Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Feb 6 - Feb 8
In two months
Mar 20 - Mar 22
In three months
Apr 17 - Apr 19
In four months
May 15 - May 17

Our top choices for Chicago vacation rentals

Indoor pool

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,061 reviews)
"Ideal location "
United States
David
The price is ￥17,074
￥24,613 total
includes taxes & fees
Jan 25 - Jan 26
Sentral Michigan Avenue
Desk, iron/ironing board, travel crib, WiFi

Apartment in Downtown Chicago

Chic Studio in the Heart of the Gold Coast
10.0 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!"
United States
Seynabou
The price is ￥10,743
￥25,770 total
includes taxes & fees
Jan 25 - Jan 26
Chic Studio in the Heart of the Gold Coast
Full-size fridge, microwave, oven, stovetop

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (415 reviews)
"Property was clean, welcoming, pet friendly "
United States
Heather
Level Chicago – Old Town
1 bedroom, iron/ironing board, travel crib, WiFi

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 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."
United States
Jeffrey
The price is ￥9,809
￥26,232 total
includes taxes & fees
Jan 26 - Jan 27
West Loop Living – Bright 1BR
1 bedroom, WiFi, bed sheets

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ￥9,809
￥26,232 total
includes taxes & fees
Jan 27 - Jan 28
1BR Modern Luxe Apt with In-Unit Laundry
TV, offices

Apartment in Downtown Chicago

Chicago-Themed 1BR in a Central Spot near Downtown
The price is ￥9,809
￥26,232 total
includes taxes & fees
Jan 26 - Jan 27
Chicago-Themed 1BR in a Central Spot near Downtown
Interior

Apartment in Downtown Chicago

River North Rooftop With In and Out Parking 3
9.6 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!"
United States
Jennifer M.
The price is ￥15,570
￥49,485 total
includes taxes & fees
Jan 26 - Jan 27
River North Rooftop With In and Out Parking 3
TV, offices

Apartment in Downtown Chicago

Complete 1BR Home Sum
The price is ￥10,938
￥27,822 total
includes taxes & fees
Feb 2 - Feb 3
Complete 1BR Home Sum
Lounge

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
TV, offices

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very Good, (5 reviews)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is ￥9,987
￥26,708 total
includes taxes & fees
Jan 29 - Jan 30
The One: A 1BR Stay That Feels Like Home
TV, offices

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
10.0 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. "
United States
Tyler B.
The price is ￥9,809
￥26,232 total
includes taxes & fees
Jan 26 - Jan 27
Sun-Drenched 1BR Apartment
TV, offices

Apartment in Downtown Chicago

Modern Comfort: 1BR Unit w/ Laundry
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is ￥9,809
￥26,232 total
includes taxes & fees
Jan 26 - Jan 27
Modern Comfort: 1BR Unit w/ Laundry
Living area

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.4 out of 10, Exceptional, (28 reviews)
"Nice place "
United States
Barry
The price is ￥23,122
￥27,144 total
includes taxes & fees
Jan 30 - Jan 31
Wrigleyville Suites
Interior

Apartment in Downtown Chicago

Stylish Japanese-Themed 2BR Apt Close to Downtown
The price is ￥14,108
￥33,912 total
includes taxes & fees
Feb 2 - Feb 3
Stylish Japanese-Themed 2BR Apt Close to Downtown
Fridge, microwave, oven, stovetop

Apartment in Downtown Chicago

Sleek 1BR Apt w/ Laundry
10.0 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."
United States
Anonymous traveler
The price is ￥9,809
￥26,232 total
includes taxes & fees
Jan 27 - Jan 28
Sleek 1BR Apt w/ Laundry
Interior

Apartment in Downtown Chicago

Twice as Nice: Chic 2BR Stay with Style & Space
9.6 out of 10, Exceptional, (20 reviews)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is ￥10,743
￥30,047 total
includes taxes & fees
Jan 26 - Jan 27
Twice as Nice: Chic 2BR Stay with Style & Space
Smart TV, books

Apartment in West Town

Flexhome Ukrainian Village 2BR D1
9.6 out of 10, Exceptional, (5 reviews)
"It was clean and ready for our arrival. A big plus is having a washer and dryer on the premises."
United States
Ray R.
The price is ￥11,818
￥28,033 total
includes taxes & fees
Jan 26 - Jan 27
Flexhome Ukrainian Village 2BR D1
Fridge, microwave, oven, stovetop

Apartment in Uptown

Majestic Modern Style|13 mins DT|4 mins Lake
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful property, fabulous location, well-stocked with amenities, great gym, wonderful view, small but very comfortable, "
United States
Walt K.
The price is ￥12,705
￥44,363 total
includes taxes & fees
Feb 1 - Feb 2
Majestic Modern Style|13 mins DT|4 mins Lake
Smart TV, books

Apartment in West Ridge

Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer
10.0 out of 10, Exceptional, (5 reviews)
"This spot was perfect for our Chicago visit where we mostly needed a place to sleep, not hang out. It seemed to have been refinished recently, so beds were comfy, bathroom lovely, and sitting area big enough for the two of us. "
United States
Deb B.
The price is ￥13,312
￥43,515 total
includes taxes & fees
Jan 26 - Jan 27
Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer
Terrace/patio

Apartment in Uptown

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
10.0 out of 10, Exceptional, (49 reviews)
"It was perfect for a concert at the aragon ballroom, it was only a block away!"
United States
Maria G.
The price is ￥7,474
￥36,934 total
includes taxes & fees
Feb 1 - Feb 2
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
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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Top Chicago Hotel Reviews

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"Incredible location and wonderful satff"
Michael 1-night trip
Posted 9 hours ago
Hotel Riu Plaza Chicago

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!

Frequently asked questions

Can I find vacation rentals in Chicago?

Yes, we give you a choice of vacation rentals in Chicago near Six Flags Great America, or you can choose a more secluded option if you want a relaxing stay. Tourists who visit Chicago like the notable monuments and entertainment choices. The array of shops and fascinating museums are some other things you might want to check out while you're here.

What are some of the best vacation rentals in Chicago?

A Home Away From Home!: This highly rated vacation home rental in Chicago offers a fireplace, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave. Other favorite homes for rent in Chicago are Cozy 3-bedroom house in family-oriented Melrose Park. and Belmont House, Classy & Chic/walk to Wrigley Field.

How many vacation rentals are there in Chicago?

With 937 Expedia vacation rentals, you're sure to find just the right place for your Chicago stay.

What can I see and do in Chicago?

Cultural attractions include CIBC Theatre and Symphony Center, whereas Millennium Park and Grant Park are a couple of picturesque spots to enjoy the outdoors. You can also visit some other popular places in town, such as Michigan Avenue and Wrigley Field.

What are vacation rentals like in Chicago?

Vacation rentals are private properties you can stay in for a short or long stay in Chicago. Vacation rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.