Chicago Holiday Rentals

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Check prices for these dates

In two weeks
15 May - 17 May
In two months
26 Jun - 28 Jun
In three months
24 Jul - 26 Jul
In four months
21 Aug - 23 Aug

Our top choices for Chicago holiday rentals

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, (471 reviews)
"Very clean and nice place"
United States
Hector
The price is HK$1,733
HK$2,228 total
includes taxes & fees
27 May - 28 May
Level Chicago – Old Town
Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,144 reviews)
"Thank you for the stay"
United States
Marco
The price is HK$1,192
HK$1,629 total
includes taxes & fees
25 May - 26 May
Sentral Michigan Avenue
TV, offices

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"It was very clean and as described/ pictured. The location was absolutely perfect being within a short walk to millennium park, restaurants and stores. The batteries were low in the remote and the host reached out to us around the same time. We received batteries within 10 minutes of letting them know."
United States
Amber W.
The price is HK$2,108
HK$2,823 total
includes taxes & fees
7 May - 8 May
LIVN Millennium Park Downtown Chicago 2BR
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (191 reviews)
"Having a kitchen is great."
United States
Mark
The price is HK$2,158
HK$3,269 total
includes taxes & fees
19 May - 20 May
Kasa River North Chicago
TV, offices

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (21 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is HK$2,798
HK$6,626 total
includes taxes & fees
5 May - 6 May
Modern West Loop Gem-City Views & Prime Location 6
TV, offices

Downtown Chicago Stay with Free In & Out Parking 4

Downtown Chicago Stay with Free In & Out Parking 4
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Our stay was wonderful. The views were fantastic. The apartment was centrally located so we were able to walk to restaurants, museums, and theaters. We bookmarked this location for future stays."
United States
Renae S.
The price is HK$4,216
HK$7,756 total
includes taxes & fees
17 May - 18 May
Downtown Chicago Stay with Free In & Out Parking 4
Living area

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
Modern 3BR Apartment Near North Ave Shops
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (16 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is HK$1,411
HK$3,965 total
includes taxes & fees
20 May - 21 May
Spacious 4BR Central Apartment w/ Skyline Views
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, (5 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$2,124
HK$4,836 total
includes taxes & fees
26 May - 27 May
River North Rooftop With In and Out Parking 3
1 bedroom, iron/ironing board, travel cot, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is HK$1,309
HK$2,410 total
includes taxes & fees
19 May - 20 May
West Loop Living – Bright 1BR
TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
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$1,309
HK$2,343 total
includes taxes & fees
4 May - 5 May
Sunlit 1BR Apartment | Warm & Welcoming Space
TV, offices

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Everything went well"
United States
Ryan W.
The price is HK$1,442
HK$1,925 total
includes taxes & fees
3 May - 4 May
LIVN West Loop Chicago 2 BR City View
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
8.8 out of 10, Excellent, (18 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is HK$1,042
HK$2,021 total
includes taxes & fees
3 May - 4 May
Modern Comfort: 1BR Unit w/ Laundry
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$924
HK$1,795 total
includes taxes & fees
12 May - 13 May
Chic Studio in the Heart of the Gold Coast
TV, offices

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
Modern West Loop Gem-City Views & Prime Location 5
TV, offices

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
The price is HK$1,042
HK$2,039 total
includes taxes & fees
12 May - 13 May
Chicago-Themed 1BR in a Central Spot near Downtown
Interior

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
The price is HK$1,300
HK$4,602 total
includes taxes & fees
20 May - 21 May
Modern West Loop Gem-City Views & Prime Location 3
TV, offices

Modern West Loop Gem-City Views & Prime Location 1

Modern West Loop Gem-City Views & Prime Location 1
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great location, HUGE space, and great service at a great rate!"
United States
Ernest C.
The price is HK$3,033
HK$6,945 total
includes taxes & fees
10 May - 11 May
Modern West Loop Gem-City Views & Prime Location 1
TV, offices

Downtown Chicago Stay with Free In & Out Parking 2

Downtown Chicago Stay with Free In & Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location and the in/out parking was very convenient. The apartment was clean and had plenty of room. The Host was very attentive to our needs. "
United States
Patty H.
The price is HK$2,343
HK$5,303 total
includes taxes & fees
3 May - 4 May
Downtown Chicago Stay with Free In & Out Parking 2
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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

8/10 Good
"Rooms were infrequently cleaned and we had to request soap and new towels (no we didn’t have our (no housekeeping) sign up). Other than that it was a nice stay."
Garrett 4-night trip
Posted 1 hour ago
Hotel Felix River North/Magnificent 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 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 theatre 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This highly rated holiday home rental in Chicago is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Other favourite homes for rent in Chicago are A Home Away From Home! and Luxury Home Away From Your Home.

How many holiday rentals are there in Chicago?

With 939 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 Navy Pier 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.