Chicago Holiday Rentals

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 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, (1,087 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is HK$857
HK$1,235 total
includes taxes & fees
22 Feb - 23 Feb
Sentral Michigan Avenue
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, (430 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town
TV, offices

Complete 1BR Fully Furnished Home

Complete 1BR Fully Furnished Home
Downtown Chicago
The price is HK$688
HK$1,545 total
includes taxes & fees
2 Mar - 3 Mar
Complete 1BR Fully Furnished Home
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$1,063
HK$2,831 total
includes taxes & fees
1 Mar - 2 Mar
River North Rooftop With In and Out Parking 3
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
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
22 Feb - 23 Feb
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$539
HK$1,372 total
includes taxes & fees
22 Feb - 23 Feb
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$539
HK$1,372 total
includes taxes & fees
22 Feb - 23 Feb
Sun-Drenched 1BR Apartment
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$719
HK$1,582 total
includes taxes & fees
2 Mar - 3 Mar
1BR Modern Luxe Apt with 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$5,462
HK$9,460 total
includes taxes & fees
2 Mar - 3 Mar
Spacious 4BR Central Apartment w/ Skyline Views
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
22 Feb - 23 Feb
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$539
HK$1,372 total
includes taxes & fees
26 Feb - 27 Feb
Sleek 1BR Apartment w/ In-unit Laundry
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$1,039
HK$2,997 total
includes taxes & fees
23 Mar - 24 Mar
5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10
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$680
HK$1,741 total
includes taxes & fees
22 Feb - 23 Feb
Your Perfect 2BR Home
TV, offices

Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
The price is HK$539
HK$1,372 total
includes taxes & fees
22 Feb - 23 Feb
Stylish Gold Coast 1BR with Vintage Flair
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$696
HK$2,016 total
includes taxes & fees
22 Feb - 23 Feb
2-bedroom apartment just 2 minutes drive to Wrigley Field
Smart TV, stereo

Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
Irving Park
10.0 out of 10, Exceptional, (5 reviews)
"Beautifully decorated, spotless unit. Conveniently located."
United States
Holly G.
The price is HK$883
HK$1,937 total
includes taxes & fees
22 Feb - 23 Feb
Pine Beam Sloth Apartment next to Blue Line
Exterior

Cozy Train Vibes + Rare Parking x3

Cozy Train Vibes + Rare Parking x3
North Center
10.0 out of 10, Exceptional, (17 reviews)
"Nice place. Very responsive hosts"
United States
Charles H.
Cozy Train Vibes + Rare Parking x3
TV, offices

Smart & Stylish 2-Bedroom Unit

Smart & Stylish 2-Bedroom Unit
Lakeview
9.4 out of 10, Exceptional, (3 reviews)
"Good, walkable neighborhood. Nice room. "
United States
Dawn N.
The price is HK$1,555
HK$2,717 total
includes taxes & fees
22 Mar - 23 Mar
Smart & Stylish 2-Bedroom Unit
1 bedroom, iron/ironing board, free WiFi, bed sheets

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (62 reviews)
"Great room and host"
United States
Kathy T.
The price is HK$469
HK$1,061 total
includes taxes & fees
23 Feb - 24 Feb
Cozy studio in Andersonville Chicago
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

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Clean room"
Jesus 1-night trip
Posted 2 days ago
The Royal Sonesta Chicago Downtown

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.