Chicago Vacation Rentals

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Our top choices for Chicago vacation rentals

Exterior
Chicago luxury home suites

Chicago luxury home suites

Chicago luxury home suites
2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Amazing stay! The location is very central and close to everything. The room was spotless, and the mattress was very comfortable. I really appreciated that the property is pet friendly. I was able to bring my dog along, which made the trip even better. The view was absolutely stunning. The hosts were very responsive and helpful throughout our stay. Highly recommend!"
Canada
Alex
$97 nightly
The price is $114
Jan 8 - Jan 9
Total with taxes and fees
Chicago luxury home suites
Full-size fridge, microwave, oven, stovetop
Level Chicago – Old Town

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (408)
"Great location, clean room and friendly staff!"
United States
Scott
$222 nightly
The price is $261
Jan 11 - Jan 12
Total with taxes and fees
Level Chicago – Old Town
Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1036)
"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
$154 nightly
The price is $181
Jan 8 - Jan 9
Total with taxes and fees
Sentral Michigan Avenue
Lounge
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (182)
"Awesome stay "
United States
Sally
$218 nightly
The price is $256
Jan 11 - Jan 12
Total with taxes and fees
Kasa River North Chicago
Living area
Wrigleyville Suites

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.6 out of 10, Exceptional, (27)
"Nice place "
United States
Barry
$140 nightly
The price is $165
Jan 11 - Jan 12
Total with taxes and fees
Wrigleyville Suites
Interior
River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts

River West, Third Floor Chicago by 747 Lofts
2.0 star property
West Town
9.0 out of 10, Wonderful, (17)
"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
Breakfast, lunch, dinner served; Greek cuisine
The Gem Museum Suites

The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, Exceptional, (103)
"This is a fantastic hotel with super friendly staff"
United States
German
$168 nightly
The price is $193
Jan 13 - Jan 14
Total with taxes and fees
The Gem Museum Suites
House (3 Bedrooms) | Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
$387 nightly
The price is $412
Jan 8 - Jan 9
Total with taxes and fees
Classic Forest Park Foursquare < 1 Mi to Blue Line
Comfort Double Room | Desk, laptop workspace, blackout drapes, free WiFi
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Comfort Inn Chicago Southland I-80 & I-294 Near Casino
3.0 star property
Harvey
4.0 out of 10, (69)
"Under renovations so some rooms have missing appliances, even through an app they require a deposit. Utter wise nice room and workers"
United States
Destin
$94 nightly
The price is $106
Jan 8 - Jan 9
Total with taxes and fees
Comfort Inn Chicago Southland I-80 & I-294 Near Casino
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

Hyatt Regency Chicago

Hyatt Regency Chicago

10/10 Excellent
"The room was clean staff was very nice. I enjoyed the view of the fireworks it was great. I enjoyed the restaurant and food drinks were also good!! Great New Years Eve"
Queen 1-night trip
Posted 9 hours ago
Hyatt Regency Chicago

Price trends for vacation rentals in Chicago

Less expensive
More expensive
This month
Next month
January
July
$279
$291
Month
Price
January
$279
February
$291
March
$302
April
$344
May
$404
June
$376
July
$422
August
$409
September
$342
October
$378
November
$308
December
$282
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 Home -2 bedroom, 4k projector and Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!.

How many vacation rentals are there in Chicago?

With 917 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.