Chicago Holiday Rentals

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Check prices for these dates

Tonight
19 Nov - 20 Nov
Tomorrow
20 Nov - 21 Nov
This weekend
21 Nov - 23 Nov
Next weekend
28 Nov - 30 Nov

Holiday Rentals in Chicago

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (986)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is HK$783
HK$1,148 total
includes taxes & fees
17 Dec - 18 Dec
Sentral Michigan Avenue
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (623)
"Room was very nice, location was wonderful."
United States
Nicholas
Kasa Magnificent Mile Chicago
Front of property – evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (383)
"Property was clean, centrally located with wonderful staff. Will definitely stay again."
United States
Michelle
Level Chicago – Old Town
1 bedroom, individually decorated, individually furnished, desk
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
Downtown Chicago
8.0 out of 10, Very good, (402)
"Great location. Was there for the marathon and had a great stay. "
United States
HELGA
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Balcony
Kasa South Loop Chicago

Kasa South Loop Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (376)
"An excellent place to stay in Chicago downtown."
United States
ABDULHAFEEZ
Kasa South Loop Chicago
Lobby
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (254)
"Great stay. "
United States
Teresa
Sonder by Marriott Bonvoy The Burnham Apartments Loop
36-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
Near South Side
8.6 out of 10, Excellent, (713)
"Love the unit and location close to multiple restaurants and shopping."
United States
Jessie
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
Downtown Chicago
8.2 out of 10, Very good, (188)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
1 bedroom, individually furnished, desk, iron/ironing board
Sonder by Marriott Bonvoy The Opal Apartments River North

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
Downtown Chicago
8.4 out of 10, Very good, (57)
"Worked great for a work and family trip."
United States
David
Sonder by Marriott Bonvoy The Opal Apartments River North
Front of property
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4.0 star property
Near West Side
9.6 out of 10, Exceptional, (219)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy
Business centre
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (179)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Living area
Wrigleyville Suites

Wrigleyville Suites

2.0 star property
Lakeview
9.6 out of 10, Exceptional, (25)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is HK$584
HK$686 total
includes taxes & fees
20 Nov - 21 Nov
Wrigleyville Suites
Living room
Sonder by Marriott Bonvoy Greektown Apartments

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
Downtown Chicago
8.6 out of 10, Excellent, (65)
"The kitchen had everything we needed, great space overall, safe location, clean, near everything we needed, access to bus and rail very close, we really enjoyed our stay. "
United States
Samuel
Sonder by Marriott Bonvoy Greektown Apartments
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
The price is HK$2,209
HK$2,593 total
includes taxes & fees
20 Nov - 21 Nov
Chicago luxury home suites
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt

Clean & Equipped 1BR Apt

Lakeview
9.2 out of 10, Wonderful, (35)
"Amazing location and even nicer place inside. Enjoyed my time there a lot!"
United States
Camron K.
The price is HK$428
HK$1,239 total
includes taxes & fees
30 Nov - 1 Dec
Clean & Equipped 1BR Apt
Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
The price is HK$1,887
HK$3,019 total
includes taxes & fees
18 Dec - 19 Dec
Stylish Apartment near Chicago Downtown
Fridge, microwave, oven, stovetop
Lakeview 2BR Apartment

Lakeview 2BR Apartment

Lakeview
9.4 out of 10, Exceptional, (24)
"The apartment was as described and the customer service was amazing! "
United States
Michael M.
The price is HK$483
HK$1,429 total
includes taxes & fees
30 Nov - 1 Dec
Lakeview 2BR Apartment
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop

Stylish 1BR in West Loop

Downtown Chicago
10.0 out of 10, Exceptional, (9)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is HK$428
HK$1,239 total
includes taxes & fees
30 Nov - 1 Dec
Stylish 1BR in West Loop
Outdoor dining
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Near West Side
10.0 out of 10, Exceptional, (267)
"Lovely place! Very clean and has all of the amenities necessary for a good stay. Lots of fresh towels, a fully stocked kitchen and the location is excellent. "
United States
Angela C.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
Interior
Remodeled West Loop Apartment Near United Center

Remodeled West Loop Apartment Near United Center

Near West Side
9.0 out of 10, Wonderful, (56)
"This apartment is very close to downtown with easy parking right outside! The unit is very well maintained with spacious rooms and amenities! The host has thought of everything to make it feel like your own home! Would love to come back and stay here again!"
United States
kiran
Remodeled West Loop Apartment Near United Center
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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"I like the place was a good place and the staff are very welcoming. As one thing I didn't like I booked one bedroom King bed, I end up with two single beds. But they promise me to change in the morning and they didn't. I was not happy about it."
Regina 3-night trip
Posted 16 hours ago
Embassy Suites by Hilton Chicago Downtown River North

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 Field Museum of Natural History, 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 entertainment choices. 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?

Belmont House, Classy & Chic/walk to Wrigley Field: This highly rated holiday home rental in Chicago is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Other favourite homes for rent in Chicago are Wrigley Field/Lakeview -Entire Home- Large Groups! and Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed.

How many holiday rentals are there in Chicago?

With 1137 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 Lake Michigan 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.