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Check prices for these dates

In two weeks
21 Nov - 23 Nov
In two months
2 Jan - 4 Jan
In three months
30 Jan - 1 Feb
In four months
27 Feb - 1 Mar

Top Holiday Rentals in Chicago

Front of property – evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (375)
"Great place to stay. Loved it!"
United States
Peter
The price is Rp3.546.679
Rp4.536.570 total
includes taxes & fees
10 Nov - 11 Nov
Level Chicago – Old Town
Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (974)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is Rp2.241.750
Rp3.122.234 total
includes taxes & fees
10 Nov - 11 Nov
Sentral Michigan Avenue
Business centre
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.4 out of 10, Exceptional, (176)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Lobby
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Sonder by Marriott Bonvoy The Burnham Apartments Loop
3.5 star property
8.8 out of 10, Excellent, (251)
"Great stay. "
United States
Teresa
The price is Rp2.117.208
Rp2.485.390 total
includes taxes & fees
13 Nov - 14 Nov
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Free WiFi
Chicago luxury home suites
Chicago luxury home suites
2.0 star property
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 Rp16.708.000
Rp19.613.521 total
includes taxes & fees
7 Dec - 8 Dec
Chicago luxury home suites
Business Apartment, City View | Private kitchen | Fridge, microwave, oven, stovetop
4BR Corporate Suite Central and Modern
4BR Corporate Suite Central and Modern
2.0 star property
10.0 out of 10, Exceptional, (6)
"Great location in Lincoln Park. Easy walk to several shops and restaurants. And about a 5 minute walk to the redline station (North/Clybourn). Very clean and quiet inside the unit. Building is very new. Room access through the Latch app is simple. I would definitely stay here again. The overall experience was excellent and my other guests would agree. "
United States
Phillip
The price is Rp3.293.249
Rp7.378.658 total
includes taxes & fees
16 Nov - 17 Nov
4BR Corporate Suite Central and Modern
Studio | Exterior
Chicago Third Floor Studio by 747 Lofts
Chicago Third Floor Studio by 747 Lofts
2.0 star property
9.6 out of 10, Exceptional, (5)
"Excellent facility with great amenities: laundry, kitchen and a great location close to the Loop and easy access to O’Hare airport via Blue Line or Kennedy Expressway."
United States
Philip
The price is Rp973.598
Rp3.632.604 total
includes taxes & fees
9 Nov - 10 Nov
Chicago Third Floor Studio by 747 Lofts
Living area
Wrigleyville Suites
Wrigleyville Suites
2.0 star property
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
The price is Rp2.587.792
Rp3.037.810 total
includes taxes & fees
7 Nov - 8 Nov
Wrigleyville Suites
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown
Stylish Apartment near Chicago Downtown
2.0 star property
The price is Rp4.160.292
Rp6.609.758 total
includes taxes & fees
7 Dec - 8 Dec
Stylish Apartment near Chicago Downtown
Room, 1 Queen Bed, Non Smoking | Free WiFi
Logan Square SRO Hotel
Logan Square SRO Hotel
2.0 star property
The price is Rp3.343.400
Rp5.178.591 total
includes taxes & fees
8 Nov - 9 Nov
Logan Square SRO Hotel
Interior
Art Villa
Art Villa
5.0 star property
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
The price is Rp9.005.612
Rp17.220.636 total
includes taxes & fees
7 Dec - 8 Dec
Art Villa
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
8.2 out of 10, Very good, (187)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
The price is Rp1.833.019
Rp2.151.781 total
includes taxes & fees
10 Nov - 11 Nov
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Apartment, 1 Bedroom | Living room | 40-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Greektown Apartments
Sonder by Marriott Bonvoy Greektown Apartments
3.5 star property
8.6 out of 10, Excellent, (65)
"I enjoyed my stay! Thanks!"
United States
Jonathan
The price is Rp1.975.114
Rp2.318.586 total
includes taxes & fees
16 Nov - 17 Nov
Sonder by Marriott Bonvoy Greektown Apartments
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
8.4 out of 10, Very good, (56)
"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."
United States
Swastika
The price is Rp1.974.050
Rp2.317.338 total
includes taxes & fees
7 Dec - 8 Dec
Sonder by Marriott Bonvoy The Opal Apartments River North
Studio | Exterior
Ground Floor Studios in Chicago by 747 Lofts
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (21)
"This property is excellent!"
United States
Philip
Ground Floor Studios in Chicago by 747 Lofts
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
8.0 out of 10, Very good, (399)
"Quite and low key spot"
United States
Shunica
The price is Rp1.690.925
Rp1.984.978 total
includes taxes & fees
10 Nov - 11 Nov
Sonder by Marriott Bonvoy Market Hall Apartments West 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
8.6 out of 10, Excellent, (708)
"Location was nice."
United States
Juliet
The price is Rp2.117.208
Rp2.485.390 total
includes taxes & fees
10 Nov - 11 Nov
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Studio | Private kitchen | Fridge, oven, coffee/tea maker, toaster
Chicago Second Floor Studio by 747 Lofts
Chicago Second Floor Studio by 747 Lofts
2.0 star property
8.8 out of 10, Excellent, (13)
"Great location, convenient to downtown and blue line to airport. Everything necessary in unit, comfortable temperature and full kitchen with unique grocery store nearby."
United States
Barbara
The price is Rp956.714
Rp2.195.611 total
includes taxes & fees
9 Nov - 10 Nov
Chicago Second Floor Studio by 747 Lofts
House (3 Bedrooms) | Floor plan
Spacious 3BR Home Firepit & Grill
Spacious 3BR Home Firepit & Grill
2.0 star property
The price is Rp2.591.135
Rp7.014.453 total
includes taxes & fees
11 Nov - 12 Nov
Spacious 3BR Home Firepit & Grill
Exclusive Apartment, Private Bathroom, Garden View (1st Floor) | Interior
Historic Oak Park Home
Historic Oak Park Home
2.0 star property
10.0 out of 10, Exceptional, (5)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is Rp2.585.451
Rp4.816.168 total
includes taxes & fees
9 Nov - 10 Nov
Historic Oak Park Home
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
"Room clean and welcoming staff. The room has a great layout. perfect hotel to be downtown"
Gwenola 3-night trip
Posted 18 hours ago
Hilton Chicago/Magnificent Mile Suites

Find out more about Chicago

Search for holiday rentals in Chicago on Expedia.co.id! 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.

How many holiday rentals are there in Chicago?

With 1140 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.