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Chicago Vacation Rentals

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Our top choices for Chicago vacation rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,193 reviews)
"Great location"
United States
JAVIER
The price is ¥28,107
¥37,727 total
includes taxes & fees
Jul 5 - Jul 6
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (796 reviews)
"Great place to stay."
United States
Benedictine
The price is ¥41,799
¥58,533 total
includes taxes & fees
Jun 21 - Jun 22
Kasa Magnificent Mile Chicago

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (495 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is ¥37,318
¥47,788 total
includes taxes & fees
Jun 29 - Jun 30
Level Chicago – Old Town

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
10.0 out of 10, Exceptional, (9 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is ¥84,199
¥173,191 total
includes taxes & fees
Jul 2 - Jul 3
Modern West Loop Gem-City Views & Prime Location 4

870 1&2 - 2 Separate Suites in same building

870 1&2 - 2 Separate Suites in same building
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Great spot in a great area"
United States
Jesse H.
The price is ¥79,037
¥177,348 total
includes taxes & fees
Jul 3 - Jul 4
870 1&2 - 2 Separate Suites in same building

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"We loved the location."
United States
Nicoll M.
The price is ¥45,164
¥60,786 total
includes taxes & fees
Jun 21 - Jun 22
LIVN Millennium Park Downtown Chicago Superior 2 BR

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
10.0 out of 10, Exceptional, (3 reviews)
"Excellent place and great location. Very clean!"
United States
Amber S.
The price is ¥42,422
¥99,325 total
includes taxes & fees
Jun 23 - Jun 24
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
The price is ¥61,294
¥124,419 total
includes taxes & fees
Jul 17 - Jul 18
South Loop Rooftop With In and Out Parking 2

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.2 out of 10, Wonderful, (7 reviews)
"The parking situation is pretty rough. You have to park a half a mile away from the property. The room looks very luxurious in the pictures. However, once you get there, it does show some age and you can hear the other guest from above and below at all night not to mention that the city sounds are in full effect horns and traffic all night long and it’s difficult to get the room dark"
United States
Robert
The price is ¥66,940
¥89,735 total
includes taxes & fees
Jun 24 - Jun 25
LIVN West Loop Chicago 2 BR City View

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is ¥42,745
¥96,551 total
includes taxes & fees
Jun 28 - Jun 29
River North Rooftop With In and Out Parking 3

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (196 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
The price is ¥24,310
¥41,788 total
includes taxes & fees
Jun 21 - Jun 22
Kasa River North Chicago

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
9.8 out of 10, Exceptional, (7 reviews)
"This was a great stay! Great size and location. Would recommend it a lot."
United States
Dulce
The price is ¥29,679
¥51,213 total
includes taxes & fees
Jul 19 - Jul 20
Chic Studio in the Heart of the Gold Coast

Beautiful Unit CHI in Prime River North - 2

Beautiful Unit CHI in Prime River North - 2
Downtown Chicago
8.6 out of 10, Excellent, (25 reviews)
"Great place to stay for our girls weekend. Very convenient to everything in the city! We had the second unit and just to know this is a walk up with about 40-45 stairs to get to the unit. "
United States
Dawn P.
The price is ¥30,970
¥76,831 total
includes taxes & fees
Jul 3 - Jul 4
Beautiful Unit CHI in Prime River North - 2

Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
Downtown Chicago
The price is ¥36,454
¥64,375 total
includes taxes & fees
Jun 30 - Jul 1
Stylish Japanese-Themed 2BR Apt Close to Downtown

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
8.0 out of 10, Very Good, (3 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is ¥20,163
¥40,287 total
includes taxes & fees
Jun 21 - Jun 22
Sunlit 1BR Apartment | Warm & Welcoming Space

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.2 out of 10, Wonderful, (12 reviews)
"The host was great at communicating and the apartment was very clean! "
United States
Hannah C.
The price is ¥28,389
¥50,915 total
includes taxes & fees
Jun 28 - Jun 29
West Loop Living – Bright 1BR

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ¥27,744
¥49,563 total
includes taxes & fees
Jun 22 - Jun 23
1BR Modern Luxe Apt with In-Unit Laundry

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
LIVN Millennium Park Downtown Chicago 2BR

Gold Coast Hideaway | Vintage & Inviting Studio

Gold Coast Hideaway | Vintage & Inviting Studio
Downtown Chicago
The price is ¥21,614
¥39,975 total
includes taxes & fees
Jul 1 - Jul 2
Gold Coast Hideaway | Vintage & Inviting Studio
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

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:

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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 art scene. 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 vacation rentals in Chicago?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This highly rated vacation home rental in Chicago is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Other favorite homes for rent in Chicago are King Comfort apartment, Quiet, Clean, AC & WiFi and Chic Chicago Retreat (2-Bedroom Home) by RedAwning.

How many vacation rentals are there in Chicago?

With 931 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 Wrigley Field and Michigan Avenue.

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.