Chicago Vacation Rentals

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Jul 30 - Jul 31
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Vacation Rentals in Chicago

Sentral Michigan Avenue
Relax in a spacious area with comfortable seating and lush greenery.

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (845)
"We would stay here again. Very happy with our stay "
The price is P9,700
P13,070 total
includes taxes & fees
Aug 4 - Aug 5
Sentral Michigan Avenue
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Enjoy a minimalist retreat with a large bed, desk, and compact kitchenette.

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very Good, (335)
"The property canceled on us 4 hours prior to check in"
The price is P7,263
P8,526 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
Kasa Magnificent Mile Chicago
Relax on the spacious balcony with a city view, featuring a sofa, armchair, and outdoor seating area.

Kasa Magnificent Mile Chicago

4.0 star property
9.4 out of 10, Exceptional, (453)
"Nice views and convenient location to transit and dining"
Kasa Magnificent Mile Chicago
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Enjoy a city view from the large window, with a comfortable sofa and potted plant adding to the inviting atmosphere.

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (593)
"I would stay again. "
The price is P8,628
P10,128 total
includes taxes & fees
Aug 25 - Aug 26
Sonder by Marriott Bonvoy South Wabash Apartments South Loop
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Enjoy the city view from this stylish balcony with a sofa, chair, and table.

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (124)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is P7,507
P8,812 total
includes taxes & fees
Aug 25 - Aug 26
Sonder by Marriott Bonvoy The Plymouth Apartments Loop
Kasa South Loop Chicago
Enjoy the city view from this balcony with a comfortable Adirondack chair and a small table.

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (322)
"Great stay"
Kasa South Loop Chicago
Sonder by Marriott Bonvoy The Burnham Apartments Loop
Relax in style with plush armchairs and a natural centerpiece, surrounded by a contemporary design.

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (200)
"Clean, new, spacious "
The price is P12,576
P14,763 total
includes taxes & fees
Aug 24 - Aug 25
Sonder by Marriott Bonvoy The Burnham Apartments Loop
The Gem Museum Suites
Kitchen area with dining space, featuring a refrigerator, round table, and two chairs.

The Gem Museum Suites

3.5 star property
9.4 out of 10, Exceptional, (80)
"Had a good and comfortable stay "
The price is P11,871
P13,590 total
includes taxes & fees
Aug 12 - Aug 13
The Gem Museum Suites
The Neighborhood Hotel-Little Italy
Welcome to The Neighborhood Hotel, where guests enter through a distinctive black brick facade with the hotel's name prominently displayed.

The Neighborhood Hotel-Little Italy

4.0 star property
9.8 out of 10, Exceptional, (181)
"Great suite"
The Neighborhood Hotel-Little Italy
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Relax in this stylish living room with a sofa, armchair, and coffee table, offering a view of the city outside.

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very Good, (169)
"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 P9,213
P10,815 total
includes taxes & fees
Aug 17 - Aug 18
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Two single beds with white linens, a small armchair, and a bedside table with a lamp.

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

2.5 star property
3.6 out of 10, (50)
"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 P4,837
P5,465 total
includes taxes & fees
Aug 4 - Aug 5
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
Kasa River North Chicago
Meetings take place around a large, rectangular table surrounded by six chairs with chrome legs.

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (157)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago
Wrigleyville Suites
Enjoy meals in this cozy dining area with a long table and six chairs, surrounded by framed photographs and a potted plant.

Wrigleyville Suites

2.0 star property
9.8 out of 10, Exceptional, (10)
"Excellent location and very clean! Would stay again!"
The price is P10,807
P15,545 total
includes taxes & fees
Jul 31 - Aug 1
Wrigleyville Suites
Sonder by Marriott Bonvoy Greektown Apartments
Relax in this stylish living space with a sofa, armchair, and dining area.

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.8 out of 10, Excellent, (56)
"Great location, easy stay!"
The price is P12,138
P14,248 total
includes taxes & fees
Aug 24 - Aug 25
Sonder by Marriott Bonvoy Greektown Apartments
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

The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

10/10 Excellent
"Always stay there! Location is a plus "
Karin 2-night trip
Posted 5 hours ago
The Whitehall Hotel, BW Premier Collection

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.

How many vacation rentals are there in Chicago?

With 1501 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.