Chicago Vacation Rentals

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Jan 14 - Jan 15
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Jan 16 - Jan 18
Next weekend
Jan 23 - Jan 25

Our top choices for Chicago vacation rentals

Indoor pool

Aparthotel in Downtown Chicago

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (1,048 reviews)
"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "
United States
Khalid
$135 nightly
The price is $158
Jan 19 - Jan 20
Total with taxes and fees
Sentral Michigan Avenue
TV, offices

Apartment in Downtown Chicago

Chicago-Themed 1BR in a Central Spot near Downtown
2.0 star property
$153 nightly
The price is $168
Jan 26 - Jan 27
Total with taxes and fees
Chicago-Themed 1BR in a Central Spot near Downtown
Full-size fridge, microwave, oven, stovetop

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (411 reviews)
"Great location, clean room and friendly staff!"
United States
Scott
$167 nightly
The price is $196
Jan 19 - Jan 20
Total with taxes and fees
Level Chicago – Old Town
Desk, iron/ironing board, travel crib, WiFi

Apartment in Downtown Chicago

Chic Studio in the Heart of the Gold Coast
10.0 out of 10, Exceptional, (5 reviews)
"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
$149 nightly
The price is $166
Jan 27 - Jan 28
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast
TV, offices

Apartment in Downtown Chicago

Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
$153 nightly
The price is $168
Jan 19 - Jan 20
Total with taxes and fees
Sun-Drenched 1BR Apartment
TV, offices

Apartment in Downtown Chicago

Complete 1BR Home Sum
$153 nightly
The price is $168
Jan 19 - Jan 20
Total with taxes and fees
Complete 1BR Home Sum
1 bedroom, WiFi, bed sheets

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$153 nightly
The price is $168
Jan 19 - Jan 20
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
Interior

Apartment in Downtown Chicago

River North Rooftop With In and Out Parking 3
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
$282 nightly
The price is $313
Feb 3 - Feb 4
Total with taxes and fees
River North Rooftop With In and Out Parking 3
TV, offices

Apartment in Downtown Chicago

Modern Comfort: 1BR Unit w/ Laundry
9.8 out of 10, Exceptional, (11 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
$153 nightly
The price is $168
Jan 19 - Jan 20
Total with taxes and fees
Modern Comfort: 1BR Unit w/ Laundry
Lounge

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
$218 nightly
The price is $256
Jan 22 - Jan 23
Total with taxes and fees
Kasa River North Chicago
TV, offices

Apartment in Downtown Chicago

The One: A 1BR Stay That Feels Like Home
8.4 out of 10, Very Good, (5 reviews)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
$243 nightly
The price is $275
Feb 15 - Feb 16
Total with taxes and fees
The One: A 1BR Stay That Feels Like Home
1 bedroom, iron/ironing board, travel crib, WiFi

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (6 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
$153 nightly
The price is $168
Jan 22 - Jan 23
Total with taxes and fees
West Loop Living – Bright 1BR
Interior

Apartment in Downtown Chicago

Stylish Japanese-Themed 2BR Apt Close to Downtown
2.0 star property
$174 nightly
The price is $191
Jan 19 - Jan 20
Total with taxes and fees
Stylish Japanese-Themed 2BR Apt Close to Downtown
Interior

Apartment in Downtown Chicago

Twice as Nice: Chic 2BR Stay with Style & Space
9.6 out of 10, Exceptional, (20 reviews)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
$174 nightly
The price is $191
Jan 19 - Jan 20
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
Fridge, microwave, oven, stovetop

Apartment in Downtown Chicago

Sleek 1BR Apt w/ Laundry
10.0 out of 10, Exceptional, (1 review)
"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
$153 nightly
The price is $168
Jan 21 - Jan 22
Total with taxes and fees
Sleek 1BR Apt w/ Laundry
View from property

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments
2.0 star property
9.4 out of 10, Exceptional, (10 reviews)
"Good for family, enjoyed the stay"
United States
Karthik
$1,602 nightly
The price is $1,881
Jan 16 - Jan 17
Total with taxes and fees
ENVITAE Hotel 4 Bedroom Luxury Apartments
Interior

Apartment in Irving Park

Pine Beam Sloth Apartment next to Blue Line
2.0 star property
10.0 out of 10, Exceptional, (4 reviews)
"Amazing stay! So comfortable, clean, and the sushi underneath was the icing on the cake! We will definitely stay again when we come back! "
United States
Emily s.
$205 nightly
The price is $209
Jan 20 - Jan 21
Total with taxes and fees
Pine Beam Sloth Apartment next to Blue Line
TV, offices

Apartment in Lakeview

Clean and Equipped 2BR Apartment
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Excellent property and location!"
United States
Chris F.
$177 nightly
The price is $194
Jan 19 - Jan 20
Total with taxes and fees
Clean and Equipped 2BR Apartment
Interior

Aparthotel in West Town

River West, Third Floor Chicago by 747 Lofts
2.0 star property
9.0 out of 10, Wonderful, (17 reviews)
"Loved the space and location "
United States
Caroline
$294 nightly
The price is $345
Jan 25 - Jan 26
Total with taxes and fees
River West, Third Floor Chicago by 747 Lofts
2 bedrooms, iron/ironing board, travel crib, WiFi

Apartment in Hyde Park

Explore Hyde Park: 2BR Apt on Blackstone Ave
8.4 out of 10, Very Good, (5 reviews)
"Host was responsive to my questions. Apartment is located in a great area of Hyde Park. "
United States
Lind A.
$168 nightly
The price is $183
Jan 28 - Jan 29
Total with taxes and fees
Explore Hyde Park: 2BR Apt on Blackstone Ave
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

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent
"Excellent view"
Maria 1-night trip
Posted 17 hours ago
InterContinental Chicago Magnificent Mile by IHG

Price trends for vacation rentals in Chicago

Less expensive
More expensive
Next month
February
August
$277
Month
Price
January
$282
February
$277
March
$303
April
$308
May
$376
June
$382
July
$423
August
$435
September
$395
October
$346
November
$287
December
$311
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 $106 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 Field Museum of Natural History, or you can choose a more secluded option if you want a relaxing stay. Tourists who visit Chicago like the notable monuments and entertainment choices. 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 Pleasant 3-bedroom house with AC in charming Mundelein and Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!.

How many vacation rentals are there in Chicago?

With 925 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 Lake Michigan 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 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.