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All Vacation Rentals
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Chicago
Chicago Apartment Rentals
598
Chicago Apartment Rentals
Tripping.com is the world's top vacation rental search engine, rated 9.6 out of 10 based on 50 user reviews.
Compare Chicago apartment rentals from 9 rental sites including Booking.com, HomeAway, HRS Holidays and more, from $25 a night.
Apartment in River North Downtown Chicago
1
1
Booking.com
Celeste Celebrity Theme Unit In Gold Coast. In 7 Unit Building Gold Coast!
1
1
$249
HomeAway
$249
VRBO
Listed on 4 Sites
All rental sites
$249
/
night
HomeAway
View
$249
/
night
VRBO
View
$249
/
night
VacationRentals
View
$249
/
night
OwnersDirect
View
WINTER SPECIALS. SAFE, CLOSE to Everything. HOT TUB. PARKING
3
1
$150
Tripz
Oakwood 200 Squared
1
1
Booking.com
Gold Coast Wow Celebrity Themed Unit On Cedar!
2
1
$399
HomeAway
$399
VRBO
Listed on 4 Sites
All rental sites
$399
/
night
HomeAway
View
$399
/
night
VRBO
View
$399
/
night
VacationRentals
View
$399
/
night
OwnersDirect
View
SPECIALS March, April. VERY SAFE. CLOSE to Everything. PARKING. View. Hot Tub
2
1
$132
Tripz
Stay Alfred Apartments on Ohio Street
1
1
Booking.com
Al Capone Unit In Beautiful Vintage Building In The Gold Coast!
1
2
$249
HomeAway
$249
VRBO
Listed on 4 Sites
All rental sites
$249
/
night
HomeAway
View
$249
/
night
VRBO
View
$249
/
night
VacationRentals
View
$249
/
night
OwnersDirect
View
Stay Alfred Apartments on Lake Street
1
1
Booking.com
Celeste Celebrity Suites GOLD COAST!
1
1
$249
HomeAway
$249
VRBO
Listed on 4 Sites
All rental sites
$249
/
night
HomeAway
View
$249
/
night
VRBO
View
$249
/
night
VacationRentals
View
$249
/
night
OwnersDirect
View
Furnished Suites Near Navy Pier
2
1
Booking.com
AMAZING 38TH FLOOR PENTHOUSE IN LOOP THEATRE DISTRICT HIGH RISE!
2
2
$315
HomeAway
$315
VRBO
Listed on 4 Sites
All rental sites
$315
/
night
HomeAway
View
$315
/
night
VRBO
View
$315
/
night
VacationRentals
View
$315
/
night
OwnersDirect
View
Corporate Suites in the Heart of Magnificent Mile
1
1
Booking.com
Gorgeous Vintage and Modernized 4 Bedroom in Heart of Gallery District! 4600 SF
4
4
$599
HomeAway
$599
VRBO
Listed on 4 Sites
All rental sites
$599
/
night
HomeAway
View
$599
/
night
VRBO
View
$599
/
night
VacationRentals
View
$599
/
night
OwnersDirect
View
Furnished Suites in South Loop Chicago
1
1
Booking.com
Fantastic Large 3 BR, Safe, Close to EVERYTHING & McCormick Place. Hot Tube
3
2
$170
HomeAway
$170
VRBO
Listed on 4 Sites
All rental sites
$170
/
night
HomeAway
View
$170
/
night
VRBO
View
$170
/
night
VacationRentals
View
$170
/
night
OwnersDirect
View
Modern River View Apartment
1
1
Booking.com
Beautiful and Large Apt. 3 Queen Beds. Close to Everything & McCormick Place
2
2
$170
HomeAway
$170
VRBO
Listed on 4 Sites
All rental sites
$170
/
night
HomeAway
View
$170
/
night
VRBO
View
$170
/
night
VacationRentals
View
$170
/
night
OwnersDirect
View
Lavish 2BR Apartment in South Loop
2
1
Booking.com
Sleek 2BR near Restaurant Row by Sonder
2
2
$126
HomeAway
$126
VRBO
Listed on 4 Sites
All rental sites
$126
/
night
HomeAway
View
$126
/
night
VRBO
View
$126
/
night
VacationRentals
View
$126
/
night
OwnersDirect
View
Modern Greek Town Apartments
1
1
Booking.com
53/54th Floor MagMile Penthouse - Fitness Center, VIEWS, Fireplace, Balcony
3
3
$675
HomeAway
$675
VRBO
Listed on 4 Sites
All rental sites
$675
/
night
HomeAway
View
$675
/
night
VRBO
View
$675
/
night
VacationRentals
View
$675
/
night
OwnersDirect
View
Bespoke Bucktown Couch House No. 2 by Chicagoan
2
2
$252
Booking.com
51/52nd Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Fitness Center
2
2
$515
HomeAway
$515
VRBO
Listed on 4 Sites
All rental sites
$515
/
night
HomeAway
View
$515
/
night
VRBO
View
$515
/
night
VacationRentals
View
$515
/
night
OwnersDirect
View
Royal Living Group - Union Station
1
1
Booking.com
53/54th Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Balcony
2
3
$525
HomeAway
$525
VRBO
Listed on 4 Sites
All rental sites
$525
/
night
HomeAway
View
$525
/
night
VRBO
View
$525
/
night
VacationRentals
View
$525
/
night
OwnersDirect
View
Stay Alfred Apartments on LaSalle
1
1
Booking.com
Stay Alfred Apartments on Wabash
1
1
Booking.com
Stay Alfred on South State Street
1
1
Booking.com
The Hudson
1
1
$117
Booking.com
Forrestville Ave Apartment
2
1
$85
Booking.com
55th Floor MagMile Penthouse - VIEWS, Balcony, Pool, WiFi
2
2
$375
HomeAway
$375
VRBO
Listed on 4 Sites
All rental sites
$375
/
night
HomeAway
View
$375
/
night
VRBO
View
$375
/
night
VacationRentals
View
$375
/
night
OwnersDirect
View
Bucktown, Urban Luxury and Convenience
3
2
$215
Tripz
2BR Apartment Heart of Lincoln Park
2
1
Booking.com
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
1
1
$250
HomeAway
$250
VRBO
Listed on 4 Sites
All rental sites
$250
/
night
HomeAway
View
$250
/
night
VRBO
View
$250
/
night
VacationRentals
View
$250
/
night
OwnersDirect
View
Luxury Chicago Apt Mins To Downtown
2
2
$86
Tripz
1
2
...
16
17
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