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, (1,102 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is ￥19,984
￥28,091 total
includes taxes & fees
Apr 5 - Apr 6
Sentral Michigan Avenue
TV, offices

Apartment in Downtown Chicago

Stylish Gold Coast 1BR with Vintage Flair
The price is ￥17,829
￥36,409 total
includes taxes & fees
Mar 10 - Mar 11
Stylish Gold Coast 1BR with Vintage Flair
Full-size fridge, microwave, oven, stovetop

Aparthotel in Downtown Chicago

Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (441 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
Level Chicago – Old Town
Lounge

Aparthotel in Downtown Chicago

Kasa River North Chicago
4.0 star property
9.4 out of 10, Exceptional, (185 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
1 bedroom, iron/ironing board, travel crib, WiFi

Apartment in Downtown Chicago

West Loop Living – Bright 1BR
10.0 out of 10, Exceptional, (7 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
The price is ￥17,829
￥36,409 total
includes taxes & fees
Mar 10 - Mar 11
West Loop Living – Bright 1BR
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 ￥17,829
￥36,409 total
includes taxes & fees
Mar 10 - Mar 11
Sun-Drenched 1BR Apartment
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 ￥17,829
￥36,409 total
includes taxes & fees
Mar 10 - Mar 11
Modern Comfort: 1BR Unit w/ Laundry
Exterior

Apartment in Near North Side

Spacious 4BR Central Apartment w/ Skyline Views
10.0 out of 10, Exceptional, (10 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is ￥99,259
￥177,392 total
includes taxes & fees
Mar 11 - Mar 12
Spacious 4BR Central Apartment w/ Skyline Views
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
The price is ￥17,829
￥36,409 total
includes taxes & fees
Mar 10 - Mar 11
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.
The price is ￥30,767
￥71,174 total
includes taxes & fees
Mar 18 - Mar 19
River North Rooftop With In and Out Parking 3
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 ￥17,829
￥34,636 total
includes taxes & fees
Mar 10 - Mar 11
Chic Studio in the Heart of the Gold Coast
Outdoor dining

Apartment in Edgewater

Relaxing Chicago Studio
10.0 out of 10, Exceptional, (52 reviews)
"Easy to find, great location, very clean and cozy"
United States
Riley R.
The price is ￥10,256
￥25,310 total
includes taxes & fees
Mar 30 - Mar 31
Relaxing Chicago Studio
TV

Apartment in Lincoln Square

Nice 1BR Spot, Unwind & Relax
9.8 out of 10, Exceptional, (27 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
The price is ￥10,887
￥27,692 total
includes taxes & fees
Mar 11 - Mar 12
Nice 1BR Spot, Unwind & Relax
Iron/ironing board, travel crib, WiFi, bed sheets

Apartment in Uptown

Sunny Studio in Heart of Ravenswood
9.4 out of 10, Exceptional, (6 reviews)
"Great neighborhood, easy check in/out. "
United States
Leah B.
The price is ￥9,782
￥24,820 total
includes taxes & fees
Mar 10 - Mar 11
Sunny Studio in Heart of Ravenswood
Iron/ironing board, travel crib, WiFi, bed sheets

Apartment in Hyde Park

Modern Studio Unit Near UChicago
8.8 out of 10, Excellent, (15 reviews)
"Clean room and convenient location! "
United States
Gabriela
The price is ￥12,938
￥28,516 total
includes taxes & fees
Mar 11 - Mar 12
Modern Studio Unit Near UChicago
TV, offices

Apartment in Hyde Park

Bright & Modern 1BR in a Prime Area
8.8 out of 10, Excellent, (3 reviews)
"Property was very clean. We enjoyed ourselves, Thank you!"
United States
Charles S.
The price is ￥13,885
￥31,203 total
includes taxes & fees
Mar 10 - Mar 11
Bright & Modern 1BR in a Prime Area
TV, offices

Apartment in Irving Park

Stylish 1BR Stay in Irving Vibes
9.0 out of 10, Wonderful, (4 reviews)
"The apartment was in a nice area. It was clean and included appropriate amenities. Bed was comfortable. Thanks!"
United States
Chris C.
The price is ￥12,149
￥29,170 total
includes taxes & fees
Apr 7 - Apr 8
Stylish 1BR Stay in Irving Vibes
Dining

Apartment in West Town

Urban Comfort • 2BR in West Town
9.6 out of 10, Exceptional, (7 reviews)
"The place was very clean and accommodating."
United States
Mark E.
The price is ￥14,831
￥35,264 total
includes taxes & fees
Mar 11 - Mar 12
Urban Comfort • 2BR in West Town
Game room

Apartment in Brighton Park

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
9.4 out of 10, Exceptional, (9 reviews)
"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "
United States
Jessica H.
The price is ￥13,569
￥44,043 total
includes taxes & fees
Mar 17 - Mar 18
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
1 bedroom, iron/ironing board, travel crib, WiFi

Apartment in Irving Park

Charming Sunlit 1BR Apartment
9.2 out of 10, Wonderful, (12 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
The price is ￥10,887
￥27,692 total
includes taxes & fees
Mar 10 - Mar 11
Charming Sunlit 1BR Apartment
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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

10/10 Excellent
"The breakfast menu was excellent. The hotel had a small pool and gym in a nice location. The room was clean and well-equipped with a refrigerator, coffee machine, and microwave. The bathroom was luxurious with Crab Tree The staff was friendly, and it was close to everything. However, there was no jacuzzi. We enjoyed the welcome reception with finger foods. We would definitely book this hotel again if we return to Chicago."
Jocelyn 3-night trip
Posted 3 hours ago
Embassy Suites by Hilton Chicago Downtown River North

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?

Wrigley Field/Lakeview -Entire Home- Large Groups!: This highly rated vacation home rental in Chicago is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. Other favorite homes for rent in Chicago are A Home Away From Home! and Heart of the City Group Hub • Patio • Fireplace • Parking.

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.