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Top Holiday Rentals in Chicago
Estimated price for 1 night/2 adults
Per night/room
7 Jun-8 Jun
I Wanted To Live There. It Was Very Homey. I’ll Be Back Soon.
Per night/room
2 Jun-3 Jun
Better than Extended Stay with the same luxuries and then some.
Per night/room
7 Jun-8 Jun
I liked the kitchen and the bedroom space. Could of used more towels
Per night/room
27 Jun-28 Jun
We were unexpectedly delayed at MDW and had to get lodging for the night. Everyone at the hotel was accommodating and helpful, making our stay a mini-vacation despite the complicated social difficulties of the COVID-19 crisis. We had not considered going to Chicago as a vacation spot, but we now ...
Nice neighborhood easy access & a great place for kids
Per night/room
5 Jun-6 Jun
Great place to stay. It was quiet and we enjoyed our stay there. The kitchen had everything we needed and breakfast was served too. Very kind people too.
Per night/room
22 Jun-23 Jun
I liked that it was quiet and there was a kitchenette. I didn't like that the parking was down the block, and you had to pay cash. I ended up parking in the Grant Park garages.
Per night/room
30 May-31 May
Very cosy, modern and spacious apartment in central downtown. The team addressed our concerns in a very professional manner. The building has a bicycle dock right in the front and parking lot is across the street. However, the parking lot rates are expensive.
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.
Other types of properties in Chicago you may be interested in
Estimated price for 1 night/2 adults
The Godfrey Hotel Chicago
127 West Huron, at LaSalle, Chicago, IL
LondonHouse Chicago, Curio Collection by Hilton
85 East Wacker Drive, Chicago, ILLondonHouse Chicago, Curio Collection by Hilton£94
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.
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Explore Chicago
Expedia Latest Trends
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- Hotels in Hyde Park
- Hotels in Magnificent Mile
- Elgin accommodation
- Chicago Airport Hotels
- The Ambassador Chicago, a Joie de Vivre Hotel
- Homewood Suites by Hilton Chicago Downtown
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- Kinzie Hotel
- The Langham, Chicago
- Eurostars Magnificent Mile, previously Dana Hotel
- Hilton Hotels Hotels in Geneva
- Best Western Grant Park Hotel
- Hilton Hotels Hotels in Chicago
- The Hoxton Chicago
- Sophy Hyde Park
- The Talbott Hotel
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- City Suites Hotel
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- Trump International Hotel & Tower Chicago
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- Travelodge by Wyndham Downtown Chicago
