Chicago Vacation Rentals

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Vacation Rentals in Chicago

Fridge, microwave, oven, stovetop
West Loop Living – Bright 1BR
West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (1)
"Thorough and easy to follow parking and check in instructions. Clean apartment. "
United States
Kira V.
$186 nightly
The price is $207
Nov 3 - Nov 4
Total with taxes and fees
West Loop Living – Bright 1BR
TV, offices
Complete 1BR Home Sum
Complete 1BR Home Sum
$187 nightly
The price is $208
Nov 9 - Nov 10
Total with taxes and fees
Complete 1BR Home Sum
Indoor pool
Sentral Michigan Avenue
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (967)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
$174 nightly
The price is $204
Nov 10 - Nov 11
Total with taxes and fees
Sentral Michigan Avenue
Iron/ironing board, travel crib, WiFi, bed sheets
Chic Vintage Studio in the Gold Coast
Chic Vintage Studio in the Gold Coast
$177 nightly
The price is $198
Nov 4 - Nov 5
Total with taxes and fees
Chic Vintage Studio in the Gold Coast
Fridge, microwave, oven, stovetop
The One: A 1BR Stay That Feels Like Home
The One: A 1BR Stay That Feels Like Home
9.0 out of 10, Wonderful, (2)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
$187 nightly
The price is $208
Nov 3 - Nov 4
Total with taxes and fees
The One: A 1BR Stay That Feels Like Home
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 1
River North Rooftop With In and Out Parking 1
9.0 out of 10, Wonderful, (2)
"Clean rooms Adequate kitchen space Dishwasher Fast wifi with desk area to work. Near to many restaurants. Area felt safe. Communication with hosts was excellent. Minor misunderstandings resolved efficiently and completely. Beds are firm. Shower head was a little odd, almost like a strong mist and couldn't turn the showerhead to change the output. Not a real issue for me with little hair, but if you were a woman with long, thick hair, I could see it potentially being an issue. Upstairs...
United States
Ryan M.
$286 nightly
The price is $310
Nov 19 - Nov 20
Total with taxes and fees
River North Rooftop With In and Out Parking 1
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry
1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$186 nightly
The price is $207
Nov 6 - Nov 7
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
Fridge, microwave, oven, stovetop
Sun-Drenched 1BR Apartment
Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (1)
"The location was fantastic. We were just a couple blocks from the Green and Pink line on Clinton. There was a code to get into the building so it felt safe. The code to the door was great because there was no key to worry about since I had to work and my hubby was in and out of the apartment all day. There were a couple small things, the bed squeaks a lot. Also, it is very clear in the listing that the train is close. It is about 30ft straight out from the window. I'm not a light sleeper so I...
United States
Jennifer A.
$186 nightly
The price is $207
Nov 5 - Nov 6
Total with taxes and fees
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop
River North Rooftop With In and Out Parking 5
River North Rooftop With In and Out Parking 5
10.0 out of 10, Exceptional, (2)
"As advertised. Beautiful, well appointed apartment. Centrally located to restaurants, shopping and the L train. Hosts were very communicative and attentive to our needs. Highly recommend. "
United States
Mike S.
$364 nightly
The price is $402
Nov 16 - Nov 17
Total with taxes and fees
River North Rooftop With In and Out Parking 5
Fridge, microwave, oven, stovetop
Stylish 1BR in West Loop
Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (7)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
$186 nightly
The price is $207
Nov 3 - Nov 4
Total with taxes and fees
Stylish 1BR in West Loop
Lobby
South Loop Rooftop With In and Out Parking 2
South Loop Rooftop With In and Out Parking 2
$286 nightly
The price is $310
Nov 17 - Nov 18
Total with taxes and fees
South Loop Rooftop With In and Out Parking 2
50-inch flat-screen TV with digital channels, TV
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
3.5 star property
8.2 out of 10, Very Good, (186)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
$110 nightly
The price is $129
Nov 16 - Nov 17
Total with taxes and fees
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Business center
Kasa River North Chicago
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (174)
"Awesome stay "
United States
Sally
$226 nightly
The price is $266
Nov 11 - Nov 12
Total with taxes and fees
Kasa River North Chicago
Front of property - evening/night
Level Chicago – Old Town
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (375)
"Great place to stay. Loved it!"
United States
Peter
$225 nightly
The price is $264
Nov 4 - Nov 5
Total with taxes and fees
Level Chicago – Old Town
Free WiFi
Chicago luxury home suites
Chicago luxury home suites
2.0 star property
10.0 out of 10, Exceptional, (1)
"This was Amazing stay I have ever had in my life. Wonderful host, super clean. Stunning views, close to everything that you would needed. "
New Zealand
Moha
$975 nightly
The price is $1,145
Nov 3 - Nov 4
Total with taxes and fees
Chicago luxury home suites
Iron/ironing board, travel crib, WiFi, bed sheets
Studio Gold Coast City Living
Studio Gold Coast City Living
6.0 out of 10, (1)
"Key pad issues with entry, but overall good "
United States
Andrew U.
$178 nightly
The price is $200
Nov 9 - Nov 10
Total with taxes and fees
Studio Gold Coast City Living
Desk, iron/ironing board, travel crib, WiFi
Cozy Gold Coast Studio Stay
Cozy Gold Coast Studio Stay
10.0 out of 10, Exceptional, (2)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
$177 nightly
The price is $198
Nov 3 - Nov 4
Total with taxes and fees
Cozy Gold Coast Studio Stay
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry
Sleek 1BR Apt w/ Laundry
10.0 out of 10, Exceptional, (1)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
$189 nightly
The price is $211
Nov 13 - Nov 14
Total with taxes and fees
Sleek 1BR Apt w/ Laundry
Interior
Twice as Nice: Chic 2BR Stay with Style & Space
Twice as Nice: Chic 2BR Stay with Style & Space
9.6 out of 10, Exceptional, (13)
"Had a very nice time in Chicago!"
United States
Valerie S.
$214 nightly
The price is $238
Nov 11 - Nov 12
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
TV, offices
1BR Gold Coast Vintage Gem
1BR Gold Coast Vintage Gem
$189 nightly
The price is $211
Nov 3 - Nov 4
Total with taxes and fees
1BR Gold Coast Vintage Gem
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.
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Top Chicago Hotel Reviews

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

10/10 Excellent
"Clean room and loved the atmosphere"
Madison 1-night trip
Posted 12 hours ago
Aloft Chicago Mag Mile

Price trends for vacation rentals in Chicago

Less expensive
More expensive
This month
Next month
September
October
$299
$305
Month
Price
January
$242
February
$252
March
$267
April
$237
May
$268
June
$317
July
$322
August
$338
September
$230
October
$368
November
$299
December
$305
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Chicago. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Chicago

Everything you need to know about Chicago vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chicago vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chicago vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chicago vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chicago. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chicago in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $94 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chicago rentals

At Expedia, we put the best Chicago vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chicago rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chicago vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chicago. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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 theater 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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This highly rated vacation home rental in Chicago offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave. Other favorite homes for rent in Chicago are Wrigley Field/Lakeview -Entire Home- Large Groups! and Belmont House, Classy & Chic/walk to Wrigley Field.

How many vacation rentals are there in Chicago?

With 1140 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 CIBC Theatre and Symphony Center, 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 Michigan Avenue and Navy Pier.

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.