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Vacation Rentals in Chicago, IL

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All 210 Rentals in Chicago
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From
$299
Per Night
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 6
Bookings
34 photos Details Reviews (1) Make Inquiry
From
$175
Per Night
Near North Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
4 photos Details Reviews (1) Make Inquiry
From
$160
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
Booking
19 photos Details Reviews (1) Make Inquiry
Also consider
Huge And Modern: The Penthouse At Lex!!
1 Bedroom, sleeps 5
$400 / night
Chicago Loop Residences
1 Bedroom, sleeps 3
$89 - $180 / night
Penthouse LUXURY LOFT 27th FL Amazing A+ City View
2 Bedrooms, sleeps 5
$300 / night
Modern duplex. Great accommodations, great value!
3 Bedrooms, sleeps 12
$175 / night
From
$159
Per Night
Roscoe Village
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
11 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed September 25, 2014
My wife and I travel to Chicago 4-6 times per year to visit our daughter and her family. We usually stay with her but this time she hosted her sister and their family which made...
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From
$197
Per Night
Northwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 8
Booking
7 photos Details Reviews (1) Make Inquiry
From
$139
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
14 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed July 18, 2014
Nice location. Everyone got their own beds. Easy to downtown. Kitchen and free laundry. Free Tide detergent too (not expected). Will stay again.
3 of 5 stars Reviewed May 7, 2014
The location of this property was great. It was about 12-15 minutes from downtown, which is where we wanted to be. There was plenty of on-street parking right in front of the...
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From
$80
Per Night
Lakeview
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
19 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed October 19, 2014
The location was great! There are a lot of restaurants in the neighborhood and cute local stores. It's easy to go downtown from the apartment. The apartment was clean and...
5 of 5 stars Reviewed June 14, 2014
This apartment was the perfect place for my husband and I to stay. We felt right at home. 5 minute walk to the lake front and 15 minute walk to the Red Line, so you can get...
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From
$115
Per Night
Rogers Park
2 Bedrooms, 1 Bathroom, Sleeps 7
Bookings
28 photos Details Reviews (4) Make Inquiry
4 of 5 stars Reviewed October 2, 2014
Three of us stayed at at Devon property and were thrilled with the accommodations. The location to the local bus and train stops were very convenient. The hosts, Lisa and...
4 of 5 stars Reviewed September 3, 2014
Stayed here with a few friends for the weekend. Had a great time, The location is perfect, its close to everything, yet still residential. Lisa was the main contact, she was...
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From
$99
Per Night
1 Bedroom, 1 Bathroom, Sleeps 6
Bookings
20 photos Details Reviews (4) Make Inquiry
4 of 5 stars Reviewed September 3, 2014
This was my first experience using Trip Advisor and renting a private home to stay in. The weekend was great. The apartment was located in a safe neighborhood to walk around in...
5 of 5 stars Reviewed November 11, 2013
From start to finish this rental was perfect. I was hesitant to rent from a private party, however great communication early on helped put me at ease. As a solo traveling female I...
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From
$149
Per Night
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
10 photos Details Reviews (2) Make Inquiry
4 of 5 stars Reviewed July 10, 2014
I really enjoyed staying here. A great property. The sink did break while we were there but Jackie was right on getting it fixed for us! Great place, big enough for our group!
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From
$85
Per Night
Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
14 photos Details Reviews (6) Make Inquiry
5 of 5 stars Reviewed September 20, 2014
Hanne was very easy to work with and extremely nice. Nice roomy apt and pretty close to everything. I would definitely stay here again when traveling to Chicago. Very quiet...
5 of 5 stars Reviewed September 11, 2014
Roomy 2 bedroom was in walking distance to great bars and restaurants and was a ten minute drive to many "Lincoln Park" area attractions such as the zoo, aquarium and...
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From
$250
Per Night
Lakeview
2 Bedrooms, 1 Bathroom, Sleeps 6
Booking
15 photos Details Reviews (2) Make Inquiry
From
$80
Per Night
Studio, 1 Bathroom, Sleeps 2
Bookings
14 photos Details Reviews (3) Make Inquiry
4 of 5 stars Reviewed September 3, 2014
Great stay, close to the El train and cheaper than a hotel! Able to stay parked out front for free and take the El where ever we wanted to. If you want a great stuffed pizza...
5 of 5 stars Reviewed July 8, 2014
the location of the apartment we stayed was convenient enough:only some min away from the red line train and a min from the bus stop,so getting to downtown is easy.we got a great...
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From
$85
Per Night
Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
16 photos Details Reviews (29) Make Inquiry
4 of 5 stars Reviewed October 20, 2014
This one bedroom apartment was perfect for our visit to Chicago. It sits in a quiet neighborhood, a block from the Kedsie Brown Line stop. Getting to downtown could not have...
