Search Holiday Rentals in Chicago

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Tonight
2 Jul - 3 Jul
Tomorrow
3 Jul - 4 Jul
This weekend
4 Jul - 6 Jul
Next weekend
11 Jul - 13 Jul

Top Holiday Rentals in Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (804)
"Great stay!"
The price is ₹13,013
₹17,786 total
includes taxes & fees
7 Jul - 8 Jul
Sentral Michigan Avenue
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (322)
"Hotel was nice"
The price is ₹38,299
₹46,868 total
includes taxes & fees
30 Jul - 31 Jul
Level Chicago – Old Town
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
1 bedroom, individually decorated, individually furnished, desk

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.4 out of 10, Very good, (314)
"Super cool spot in a great part of the city."
The price is ₹11,889
₹13,956 total
includes taxes & fees
6 Jul - 7 Jul
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
36-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (556)
"Great place and location. "
The price is ₹12,744
₹14,960 total
includes taxes & fees
6 Jul - 7 Jul
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
2 bedrooms, premium bedding, individually decorated

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (192)
"Fantastically located snd brilliantly appointed aparthotel. Absolutely perfect for our stay, where we were competing at the HYROX world championships. The room was super spacious and had all amenities you could wish for. "
The price is ₹19,586
₹22,992 total
includes taxes & fees
6 Jul - 7 Jul
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (435)
"We had an amazing week staying here. Highly recommend!!"
Kasa Magnificent Mile Chicago
The Gem Museum Suites
Reception

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (69)
"Very clean, the room was very spacious and everyone was very friendly and the complementary breakfast was good. We also like the location. "
The price is ₹18,976
₹21,724 total
includes taxes & fees
9 Jul - 10 Jul
The Gem Museum Suites
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Property amenity

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
8.2 out of 10, Very good, (108)
"We love staying at Sonder properties. The apartment has a full kitchen with everything you need, the shower is so refreshing, and the in-room washer/dryer is super handy when traveling."
The price is ₹11,889
₹13,956 total
includes taxes & fees
6 Jul - 7 Jul
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (172)
"Great spot. "
The Neighborhood Hotel-Little Italy
Kasa South Loop Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | City view

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (317)
"Great stay"
Kasa South Loop Chicago
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
50-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (167)
"Great location and much larger space than I expected. Great location in the Loop with access to public transit and walkable. "
The price is ₹13,599
₹15,964 total
includes taxes & fees
6 Jul - 7 Jul
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy The Opal Apartments River North
1 bedroom, individually furnished, desk, iron/ironing board

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.6 out of 10, Excellent, (40)
"Our stay was amazing. "
The price is ₹13,599
₹15,964 total
includes taxes & fees
6 Jul - 7 Jul
Sonder by Marriott Bonvoy The Opal Apartments River North
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.2 out of 10, Wonderful, (7)
"Absolutely loved staying here! Would 10/10 recommend this place!"
Wrigleyville Suites
Kasa River North Chicago
Library

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (152)
"Great stay, clean room!"
Kasa River North Chicago
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Comfort Double Room | 1 bedroom, desk, laptop workspace, blackout curtains

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

2.5 star property
3.8 out of 10, (42)
"They cancel my reservation same day just getting there a terrible experience because i was traveling with my kid and need a place to rest and still waiting for my refund I need help for reund"
The price is ₹8,040
₹9,083 total
includes taxes & fees
6 Jul - 7 Jul
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Sonder by Marriott Bonvoy Greektown Apartments
40-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
9.0 out of 10, Wonderful, (55)
"Great location, easy stay!"
The price is ₹18,829
₹22,104 total
includes taxes & fees
27 Jul - 28 Jul
Sonder by Marriott Bonvoy Greektown Apartments
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 entertainment choices. The array of shops and fascinating museums are some other things you might want to check out while you're here.

How many holiday rentals are there in Chicago?

With 1451 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 Art Institute of Chicago and CIBC Theatre, 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 Soldier 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.