Chicago Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

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, (1,129 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is ¥21,384
¥29,778 total
includes taxes & fees
Apr 14 - Apr 15
Sentral Michigan Avenue

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (460 reviews)
"Would definitely stay again. Everything was great!"
United States
Michelle
The price is ¥36,466
¥46,734 total
includes taxes & fees
Apr 14 - Apr 15
Level Chicago – Old Town

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (188 reviews)
"Great place! Would definitely stay again!"
United States
Katherine
The price is ¥24,225
¥43,397 total
includes taxes & fees
Apr 30 - May 1
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, (18 reviews)
"Great place"
United States
Daniel L.
The price is ¥33,606
¥102,814 total
includes taxes & fees
Apr 19 - Apr 20
Modern West Loop Gem-City Views & Prime Location 6

Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Plymouth Collection: 2BD with Lobby, Gym, Rooftop
Chicago
Plymouth Collection: 2BD with Lobby, Gym, Rooftop

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (13 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is ¥22,935
¥71,543 total
includes taxes & fees
Apr 26 - Apr 27
Spacious 4BR Central Apartment w/ Skyline Views

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Everything went well"
United States
Ryan W.
The price is ¥27,713
¥36,466 total
includes taxes & fees
Apr 13 - Apr 14
LIVN West Loop Chicago 2 BR City View

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.
The price is ¥25,483
¥72,734 total
includes taxes & fees
Apr 14 - Apr 15
River North Rooftop With In and Out Parking 3

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)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is ¥21,024
¥39,098 total
includes taxes & fees
May 3 - May 4
Chic Studio in the Heart of the Gold Coast

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (9 reviews)
"Great spot next to the green line train a few restaurants and a Starbucks right up the street I will book again for sure "
United States
2k G.
The price is ¥15,608
¥33,363 total
includes taxes & fees
Apr 13 - Apr 14
West Loop Living – Bright 1BR

Sunlit 1BR Apartment | Warm & Welcoming Space

Sunlit 1BR Apartment | Warm & Welcoming Space
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 ¥17,998
¥36,362 total
includes taxes & fees
Apr 13 - Apr 14
Sunlit 1BR Apartment | Warm & Welcoming Space

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.0 out of 10, Wonderful, (17 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is ¥11,467
¥28,512 total
includes taxes & fees
Apr 19 - Apr 20
Modern Comfort: 1BR Unit w/ Laundry

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 ¥17,998
¥36,362 total
includes taxes & fees
Apr 13 - Apr 14
1BR Modern Luxe Apt with In-Unit Laundry

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is ¥17,488
¥64,033 total
includes taxes & fees
Apr 15 - Apr 16
Premium Urban 4BR - Perfect Mix of Comfort & Location

Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 3
Downtown Chicago
10.0 out of 10, Exceptional, (5 reviews)
"Loved the place 4 bedroom & 4 bathrooms was ideal for our stayGreat locationLoved the well stocked convenience store a block away "
United States
Tina Y.
Modern West Loop Gem-City Views & Prime Location 3

Luxury Lincoln Park Apartment with Gourmet Kitchen

Luxury Lincoln Park Apartment with Gourmet Kitchen
Lincoln Park
10.0 out of 10, Exceptional, (11 reviews)
"Home was well maintained and clean. Location was fantastic with an easy walk to shops and restaurants. "
United States
Nikki R.
Luxury Lincoln Park Apartment with Gourmet Kitchen

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
The price is ¥20,864
¥28,426 total
includes taxes & fees
Apr 26 - Apr 27
LIVN West Loop Chicago King Studio

Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom

Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom
Lakeview
10.0 out of 10, Exceptional, (22 reviews)
"Place is freaking perfect if you're in town for some sight seeing and a ball game."
United States
Elbert C.
The price is ¥76,290
¥172,954 total
includes taxes & fees
Apr 20 - Apr 21
Wrigley Field Stadium Suite 4 Bedroom 2 Bathroom

Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms
Lakeview
9.6 out of 10, Exceptional, (29 reviews)
"Host was great! Let us check in early, it was an easy check in/out! We'll be back for a Cubs game! "
United States
Caroline B.
The price is ¥76,290
¥173,935 total
includes taxes & fees
Apr 13 - Apr 14
Wrigley Field Legend Suite 4 Bedrooms, 2 Bathrooms

Aloha 2.0 Tropical Oasis in the heart of Wicker Park that sleeps 23 + backyard patio

Aloha 2.0 Tropical Oasis in the heart of Wicker Park that sleeps 23 + backyard patio
West Town
10.0 out of 10, Exceptional, (12 reviews)
"We booked this apartment and their other one for a bachelorette. It was such an amazing time and everything Was so thoughtful . Perfect location too!"
United States
Lita T.
Aloha 2.0 Tropical Oasis in the heart of Wicker Park that sleeps 23 + backyard patio
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.
Save an average of 15% on thousands of hotels when you're signed in

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:

  • 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 theater 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?

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony: This highly rated vacation home rental in Chicago is located in the city center and has a balcony, an arcade game room, 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. Other favorite homes for rent in Chicago are Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown! and A Home Away From Home!.

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 Navy Pier 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.