5 of 5 stars Reviewed October 9, 2014
I've traveled all over the world - from cruises to the Greek Isles to resorts in Hawaii - and this was easily the best vacation stay I've ever experienced. Every aspect of our...
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From
$199
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
9 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed September 29, 2014
The apartment was more spacious and comfty than it appeared in photos. The location was excellent, we had everything we could need at much 2 blocks away (restaurants, bars...
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From
$199
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 2
15 photos Details Reviews (1) Make Inquiry
4 of 5 stars Reviewed September 20, 2012
We rented a one-bedroom apartment in this six-apartment building for the entire summer, so we could experience Chicago without exhausting ourselves. Cozy apartment, comfortably...
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From
$79
Per Night
Northwest Side
Studio, 1 Bathroom, Sleeps 2
Bookings
14 photos Details Reviews (9) Make Inquiry
5 of 5 stars Reviewed September 20, 2014
The place is immaculate. Super clean and fully equipped. The location is great. You have the subway blue line (to downtown) in a short walk from the house to the station. The...
5 of 5 stars Reviewed September 1, 2014
I enjoyed my stay here and the hosts are warm, friendly and welcoming people. Hanne is just the sweetest person and I feel as if I have known her for many years. She always made...
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From
$165
Per Night
Southwest Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
49 photos Details Reviews (13) Make Inquiry
5 of 5 stars Reviewed April 7, 2014
Our family of four (two teens) spent 5 days here during spring break and had an excellent experience. We went downtown every day by catching the red line train at the 35th/Sox...
5 of 5 stars Reviewed May 2, 2012
We couldn’t be more pleased with our stay, everyone had a fantastic time. Our visit took place April 12-15 and there were six of us; my parents (early 50’s), younger brother and...
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From
$89
Per Night
The Loop
Studio, 1 Bathroom, Sleeps 2
Bookings
40 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed July 19, 2014
Beautiful furnished apartments with kitchennete and in the heart of downtown, just a few blocks away from State st and michigan ave. I had a very pleasant and comfortable stay...
5 of 5 stars Reviewed May 7, 2014
The location is so convenient, the blue line train from O'hare airport takes you right to the stop of which is about 5 minutes walk to the building. The unit is clean and with...
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From
$89
Per Night
Northwest Side
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
7 photos Details Reviews (1) Make Inquiry
From
$199
Per Night
West Town
3 Bedrooms, 2 Bathrooms, Sleeps 5
Bookings
14 photos Details Reviews (3) Make Inquiry
3 of 5 stars Reviewed September 17, 2014
Nice place, only one bed and couldn't use the garage as advertised. Parking is a bit tricky, had to park several blocks away on Hubbard, but when rush hour ends it is good. No...
4 of 5 stars Reviewed July 10, 2014
This was a beautiful condo in a great location in Chicago. We rented the condo for one day for a video shoot and the couple renting it to us were so helpful and flexible with our...
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From
$199
Per Night
Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
41 photos Details Make Inquiry
From
$150
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 3
4 photos Details Make Inquiry
From
$95
Per Night
Lincoln Square
1 Bedroom, 1 Bathroom, Sleeps 3
Booking
11 photos Details Make Inquiry
From
$167
Per Night
Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
13 photos Details Make Inquiry
From
$249
Per Night
Near North Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Bookings
17 photos Details Make Inquiry
From
$100
Per Night
Rogers Park
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
18 photos Details Make Inquiry
From
$395
Per Night
DePaul
3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
8 photos Details Make Inquiry
From
$199
Per Night
Roscoe Village
2 Bedrooms, 1 Bathroom, Sleeps 6
16 photos Details Make Inquiry
From
$195
Per Night
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
Booking
10 photos Details Make Inquiry
From
$169
Per Night
Lakeview
1 Bedroom, 1 Bathroom, Sleeps 4
16 photos Details Make Inquiry
From
$120
Per Night
Northwest Side
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
23 photos Details Make Inquiry
From
$150
Per Night
Gold Coast, Near North Side
2 Bedrooms, 2 Bathrooms, Sleeps 6
33 photos Details Make Inquiry
From
$249
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
13 photos Details Make Inquiry
From
$300
Per Night
The Loop
2 Bedrooms, 2 Bathrooms, Sleeps 5
35 photos Details Make Inquiry
From
$120
Per Night
Rogers Park
3 Bedrooms, 1 Bathroom, Sleeps 8
Bookings
20 photos Details Make Inquiry
From
$120
Per Night
Rogers Park
3 Bedrooms, 1 Bathroom, Sleeps 8
Booking
14 photos Details Make Inquiry
From
$125
Per Night
Northwest Side, Wicker Park / Bucktown
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
4 photos Details Make Inquiry
From
$200
Per Night
The Loop
1 Bedroom, 1 Bathroom, Sleeps 4
10 photos Details Make Inquiry
From
$299
Per Night
Near North Side
1 Bedroom, 1 Bathroom, Sleeps 1
30 photos Details Make Inquiry
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Learn about Chicago neighborhoods

