Chicago Holiday 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 holiday rentals
Aparthotel in Downtown Chicago
Sentral Michigan Avenue9.2 out of 10, Wonderful, (1,066 reviews)
"Best full kitchen multi-room family lodging"
Lee
The price is HK$855
HK$1,233 total
includes taxes & fees
1 Feb - 2 Feb
Apartment in Downtown Chicago
Chic Studio in the Heart of the Gold Coast10.0 out of 10, Exceptional, (5 reviews)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
Seynabou
The price is HK$522
HK$1,272 total
includes taxes & fees
1 Feb - 2 Feb
Apartment in Downtown Chicago
Sleek 1BR Apt w/ Laundry10.0 out of 10, Exceptional, (1 review)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
Anonymous traveller
The price is HK$538
HK$1,369 total
includes taxes & fees
1 Feb - 2 Feb
Aparthotel in Downtown Chicago
Level Chicago – Old Town9.0 out of 10, Wonderful, (416 reviews)
"Property was clean, welcoming, pet friendly "
Heather
Apartment in Downtown Chicago
West Loop Living – Bright 1BR10.0 out of 10, Exceptional, (7 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
Jeffrey
The price is HK$491
HK$1,314 total
includes taxes & fees
29 Jan - 30 Jan
Apartment in Downtown Chicago
1BR Modern Luxe Apt with In-Unit Laundry10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
ShowtimeFam1
The price is HK$538
HK$1,369 total
includes taxes & fees
1 Feb - 2 Feb
Apartment in Downtown Chicago
River North Rooftop With In and Out Parking 39.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
Jennifer M.
The price is HK$780
HK$2,441 total
includes taxes & fees
8 Feb - 9 Feb
Apartment in Downtown Chicago
Sun-Drenched 1BR Apartment10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
Tyler B.
The price is HK$538
HK$1,369 total
includes taxes & fees
1 Feb - 2 Feb
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 holiday rentals that suit your style
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Chicago Hotel Reviews
The Royal Sonesta Chicago Downtown
10/10 Excellent
Find out more about Chicago
Search for holiday rentals in Chicago on Expedia! You can easily find your home rentals, villas, holiday apartments in Chicago using one of the methods below:
- View our selection of featured holiday rentals in Chicago
- Use the map to find apartments and other holiday homes in the Chicago neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in Chicago while they last
Look no further and take a look at our great range of rental properties in Chicago!
