Chicago Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Chicago vacation homes
ENVITAE Hotel, 4BR Luxury Modern Apartments
ENVITAE Hotel, 4BR Luxury Modern ApartmentsNear North Side
9.6 out of 10, Exceptional, (13 reviews)
"Un superbe building avec des prestations sympas, un chouette appartement avec tout ce qu’il faut pour être confortable et les petits détails qui font la différence, notamment pour un court séjour car cela évite de voyager avec ou de courir en acheter: savon pour les mains, shampooing, gel douche, lessive, café etc il est très proche de la ligne rouge du métro et d’un arrêt de bus. "
Emeline B.
The price is CA $733
CA $1,303 total
includes taxes & fees
Jun 25 - Jun 26
Quaint Bungalow, near Great Lakes Naval Base
Quaint Bungalow, near Great Lakes Naval BaseMundelein
9.8 out of 10, Exceptional, (72 reviews)
"We had a great stay! The area was peaceful and felt safe. "
Yoselin V.
The price is CA $188
CA $498 total
includes taxes & fees
Jul 5 - Jul 6
Attractive Coach House Apartment for rent in Oak Park.
Attractive Coach House Apartment for rent in Oak Park.Oak Park
10.0 out of 10, Exceptional, (1 review)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
kerston b.
The price is CA $226
CA $294 total
includes taxes & fees
Jun 30 - Jul 1
Master qtr close to nature & easy urban facilities
Master qtr close to nature & easy urban facilitiesRiverwoods
9.8 out of 10, Exceptional, (84 reviews)
"nice little place! quiet area "
Nayeli A.
The price is CA $166
CA $306 total
includes taxes & fees
Jun 30 - Jul 1
✽ Charming Cottage ✽ close to College/Town/Station
✽ Charming Cottage ✽ close to College/Town/StationWheaton
9.8 out of 10, Exceptional, (69 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
Nancy F.
The price is CA $251
CA $448 total
includes taxes & fees
Jul 8 - Jul 9
The price is CA $167
CA $301 total
includes taxes & fees
Jul 6 - Jul 7
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bedMaywood
8.0 out of 10, Very good, (28 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
Eduardo
The price is CA $207
CA $425 total
includes taxes & fees
Jun 16 - Jun 17
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
*The Comfy King Ranch*King Bed Suite*Fast Wi-FiWorth
9.6 out of 10, Exceptional, (62 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
Stephanie H.
The price is CA $267
CA $561 total
includes taxes & fees
Jul 9 - Jul 10
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Find vacation rentals that suit your style
Cabins
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Chicago Hotel Reviews
Freehand Chicago
8/10 Good
Find out more about Chicago
Chicago Vacation Homes information
Number of reviews | 456 |
|---|---|
Accommodation | 857 Vacation Homes |
Lowest Price | CA $294 |
Highest Price | CA $1,357 |
Explore a world of travel with Expedia
- 3 Star Hotels in The Loop
- 4 Star Hotels in The Loop
- 5 Star Hotels in The Loop
- Hotels near Adams-Wabash Station
- Houseboats in Adams-Wabash Station
- Hotels near Art Institute of Chicago
- Hotels near CIBC Theatre
- Aparthotels in Central Chicago
- B&B in Central Chicago
- Guest Houses in Central Chicago
- Hostels in Central Chicago
- Hotels near Chagall's Four Seasons
- Hotels near Chase Tower
- Hotels near Chicago Temple
- Hotels near Chicago Theatre
- Aparthotels in Chicago Union Station
- B&B in Chicago Union Station
- Hostels in Chicago Union Station
- Motels in Chicago Union Station
- Vacation Homes in Chicago Union Station
- Condo Rentals in Clark-Lake Station
- Resorts in Clark-Lake Station
- Downtown Chicago Hotels
- Aparthotels in LaSalle Street Station
- B&B in LaSalle Street Station
- Guest Houses in LaSalle Street Station
- Inns in LaSalle Street Station
- Resorts in LaSalle Street Station
- Aparthotels in Madison-Wabash Station
- Hotels near Madison-Wabash Station
- Inns in Madison-Wabash Station
- Magnificent Mile Hotels
- Resorts in Merchandise Mart Station
- Hotels near Millennium Park
- Guest Houses in Millennium Station
- Resorts in Millennium Station
- Hotels near Monroe Station
- Houseboats in Monroe Station
- Aparthotels in Ogilvie Transportation Center
- Castles in Ogilvie Transportation Center
- Vacation Homes in Ogilvie Transportation Center
- Motels in Quincy Metro Station
- Aparthotels in Randolph-Wabash Station
- B&B in Randolph-Wabash Station
- Hotels near Richard J. Daley Center
- Hotels near State Street
- Adults Only Resorts & in The Loop
- All Inclusive Resorts and in The Loop
- Beach Hotel Hotels in The Loop
- Best Western Hotels in The Loop
- Boutique Hotels in The Loop
- Cheap Hotels in The Loop
- Destination Hotels in The Loop
- Fairmont Hotels in The Loop
- Family Hotels in The Loop
- Golf Hotels in The Loop
- Hilton Hotels in The Loop
- Honeymoon Resorts and in The Loop
- Hotels with a Pool in The Loop
- Hotels with Bar in The Loop
- Hotels with Free Airport Shuttle in The Loop
- Hotels with Free Breakfast in The Loop
- Hotels with Free Parking in The Loop
- Hotels with Hot Tubs in The Loop
- Hotels with an Indoor Pool in The Loop
- Hotels with Tennis Courts in The Loop
- Kimpton Hotels in The Loop
- Lake Hotels in The Loop
- Luxury Hotels in The Loop
- Marriott Hotels & Resorts in The Loop
- Oceanfront Hotels in The Loop
- Pet-Friendly Hotels in The Loop
- Romantic Hotels in The Loop
- Shopping Hotels in The Loop
- Spa Hotels in The Loop
- The Loop Hotels
- Cheap Hotels in Theatre District
- Luxury Hotels in Theatre District
- Theatre District Hotels
- Houseboats in Washington-Wells Station
- Alamo Rent A Car Rental Cars in The Loop
- Avis Rental Cars in The Loop
- Car rentals near Richard J. Daley Center
- Car rentals near The Loop
- Dollar Rent A Car Rental Cars in The Loop
- Enterprise Rental Cars in The Loop
- Fox Rental Cars Rental Cars in The Loop
- Oryx Rent A Car Rental Cars in The Loop
- Payless Rental Cars in The Loop
- Rent A Wreck Rental Cars in The Loop
- Routes Rental Cars in The Loop
- Sixt Rental Cars in The Loop
- Thrifty Car Rental Rental Cars in The Loop