Chicago Vacation Rentals

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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 ¥20,135
¥28,299 total
includes taxes & fees
Apr 16 - Apr 17
Sentral Michigan Avenue

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 ¥16,996
¥33,360 total
includes taxes & fees
Apr 29 - Apr 30
Chic Studio in the Heart of the Gold Coast

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 ¥33,308
¥101,697 total
includes taxes & fees
Apr 19 - Apr 20
Modern West Loop Gem-City Views & Prime Location 6

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 ¥15,618
¥33,385 total
includes taxes & fees
Apr 16 - Apr 17
West Loop Living – Bright 1BR

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 ¥25,414
¥72,145 total
includes taxes & fees
Apr 29 - Apr 30
River North Rooftop With In and Out Parking 3

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (464 reviews)
"Would definitely stay again. Everything was great!"
United States
Michelle
The price is ¥28,013
¥36,816 total
includes taxes & fees
Apr 16 - Apr 17
Level Chicago – Old Town

Envitae Hotel, 4BR Modern Sleek Apartment

Envitae Hotel, 4BR Modern Sleek Apartment
Near North Side
The price is ¥24,938
¥74,876 total
includes taxes & fees
May 13 - May 14
Envitae Hotel, 4BR Modern Sleek Apartment

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (190 reviews)
"Great place! Would definitely stay again!"
United States
Katherine
The price is ¥22,949
¥41,907 total
includes taxes & fees
Apr 30 - May 1
Kasa River North Chicago

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
The price is ¥24,224
¥32,373 total
includes taxes & fees
May 11 - May 12
LIVN West Loop Chicago King Studio

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 ¥17,949
¥37,046 total
includes taxes & fees
Apr 26 - Apr 27
Sunlit 1BR Apartment | Warm & Welcoming Space

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"This VRBO was perfect for our family as we visited our college student in downtown Chicago. Plenty of space, sparkling clean, comfy beds. Only two things that I think could be improved/better communicated: only one key card is provided, and the beds are full size not queen (but they were SUPER comfortable!!!)"
United States
Gina C.
The price is ¥30,180
¥79,986 total
includes taxes & fees
Apr 29 - Apr 30
Downtown Chicago Stay with Free In & Out Parking 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 ¥21,126
¥40,376 total
includes taxes & fees
Apr 27 - Apr 28
Chicago-Themed 1BR in a Central Spot near Downtown

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 ¥11,475
¥28,531 total
includes taxes & fees
Apr 19 - Apr 20
Modern Comfort: 1BR Unit w/ Laundry

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (14 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
The price is ¥22,714
¥71,738 total
includes taxes & fees
Apr 26 - Apr 27
Spacious 4BR Central Apartment w/ Skyline Views

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 ¥20,967
¥68,800 total
includes taxes & fees
Apr 27 - Apr 28
Premium Urban 4BR - Perfect Mix of Comfort & Location

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"It was very clean and as described/ pictured. The location was absolutely perfect being within a short walk to millennium park, restaurants and stores. The batteries were low in the remote and the host reached out to us around the same time. We received batteries within 10 minutes of letting them know."
United States
Amber W.
The price is ¥47,014
¥63,260 total
includes taxes & fees
Apr 19 - Apr 20
LIVN Millennium Park Downtown Chicago 2BR

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

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (34 reviews)
"Great location and space ! Will use again "
United States
Vanessa
The price is ¥21,063
¥24,725 total
includes taxes & fees
Apr 19 - Apr 20
Wrigleyville Suites

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 ¥27,162
¥74,693 total
includes taxes & fees
Apr 28 - Apr 29
Downtown Chicago Stay with Free In & Out Parking 4

2-bedroom apartment just 2 minutes drive to Wrigley Field

2-bedroom apartment just 2 minutes drive to Wrigley Field
North Center
9.6 out of 10, Exceptional, (66 reviews)
"Nice property, great location, super helpful host!"
United States
Carin O.
The price is ¥21,300
¥52,151 total
includes taxes & fees
Apr 26 - Apr 27
2-bedroom apartment just 2 minutes drive to Wrigley Field
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?

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.