Chicago Holiday Rentals

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

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, (1,129 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is HK$1,051
HK$1,464 total
includes taxes & fees
14 Apr - 15 Apr
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, (462 reviews)
"Would definitely stay again. Everything was great!"
United States
Michelle
The price is HK$1,827
HK$2,338 total
includes taxes & fees
15 Apr - 16 Apr
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, (190 reviews)
"Great place! Would definitely stay again!"
United States
Katherine
The price is HK$1,191
HK$2,134 total
includes taxes & fees
30 Apr - 1 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, (18 reviews)
"Great place"
United States
Daniel L.
The price is HK$1,644
HK$5,007 total
includes taxes & fees
19 Apr - 20 Apr
Modern West Loop Gem-City Views & Prime Location 6
Living area

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Plymouth Collection: 2BD with Lobby, Gym, Rooftop
Chicago
Plymouth Collection: 2BD with Lobby, Gym, Rooftop
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (13 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is HK$1,128
HK$3,556 total
includes taxes & fees
26 Apr - 27 Apr
Spacious 4BR Central Apartment w/ Skyline Views
Living area

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Everything went well"
United States
Ryan W.
The price is HK$1,519
HK$1,977 total
includes taxes & fees
19 Apr - 20 Apr
LIVN West Loop Chicago 2 BR City View
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$1,253
HK$3,557 total
includes taxes & fees
14 Apr - 15 Apr
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$1,034
HK$1,942 total
includes taxes & fees
5 May - 6 May
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, (9 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$767
HK$1,640 total
includes taxes & fees
14 Apr - 15 Apr
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$885
HK$1,778 total
includes taxes & fees
16 Apr - 17 Apr
Sunlit 1BR Apartment | Warm & Welcoming Space
TV, offices

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.0 out of 10, Wonderful, (17 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is HK$564
HK$1,402 total
includes taxes & fees
19 Apr - 20 Apr
Modern Comfort: 1BR Unit w/ Laundry
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.0 out of 10, Very good, (2 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$885
HK$1,788 total
includes taxes & fees
14 Apr - 15 Apr
1BR Modern Luxe Apt with In-Unit Laundry
Interior

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is HK$839
HK$3,122 total
includes taxes & fees
15 Apr - 16 Apr
Premium Urban 4BR - Perfect Mix of Comfort & Location
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, (5 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.
Modern West Loop Gem-City Views & Prime Location 3
Beach

Luxury Lincoln Park Apartment with Gourmet Kitchen

Luxury Lincoln Park Apartment with Gourmet Kitchen
Lincoln Park
10.0 out of 10, Exceptional, (11 reviews)
"Home was well maintained and clean. Location was fantastic with an easy walk to shops and restaurants. "
United States
Nikki R.
The price is HK$8,575
HK$16,349 total
includes taxes & fees
11 May - 12 May
Luxury Lincoln Park Apartment with Gourmet Kitchen
Room

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
The price is HK$1,042
HK$1,416 total
includes taxes & fees
10 May - 11 May
LIVN West Loop Chicago King Studio
Living area

Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom

Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
Lakeview
10.0 out of 10, Exceptional, (22 reviews)
"Place is freaking perfect if you're in town for some sight seeing and a ball game."
United States
Elbert C.
The price is HK$3,751
HK$8,542 total
includes taxes & fees
15 Apr - 16 Apr
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
Fireplace

Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
Lakeview
9.6 out of 10, Exceptional, (29 reviews)
"Host was great! Let us check in early, it was an easy check in/out! We'll be back for a Cubs game! "
United States
Caroline B.
The price is HK$3,751
HK$8,542 total
includes taxes & fees
15 Apr - 16 Apr
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
Dining

Aloha 2.0 Tropical Oasis in the heart of Wicker Park that sleeps 23 + backyard patio

Aloha 2.0 Tropical Oasis in the heart of Wicker Park that sleeps 23 + backyard patio
West Town
10.0 out of 10, Exceptional, (12 reviews)
"We booked this apartment and their other one for a bachelorette. It was such an amazing time and everything Was so thoughtful . Perfect location too!"
United States
Lita T.
The price is HK$7,048
HK$13,350 total
includes taxes & fees
3 May - 4 May
Aloha 2.0 Tropical Oasis in the heart of Wicker Park that sleeps 23 + backyard patio
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

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

10/10 Excellent
"Very nice I always stay here! "
Bennie 2-night trip
Posted 1 hour ago
Hilton Chicago/Magnificent Mile Suites

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?

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony: This highly rated holiday home rental in Chicago is located in the city centre, and has a balcony, an arcade/games room and a BBQ to put you at ease in your new surroundings. It has 3 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 Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown! and A Home Away From Home!.

How many holiday rentals are there in Chicago?

With 931 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.