Chicago Holiday Rentals

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Check prices for these dates

In two weeks
27 Feb - 1 Mar
In two months
10 Apr - 12 Apr
In three months
8 May - 10 May
In four months
5 Jun - 7 Jun

Our top choices for Chicago holiday rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,074 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is HK$857
HK$1,236 total
includes taxes & fees
22 Feb - 23 Feb
Sentral Michigan Avenue
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
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 HK$539
HK$1,372 total
includes taxes & fees
17 Feb - 18 Feb
West Loop Living – Bright 1BR
Desk, iron/ironing board, travel cot, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
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 HK$524
HK$1,275 total
includes taxes & fees
18 Feb - 19 Feb
Chic Studio in the Heart of the Gold Coast
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
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 HK$539
HK$1,372 total
includes taxes & fees
15 Feb - 16 Feb
1BR Modern Luxe Apt with In-Unit Laundry
TV, offices

Complete 1BR Fully Furnished Home

Complete 1BR Fully Furnished Home
Downtown Chicago
The price is HK$688
HK$1,546 total
includes taxes & fees
2 Mar - 3 Mar
Complete 1BR Fully Furnished Home
Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (426 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (693 reviews)
"Big, luxury, easy parking "
United States
Chanel
Kasa Magnificent Mile Chicago
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
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 HK$868
HK$2,590 total
includes taxes & fees
19 Feb - 20 Feb
River North Rooftop With In and Out Parking 3
TV, offices

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
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 HK$539
HK$1,372 total
includes taxes & fees
17 Feb - 18 Feb
Sun-Drenched 1BR Apartment
Beach

Guild #2 | Gold Coast Mag Mile Best Location

Guild #2 | Gold Coast Mag Mile Best Location
Downtown Chicago
9.8 out of 10, Exceptional, (19 reviews)
"We loved our stay at this property. It’s in a fantastic location and is roomy and comfortable. We would definitely stay again!"
United States
laura s.
Guild #2 | Gold Coast Mag Mile Best Location
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$539
HK$1,372 total
includes taxes & fees
17 Feb - 18 Feb
Modern Comfort: 1BR Unit w/ Laundry
Living area

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.2 out of 10, Wonderful, (29 reviews)
"Nice place "
United States
Barry
The price is HK$929
HK$1,090 total
includes taxes & fees
15 Feb - 16 Feb
Wrigleyville Suites
Fridge, microwave, oven, stovetop

Sleek 1BR Apartment w/ In-unit Laundry

Sleek 1BR Apartment w/ In-unit Laundry
Downtown Chicago
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 traveller
The price is HK$539
HK$1,372 total
includes taxes & fees
17 Feb - 18 Feb
Sleek 1BR Apartment w/ In-unit Laundry
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (9 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is HK$5,463
HK$9,462 total
includes taxes & fees
2 Mar - 3 Mar
Spacious 4BR Central Apartment w/ Skyline Views
Interior

Chicago Third Floor Studio by 747 Lofts

Chicago Third Floor Studio by 747 Lofts
2.0 star property
West Town
9.8 out of 10, Exceptional, (7 reviews)
"Clean, easy to check in, all the household items you’d expect"
United States
Jason
The price is HK$511
HK$2,609 total
includes taxes & fees
15 Feb - 16 Feb
Chicago Third Floor Studio by 747 Lofts
Smart TV, books

Flexhome Ukrainian Village 2BR D1

Flexhome Ukrainian Village 2BR D1
West Town
9.2 out of 10, Wonderful, (7 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 HK$600
HK$1,416 total
includes taxes & fees
15 Feb - 16 Feb
Flexhome Ukrainian Village 2BR D1
Lounge

Kasa River North Chicago

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

Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer

Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer
West Ridge
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 HK$703
HK$2,238 total
includes taxes & fees
17 Feb - 18 Feb
Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer
Dining

Urban Comfort • 2BR in West Town

Urban Comfort • 2BR in West Town
West Town
9.6 out of 10, Exceptional, (7 reviews)
"Good location, close to airport, downtown Chicago, Wrigleyville and United Center. "
United States
David M.
The price is HK$586
HK$1,544 total
includes taxes & fees
17 Feb - 18 Feb
Urban Comfort • 2BR in West Town
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Great location, beautiful historic hotel with clean, updated rooms. "
Jennifer 4-night trip
Posted 2 days ago
Congress Plaza Hotel

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 holiday rentals in Chicago?

Yes, there are holiday rentals in Chicago close to Six Flags Great America, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Chicago like the notable monuments and fascinating museums. The array of shops and acclaimed art scene are some other things you might want to check out while you're here.

What are some of the best holiday rentals that Chicago has to offer?

A Home Away From Home!: This highly rated holiday 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 favourite homes for rent in Chicago are Belmont House, Classy & Chic/walk to Wrigley Field and Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!.

How many holiday rentals are there in Chicago?

With 955 Expedia holiday rentals, you're guaranteed 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 United Center.

What are holiday rentals like in Chicago?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chicago. Holiday rentals offer extras like WiFi and washers and dryers so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for a small group gathering.