to call home during your trip to Chicago? This Apartment offers a comfort and style with top-notch amenities, including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Facade/entrance
4.7 / 5.0
Outstanding(7 Ratings)
webster house
Apartment
 in Chicago
Garden · Pets allowed · Kitchen or Kitchenette

Experience vacation in Chicago with our Apartment, webster house. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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TV, books
5.0 / 5.0
Outstanding(1 Rating)
Blue Island Apartment: Walk to Metra!
Apartment
 in Blue Island
2 guests
Pets allowed · Kitchen or Kitchenette · Air conditioner

This Apartment in Chicago, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

$$$$
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Property view
4.8 / 5.0
Outstanding(12 Ratings)
The Avondale Attic
Apartment
 in Chicago
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Enjoy the best of Chicago in our Apartment, The Avondale Attic. A stunning property with amenities including Air conditioner, Internet / Wifi and Kitchen or Kitchenette, and more.

$$$$
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Living room
4.6 / 5.0
Outstanding(100 Ratings)
Forrestville Ave Large Suite
Apartment
 in Chicago
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Indulge in a peaceful retreat at Forrestville Ave Large Suite, our elegant Apartment in Chicago. Enjoy amenities including Air conditioner, Internet / Wifi and Kitchen or Kitchenette, and more.

$$$$
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Apartment (3 Bedrooms) | Interior
5.0 / 5.0
Outstanding(1 Rating)
Spacious Oak Park Home, 11 Mi to Downtown Chicago!
Apartment
 in Oak Park
2 guests
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

This attractive Apartment in Chicago, $491 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Photo of the whole room, Bedroom
4.3 / 5.0
Excellent(38 Ratings)
My Cozy Heavon
Apartment
 in Chicago
Kitchen or Kitchenette · Air conditioner · Internet / Wifi

Discover the beauty of Chicago with a stay at My Cozy Heavon, a top rated Apartment with amenities such as Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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