Chicago Vacation Rentals

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Vacation Rentals in Chicago

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
Desk, iron/ironing board, WiFi, bed sheets
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
10.0 out of 10, Exceptional, (20)
"Very cool penthouse apartment with two balconies and access to additional rooftop patio having amazing views of the Chicago skyline. Highly recommend!"
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
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Exterior
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
10.0 out of 10, Exceptional, (176)
"We had family coming from 3 different states for my daughter's graduation from UIC. The apartment was perfect for us! We could walk to the ceremony and great restaurants through the beautiful tree-lined streets. The interior is beautifully decorated with interesting and thoughtful artwork and touches. Kitchen had everything we could need. Bathrooms are stocked well. The entire place was comfortable, clean and perfect! When we are in Chicago again, we would definitely stay in this wonderful place...
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Exterior
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 CA $113
CA $200 total
includes taxes & fees
May 22 - May 23
Ground Floor Studios in Chicago by 747 Lofts
Lobby
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
10.0 out of 10, Exceptional, (2)
"very close to Michigan Avenue convenience store like a block away. It was a great stay."
The price is CA $224
CA $292 total
includes taxes & fees
May 27 - May 28
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, (28)
"Beautiful, spacious, clean rooms. Cozy safe neighborhood. Prompt and responsive communication. Would absolutely stay here again!!"
The Neighborhood Hotel-Little Italy
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (156)
"We stayed here for our daughter's graduation. It was a perfect home base for everything we needed to do. Ross was attentive and thorough in explaining everything we needed to know about the unit, garage parking was a plus, beds were comfortable...overall a great stay."
Walking distance to restaurants, shops and Lake Michigan,
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!
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
Smart TV, books
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, (7)
"Great unit! Spacious and clean. We were able to have the best family mini vacay sharing tons of laughs and memories. I believe it is family owned, which is a bonus for us. We even crossed paths with the grandmother who was very kind and accommodating. The only downside was that the neighborhood looked a bit rough in the harsh light of day. However, we only encountered polite neighbors and an adorable doggo next door."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
Exterior
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, (18)
"It’s really confortable clean and accesible easy"
Cozy modern unit w/ easy access to downtown Chi
Exterior
Chic Suite/Mins to L Train /Laundry/Free Parking
9.6 out of 10, Exceptional, (17)
"My wife and I spent a long weekend here. The apartment had plenty of room, was nicely decorated. The kitchen contained everything we needed to cook a full meal (which we did not). The bed is very comfortable. Ride service to downtown averaged $25. It was perfect."
The price is CA $109
CA $255 total
includes taxes & fees
May 27 - May 28
Chic Suite/Mins to L Train /Laundry/Free Parking
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | 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
Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (397)
"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 CA $171
CA $241 total
includes taxes & fees
May 27 - May 28
Sentral Michigan Avenue
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)
"Everything was great. From easy check in to easy check out. The room was very nice and cozy. Very clean. Amazing view of downtown from the bedroom and balcony. I will be staying here again! "
Kasa Magnificent Mile Chicago
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Excellent"
The price is CA $205
CA $263 total
includes taxes & fees
May 19 - May 20
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Private kitchen
LUXE 3 BR, 2 BA + Hot Tub
9.2 out of 10, Wonderful, (9)
"Nice house in a nice, quiet neighborhood. Plenty of room for the whole family. Liked being able to park our car in the attached garage. Using the hot tub in backyard was very enjoyable. Our host was very pleasant and quick to respond."
The price is CA $226
CA $371 total
includes taxes & fees
May 19 - May 20
LUXE 3 BR, 2 BA + Hot Tub
Private kitchen
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"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
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 CA $265
CA $311 total
includes taxes & fees
May 28 - May 29
Sonder South Wabash
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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

View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2871)
"We stayed here for two nights and it was amazing! We will come back again)"
The price is CA $232
CA $273 total
includes taxes & fees
May 27 - May 28
River Hotel
Exterior
The Westin Michigan Avenue Chicago
4.5 star property
8.6 out of 10, Excellent, (1002)
"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 CA $257
CA $335 total
includes taxes & fees
May 23 - May 24
The Westin Michigan Avenue Chicago
Front of property
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2582)
"Very clean"
The price is CA $143
CA $189 total
includes taxes & fees
May 27 - May 28
Warwick Allerton - 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.

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.