Chicago Holiday Rentals

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Our top choices for Chicago holiday rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,052 reviews)
"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "
United States
Khalid
The price is HK$855
HK$1,233 total
includes taxes & fees
20 Jan - 21 Jan
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (414 reviews)
"Property was clean, welcoming, pet friendly "
United States
Heather
The price is HK$1,138
HK$1,528 total
includes taxes & fees
22 Jan - 23 Jan
Level Chicago – Old Town

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$538
HK$1,290 total
includes taxes & fees
25 Jan - 26 Jan
Chic Studio in the Heart of the Gold Coast

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$491
HK$1,314 total
includes taxes & fees
22 Jan - 23 Jan
West Loop Living – Bright 1BR

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$780
HK$2,478 total
includes taxes & fees
26 Jan - 27 Jan
River North Rooftop With In and Out Parking 3

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ 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$491
HK$1,314 total
includes taxes & fees
26 Jan - 27 Jan
Sleek 1BR Apt w/ Laundry

Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
2.0 star property
Downtown Chicago
The price is HK$538
HK$1,485 total
includes taxes & fees
20 Jan - 21 Jan
Stylish Japanese-Themed 2BR Apt Close to Downtown

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$491
HK$1,314 total
includes taxes & fees
20 Jan - 21 Jan
1BR Modern Luxe Apt with In-Unit Laundry

Downtown 2bd #5 +Gym near Park, Lake, Museums

Downtown 2bd #5 +Gym near Park, Lake, Museums
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
The price is HK$734
HK$2,270 total
includes taxes & fees
22 Jan - 23 Jan
Downtown 2bd #5 +Gym near Park, Lake, Museums

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very good, (5 reviews)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is HK$756
HK$1,624 total
includes taxes & fees
17 Feb - 18 Feb
The One: A 1BR Stay That Feels Like Home

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$491
HK$1,314 total
includes taxes & fees
22 Jan - 23 Jan
Sun-Drenched 1BR Apartment

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.8 out of 10, Exceptional, (11 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$491
HK$1,314 total
includes taxes & fees
20 Jan - 21 Jan
Modern Comfort: 1BR Unit w/ Laundry

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
The price is HK$1,076
HK$1,995 total
includes taxes & fees
22 Jan - 23 Jan
Kasa River North Chicago

Downtown Mag Mile Sleep 20 | 6bd/6ba

Downtown Mag Mile Sleep 20 | 6bd/6ba
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Great units, fabulous location, very attentive property managers. Loved the place. Only downside was a grumpy downstairs neighbor who complained about the noise of the children and noise of adults even before quiet hours and no music playing."
United States
Cathy E.
The price is HK$2,703
HK$8,842 total
includes taxes & fees
21 Jan - 22 Jan
Downtown Mag Mile Sleep 20 | 6bd/6ba

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (27 reviews)
"Nice place "
United States
Barry
The price is HK$1,158
HK$1,359 total
includes taxes & fees
20 Jan - 21 Jan
Wrigleyville Suites

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is HK$491
HK$1,314 total
includes taxes & fees
20 Jan - 21 Jan
Complete 1BR Home Sum

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
2.0 star property
Downtown Chicago
The price is HK$491
HK$1,314 total
includes taxes & fees
26 Jan - 27 Jan
Chicago-Themed 1BR in a Central Spot near Downtown

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
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 HK$538
HK$1,485 total
includes taxes & fees
20 Jan - 21 Jan
Twice as Nice: Chic 2BR Stay with Style & Space

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (49 reviews)
"Clean and quiet, perfect for nights to rest after exploring the city"
United States
Joe T.
The price is HK$627
HK$2,182 total
includes taxes & fees
2 Feb - 3 Feb
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Flexhome Ukrainian Village 2BR D1

Flexhome Ukrainian Village 2BR D1
West Town
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 HK$1,166
HK$2,190 total
includes taxes & fees
13 Feb - 14 Feb
Flexhome Ukrainian Village 2BR D1
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

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:

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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 Field Museum of Natural History, 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 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 holiday rentals that Chicago has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This highly rated holiday home rental in Chicago offers a patio, a BBQ 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 Pleasant 3-bedroom house with AC in charming Mundelein and Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!.

How many holiday rentals are there in Chicago?

With 931 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 Wrigley Field.

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.