Suitability

  • Wheelchair access (58)
  • Elder access (101)
  • Suitable for children (111)
  • Pet friendly (52)
  • Smoking allowed (1)

Amenities

  • Air Conditioning (141)
  • Internet (137)
  • Other outdoor space (103)
  • Washer/Dryer (92)
  • Parking (67)
  • View all amenities
Chicago Vacation Rentals

Planning a visit to Chicago? A Chicago vacation rental is a great hotel alternative. From modern apartments on the Magnificent Mile to cozy coach houses in Lincoln Park and everything in between, we’ve got a wide variety of Chicago vacation rentals so there’s sure to be one that’s just right for you. Whatever your budget, we’ll help you find a great deal. Plus, you can book with confidence - we have plenty of unbiased user reviews of Chicago vacation rentals!

Chicago family vacations

Chicago is a great city for families and a vacation home rental makes it easy to explore all that the second city has to offer. If it’s baseball season, catch a Chicago Cubs game at historic Wrigley Field, one of the oldest ball parks in the country. Or take the kids out to Navy Pier, which features amusement rides, shops and restaurants right on Lake Michigan. If you’re kids are animal lovers, visit the Great Ape House at the Lincoln Park Zoo, where admission is still free. Or see dinosaurs at The Field Museum of Natural History.

Chicago attractions

There's plenty to do in Chicago and a vacation rental in the city will put you within walking distance of most of the city's many attractions. Art lovers will enjoy the Art Institute of Chicago where they can browse the large collection of impressionist and post-impressionist paintings before heading to the newer Modern Wing. After, you’ll want to head over to nearby Millennium Park, which features public art and cultural events year-round. During the warmer months, find a spot on the sand at Oak Street Beach, a great place to people watch with views of downtown skyscrapers and Lake Michigan.

Chicago day trips

For those who want to explore Chicago beyond the city center, there are plenty of short getaways worth exploring, all within an hour or two of your vacation rental. Nearby Oak Park is home to the Frank Lloyd Wright Home and Studio. It’s also the birthplace of Ernest Hemingway. For those looking for outdoor adventure, head south to Starved Rock State Park where you can hike miles of trails through rolling hills or go fishing, boating or horseback riding. Other popular getaways include Lake Geneva in southern Wisconsin or the shores along Lake Michigan outside the city.

Saving money on Chicago vacation rentals

Whether you want to stay in a chic downtown apartment rental in Chicago or a spacious house in the suburbs, we can help you find a deal that fits your budget. There are discounts on every type of property to help you get the most bang for your buck.