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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, (1,200 reviews)
"Great location"
United States
JAVIER
The price is ¥24,608
¥33,636 total
includes taxes & fees
Jul 1 - Jul 2
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (497 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
The price is ¥39,358
¥50,193 total
includes taxes & fees
Jul 6 - Jul 7
Level Chicago – Old Town

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (24 reviews)
"Great location. "
United States
Tom S.
The price is ¥89,766
¥180,447 total
includes taxes & fees
Jul 23 - Jul 24
Modern West Loop Gem-City Views & Prime Location 6

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.8 out of 10, Exceptional, (6 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
The price is ¥38,818
¥80,744 total
includes taxes & fees
Jul 26 - Jul 27
River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
The price is ¥33,318
¥83,839 total
includes taxes & fees
Jul 19 - Jul 20
River North Rooftop With In and Out Parking 6

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is ¥32,348
¥43,165 total
includes taxes & fees
Jul 1 - Jul 2
LIVN Millennium Park Downtown Chicago 2BR

South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3
Downtown Chicago
8.8 out of 10, Excellent, (5 reviews)
"Clean place. Family friendly. Location was great. A lot of restaurants close by. Great communication from the host."
United States
jaspreet
The price is ¥42,376
¥96,417 total
includes taxes & fees
Jul 19 - Jul 20
South Loop Rooftop With In and Out Parking 3

Beautiful Unit CHI in Prime River North - 1

Beautiful Unit CHI in Prime River North - 1
Downtown Chicago
9.2 out of 10, Wonderful, (23 reviews)
Beautiful Unit CHI in Prime River North - 1

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (9 reviews)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
The price is ¥25,231
¥34,012 total
includes taxes & fees
Jun 30 - Jul 1
LIVN West Loop Chicago Queen Superior Studio

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 ¥80,870
¥167,875 total
includes taxes & fees
Jul 2 - Jul 3
Modern West Loop Gem-City Views & Prime Location 4

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 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 ¥42,861
¥97,212 total
includes taxes & fees
Jul 1 - Jul 2
River North Rooftop With In and Out Parking 3

Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
Downtown Chicago
9.4 out of 10, Exceptional, (9 reviews)
"Excellent location, very clean & comfortable. West Loop is an awesome area to stay in Chicago. Seamless check in process."
United States
Dean R.
The price is ¥73,268
¥156,896 total
includes taxes & fees
Jul 26 - Jul 27
Modern West Loop Gem-City Views & Prime Location 2

River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
The price is ¥68,416
¥124,452 total
includes taxes & fees
Jul 2 - Jul 3
River North Private Balcony With In and Out Parking

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We loved the location."
United States
Nicoll M.
The price is ¥36,230
¥48,323 total
includes taxes & fees
Jul 1 - Jul 2
LIVN Millennium Park Downtown Chicago Superior 2 BR

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 ¥45,287
¥101,403 total
includes taxes & fees
Jul 21 - Jul 22
South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
The price is ¥58,065
¥119,767 total
includes taxes & fees
Jul 29 - Jul 30
South Loop Rooftop With In & Out Parking 1

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
The price is ¥24,261
¥32,676 total
includes taxes & fees
Jun 30 - Jul 1
LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
The price is ¥25,555
¥34,392 total
includes taxes & fees
Jun 30 - Jul 1
LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excelente, well located. Recommended."
United States
Sandra S.
The price is ¥29,760
¥38,931 total
includes taxes & fees
Jul 1 - Jul 2
LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
The price is ¥26,849
¥35,512 total
includes taxes & fees
Jul 1 - Jul 2
LIVN West Loop Chicago King 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 ENVITAE Hotel, 4BR Luxury Modern Apartments and King Comfort apartment, Quiet, Clean, AC & WiFi.

How many vacation rentals are there in Chicago?

With 889 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 Lake Michigan 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.