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 4507 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 $20,000. Top features often include Internet / Wifi, offering a unique stay.

Top Features: Internet / Wifi, Air conditioner, TV, Kitchen / Kitchenette 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
3.6
Good(17 Reviews)
Condo
 in Chicago
Perfect Wrigleyville Stay
Pets allowed · Kitchen / Kitchenette · Air conditioner

This Condo 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(28 Reviews)
Condo
 in Chicago
✪ Cozy 1 Bedroom close to Downtown Chicago ✪
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Condo 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
4.3
Excellent(246 Reviews)
Condo
 in Chicago
The Double Play Wrigley Field Flats - Located Right next to Wrigley and Transit - Cubs!
Pets allowed · Kitchen / Kitchenette · Air conditioner

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

$$$$
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Property view
3.4
Average(6 Reviews)
Condo
 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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Property view
4.4
Excellent(58 Reviews)
Condo
 in Chicago
1549 North Maplewood Avenue
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

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

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Property view
4.2
Excellent(20 Reviews)
Condo
 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 Condo, 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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Lounge
5.0
Outstanding(3 Reviews)
Condo
 in Oak Park
At Home in Oak Park
Internet / Wifi · Parking

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

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Living Room
5.0
Outstanding(225 Reviews)
Condo
 in Chicago
Bella Villa on Taylor Street Chicago’s Little Italy 1 mile west the Loop & UIC
6 guests · 3 bedrooms · 2 baths
Garden · Kitchen / Kitchenette · Air conditioner

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

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Property view
4.3
Excellent(12 Reviews)
Condo
 in Chicago
Uptown Gem
Garden · Pool · Kitchen / Kitchenette

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

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Property view
3.4
Average(17 Reviews)
Condo
 in Chicago
Wrigley Garden Unit
Garden · Pets allowed · Kitchen / Kitchenette

Experience the best of Chicago with this Condo 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
4.8
Outstanding(35 Reviews)
Condo
 in Chicago
Wrigley Oasis! Steps from the Field! - 3BD 1BA
Pets allowed · Kitchen / Kitchenette · Air conditioner

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

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Property view
4.5
Excellent(77 Reviews)
Condo
 in Chicago
Perfect place to enjoy the city or just relax
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

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

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Vacation rentals with internet & wifi in Chicago

Property view
4.3
Excellent(12 Reviews)
Condo
 in Chicago
Wrigleyville Friends Unit - 5bdrm
Pets allowed · Kitchen / Kitchenette · Air conditioner

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

$$$$
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Condo
 in Dunning
Spacious 2BR Apartment near Airport - Central Charming
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking to create some memories in Chicago? Look no further than our Condo, Spacious 2BR Apartment near Airport - Central Charming. Enjoy top-rated amenities including Air conditioner, Internet / Wifi and Laundry, and more.

$$$$
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Property view
4.7
Outstanding(10 Reviews)
Condo
 in Chicago
Superior
Garden · Kitchen / Kitchenette · Air conditioner

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

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Property view
3.4
Average(18 Reviews)
Condo
 in Chicago
Modern 1BR Oasis in the Heart of the City - Marshfield G
Kitchen / Kitchenette · Internet / Wifi · Parking

The best choice in Chicago for Condo, for $75 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

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Condo
 in Chicago
1BR Magnificent Apartment in Chicago - Belmont B3
Kitchen / Kitchenette · Internet / Wifi · TV

Discover the beauty of Chicago with a stay at 1BR Magnificent Apartment in Chicago - Belmont B3, a top rated Condo with amenities such as Dishwasher, Internet / Wifi and Laundry, and more.

$$$$
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Property view
3.9
Good(5 Reviews)
Condo
 in Chicago
Stylish 1BR Apt in Lakeview, Perfect for Getaway - Oakdale 201
Kitchen / Kitchenette · Internet / Wifi · TV

This Condo for $76 in Chicago, is perfect for your next (business stay, family stay, couples stay, getaway vacation, etc.)

$$$$
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Property view
4.6
Outstanding(85 Reviews)
Condo
 in Chicago
Forrestville Ave Large Suite
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

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

$$$$
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Property view
4.8
Outstanding(3 Reviews)
Condo
 in Chicago
webster house
Garden · Pets allowed · Kitchen / Kitchenette

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

$$$$
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Condo
 in Chicago
Stylishly Furnished 1BR Apartment in Lakeview - Oakdale 1S
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

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

$$$$
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Condo
 in Dunning
3BR Suburban Home Parking near O'Hare & Downtown - Central Stylish
Kitchen / Kitchenette · Air conditioner · Internet / Wifi

Looking for a memorable stay in Chicago? Our Condo might just be what you're looking for. Enjoy amenities including Air conditioner, Internet / Wifi and Laundry, and more during your stay.

$$$$
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Property view
3.6
Good(17 Reviews)
Condo
 in Chicago
Newly Decorated 1BR 1BA Convenient Apartment - Roscoe 1D
Kitchen / Kitchenette · Internet / Wifi · Parking

Looking for the perfect place to call home during your trip to Chicago? This Condo offers a comfort and style with top-notch amenities, including Dishwasher, Internet / Wifi and Laundry, and more.

$$$$
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Property view
3.9
Good(4 Reviews)
Condo
 in Chicago
ENVITAE 3BR Spacious Lux Skyview Of Navy Pier
Pool · Pets allowed · Kitchen / Kitchenette

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

$$$$
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