Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

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, (1,104 reviews)
"The kitchen was great and check-in was easy."
United States
Marshal
The price is ￥18,875
￥26,844 total
includes taxes & fees
Mar 19 - Mar 20
Sentral Michigan Avenue
Full-size fridge, microwave, oven, stovetop

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (443 reviews)
"Great value, friendly staff"
United States
Marcus
The price is ￥21,866
￥29,610 total
includes taxes & fees
Apr 5 - Apr 6
Level Chicago – Old Town
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.
The price is ￥31,147
￥81,618 total
includes taxes & fees
Mar 18 - Mar 19
River North Rooftop With In and Out Parking 3
TV, offices

Apartment in Downtown Chicago

Modern West Loop Gem-City Views & Prime Location 6
10.0 out of 10, Exceptional, (15 reviews)
"Great place"
United States
Daniel L.
The price is ￥32,745
￥101,138 total
includes taxes & fees
Mar 29 - Mar 30
Modern West Loop Gem-City Views & Prime Location 6
Lounge

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.4 out of 10, Exceptional, (186 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
The price is ￥22,138
￥39,114 total
includes taxes & fees
Apr 12 - Apr 13
Kasa River North Chicago
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.
The price is ￥14,855
￥33,312 total
includes taxes & fees
Mar 22 - Mar 23
Sun-Drenched 1BR Apartment
1 bedroom, iron/ironing board, travel crib, WiFi

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (8 reviews)
"Great communication and hosts. Location and unit was perfect."
United States
Greg C.
The price is ￥14,056
￥32,181 total
includes taxes & fees
Mar 16 - Mar 17
West Loop Living – Bright 1BR
Interior

Aparthotel in Near North Side

Premium Urban 4BR - Perfect Mix of Comfort & Location
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is ￥111,651
￥193,362 total
includes taxes & fees
Mar 25 - Mar 26
Premium Urban 4BR - Perfect Mix of Comfort & Location
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)
"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 ￥18,049
￥34,669 total
includes taxes & fees
Mar 24 - Mar 25
Chic Studio in the Heart of the Gold Coast
TV, offices

Apartment in Downtown Chicago

Modern Comfort: 1BR Unit w/ Laundry
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is ￥14,056
￥32,181 total
includes taxes & fees
Mar 16 - Mar 17
Modern Comfort: 1BR Unit w/ Laundry
TV, offices

Apartment in Downtown Chicago

Chicago-Themed 1BR in a Central Spot near Downtown
The price is ￥14,056
￥31,588 total
includes taxes & fees
Mar 25 - Mar 26
Chicago-Themed 1BR in a Central Spot near Downtown
1 bedroom, WiFi, bed sheets

Apartment in Downtown Chicago

1BR Modern Luxe Apt with In-Unit Laundry
8.0 out of 10, Very Good, (2 reviews)
"The apartment was clean. Fine for a short vacation. I however was working from the apartment while relocating and there were significant WiFi issues. It should also be noted that it is right next to the El so there is train noise - didn’t bother me but should be known."
United States
John L.
The price is ￥14,056
￥32,181 total
includes taxes & fees
Mar 17 - Mar 18
1BR Modern Luxe Apt with In-Unit Laundry
Interior

Apartment in Downtown Chicago

Modern West Loop Gem-City Views & Prime Location 3
10.0 out of 10, Exceptional, (5 reviews)
"The host communicated everything very well. The short videos sent giving info about all the things you'd need to know were super helpful!"
United States
Laurie A.
The price is ￥33,384
￥101,927 total
includes taxes & fees
Mar 30 - Mar 31
Modern West Loop Gem-City Views & Prime Location 3
TV, offices

Apartment in Downtown Chicago

Modern West Loop Gem-City Views & Prime Location 4
10.0 out of 10, Exceptional, (8 reviews)
"Amazing accommodation"
United States
Jiri N.
The price is ￥32,265
￥100,348 total
includes taxes & fees
Mar 22 - Mar 23
Modern West Loop Gem-City Views & Prime Location 4
Living area

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.2 out of 10, Wonderful, (29 reviews)
"Very nice place to stay at. "
United States
ANDRO
The price is ￥17,837
￥20,939 total
includes taxes & fees
Mar 17 - Mar 18
Wrigleyville Suites
TV, offices

Apartment in Downtown Chicago

Modern West Loop Gem-City Views & Prime Location 2
9.4 out of 10, Exceptional, (8 reviews)
"Apartment was clean and nice. Nice to have off street parking and the hosts were quick to respond. "
United States
Erik R.
The price is ￥34,342
￥103,304 total
includes taxes & fees
Mar 19 - Mar 20
Modern West Loop Gem-City Views & Prime Location 2
Terrace/patio

Apartment in Uptown

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
9.0 out of 10, Wonderful, (19 reviews)
"Had a great stay! Perfect for our needs. Great location. It was an easy walk to the lake and lots of great restaurants nearby!"
United States
Rodney S.
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
TV, offices

Apartment in Downtown Chicago

Stylish Gold Coast 1BR with Vintage Flair
The price is ￥14,056
￥31,788 total
includes taxes & fees
Mar 22 - Mar 23
Stylish Gold Coast 1BR with Vintage Flair
Iron/ironing board, WiFi

Apartment in Uptown

Uptown Studio Gem Sum
7.4 out of 10, Good, (6 reviews)
"The neighborhood was perfect for me. I’d like to book the same property again because of the location.The only problem was checking in. The address was wrong and if I wasn’t raised in that part of Chicago I would have been very confused.Plus I checked in late at night. It wasn’t an easy process. Next time it will be diffeeent."
United States
Darryl C.
The price is ￥15,015
￥31,114 total
includes taxes & fees
Mar 16 - Mar 17
Uptown Studio Gem Sum
Interior

Apartment in Near West Side

Your Perfect 2BR Home
8.4 out of 10, Very Good, (15 reviews)
"Great location! "
United States
Kourtney K.
The price is ￥15,015
￥36,499 total
includes taxes & fees
Mar 16 - Mar 17
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

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

10/10 Excellent
"Employees were very friendly. Website states restaurant on site but there is no restaurant. Only a small kitchen to order breakfast-type sandwiches."
Sally 1-night trip
Posted 2 hours ago
Aloft Chicago Mag Mile

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:

  • View our selection of featured holiday rentals in Chicago
  • Use the map to find apartments and other holiday homes in the Chicago neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chicago while they last

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 Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown! and HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony.

How many vacation rentals are there in Chicago?

With 945 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.