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, (395)
"It was amazing to have a whole apartment for the price of a hotel room... less actually. Their system is simple and painless. I will book here again!"
The price is ￥19,544
￥27,529 total
includes taxes & fees
May 27 - May 28
Sentral Michigan Avenue
Interior
Sonder Market Hall
3.5 star property
8.2 out of 10, Very Good, (77)
"Gorgeous rooms. Simple and quiet property. "
The price is ￥16,741
￥19,655 total
includes taxes & fees
May 27 - May 28
Sonder Market Hall
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (222)
"Nice location and nice property. We enjoyed our visit there."
Kasa Magnificent Mile Chicago
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City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (295)
"Overall the stay was amazing. We will definitely be booking here again."
The price is ￥30,317
￥35,593 total
includes taxes & fees
May 28 - May 29
Sonder South Wabash
Exterior
Sonder The Burnham
3.5 star property
8.8 out of 10, Excellent, (53)
"We loved the space, very clean, great amenities, looks like a perfect combo of a cozy apartment and a hotel room. The only problem is that it’s not very soundproof, and you can hear people using restrooms or showering in the neighboring rooms. But would definitely stay again!"
The price is ￥30,309
￥35,584 total
includes taxes & fees
May 28 - May 29
Sonder The Burnham
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (126)
"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 ￥33,022
￥38,767 total
includes taxes & fees
Jun 6 - Jun 7
Found Chicago powered by Sonder
Front of property - evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (207)
"Nice"
The price is ￥47,647
￥58,594 total
includes taxes & fees
May 15 - May 16
Level Chicago – Old Town
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, (28)
"Great location, Great Neighborhood, plenty of dining options within walking distance. You can park by the hotel to unload and load and there is limited time meter parking or late night early am free parking streetside... When you can find it. There is a parking garage at the corner of Taylor and Paulina that is only $9 if in after 3p and out before 8a... Which is a steal by Chicago parking costs. It's a short 3 block walk to the hotel... Well lit and sidewalks. The only nitpick I can even...
The Neighborhood Hotel-Little Italy
1 bedroom, premium bedding, pillowtop beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"Very nice property "
The price is ￥11,247
￥11,922 total
includes taxes & fees
May 15 - May 16
WoodSpring Suites Chicago Addison
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very Good, (100)
"This is an overall very convenient, clean and well maintained apartment hotel. Transportation is convenient, there are restaurants and other amenities nearby, and the facilities within the hotel are also good. However, the only downside is that it is close to the station and there is construction nearby, so it is very noisy. However, if I had the chance to choose again, I would choose this hotel. I am satisfied."
The price is ￥32,877
￥38,599 total
includes taxes & fees
May 28 - May 29
Sonder Jewelers Row
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (65)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | Living area | Smart TV, streaming services
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, (66)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is ￥41,143
￥48,302 total
includes taxes & fees
May 27 - May 28
Sonder The Plymouth
3 bedrooms, WiFi, bed sheets
Your Home Away From Home
2.0 out of 10, (1)
"No me agradó"
The price is ￥23,367
￥26,905 total
includes taxes & fees
May 17 - May 18
Your Home Away From Home
Private kitchen | Fridge, microwave, oven, stovetop
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (107)
"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
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (156)
"This is a fantastic location just outside of the city on a quiet street but close to everything. The Property Manager (Ross) is fantastic with communication and even after our flight was delayed three times, he met us at the door, gave us a thorough tour of where everything is located, and some great tips on where to eat. It's a $20 UBER to the heart of the city (Millenium Park) and the place is spotless! Highly recommend if you're looking for a place to hang your hat for a few days!"
Walking distance to restaurants, shops and Lake Michigan,
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Excellent"
The price is ￥22,966
￥29,535 total
includes taxes & fees
May 19 - May 20
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (36)
"Great access to Wrigley/ South Port & Lake view neighborhoods. Very Clean and laid out space that maximizes the space in this unit. Will be back soon!"
Wrigley/Southport Corridor Garden Oasis +parking!
Fridge, microwave, oven, stovetop
LakeHouse
10.0 out of 10, Exceptional, (6)
"I loved this house. It was clean, spacious, the piano made it that much better. I will definitely be back again."
LakeHouse
Outdoor pool
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (198)
"This was an amazing place, in a great location, the view was unbelievable, and there was lots of things to do in the area our host, we’re great to work with, they had great insight, and information to share with us to make our stay even more enjoyable. we would definitely use their property again"
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Don't see what you're looking for?
See all available properties in Chicago
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, (6732)
"The Congress is a short wall to the Symphony, and the art museum. It's an old hotel but clean and everything worked. Mattresses were a little too firm for me. "
The price is ￥26,122
￥30,666 total
includes taxes & fees
May 27 - May 28
Congress Plaza Hotel
Front of property
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2584)
"Nice view. Great location. I just bounced in and out for a concert but I would totally stay here again. "
The price is ￥17,966
￥23,437 total
includes taxes & fees
May 27 - May 28
Warwick Allerton - Chicago
Exterior
The Westin Michigan Avenue Chicago
4.5 star property
8.6 out of 10, Excellent, (1009)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"
The price is ￥32,652
￥42,238 total
includes taxes & fees
May 27 - May 28
The Westin Michigan Avenue Chicago
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 fascinating museums. The array of shops and acclaimed art scene are some other things you might want to check out while you're here.

What are some of the best vacation rentals in Chicago?

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking: Visitors give good reviews to this Chicago vacation home rental, which is located in the city center and offers a barbecue grill, air-conditioning, and cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Chicago?

With 1366 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.

Recent reviews of Chicago properties
Expedia verified reviews

Eurostars Magnificent Mile

Eurostars Magnificent Mile

5/5 Excellent
"Very nice and clean! Great customer service."
A verified traveler stayed at Eurostars Magnificent Mile
Posted 5 hours ago
Eurostars Magnificent Mile