Chicago Vacation Rentals

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Nov 5 - Nov 6
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Nov 6 - Nov 7
This weekend
Nov 7 - Nov 9
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Nov 14 - Nov 16

Vacation 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 P12,114
P15,533 total
includes taxes & fees
Nov 10 - Nov 11
Level Chicago – Old Town
Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (972)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is P7,849
P10,931 total
includes taxes & fees
Nov 25 - Nov 26
Sentral Michigan Avenue
Business center
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 P7,413
P8,702 total
includes taxes & fees
Dec 4 - Dec 5
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 P58,529
P68,707 total
includes taxes & fees
Nov 6 - Nov 7
Chicago luxury home suites
Private kitchen
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 P5,897
P19,276 total
includes taxes & fees
Nov 6 - Nov 7
4BR Corporate Suite Central and Modern
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 P3,424
P12,776 total
includes taxes & fees
Nov 9 - Nov 10
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 P4,635
P5,442 total
includes taxes & fees
Nov 6 - Nov 7
Wrigleyville Suites
Private kitchen
Stylish Apartment near Chicago Downtown
Stylish Apartment near Chicago Downtown
2.0 star property
The price is P14,574
P23,154 total
includes taxes & fees
Nov 16 - Nov 17
Stylish Apartment near Chicago Downtown
Free WiFi
Logan Square SRO Hotel
Logan Square SRO Hotel
2.0 star property
The price is P10,243
P16,413 total
includes taxes & fees
Nov 6 - Nov 7
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 P31,547
P60,325 total
includes taxes & fees
Nov 17 - Nov 18
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 P6,447
P7,568 total
includes taxes & fees
Nov 20 - Nov 21
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Living room
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 P6,915
P8,118 total
includes taxes & fees
Nov 17 - Nov 18
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 P6,915
P8,118 total
includes taxes & fees
Nov 19 - Nov 20
Sonder by Marriott Bonvoy The Opal Apartments River North
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, (398)
"Quite and low key spot"
United States
Shunica
The price is P5,920
P6,950 total
includes taxes & fees
Nov 17 - Nov 18
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, (707)
"Location was nice."
United States
Juliet
The price is P7,910
P9,286 total
includes taxes & fees
Dec 4 - Dec 5
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Private kitchen
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 P3,245
P7,562 total
includes taxes & fees
Nov 9 - Nov 10
Chicago Second Floor Studio by 747 Lofts
Floor plan
Spacious 3BR Home Firepit & Grill
Spacious 3BR Home Firepit & Grill
2.0 star property
The price is P10,418
P26,066 total
includes taxes & fees
Nov 19 - Nov 20
Spacious 3BR Home Firepit & Grill
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
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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"Room was spacious, walking distance to just about anything you’d want to do in Chicago. Would highly recommend."
Anthony 3-night trip
Posted 2 days 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
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Look no further and take a look at our great range of rental properties in Chicago!

Frequently asked questions

Can I find vacation rentals in Chicago?

Yes, we give you a choice of vacation rentals in Chicago near Six Flags Great America, or you can choose a more secluded option if you want a relaxing stay. Tourists who visit Chicago like the notable monuments and acclaimed theater scene. The array of shops and fascinating museums are some other things you might want to check out while you're here.

How many vacation rentals are there in Chicago?

With 1140 Expedia vacation rentals, you're sure 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 vacation rentals like in Chicago?

Vacation rentals are private properties you can stay in for a short or long stay in Chicago. Vacation rentals provide amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.