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Chicago Vacation Rentals

Check prices for these dates

In two weeks
Jul 3 - Jul 5
In two months
Aug 14 - Aug 16
In three months
Sep 11 - Sep 13
In four months
Oct 9 - Oct 11

Our top choices for Chicago vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,192 reviews)
"Great location"
United States
JAVIER
$199 nightly
The price is $234
Jul 5 - Jul 6
Total with taxes and fees
Sentral Michigan Avenue
Dining room

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (796 reviews)
"Great place to stay."
United States
Benedictine
$315 nightly
The price is $370
Jun 21 - Jun 22
Total with taxes and fees
Kasa Magnificent Mile Chicago
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (495 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
$254 nightly
The price is $299
Jun 29 - Jun 30
Total with taxes and fees
Level Chicago – Old Town
TV, offices

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
10.0 out of 10, Exceptional, (9 reviews)
"Amazing accommodation"
United States
Jiri N.
$927 nightly
The price is $1,074
Jul 2 - Jul 3
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 4
Interior

870 1&2 - 2 Separate Suites in same building

870 1&2 - 2 Separate Suites in same building
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Great spot in a great area"
United States
Jesse H.
$891 nightly
The price is $1,099
Jul 3 - Jul 4
Total with taxes and fees
870 1&2 - 2 Separate Suites in same building
TV, offices

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"We loved the location."
United States
Nicoll M.
$319 nightly
The price is $377
Jun 21 - Jun 22
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Superior 2 BR
Interior

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Near North Side
10.0 out of 10, Exceptional, (3 reviews)
"Excellent place and great location. Very clean!"
United States
Amber S.
$462 nightly
The price is $570
Jun 21 - Jun 22
Total with taxes and fees
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
Pool

South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
$663 nightly
The price is $771
Jul 17 - Jul 18
Total with taxes and fees
South Loop Rooftop With In and Out Parking 2
TV, offices

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
9.2 out of 10, Wonderful, (7 reviews)
"The parking situation is pretty rough. You have to park a half a mile away from the property. The room looks very luxurious in the pictures. However, once you get there, it does show some age and you can hear the other guest from above and below at all night not to mention that the city sounds are in full effect horns and traffic all night long and it’s difficult to get the room dark"
United States
Robert
$412 nightly
The price is $487
Jun 24 - Jun 25
Total with taxes and fees
LIVN West Loop Chicago 2 BR City View
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 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.
$523 nightly
The price is $599
Jun 28 - Jun 29
Total with taxes and fees
River North Rooftop With In and Out Parking 3
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (196 reviews)
"Great property - would come back. Decent size rooms and generally good all around"
United States
Suyash
$475 nightly
The price is $557
Jun 22 - Jun 23
Total with taxes and fees
Kasa River North Chicago
Desk, iron/ironing board, travel crib, WiFi

Chic Studio in the Heart of the Gold Coast

Chic Studio in the Heart of the Gold Coast
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"This was a great stay! Great size and location. Would recommend it a lot."
United States
Dulce
$263 nightly
The price is $300
Jul 21 - Jul 22
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast
Fridge, microwave, oven, stovetop

Beautiful Unit CHI in Prime River North - 2

Beautiful Unit CHI in Prime River North - 2
Downtown Chicago
8.6 out of 10, Excellent, (25 reviews)
$386 nightly
The price is $476
Jul 3 - Jul 4
Total with taxes and fees
Beautiful Unit CHI in Prime River North - 2
Interior

Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
Downtown Chicago
$352 nightly
The price is $400
Jun 30 - Jul 1
Total with taxes and fees
Stylish Japanese-Themed 2BR Apt Close to Downtown
TV, offices

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
Downtown Chicago
8.0 out of 10, Very Good, (3 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.
$255 nightly
The price is $289
Jun 21 - Jun 22
Total with taxes and fees
Sunlit 1BR Apartment | Warm & Welcoming Space
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.2 out of 10, Wonderful, (12 reviews)
"The host was great at communicating and the apartment was very clean! "
United States
Hannah C.
$257 nightly
The price is $291
Jun 30 - Jul 1
Total with taxes and fees
West Loop Living – Bright 1BR
1 bedroom, WiFi, bed sheets

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
$256 nightly
The price is $290
Jun 29 - Jun 30
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
TV, offices

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
$237 nightly
The price is $280
Jun 21 - Jun 22
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 2BR
Desk, iron/ironing board, travel crib, WiFi

Gold Coast Hideaway | Vintage & Inviting Studio

Gold Coast Hideaway | Vintage & Inviting Studio
Downtown Chicago
$199 nightly
The price is $224
Jun 22 - Jun 23
Total with taxes and fees
Gold Coast Hideaway | Vintage & Inviting Studio
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 O'Hare Chicago

Hyatt Regency O'Hare Chicago

8/10 Good
"The only thing that would have made it excellent was if they had a pool/spa."
Diana 1-night trip
Posted 2 hours ago
Hyatt Regency O'Hare Chicago

Price trends for vacation rentals in Chicago

Less expensive
More expensive
Next month
May
July
$444
Month
Price
January
$297
February
$251
March
$291
April
$251
May
$249
June
$400
July
$444
August
$396
September
$367
October
$323
November
$318
December
$347
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 $111 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 art 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This highly rated vacation home rental in Chicago is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Other favorite homes for rent in Chicago are King Comfort apartment, Quiet, Clean, AC & WiFi and Chic Chicago Retreat (2-Bedroom Home) by RedAwning.

How many vacation rentals are there in Chicago?

With 931 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 Wrigley Field and Michigan Avenue.

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.