Search Holiday Rentals in Chicago

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Top Holiday 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 £177 per night from 30 May to 31 May
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 their reviews. ...
2.9/5 (37 reviews)
"Read the reviews beforehand was nervous about my stay there but I made sure to take all the necessary essentials in case you need anything there is a Walgreens near by. Self check in and self check out was simple and easy. I had an amazing stay there."

Reviewed on 28 Apr 2022

The Chicago Hotel Collection - Millennium Park
WoodSpring Suites Chicago Addison
2.5 out of 5
991 E. Lake Street, Addison, IL, 60101
Fully refundableReserve now, pay when you stay
The price is £70 per night from 30 May to 31 May
Stay at this business-friendly aparthotel in Addison. Enjoy free WiFi, free parking and a fitness centre. Our guests praise the helpful staff in their reviews. ...
3.2/5 (112 reviews)
"Overall Everything was nice..But the smell of WEED in the entire building/room was aweful...."

Reviewed on 15 Jan 2022

WoodSpring Suites Chicago Addison
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 centre and concierge services. Popular attractions Soldier Field and ...
4.4/5 Excellent! (55 reviews)
"Excellent, location is perfect!"

Reviewed on 24 May 2022

Sonder South Wabash
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Level Chicago – Old Town
4 out of 5
1140 North Wells Street, Chicago, IL, 60610
The price is £297 per night from 30 May to 31 May
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 their ...
4.3/5 Excellent! (74 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 28 Apr 2022

Level Chicago – Old Town
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 ...
3.9/5 Very Good! (30 reviews)
"The location of the property was excellent with lots of shopping and dining locations nearby, as well as a metro stop very close by to help get you to other parts of the city. The unit itself was well maintained and clean. It was small, so a long stay or having multiple people would have been difficult, ..."

Reviewed on 20 May 2022

Sonder Jewelers Row
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 (3 reviews)
"Booked a room through expedia, when I got there to check in place was closed. Never got my money back.."

Reviewed on 17 Aug 2021

InTown Suites Extended Stay Chicago IL - Elk Grove
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 a rooftop terrace, barbecues and a flat-screen TV. 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 9 Mar 2022

Sonder The Plymouth
Your✅Stylish 2BDR, ✅For Families ✅ Parking, ✅Laundry, Great for comfy long stays
The price is £604 per night from 1 Jun to 2 Jun
Stay at this holiday home in Oak Park. Enjoy free WiFi, on-site parking and a Smart TV. Popular attractions United Center and Douglas Park are located nearby. ...
5/5 Exceptional! (20 reviews)
"This apartment was so beautiful me and my friends really enjoyed our stay and really felt comfortable"

Reviewed on 16 May 2022

Your✅Stylish 2BDR, ✅For Families ✅ Parking, ✅Laundry, Great for comfy long stays
Family Townhome available - 2 Bedroom, 1.5 bath, tv, kitchen, appliances, I94
The price is £612 per night from 6 Jun to 7 Jun
Stay at this golf holiday home in Waukegan. Enjoy free WiFi, on-site parking and a garden. Popular attractions Six Flags Great America and Naval Base Great Lakes ...
4.3/5 Excellent! (3 reviews)
Just an overnight stay
"We came to this house for an overnight stay for a concert in Wakegan. The owner was very attentive. The place was pretty clean and cozy. It was pretty quiet considering it is a townhouse. Awesome water pressure in the shower. Would definetly stay here again."

Reviewed on 26 Apr 2022

Family Townhome available - 2 Bedroom, 1.5 bath, tv, kitchen, appliances, I94
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! (5 reviews)
Top notch
"We were visiting our son at the UIC campus and location couldn't be better. Beautiful, clean, and comfortable. Will definitely book again."

Reviewed on 22 Sep 2021

Sonder Greektown
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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
Fully refundableReserve now, pay when you stay
The price is £126 per night from 9 Jun to 10 Jun
Congress Plaza Hotel
21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
55 East Ontario Street, Chicago, IL, 60611
Fully refundableReserve now, pay when you stay
The price is £163 per night from 30 May to 31 May
21c Museum Hotel 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.

Choosing the perfect Chicago (and vicinity) rental

You've likely stayed at countless hotels. Maybe it's time to try a holiday rental to experience the area like a local. Stay in Chicago (and vicinity) at one of 26 holiday rentals now bookable on Expedia.com.

  • 22 apartments
  • 4 condos

Shopping, art, and dining are in for a treat, while all visitors will find something at this skyscrapers lake destination to delight in. Families won't want to miss the nearby live music and theatres.

Dining in Chicago (and vicinity)

Ada Street, University Club of Chicago, and Maria's Packaged Goods and Community Bar are a few favourite spots to grab some food. Most holiday rentals come with full-size kitchens, so eating in is always an option, too.

Sightseeing around Chicago (and vicinity)

Some of the top sights in Chicago (and vicinity) include Millennium Park, Willis Tower, and Skydeck Ledge. If you're bringing the kiddos along, save a few hours for Six Flags Great America, Navy Pier, and John G. Shedd Aquarium. Culture aficionados will have plenty to take in at Chicago Cultural Center, Ford Center for the Performing Arts Oriental Theatre, and Chicago Theater. If your holiday agenda includes shopping, consider a trip to Chicago Premium Outlets and Shops at Northbridge. Outdoor enthusiasts will appreciate a jaunt through Grant Park and Lincoln Park.

Exploring the Chicago (and vicinity) area

For those arriving without a car, nearby metro stations like Monroe Station, Monroe Station, or Adams-Wabash Station provide a convenient transportation option. To travel outside the immediate area, consider taking a train from Millennium Station, Chicago Van Buren Street Station, or Chicago Union Station.

Packing for your Chicago (and vicinity) trip

Wondering what the weather will be like on your trip? Here are the seasonal average temperatures.

  • January–March: -1°C
  • April–June: 16°C
  • July–September: 22°C
  • October–December: 5°C

Booking your rental on Expedia

Expedia makes it easy and safe to book holiday rentals in Chicago (and vicinity). We can even help you contact the property owner to make special arrangements. You're sure to have a memorable trip with the convenience of a short-term rental.

Frequently asked questions

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