Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Mar 20 - Mar 22
In two months
May 1 - May 3
In three months
May 29 - May 31
In four months
Jun 26 - Jun 28

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, (1,098 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
The price is ￥18,643
￥26,517 total
includes taxes & fees
Mar 5 - Mar 6
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, (436 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
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 ￥24,062
￥60,852 total
includes taxes & fees
Mar 10 - Mar 11
River North Rooftop With In and Out Parking 3
TV, offices

Apartment in Downtown Chicago

Complete 1BR Fully Furnished Home
The price is ￥17,772
￥35,709 total
includes taxes & fees
Mar 16 - Mar 17
Complete 1BR Fully Furnished Home
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 ￥17,772
￥34,524 total
includes taxes & fees
Mar 9 - Mar 10
Chic Studio in the Heart of the Gold Coast
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 ￥17,772
￥36,292 total
includes taxes & fees
Mar 9 - Mar 10
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 ￥17,772
￥36,292 total
includes taxes & fees
Mar 9 - Mar 10
Sun-Drenched 1BR Apartment
Fridge, microwave, oven, stovetop

Aparthotel in Near North Side

Modern 2BR Retreat Near Old Town & Lincoln Park
9.8 out of 10, Exceptional, (10 reviews)
"Great stay! "
United States
Aimee B.
Modern 2BR Retreat Near Old Town & Lincoln Park
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, 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 ￥17,772
￥36,292 total
includes taxes & fees
Mar 9 - Mar 10
1BR Modern Luxe Apt with In-Unit Laundry
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 ￥17,772
￥36,484 total
includes taxes & fees
Mar 8 - Mar 9
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, (9 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is ￥109,932
￥190,385 total
includes taxes & fees
Mar 11 - Mar 12
Spacious 4BR Central Apartment w/ Skyline Views
Fridge, microwave, oven, stovetop

Apartment in Downtown Chicago

Sleek 1BR Apartment w/ In-unit Laundry
10.0 out of 10, Exceptional, (1 review)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveler
The price is ￥17,987
￥36,009 total
includes taxes & fees
Mar 24 - Mar 25
Sleek 1BR Apartment w/ In-unit Laundry
TV, video games

Apartment in Lakeview

5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10
9.2 out of 10, Wonderful, (5 reviews)
"This was a wonderful stay! The apartment was clean, well furnished, and the communication with the manager was wonderful. My son and I really enjoyed the video games, especially golden tee. The location is fantastic, giving us access to most everything in the Lincoln Park area, as well as Wrigley Field. I can’t recommend this enough. We had a wonderful time!"
United States
Matthew B.
The price is ￥18,243
￥52,897 total
includes taxes & fees
Mar 23 - Mar 24
5 Minutes to Wrigley and Beach - Games and Arcades - Garage - Sleeps 10
Interior

Apartment in Lawndale

10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
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 ￥18,401
￥52,095 total
includes taxes & fees
Mar 29 - Mar 30
10 Minutes to Downtown Chicago - Sleeps 12 - King Beds - Games and Arcades
Living area

Aparthotel in Lakeview

Wrigleyville Suites
2.0 star property
9.2 out of 10, Wonderful, (29 reviews)
"Nice place "
United States
Barry
The price is ￥17,937
￥21,054 total
includes taxes & fees
Mar 9 - Mar 10
Wrigleyville Suites
Property grounds

Apartment in North Center

2-bedroom apartment just 2 minutes drive to Wrigley Field
9.6 out of 10, Exceptional, (59 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is ￥15,478
￥43,435 total
includes taxes & fees
Mar 5 - Mar 6
2-bedroom apartment just 2 minutes drive to Wrigley Field
Exterior

Apartment in North Center

Cozy Train Vibes + Rare Parking x3
10.0 out of 10, Exceptional, (17 reviews)
"Nice place. Very responsive hosts"
United States
Charles H.
The price is ￥30,325
￥93,169 total
includes taxes & fees
Mar 5 - Mar 6
Cozy Train Vibes + Rare Parking x3
TV, offices

Apartment in Downtown Chicago

Stylish Gold Coast 1BR with Vintage Flair
The price is ￥17,772
￥36,292 total
includes taxes & fees
Mar 10 - Mar 11
Stylish Gold Coast 1BR with Vintage Flair
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 ￥16,985
￥38,904 total
includes taxes & fees
Mar 9 - Mar 10
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

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

10/10 Excellent
"The hotel was beautiful, the rooms were clean, and the staff were amazing and friendly "
Alessiea 3-night trip
Posted 1 hour ago
Hotel Riu Plaza Chicago

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 fascinating museums. The array of shops and acclaimed art scene 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 952 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.