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, (1,060 reviews)
"Ideal location "
United States
David
The price is ¥17,377
¥25,051 total
includes taxes & fees
Jan 25 - Jan 26
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 ¥10,934
¥26,228 total
includes taxes & fees
Jan 25 - Jan 26
Chic Studio in the Heart of the Gold Coast

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (414 reviews)
"Property was clean, welcoming, pet friendly "
United States
Heather
Level Chicago – Old Town

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
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 ¥9,984
¥26,699 total
includes taxes & fees
Jan 26 - Jan 27
West Loop Living – Bright 1BR

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
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 ¥9,984
¥26,699 total
includes taxes & fees
Jan 27 - Jan 28
1BR Modern Luxe Apt with In-Unit Laundry

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
Downtown Chicago
The price is ¥9,984
¥26,699 total
includes taxes & fees
Jan 25 - Jan 26
Chicago-Themed 1BR in a Central Spot near Downtown

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, (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 ¥15,847
¥50,365 total
includes taxes & fees
Jan 26 - Jan 27
River North Rooftop With In and Out Parking 3

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is ¥10,934
¥27,813 total
includes taxes & fees
Feb 2 - Feb 3
Complete 1BR Home Sum

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very Good, (5 reviews)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is ¥11,093
¥27,999 total
includes taxes & fees
Feb 2 - Feb 3
The One: A 1BR Stay That Feels Like Home

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
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 ¥9,984
¥26,699 total
includes taxes & fees
Jan 26 - Jan 27
Sun-Drenched 1BR Apartment

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.2 out of 10, Wonderful, (15 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is ¥9,984
¥26,699 total
includes taxes & fees
Jan 25 - Jan 26
Modern Comfort: 1BR Unit w/ Laundry

Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
9.4 out of 10, Exceptional, (28 reviews)
"Nice place "
United States
Barry
The price is ¥23,533
¥27,625 total
includes taxes & fees
Jan 24 - Jan 25
Wrigleyville Suites

Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
Downtown Chicago
The price is ¥17,120
¥38,812 total
includes taxes & fees
Feb 5 - Feb 6
Stylish Japanese-Themed 2BR Apt Close to Downtown

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
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 ¥9,984
¥26,699 total
includes taxes & fees
Jan 27 - Jan 28
Sleek 1BR Apt w/ Laundry

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.6 out of 10, Exceptional, (20 reviews)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is ¥10,934
¥30,190 total
includes taxes & fees
Jan 25 - Jan 26
Twice as Nice: Chic 2BR Stay with Style & Space

Flexhome Ukrainian Village 2BR D1

Flexhome Ukrainian Village 2BR D1
West Town
9.6 out of 10, Exceptional, (5 reviews)
"It was clean and ready for our arrival. A big plus is having a washer and dryer on the premises."
United States
Ray R.
The price is ¥24,586
¥45,596 total
includes taxes & fees
Feb 13 - Feb 14
Flexhome Ukrainian Village 2BR D1

Majestic Modern Style|13 mins DT|4 mins Lake

Majestic Modern Style|13 mins DT|4 mins Lake
Uptown
9.4 out of 10, Exceptional, (13 reviews)
"Wonderful property, fabulous location, well-stocked with amenities, great gym, wonderful view, small but very comfortable, "
United States
Walt K.
The price is ¥13,125
¥45,395 total
includes taxes & fees
Feb 1 - Feb 2
Majestic Modern Style|13 mins DT|4 mins Lake

Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer

Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer
West Ridge
10.0 out of 10, Exceptional, (5 reviews)
"This spot was perfect for our Chicago visit where we mostly needed a place to sleep, not hang out. It seemed to have been refinished recently, so beds were comfy, bathroom lovely, and sitting area big enough for the two of us. "
United States
Deb B.
The price is ¥13,549
¥44,289 total
includes taxes & fees
Jan 26 - Jan 27
Private Chicago Apartment with Free Street Parking and In Unit Washer Dryer

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
10.0 out of 10, Exceptional, (49 reviews)
"It was perfect for a concert at the aragon ballroom, it was only a block away!"
United States
Maria G.
The price is ¥7,609
¥37,603 total
includes taxes & fees
Feb 1 - Feb 2
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
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 Field Museum of Natural History, or you can choose a more secluded option if you want a relaxing stay. Tourists who visit Chicago like the notable monuments and entertainment choices. 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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This highly rated vacation home rental in Chicago offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave. Other favorite homes for rent in Chicago are Pleasant 3-bedroom house with AC in charming Mundelein and Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!.

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 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.