Chicago Holiday Rentals

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Check prices for these dates

Tonight
11 Jan - 12 Jan
Tomorrow
12 Jan - 13 Jan
Next weekend
16 Jan - 18 Jan
In two weeks
23 Jan - 25 Jan

Our top choices for Chicago holiday rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,040 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$1,232 total
includes taxes & fees
13 Jan - 14 Jan
Sentral Michigan Avenue
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

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
13 Jan - 14 Jan
Chic Studio in the Heart of the Gold Coast
TV, offices
Complete 1BR Home Sum

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is HK$491
HK$1,313 total
includes taxes & fees
13 Jan - 14 Jan
Complete 1BR Home Sum
Interior
River North Rooftop With In and Out Parking 3

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$779
HK$2,439 total
includes taxes & fees
13 Jan - 14 Jan
River North Rooftop With In and Out Parking 3
TV, offices
Chicago-Themed 1BR in a Central Spot near Downtown

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$1,313 total
includes taxes & fees
13 Jan - 14 Jan
Chicago-Themed 1BR in a Central Spot near Downtown
1 bedroom, iron/ironing board, travel cot, WiFi
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (6 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$1,313 total
includes taxes & fees
22 Jan - 23 Jan
West Loop Living – Bright 1BR
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

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$1,313 total
includes taxes & fees
15 Jan - 16 Jan
1BR Modern Luxe Apt with In-Unit Laundry
Full-sized fridge, microwave, oven, stovetop
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (410 reviews)
"Great location, clean room and friendly staff!"
United States
Scott
Level Chicago – Old Town
TV, offices
The One: A 1BR Stay That Feels Like Home

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$491
HK$1,313 total
includes taxes & fees
15 Jan - 16 Jan
The One: A 1BR Stay That Feels Like Home
TV, offices
Modern Comfort: 1BR Unit w/ Laundry

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$1,313 total
includes taxes & fees
14 Jan - 15 Jan
Modern Comfort: 1BR Unit w/ Laundry
TV, offices
Sun-Drenched 1BR Apartment

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$1,313 total
includes taxes & fees
19 Jan - 20 Jan
Sun-Drenched 1BR Apartment
Lounge
Kasa River North Chicago

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

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
14 Jan - 15 Jan
Twice as Nice: Chic 2BR Stay with Style & Space
Interior
Stylish Japanese-Themed 2BR Apt Close to Downtown

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
19 Jan - 20 Jan
Stylish Japanese-Themed 2BR Apt Close to Downtown
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

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$1,313 total
includes taxes & fees
21 Jan - 22 Jan
Sleek 1BR Apt w/ Laundry
Interior
Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
2.0 star property
Irving Park
10.0 out of 10, Exceptional, (4 reviews)
"Amazing stay! So comfortable, clean, and the sushi underneath was the icing on the cake! We will definitely stay again when we come back! "
United States
Emily s.
The price is HK$575
HK$1,539 total
includes taxes & fees
13 Jan - 14 Jan
Pine Beam Sloth Apartment next to Blue Line
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

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$800
HK$2,362 total
includes taxes & fees
13 Jan - 14 Jan
Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer
1 bedroom, iron/ironing board, free WiFi, bed sheets
Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (57 reviews)
"Perfect location, parking was shockingly easy, and we were very impressed. "
United States
Samantha F.
The price is HK$468
HK$1,058 total
includes taxes & fees
14 Jan - 15 Jan
Cozy studio in Andersonville Chicago
2 bedrooms, iron/ironing board, free WiFi, bed sheets
The Lincoln Square Hideaway

The Lincoln Square Hideaway

The Lincoln Square Hideaway
Lincoln Square
10.0 out of 10, Exceptional, (15 reviews)
"Clean, good location, easy check in, very nice place, provided extras, coffee, chocolate etc."
United States
Carol H.
The price is HK$920
HK$3,059 total
includes taxes & fees
13 Jan - 14 Jan
The Lincoln Square Hideaway
Interior
River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (17 reviews)
"Loved the space and location "
United States
Caroline
The price is HK$579
HK$2,691 total
includes taxes & fees
25 Jan - 26 Jan
River West, Third Floor Chicago by 747 Lofts
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

Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

10/10 Excellent
"Super fast and easy check in / out experience, amazing location and very affordable "
Katie 2-night trip
Posted 8 hours ago
Club Quarters Hotel Wacker at Michigan, 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 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 925 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 Lake Michigan 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.