Chicago Vacation Rentals

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Our top choices for Chicago vacation rentals

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (471 reviews)
"Very clean and nice place"
United States
Hector
The price is ¥35,482
¥45,525 total
includes taxes & fees
May 27 - May 28
Level Chicago – Old Town

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,146 reviews)
"Clean spacious my go to vacation spot all year around "
United States
xavier
The price is ¥23,889
¥32,650 total
includes taxes & fees
May 25 - May 26
Sentral Michigan Avenue

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
The price is ¥36,897
¥48,552 total
includes taxes & fees
May 7 - May 8
LIVN Millennium Park Downtown Chicago 2BR

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (191 reviews)
"Having a kitchen is great."
United States
Mark
The price is ¥36,155
¥57,153 total
includes taxes & fees
May 19 - May 20
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, (21 reviews)
"Everything was walking distance and had everything needed for a comfortable stay "
United States
Daniel
The price is ¥57,181
¥135,538 total
includes taxes & fees
May 13 - May 14
Modern West Loop Gem-City Views & Prime Location 6

Downtown Chicago Stay with Free In & Out Parking 4

Downtown Chicago Stay with Free In & Out Parking 4
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Our stay was wonderful. The views were fantastic. The apartment was centrally located so we were able to walk to restaurants, museums, and theaters. We bookmarked this location for future stays."
United States
Renae S.
The price is ¥110,132
¥191,204 total
includes taxes & fees
May 17 - May 18
Downtown Chicago Stay with Free In & Out Parking 4

Modern 3BR Apartment Near North Ave Shops

Modern 3BR Apartment Near North Ave Shops
Near North Side
The price is ¥26,162
¥74,622 total
includes taxes & fees
May 3 - May 4
Modern 3BR Apartment Near North Ave Shops

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (16 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is ¥26,535
¥77,114 total
includes taxes & fees
May 20 - May 21
Spacious 4BR Central Apartment w/ Skyline Views

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 ¥42,142
¥96,287 total
includes taxes & fees
May 26 - May 27
River North Rooftop With In and Out Parking 3

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
9.8 out of 10, Exceptional, (10 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 ¥26,476
¥48,363 total
includes taxes & fees
May 26 - May 27
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 ¥26,476
¥48,363 total
includes taxes & fees
May 26 - May 27
Sunlit 1BR Apartment | Warm & Welcoming Space

LIVN West Loop Chicago 2 BR City View

LIVN West Loop Chicago 2 BR City View
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"We spent most of this trip discussing our NEXT trip - this stay was one of the simplest, easiest, and most satisfying we've ever experienced with a short-term rental. Hands-down will stay again!Unit incredibly clean, close proximity to the areas we needed to be in, and the host was next-level communicative and kind! Thank you for making it so easy for us!"
United States
Stephanie G.
The price is ¥37,996
¥50,032 total
includes taxes & fees
May 7 - May 8
LIVN West Loop Chicago 2 BR City View

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
8.8 out of 10, Excellent, (18 reviews)
"Great location, apt well equipped and host very responsive. Wonderful stay. "
United States
Gina G.
The price is ¥20,836
¥40,400 total
includes taxes & fees
May 3 - May 4
Modern Comfort: 1BR Unit w/ Laundry

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 ¥19,583
¥36,979 total
includes taxes & fees
May 26 - May 27
Chic Studio in the Heart of the Gold Coast

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.4 out of 10, Exceptional, (3 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is ¥83,813
¥173,040 total
includes taxes & fees
May 13 - May 14
Modern West Loop Gem-City Views & Prime Location 5

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Clean spacious great location easy to get everywhere "
United States
Melissa M.
The price is ¥29,139
¥52,058 total
includes taxes & fees
May 13 - May 14
Chicago-Themed 1BR in a Central Spot near Downtown

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, (7 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.
The price is ¥25,379
¥91,073 total
includes taxes & fees
May 20 - May 21
Modern West Loop Gem-City Views & Prime Location 3

Modern West Loop Gem-City Views & Prime Location 1

Modern West Loop Gem-City Views & Prime Location 1
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great location, HUGE space, and great service at a great rate!"
United States
Ernest C.
The price is ¥45,588
¥117,945 total
includes taxes & fees
May 10 - May 11
Modern West Loop Gem-City Views & Prime Location 1

Downtown Chicago Stay with Free In & Out Parking 2

Downtown Chicago Stay with Free In & Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great location and the in/out parking was very convenient. The apartment was clean and had plenty of room. The Host was very attentive to our needs. "
United States
Patty H.
The price is ¥45,588
¥104,260 total
includes taxes & fees
May 3 - May 4
Downtown Chicago Stay with Free In & Out Parking 2
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 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This highly rated vacation home rental in Chicago is located in the city center and offers a barbecue grill, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 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 HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony.

How many vacation rentals are there in Chicago?

With 927 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.