Chicago Vacation Rentals

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Vacation Rentals in Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, 429 reviews
"Nice place very nice front desk"
The price is ¥27,871
per night
Jul 1 - Jul 2
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very Good, 94 reviews
"It was perfect for my needs for the week! Great area, right across the street from a park! Within walking distance/delivery distance to several dining options! Walking distance to Rush (about 20 minutes) & had 2 bike stations within a 10 minute walk in 2 different directions! Downside was it was near a train station so it was loud when you were outside but I could barely hear it when in the apartment. Plus there was construction going on so that added to the noise. Everything in the apartment...
The price is ¥13,383
per night
Jun 30 - Jul 1
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, 310 reviews
"Pretty nice but the outlet and few other items not functioning "
The price is ¥29,823
per night
Jul 2 - Jul 3
Sonder South Wabash
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Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, 250 reviews
"Had some difficulty finding a USB charging port. It was located under the kitchen counter-top."
Kasa Magnificent Mile Chicago
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, 213 reviews
"The staff here is amazing and so helpful. Loved my stay here. "
The price is ¥44,202
per night
Jun 16 - Jun 17
Level Chicago – Old Town
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, 131 reviews
"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 ¥25,987
per night
Jun 30 - Jul 1
Found Chicago powered by Sonder
Sonder The Burnham
3.5 star property
9.0 out of 10, Wonderful, 77 reviews
"I like the hotel, I did not realize there was no cleaning services or fresh towels. After 4 days the room needed some freshing and clean wash rags and towels. There was a washing machine but doing laundry on vacation is not for me."
The price is ¥39,347
per night
Jun 14 - Jun 15
Sonder The Burnham
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, 34 reviews
"Great property, very clean, staff was only a message away and very friendly. Definitely recommend and would stay again. "
The Neighborhood Hotel-Little Italy
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, 188 reviews
"Very nice property "
The price is ¥14,004
per night
Jun 9 - Jun 10
WoodSpring Suites Chicago Addison
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, 68 reviews
"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!"
The price is ¥57,735
per night
Jun 12 - Jun 13
Kasa River North Chicago
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very Good, 107 reviews
"Loved it "
The price is ¥34,762
per night
Jun 18 - Jun 19
Sonder Jewelers Row
Kasa South Loop Chicago
4.0 star property
9.2 out of 10, Wonderful, 162 reviews
"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
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very Good, 68 reviews
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is ¥30,592
per night
Jul 2 - Jul 3
Sonder The Plymouth
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, 107 reviews
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, 157 reviews
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, 9 reviews
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is ¥26,505
per night
Jun 10 - Jun 11
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, 39 reviews
"Well renovated, nice bathroom."
Wrigley/Southport Corridor Garden Oasis +parking!
LakeHouse
10.0 out of 10, Exceptional, 7 reviews
"Great"
LakeHouse
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, 200 reviews
"Everything was perfect. Doormen so nice & helpful. The condo is warm & welcoming. Very easy to feel at home."
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Sonder The Opal
3.5 star property
8.2 out of 10, Very Good, 15 reviews
"I like that was contactless and easy to access. "
The price is ¥36,126
per night
Jul 1 - Jul 2
Sonder The Opal
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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

Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, 6,859 reviews
"Friendly check in, gorgeous historic building. Room was great, bed and pillows comfortable, fresh. Charger ports on night stands. The water - lake view was absolutely worth the sunrise over Lake Michigan! Parked in. GRANT Parking South underground lot for about half the $62 parking next to the hotel, very short walk with our bags was easy. Loved the charming room, lux plank flooring, the hallway carpets were freshly shampood. Old buildings are quirky, the hot water was neither left nor right,...
The price is ¥23,128
per night
Jun 16 - Jun 17
Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North
4.0 star property
8.0 out of 10, Very Good, 2,369 reviews
"Had a great stay. Would definitely come back"
The price is ¥33,499
per night
Jun 17 - Jun 18
Embassy Suites by Hilton Chicago Downtown River North
River Hotel
4.0 star property
8.8 out of 10, Excellent, 2,961 reviews
"Excellent stay for us. The room was clean and comfortable. The staff was exceptional. Very professional and friendly. Couldn't ask for a better experience. Thanks."
The price is ¥26,463
per night
Jun 30 - Jul 1
River Hotel
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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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?

Luxury Home Away From Your Home: This highly rated vacation home rental in Chicago has air-conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Other favorite homes for rent in Chicago are Beautiful, Remodeled Penthouse Unit in Old Town! and Lincoln Park Living - Suite 2!.

How many vacation rentals are there in Chicago?

With 1357 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 Grant Park and Millennium 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.

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