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Chicago Vacation Rentals
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Vacation Rentals in Chicago
1140 North Wells Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $218 per night from Jun 7 to Jun 8
$218
per night
Jun 7 - Jun 8
Stay at this 4-star business-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in ...
8.6/10 Excellent! (124 reviews)
"Great location and awesome amenities. Our room wasn’t ready until closer to the 4pm check in time, but we were able to use the different areas (game room, pool, etc) so it worked out fine"
Reviewed on May 29, 2023
808 SOUTH MICHIGAN AVENUE, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $209 per night from Jun 18 to Jun 19
$209
per night
Jun 18 - Jun 19
Stay at this 3.5-star aparthotel in Chicago. Enjoy free WiFi, valet parking, and a 24-hour front desk. Popular attractions Grant Park and Soldier Field are located ...
9/10 Wonderful! (158 reviews)
"The receptionist Joshua was super helpful. Made the check in process even more simple. The hotel/apartment itself is beautiful. Definitely would stay here again."
Reviewed on Jun 2, 2023
613 North Wells Street, Chicago, IL
The price is $173 per night from Jun 26 to Jun 27
$173
per night
Jun 26 - Jun 27
Stay at this aparthotel in Chicago. Enjoy free WiFi, concierge services, and a flat-screen TV. Popular attractions Millennium Park and Navy Pier are located ...
6/10 (2 reviews)
"Very clean even the floor as my white socks used as slippers attest."
Reviewed on May 13, 2023
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1419 South Wabash Avenue, Chicago, IL
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 ...
8.8/10 Excellent! (137 reviews)
"Comfortable living conditions with a view and full kitchen."
Reviewed on May 15, 2023
991 E. Lake Street, Addison, IL
Fully refundableReserve now, pay when you stay
The price is $90 per night from Jun 5 to Jun 6
$90
per night
Jun 5 - Jun 6
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. ...
6.2/10 (147 reviews)
"Nice."
Reviewed on Jun 1, 2023
19 South Wabash Avenue, Chicago, IL
The price is $355 per night from Jul 3 to Jul 4
$355
per night
Jul 3 - Jul 4
Stay at this 3.5-star aparthotel in Chicago. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Millennium Park and Grant Park ...
7.8/10 Good! (60 reviews)
"We loved it! The mixed reviews made me nervous but I chalked those up to chronic complainers and I’m glad I did because this place was awesome. It’s important to download the Sonder app to get all the necessary checkin information. Once you do that, Sonder will send you specific instructions to get ..."
Reviewed on Jan 29, 2023
La Grange Park
The price is $84 per night from Jun 6 to Jun 7
$84
per night
Jun 6 - Jun 7
Stay at this vacation home in La Grange Park. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Galloping Ghost and Oak Brook Golf Course are ...
2419 S Troy St, Chicago, IL
Stay at this 3-star apartment in Chicago. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions United Center and Soldier Field are located ...
1817 N Lawndale Ave, Chicago, IL
The price is $238 per night from Jun 5 to Jun 6
$238
per night
Jun 5 - Jun 6
Stay at this 3-star vacation home in Chicago. Enjoy free WiFi, free parking, and a garden. Popular attractions United Center and Wrigley Field are located nearby. ...
La Grange Park
Stay at this vacation home in La Grange Park. Enjoy free WiFi, onsite parking, and a garden. Popular attractions Galloping Ghost and Oak Brook Golf Course are ...
10/10 Exceptional! (1 review)
Fantastic
"Everything was great area was nice house was gorgeous easy access"
Reviewed on Apr 25, 2023
Homewood
Stay at this vacation home in Homewood. Enjoy WiFi, onsite parking, and a TV. Popular attractions Ravisloe Country Club and Oak Hill Park are located nearby. ...
10/10 Exceptional! (4 reviews)
Wonderful
"Loved it, neighborhood was great and surrounded by a lot of shopping and restaurants"
Reviewed on Mar 13, 2023
Harvey
The price is $400 per night from Jun 6 to Jun 7
$400
per night
Jun 6 - Jun 7
Stay at this vacation home in Harvey. Enjoy private pools, 2 bathrooms, and 2 bedrooms. Popular attractions Harvey Community Center and Midwest Carvers Museum ...
10/10 Exceptional! (1 review)
Riverfront stay
"This was a really nice stay. I think this home is absolutely beautiful and spacious. The beds we’re probably my favorite part haha, it was so comfy. At first I was worried about the communication between the owner and I but she was very sweet and made sure to reply as quickly as she could. I would ..."
Reviewed on Jan 9, 2023
314 South Halsted Street, Chicago, IL
Stay at this 3.5-star aparthotel in Chicago. Enjoy free WiFi, a rooftop terrace, and concierge services. Popular attractions Millennium Park and United Center ...
9.6/10 Exceptional! (16 reviews)
"The openness of the property, it was a really nice feeling."
Reviewed on Apr 10, 2023
220 W Illinois St, Chicago, IL
Stay at this 3-star apartment in Chicago. Enjoy free WiFi, concierge services, and a kitchen. Popular attractions Millennium Park and Grant Park are located ...
2/10 (1 review)
"I’m very unsatisfied with my experience with the company managing this property (Envitae). Although the apartment was nice, the lack of communication from the property management company (Envitae) made this experience very unpleasant. I was taken through an extensive process after purchasing the ..."
Reviewed on May 17, 2023
Lombard
The price is $105 per night from Jun 6 to Jun 7
$105
per night
Jun 6 - Jun 7
Stay at this hotel in Lombard. Enjoy free breakfast, a fitness center, and onsite parking. Popular attractions Yorktown Shopping Center and Lilacia Park are ...
10/10 Exceptional! (1 review)
convenient
"Good location, quiet room, nice to have breakfast available"
Reviewed on Jan 15, 2023
South Dearborn Street, Van Buren, Chicago, IL
Stay at this 3.5-star aparthotel in Chicago. Enjoy a rooftop terrace, a flat-screen TV, and cable TV. Popular attractions Grant Park and Millennium Park are ...
8.6/10 Excellent! (47 reviews)
"Me gusto todo las habitaciones, la ubicacion, la cocina y la calefacción"
Reviewed on Feb 13, 2023
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
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
Fully refundable
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 vacation rental to experience the area like a local. Stay in Chicago (and vicinity) at one of 26 vacation rentals now bookable on Expedia.com.
- 22 apartments
- 4 condos
Shoppers, art connoisseurs, and foodies are in for a treat, while all visitors will find something at this urban lakeside destination to delight in. Families won't want to miss the nearby concerts and theaters.
Dining in Chicago (and vicinity)
Ada Street, University Club of Chicago, and Maria's Packaged Goods and Community Bar are a few favorite spots to grab some food. Most vacation 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 vacation 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: 31°F
- April–June: 61°F
- July–September: 72°F
- October–December: 42°F
Booking your rental on Expedia
Expedia makes it easy and safe to book vacation 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
Recent reviews of Chicago propertiesExpedia verified reviews
River Hotel
River Hotel5/5 Excellent"Really enjoyed our stay. Front desk was staffed and efficient. Loved the layout of our room with the 2 bathrooms, very smart. Only one downside was not having an iron in the room. "A verified traveler stayed at River HotelPosted 14 hours ago
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