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 4,376 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 $5,526. Top features often include Air conditioner, offering a unique stay.

Top Features: Air conditioner, Internet / Wifi, Kitchen / 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

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4.8
Outstanding(45 Reviews)
Apartment
 in Chicago
Wrigley Oasis! Steps from the Field! - 3BD 1BA
Pets allowed · Kitchen / Kitchenette · Air conditioner

Apartment in Chicago, for $78 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

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3.6
Good(8 Reviews)
Apartment
 in Chicago
Penthouse Level, Stunning Wrigley Stay
Garden · Pets allowed · Kitchen / 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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4.4
Excellent(33 Reviews)
Apartment
 in Chicago
✪ Cozy 1 Bedroom close to Downtown Chicago ✪
Kitchen / 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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4.2
Excellent(21 Reviews)
Apartment
 in Chicago
McCormick Place spacious 3br-2ba designer suite with optional parking for 8 guests
Pets allowed · Kitchen / Kitchenette · Air conditioner

Enjoy the best of Chicago in our Apartment, McCormick Place spacious 3br-2ba designer suite with optional parking for 8 guests. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.

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Property view
3.6
Good(17 Reviews)
Apartment
 in Chicago
Perfect Wrigleyville Stay
Pets allowed · Kitchen / 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
4.4
Excellent(72 Reviews)
Apartment
 in Chicago
1549 North Maplewood Avenue
Kitchen / 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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Apartment, Private Bathroom | Lounge
5.0
Outstanding(3 Reviews)
Apartment
 in Oak Park
At Home in Oak Park
Internet / Wifi · Parking

Enjoy the best of Chicago in our Apartment, At Home in Oak Park. A stunning property with amenities including Internet / Wifi and Parking, and more.

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Exterior
5.0
Outstanding(240 Reviews)
Apartment
 in Chicago
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
6 guests · 3 bedrooms · 2 baths
Kitchen / 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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Property view
4.1
Excellent(271 Reviews)
Apartment
 in Chicago
The Double Play, Wrigley Flats - Cubs! - Located Right next to Wrigley and Transit
Pets allowed · Kitchen / Kitchenette · Air conditioner

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

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Property view
4.3
Excellent(12 Reviews)
Apartment
 in Chicago
Wrigleyville Friends Unit - 5bdrm
Pets allowed · Kitchen / 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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Property view
3.4
Average(20 Reviews)
Apartment
 in Chicago
Wrigley Garden Unit
Garden · Pets allowed · Kitchen / 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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4.5
Excellent(13 Reviews)
Apartment
 in Chicago
Uptown Gem
Garden · Pool · Kitchen / Kitchenette

This Apartment for $129 in Chicago, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

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Vacation rentals with air conditioning in Chicago

Property view
4.5
Excellent(102 Reviews)
Apartment
 in Chicago
Perfect place to enjoy the city or just relax
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

The best choice in Chicago for Apartment, for $113 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property view
4.6
Outstanding(84 Reviews)
Apartment
 in Chicago
Forrestville Ave Large Suite
Kitchen / 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 / Kitchenette, and more.

$$$$
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4.8
Outstanding(6 Reviews)
Apartment
 in Chicago
webster house
Garden · Pets allowed · Kitchen / 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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4.6
Outstanding(6 Reviews)
Apartment
 in Chicago
The Avondale Attic
Kitchen / 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 / Kitchenette, and more.

$$$$
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Property view
3.9
Good(12 Reviews)
Apartment
 in Chicago
ENVITAE Luxury Sky Loft Indoor Pool & Gym
Pool · Pets allowed · Kitchen / Kitchenette

Discover the beauty of Chicago with a stay at ENVITAE Luxury Sky Loft Indoor Pool & Gym, a top rated Apartment with amenities such as Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Property view
4.8
Outstanding(15 Reviews)
Apartment
 in Chicago
ENVITAE 3BR Luxury Corner Loft with Navy Pier Views
Pool · Pets allowed · Kitchen / Kitchenette

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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Property view
4.3
Excellent(31 Reviews)
Apartment
 in Chicago
My Cozy Heavon
Kitchen / 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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Property view
4.5
Excellent(9 Reviews)
Apartment
 in Chicago
ENVITAE 3BR Spacious Lux Skyview Of Navy Pier
Pool · Pets allowed · Kitchen / Kitchenette

This Apartment for $107 in Chicago, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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4.3
Excellent(20 Reviews)
Apartment
 in Chicago
ENVITAE 3BR Downtown Luxurious Suite Views & Pool
Pool · Pets allowed · Kitchen / Kitchenette

Looking to create some memories in Chicago? Look no further than our Apartment, ENVITAE 3BR Downtown Luxurious Suite Views & Pool. Enjoy top-rated amenities including Air conditioner, Dishwasher and Fireplace, and more.

$$$$
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Property view
4.3
Excellent(9 Reviews)
Apartment
 in Chicago
Captivating Apartment with Pier Views, Pool and Gym
Pool · Kitchen / Kitchenette · Air conditioner

This attractive Apartment in Chicago, $108 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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4.3
Excellent(14 Reviews)
Apartment
 in Chicago
Ultimate 3BR Luxury Suite near Navy Pier with Gym & Pool by ENVITAE
Pool · Kitchen / Kitchenette · Air conditioner

Business stays, family stays, couples stay, getaway vacation, and rental in Chicago at Ultimate 3BR Luxury Suite near Navy Pier with Gym & Pool by ENVITAE for $105 for your next trip.

$$$$
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Property view
3.9
Good(9 Reviews)
Apartment
 in Chicago
ENVITAE 2BR Vibrant High-Rise Penthouse
Pool · Pets allowed · Kitchen / Kitchenette
Most favorited

Apartment in Chicago, for $108 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

$$$$
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Property view
4.2
Excellent(18 Reviews)
Apartment
 in Chicago
3b/3b SkyLoft with Navy Pier View Gym & Pool by ENVITAE
Pool · Kitchen / Kitchenette · Air conditioner
Most favorited

Discover the beauty of Chicago with a stay at 3b/3b SkyLoft with Navy Pier View Gym & Pool by ENVITAE, a top rated Apartment with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.

$$$$
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