Chicago Vacation Rentals

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Vacation Rentals in Chicago

Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (415)
"Great location for museum campus area!!!"
The price is P10,902
P14,500 total
includes taxes & fees
Jun 16 - Jun 17
Sentral Michigan Avenue
Interior
Sonder Market Hall
3.5 star property
8.4 out of 10, Very Good, (88)
"I really enjoyed my stay here. I came for a bar crawl with my family and everything was in distance of the room. I really liked the fact that I could use my phone as my key for both the front door and room. I wish I could’ve stayed longer, but will definitely stay again. "
The price is P8,114
P9,526 total
includes taxes & fees
Jun 16 - Jun 17
Sonder Market Hall
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (302)
"Everything was great!"
The price is P11,250
P13,208 total
includes taxes & fees
Jun 5 - Jun 6
Sonder South Wabash
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49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (243)
"Host was easily accessible. We had a relaxing stay and the apartment is very comfortable as well as clean. Definitely will stay here again."
Kasa Magnificent Mile Chicago
Front of property - evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (209)
"Nice"
The price is P16,257
P20,074 total
includes taxes & fees
Jun 16 - Jun 17
Level Chicago – Old Town
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (130)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is P12,023
P14,115 total
includes taxes & fees
Jun 27 - Jun 28
Found Chicago powered by Sonder
Exterior
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, (64)
" Cozy "
The price is P13,268
P15,576 total
includes taxes & fees
Jun 12 - Jun 13
Sonder The Burnham
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (33)
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (67)
"The building was clean and attractive. Security on site. Breakfast options close by. All the best sites walking distance. Units was amazing. Kasa very engaged and accessible. River Walk, boat excursions etc. Tours etc. Right there. Rooftop pool and all amenities on site wow!"
Kasa River North Chicago
1 bedroom, premium bedding, pillowtop beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is P5,216
P5,529 total
includes taxes & fees
Jun 2 - Jun 3
WoodSpring Suites Chicago Addison
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very Good, (103)
"Loved it "
The price is P14,049
P16,493 total
includes taxes & fees
Jun 18 - Jun 19
Sonder Jewelers Row
Living area
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
City view from property
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very Good, (67)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is P13,737
P16,127 total
includes taxes & fees
Jun 19 - Jun 20
Sonder The Plymouth
Full-size fridge, oven, stovetop, dishwasher
Sonder The Opal
3.5 star property
8.0 out of 10, Very Good, (12)
"Overall: A nice stay in a great part of town. Pros: Walking distance to almost everything downtown Chicago. Check-in is easy, but not the most intuitive instructions for the building codes. Spacious and clean room. Cons: The view. DO NOT let the pictures of the property deceive you… Unless you are on the top floor, the view is not very good. Also, says there’s rooftop access but no way to get to the roof (door locked). The walls are thin inside the apartment. Layout was a bit bizarre. Advert...
The price is P16,168
P18,981 total
includes taxes & fees
Jun 25 - Jun 26
Sonder The Opal
40-inch flat-screen TV with digital channels, TV
Sonder Greektown
3.5 star property
8.8 out of 10, Excellent, (29)
"LOCATION was terrific - central and close to all our 'outings'. Downside was NOT being able to control the thermostat. And NO response to any of our efforts to contact the property manger(s)."
The price is P18,446
P21,655 total
includes taxes & fees
Jun 22 - Jun 23
Sonder Greektown
Iron/ironing board, free WiFi
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (7)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is P6,149
P10,306 total
includes taxes & fees
Jun 4 - Jun 5
Ground Floor Studios in Chicago by 747 Lofts
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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.

Other types of properties in Chicago you may be interested in

Lobby
Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6807)
"Very nice well maintained older classic hotel"
The price is P9,556
P11,219 total
includes taxes & fees
Jun 16 - Jun 17
Congress Plaza Hotel
View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2917)
"The facility was beautiful. The staff was extremely friendly and helpful. The views of the city were phenomenal. "
The price is P11,540
P13,548 total
includes taxes & fees
Jun 16 - Jun 17
River Hotel
Balcony
Eurostars Magnificent Mile
4.0 star property
8.4 out of 10, Very Good, (1978)
"Great service and very convenient to get into city and shopping , dining and sign seeing "
The price is P11,592
P13,609 total
includes taxes & fees
Jun 16 - Jun 17
Eurostars Magnificent Mile
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.

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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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 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 1359 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 Art Institute of Chicago and CIBC Theatre, 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 Navy Pier and Wrigley Field.

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.

Recent reviews of Chicago properties
Expedia verified reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

5/5 Excellent
"Location is excellent and walkable. Parking is expensive at $79 a night however so is parking everywhere in Chicago. Walls are pretty thin, you can hear a lot through them. Continental breakfast and complimentary cocktails in the evening were great. Rooms and property are all very clean and well maintained. Would stay again "
A verified traveler stayed at Embassy Suites by Hilton Chicago Downtown River North
Posted 5 hours ago
Embassy Suites by Hilton Chicago Downtown River North