Chicago Vacation Rentals

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Our top choices for Chicago vacation rentals

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,114 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is ¥20,168
¥28,349 total
includes taxes & fees
Apr 1 - Apr 2
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (450 reviews)
"Great value, friendly staff"
United States
Marcus
The price is ¥27,343
¥36,026 total
includes taxes & fees
Mar 29 - Mar 30
Level Chicago – Old Town

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
The price is ¥14,012
¥31,489 total
includes taxes & fees
Mar 25 - Mar 26
Chicago-Themed 1BR in a Central Spot near Downtown

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
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.
The price is ¥14,012
¥31,688 total
includes taxes & fees
Mar 25 - Mar 26
Sun-Drenched 1BR Apartment

Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (717 reviews)
"Fantastic location with great amenities and secure."
United States
Tomeka
Kasa Magnificent Mile Chicago

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 reviews)
"Great communication and hosts. Location and unit was perfect."
United States
Greg C.
The price is ¥12,420
¥29,625 total
includes taxes & fees
Mar 24 - Mar 25
West Loop Living – Bright 1BR

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, (5 reviews)
"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"
United States
Brianna K.
The price is ¥11,465
¥26,913 total
includes taxes & fees
Mar 24 - Mar 25
Chic Studio in the Heart of the Gold Coast

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, (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.
The price is ¥31,050
¥81,363 total
includes taxes & fees
Mar 30 - Mar 31
River North Rooftop With In and Out Parking 3

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.4 out of 10, Exceptional, (16 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is ¥14,012
¥31,688 total
includes taxes & fees
Mar 29 - Mar 30
Modern Comfort: 1BR Unit w/ Laundry

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, (8 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is ¥38,056
¥108,291 total
includes taxes & fees
Mar 26 - Mar 27
Modern West Loop Gem-City Views & Prime Location 4

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.0 out of 10, Very Good, (2 reviews)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is ¥12,420
¥29,625 total
includes taxes & fees
Mar 25 - Mar 26
1BR Modern Luxe Apt with In-Unit Laundry

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
The price is ¥19,108
¥26,363 total
includes taxes & fees
Apr 1 - Apr 2
LIVN West Loop Chicago Queen Superior Studio

Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
The price is ¥11,942
¥29,066 total
includes taxes & fees
Mar 26 - Mar 27
Stylish Gold Coast 1BR with Vintage Flair

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is ¥12,101
¥81,716 total
includes taxes & fees
Mar 29 - Mar 30
Near Lake and Museum • Modern • Game Area

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (187 reviews)
"Nice area if you are renting a car, be aware that you would have to pay for street parking or go over a few blocks and park in a parking lot."
United States
Daysha
Kasa River North Chicago

Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6
Downtown Chicago
10.0 out of 10, Exceptional, (17 reviews)
"Great place"
United States
Daniel L.
The price is ¥30,094
¥96,694 total
includes taxes & fees
Mar 29 - Mar 30
Modern West Loop Gem-City Views & Prime Location 6

Cozy Well-Equipped Studio Apartment

Cozy Well-Equipped Studio Apartment
Hyde Park
The price is ¥11,465
¥26,913 total
includes taxes & fees
Mar 24 - Mar 25
Cozy Well-Equipped Studio Apartment

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
Lawndale
8.8 out of 10, Excellent, (3 reviews)
"While it was a great price, you get what you pay for. "
United States
Deya R.
The price is ¥17,675
¥53,755 total
includes taxes & fees
Apr 1 - Apr 2
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (65 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is ¥21,353
¥52,481 total
includes taxes & fees
Mar 24 - Mar 25
2-bedroom apartment just 2 minutes drive to Wrigley Field

Your Perfect 2BR Home

Your Perfect 2BR Home
Near West Side
8.4 out of 10, Very Good, (15 reviews)
"Great location! "
United States
Kourtney K.
The price is ¥14,012
¥35,264 total
includes taxes & fees
Mar 24 - Mar 25
Your Perfect 2BR Home
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

Find out more about Chicago

Search for holiday rentals in Chicago on Expedia! You can easily find your home rentals, villas, holiday apartments in Chicago using one of the methods below:

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Look no further and take a look at our great range of rental properties in Chicago!

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?

A Home Away From Home!: This highly rated vacation home rental in Chicago offers a fireplace, a garden, 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 HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony and Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!.

How many vacation rentals are there in Chicago?

With 939 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 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.