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
14 Aug - 15 Aug
Tomorrow
15 Aug - 16 Aug
This weekend
15 Aug - 17 Aug
Next weekend
22 Aug - 24 Aug

Top Holiday Rentals in Chicago

Sentral Michigan Avenue
Interior

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (875)
"Great stay!"
The price is ฿4,665
฿6,430 total
includes taxes & fees
2 Sept - 3 Sept
Sentral Michigan Avenue
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
8.2 out of 10, Very good, (341)
"Great stay!"
The price is ฿4,113
฿4,828 total
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Level Chicago – Old Town
Front of property – evening/night

Level Chicago – Old Town

4.0 star property
9.0 out of 10, Wonderful, (338)
"A lot of good food options walkable distance. "
Level Chicago – Old Town
Kasa Magnificent Mile Chicago
49-inch Smart TV with digital channels, TV, streaming services

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (469)
"Great location and great property will stay again "
Kasa Magnificent Mile Chicago
The Neighborhood Hotel-Little Italy
Front of property

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (189)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy
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, (613)
"I would stay again. "
The price is ฿3,561
฿4,180 total
includes taxes & fees
2 Sept - 3 Sept
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Kasa South Loop Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (330)
"Great stay"
Kasa South Loop Chicago
The Gem Museum Suites
Suite, 2 Bedrooms, Kitchen (Three Beds, Washer/Dryer) | Private kitchen | Full-sized fridge, microwave, stovetop, dishwasher

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (83)
"Super nice hotel and staff "
The price is ฿6,693
฿7,662 total
includes taxes & fees
2 Sept - 3 Sept
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
7.8 out of 10, Good, (129)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is ฿5,456
฿6,404 total
includes taxes & fees
2 Sept - 3 Sept
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Lobby

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (205)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is ฿4,815
฿5,652 total
includes taxes & fees
17 Aug - 18 Aug
Sonder by Marriott Bonvoy The Burnham Apartments Loop
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, (171)
"Great location. Clean (very clean) and comfortable apartments with everything you need. Cons: soundproofing from the city center is weak, all sounds are heard quite well. In terms of price per room ratio - a super option. I will book next time, and I recommend it to everyone."
The price is ฿4,389
฿5,152 total
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Wrigleyville Suites
Living area

Wrigleyville Suites

2.0 star property
9.6 out of 10, Exceptional, (14)
"Excellent location and very clean! Would stay again!"
Wrigleyville Suites
Kasa River North Chicago
Business centre

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (161)
"Great location and very clean! Will definitely be staying again. "
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
3.6 out of 10, (51)
"Property is advertised as a Comfort Inn, but is actually undergoing the transformation of becoming a Comfort Inn. It is still very much so operating as a motel on the south side of Chicago. Be safe. "
The price is ฿2,734
฿3,089 total
includes taxes & fees
18 Aug - 19 Aug
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
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
8.4 out of 10, Very good, (46)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is ฿4,389
฿5,152 total
includes taxes & fees
3 Sept - 4 Sept
Sonder by Marriott Bonvoy The Opal Apartments River North
Sonder by Marriott Bonvoy Greektown Apartments
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (59)
"Great location, easy stay!"
The price is ฿6,873
฿8,068 total
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy Greektown Apartments
Ground Floor Studios in Chicago by 747 Lofts
Exterior

Ground Floor Studios in Chicago by 747 Lofts

2.0 star property
9.4 out of 10, Exceptional, (16)
"Its was in a good location for anyone who has family close by. Bed was wonderful. "
The price is ฿2,395
฿7,688 total
includes taxes & fees
17 Aug - 18 Aug
Ground Floor Studios in Chicago by 747 Lofts
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

Top Chicago Hotel Reviews

Hilton Chicago

Hilton Chicago

10/10 Excellent
"Hilton honors member so they treated me extra special will be booking when I go back to Chicago "
Jasmine 1-night trip
Posted 10 hours ago
Hilton 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.

How many holiday rentals are there in Chicago?

With 1514 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 Navy Pier.

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.