Chicago Holiday Rentals

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Check prices for these dates

In two weeks
13 Mar - 15 Mar
In two months
24 Apr - 26 Apr
In three months
22 May - 24 May
In four months
19 Jun - 21 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, (1,094 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is HK$857
HK$1,236 total
includes taxes & fees
3 Mar - 4 Mar
Sentral Michigan Avenue
TV, offices

Complete 1BR Fully Furnished Home

Complete 1BR Fully Furnished Home
Downtown Chicago
The price is HK$884
HK$1,814 total
includes taxes & fees
1 Mar - 2 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, (433 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town
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$1,048
HK$2,823 total
includes taxes & fees
1 Mar - 2 Mar
River North Rooftop With In and Out Parking 3
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$884
HK$1,717 total
includes taxes & fees
1 Mar - 2 Mar
Chic Studio in the Heart of the Gold Coast
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$884
HK$1,814 total
includes taxes & fees
1 Mar - 2 Mar
West Loop Living – Bright 1BR
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$884
HK$1,775 total
includes taxes & fees
10 Mar - 11 Mar
Sun-Drenched 1BR Apartment
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (184 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
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$884
HK$1,814 total
includes taxes & fees
1 Mar - 2 Mar
1BR Modern Luxe Apt with In-Unit Laundry
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$884
HK$1,814 total
includes taxes & fees
1 Mar - 2 Mar
Modern Comfort: 1BR Unit w/ Laundry
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$978
HK$1,886 total
includes taxes & fees
18 Mar - 19 Mar
Sleek 1BR Apartment w/ In-unit Laundry
TV, offices

Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
The price is HK$884
HK$1,775 total
includes taxes & fees
11 Mar - 12 Mar
Stylish Gold Coast 1BR with Vintage Flair
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$5,466
HK$9,466 total
includes taxes & fees
11 Mar - 12 Mar
Spacious 4BR Central Apartment w/ Skyline Views
TV, video games

5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10

5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10
Lakeview
9.2 out of 10, Wonderful, (5 reviews)
"This was a wonderful stay! The apartment was clean, well furnished, and the communication with the manager was wonderful. My son and I really enjoyed the video games, especially golden tee. The location is fantastic, giving us access to most everything in the Lincoln Park area, as well as Wrigley Field. I can’t recommend this enough. We had a wonderful time!"
United States
Matthew B.
The price is HK$720
HK$2,394 total
includes taxes & fees
27 Feb - 28 Feb
5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10
WiFi, bed sheets

Trendy Studio in Vibrant Area

Trendy Studio in Vibrant Area
Hyde Park
The price is HK$641
HK$1,414 total
includes taxes & fees
2 Mar - 3 Mar
Trendy Studio in Vibrant Area
Interior

Your Perfect 2BR Home

Your Perfect 2BR Home
Near West Side
8.2 out of 10, Very good, (14 reviews)
"Great location! "
United States
Kourtney K.
The price is HK$845
HK$1,944 total
includes taxes & fees
1 Mar - 2 Mar
Your Perfect 2BR Home
2 bedrooms, iron/ironing board, travel cot, WiFi

Modern 2BR with Reliable Wi-Fi

Modern 2BR with Reliable Wi-Fi
Lakeview
9.0 out of 10, Wonderful, (6 reviews)
"Great location for seeing a Cubs game. Easy to follow "
United States
David A.
The price is HK$837
HK$1,838 total
includes taxes & fees
11 Mar - 12 Mar
Modern 2BR with Reliable Wi-Fi
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$744
HK$874 total
includes taxes & fees
2 Mar - 3 Mar
Wrigleyville Suites
Property grounds

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (59 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is HK$908
HK$2,355 total
includes taxes & fees
1 Mar - 2 Mar
2-bedroom apartment just 2 minutes drive to Wrigley Field
Smart TV

NEW Private West Loop 1br with Backyard near Green Line and CTA

NEW Private West Loop 1br with Backyard near Green Line and CTA
East Garfield Park
9.6 out of 10, Exceptional, (4 reviews)
"Very cozy stay. Host was great with communication and the place has everything needed. Would definitely book here again!"
United States
Eric H.
The price is HK$301
HK$1,626 total
includes taxes & fees
17 Mar - 18 Mar
NEW Private West Loop 1br with Backyard near Green Line and CTA
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

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

10/10 Excellent
"Very nice. Hotel lobby has the best drinks. Nice place for couples. Room is cute"
Victor 2-night trip
Posted 1 day ago
Aloft Chicago Mag Mile

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 Chicago Cultural Center, 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 Wrigley Field/Lakeview -Entire Home- Large Groups! and HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony.

How many holiday rentals are there in Chicago?

With 947 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 Navy Pier.

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.