Chicago Holiday Rentals

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Check prices for these dates

In two weeks
27 Mar - 29 Mar
In two months
8 May - 10 May
In three months
5 Jun - 7 Jun
In four months
3 Jul - 5 Jul

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, (1,104 reviews)
"The kitchen was great and check-in was easy."
United States
Marshal
The price is HK$925
HK$1,315 total
includes taxes & fees
19 Mar - 20 Mar
Sentral Michigan Avenue
TV, offices

Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
The price is HK$837
HK$1,722 total
includes taxes & fees
24 Mar - 25 Mar
Stylish Gold Coast 1BR with Vintage Flair
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, (441 reviews)
"Great value, friendly staff"
United States
Marcus
Level Chicago – Old Town
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (186 reviews)
"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."
United States
Daysha
Kasa River North Chicago
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, (8 reviews)
"Great communication and hosts. Location and unit was perfect."
United States
Greg C.
The price is HK$689
HK$1,567 total
includes taxes & fees
15 Mar - 16 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$689
HK$1,577 total
includes taxes & fees
17 Mar - 18 Mar
Sun-Drenched 1BR Apartment
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$689
HK$1,577 total
includes taxes & fees
16 Mar - 17 Mar
Modern Comfort: 1BR Unit w/ 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, (10 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
Spacious 4BR Central Apartment w/ Skyline Views
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$689
HK$1,577 total
includes taxes & fees
17 Mar - 18 Mar
1BR Modern Luxe Apt with In-Unit Laundry
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$1,526
HK$3,530 total
includes taxes & fees
18 Mar - 19 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)
"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"
United States
Brianna K.
The price is HK$884
HK$1,699 total
includes taxes & fees
24 Mar - 25 Mar
Chic Studio in the Heart of the Gold Coast
Outdoor dining

Relaxing Chicago Studio

Relaxing Chicago Studio
Edgewater
10.0 out of 10, Exceptional, (52 reviews)
"Easy to find, great location, very clean and cozy"
United States
Riley R.
The price is HK$509
HK$1,255 total
includes taxes & fees
1 Apr - 2 Apr
Relaxing Chicago Studio
TV

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (27 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is HK$540
HK$1,373 total
includes taxes & fees
16 Mar - 17 Mar
Nice 1BR Spot, Unwind & Relax
Iron/ironing board, travel cot, WiFi, bed sheets

Sunny Studio in Heart of Ravenswood

Sunny Studio in Heart of Ravenswood
Uptown
9.4 out of 10, Exceptional, (6 reviews)
"Great neighborhood, easy check in/out. "
United States
Leah B.
The price is HK$485
HK$1,231 total
includes taxes & fees
15 Mar - 16 Mar
Sunny Studio in Heart of Ravenswood
Iron/ironing board, travel cot, WiFi, bed sheets

Modern Studio Unit Near UChicago

Modern Studio Unit Near UChicago
Hyde Park
8.8 out of 10, Excellent, (15 reviews)
"Clean room and convenient location! "
United States
Gabriela
The price is HK$642
HK$1,414 total
includes taxes & fees
18 Mar - 19 Mar
Modern Studio Unit Near UChicago
TV, offices

Bright & Modern 1BR in a Prime Area

Bright & Modern 1BR in a Prime Area
Hyde Park
8.8 out of 10, Excellent, (3 reviews)
"Property was very clean. We enjoyed ourselves, Thank you!"
United States
Charles S.
The price is HK$720
HK$1,584 total
includes taxes & fees
25 Mar - 26 Mar
Bright & Modern 1BR in a Prime Area
TV, offices

Stylish 1BR Stay in Irving Vibes

Stylish 1BR Stay in Irving Vibes
Irving Park
9.0 out of 10, Wonderful, (4 reviews)
"Great place to stay Comfy bed and setting"
United States
Steven
The price is HK$626
HK$1,474 total
includes taxes & fees
7 Apr - 8 Apr
Stylish 1BR Stay in Irving Vibes
TV, offices

Urban Comfort • 2BR in West Town

Urban Comfort • 2BR in West Town
West Town
9.6 out of 10, Exceptional, (7 reviews)
"The place was very clean and accommodating."
United States
Mark E.
The price is HK$736
HK$1,749 total
includes taxes & fees
16 Mar - 17 Mar
Urban Comfort • 2BR in West Town
Games room

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Brighton Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "
United States
Jessica H.
The price is HK$516
HK$1,992 total
includes taxes & fees
17 Mar - 18 Mar
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
1 bedroom, iron/ironing board, travel cot, WiFi

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.2 out of 10, Wonderful, (12 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
The price is HK$540
HK$1,373 total
includes taxes & fees
15 Mar - 16 Mar
Charming Sunlit 1BR Apartment
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

Swissotel - Chicago

Swissotel - Chicago

6/10 Okay
"Outdated property for the price"
Trevor 4-night trip
Posted 2 hours ago
Swissotel - 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 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 acclaimed art scene. 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?

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 Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown! and HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony.

How many holiday rentals are there in Chicago?

With 945 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.