Chicago Vacation Rentals

Save 10% or more on select stays with Expedia Rewards

Most properties are fully refundable. Because flexibility matters.

Search over 2.9 million properties and 550 airlines worldwide.

Vacation Rentals in Chicago

The Chicago Hotel Collection - Millennium Park
2.5 out of 5
55 E Washington St., Chicago, IL, 60602
Fully refundableReserve now, pay when you stay
The price is NT$2,572 per night from Jun 30 to Jul 1
Stay at this aparthotel in Chicago. Enjoy free WiFi, room service, and laundry facilities. Our guests praise the helpful staff and the quiet rooms in our reviews. ...
2.9/5 (45 reviews)
"Checking in was a little inconvenient. The kiosk wouldn't read my barcode as invalid, and checking in via confirmation number said my room wasn't available (@4:30 PM). There is no reception staff onsite so the security (there 24/7) assisted me with the customer service number. Customer service said ..."

Reviewed on 2022/6/20

The Chicago Hotel Collection - Millennium Park
Sonder South Wabash
3.5 out of 5
1419 South Wabash Avenue, Chicago, IL, 60605
Stay at this 3.5-star business-friendly aparthotel in Chicago. Enjoy free WiFi, a fitness center, and concierge services. Popular attractions Soldier Field and ...
4.3/5 Excellent! (68 reviews)
"The massive windows gave a great view of Chicago, it was a short walk to some amazing restaurants, and not far from Field Museum and Millennium Park. A fantastic apartment"

Reviewed on 2022/6/17

Sonder South Wabash
Sonder Jewelers Row
3.5 out of 5
19 South Wabash Avenue, Chicago, IL, 60603
Stay at this 3.5-star aparthotel in Chicago. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Millennium Park and Art Institute ...
4/5 Very Good! (35 reviews)
"This was a perfect stay for our Chicago visit. Despite no traditional front desk staff, we found entry into the property easy and yet secure. Luggage storage lockers were especially appreciated. The room was very clean and comfortable. Excellent downtown location at reasonable cost; exceeded our ..."

Reviewed on 2022/5/28

Sonder Jewelers Row
You could be seeing lower prices

You could be seeing lower prices

With member prices, you could save 10% or more right now on thousands of properties.
WoodSpring Suites Chicago Addison
2.5 out of 5
991 E. Lake Street, Addison, IL, 60101
The price is NT$2,872 per night from Jul 4 to Jul 5
Stay at this business-friendly aparthotel in Addison. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. ...
3.2/5 (114 reviews)
"Excellent location and clean"

Reviewed on 2022/6/11

WoodSpring Suites Chicago Addison
Level Chicago – Old Town
4 out of 5
1140 North Wells Street, Chicago, IL, 60610
Stay at this 4-star family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our ...
4.3/5 Excellent! (76 reviews)
"Loved the sauna and spa space. The space on the 8th floor was wonderful, with fitness and social spaces that are nicely done. Great distance views of the city from my unit 1109 (not backed up to a skyscraper). Sweet patio, nice set-up, big bathroom, well-outfitted kitchen. Just add a fresh bouquet ..."

Reviewed on 2022/4/28

Level Chicago – Old Town
Sonder The Plymouth
3.5 out of 5
South Dearborn Street, Van Buren, Chicago, IL, 60605
Stay at this 3.5-star business-friendly aparthotel in Chicago. Enjoy free WiFi, a rooftop terrace, and barbecue grills. Popular attractions Art Institute of ...
4.3/5 Excellent! (27 reviews)
"Great location, good communication. Easy check in and check out. Rooms have everything you need!"

Reviewed on 2022/3/9

Sonder The Plymouth
InTown Suites Extended Stay Chicago IL - Villa Park
2.5 out of 5
350 East Roosevelt, Villa Park, IL, 60181
Stay at this business-friendly aparthotel in Villa Park. Enjoy free parking, WiFi, and a flat-screen TV. Popular attractions Morton Arboretum and Drury Lane ...
4.4/5 Excellent! (5 reviews)
"No frills, but quiet, clean and excellent location, close to shopping, supermarkets and restaurants."

Reviewed on 2021/10/24

InTown Suites Extended Stay Chicago IL - Villa Park
InTown Suites Extended Stay Chicago IL - Elk Grove
3 out of 5
2411 Landmeier Road, Elk Grove Village, IL, 60007
Stay at this 3-star business-friendly aparthotel in Elk Grove Village. Enjoy WiFi, laundry facilities, and a flat-screen TV. Popular attractions Allstate Arena ...
1/5 (5 reviews)
"Booked a room through expedia, when I got there to check in place was closed. Never got my money back.."

Reviewed on 2021/8/17

InTown Suites Extended Stay Chicago IL - Elk Grove
Sonder Greektown
3.5 out of 5
314 South Halsted Street, Chicago, IL, 60661
Stay at this 3.5-star aparthotel in Chicago. Enjoy free WiFi, a rooftop terrace, and concierge services. Popular attractions Willis Tower and Chicago Theatre ...
5/5 Exceptional! (6 reviews)
"THE APRTMENT IS WELL LOCATED IN GREEKTOWN. SPACIOUS, WELL EQUIPED. PLENTY OF PARKING FACILITIES NEARBY."

Reviewed on 2022/6/20

Sonder Greektown
Sonder at 943 Crosby
3.5 out of 5
943 North Crosby Street, Chicago, IL, 60610
Stay at this 3.5-star business-friendly aparthotel in Chicago. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Michigan Avenue ...
3/5 (1 review)
"943 N. Crosby is s nice apartment building. It is an area that is undergoing a revitalization and was near where I needed to be. Everything was great until my last night when I could clearly hear the people in the apartment above me partying and then a man and woman fighting and breaking up. The ..."

Reviewed on 2020/8/23

Sonder at 943 Crosby
Don't see what you're looking for?
See all available properties in Chicago
View all properties
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.

Other types of properties in Chicago you may be interested in

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL, 60605
The price is NT$4,253 per night from Jul 4 to Jul 5
Congress Plaza Hotel
Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
701 North Michigan Avenue, Chicago, IL, 60611
The price is NT$4,131 per night from Jul 5 to Jul 6
Warwick Allerton - Chicago
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.

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!

Frequently asked questions

Recent reviews of Chicago properties
expedia verified reviews