Chicago Vacation Rentals

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Vacation Rentals in Chicago

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (998)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
$143 nightly
The price is $168
Dec 21 - Dec 22
Total with taxes and fees
Sentral Michigan Avenue
Front of property - evening/night
Level Chicago – Old Town

Level Chicago – Old Town

4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (394)
"Clean room cool staff enjoyed my stay will come stay again. "
United States
Donald
$223 nightly
The price is $262
Jan 4 - Jan 5, 2026
Total with taxes and fees
Level Chicago – Old Town
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (643)
"Clean facilities, great staff, good location "
United States
Emily
Kasa Magnificent Mile Chicago
Deluxe Apartment, 1 Bedroom, Non Smoking, Balcony (Self Check-in with Virtual Front Desk) | Balcony
Kasa South Loop Chicago

Kasa South Loop Chicago

4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (382)
"A very clean and spacious apartment with a great view. The parking garage right next to the building is very convenient. If the water pressure be improved, that will be perfect."
United States
Tammy
Kasa South Loop Chicago
Property entrance
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4.0 star property
Near West Side
9.6 out of 10, Exceptional, (221)
"Staff was courteous. Great location."
United States
Pamela
The Neighborhood Hotel-Little Italy
Free WiFi, bed sheets
Chicago luxury home suites

Chicago luxury home suites

2.0 star property
Downtown Chicago
7.4 out of 10, Good, (3)
"Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job."
Canada
pouya
$132 nightly
The price is $156
Dec 8 - Dec 9
Total with taxes and fees
Chicago luxury home suites
Business center
Kasa River North Chicago

Kasa River North Chicago

4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (181)
"Awesome stay "
United States
Sally
$347 nightly
The price is $407
Dec 9 - Dec 10
Total with taxes and fees
Kasa River North Chicago
Living area
Wrigleyville Suites

Wrigleyville Suites

2.0 star property
Lakeview
9.6 out of 10, Exceptional, (26)
"Excellent location and very clean! Would stay again!"
United States
Jacob
$88 nightly
The price is $103
Dec 8 - Dec 9
Total with taxes and fees
Wrigleyville Suites
1 bedroom, iron/ironing board, WiFi, bed sheets
Clean & Equipped 1BR Apt

Clean & Equipped 1BR Apt

Lakeview
9.0 out of 10, Wonderful, (39)
"Great location, apartment was clean, staff was very helpful."
United States
Steve H.
$150 nightly
The price is $165
Dec 8 - Dec 9
Total with taxes and fees
Clean & Equipped 1BR Apt
Terrace/patio
NEW LUXURY PENTHOUSE CONDO

NEW LUXURY PENTHOUSE CONDO

West Town
10.0 out of 10, Exceptional, (200)
"Great house with a great rooftop. "
United States
Francisco
NEW LUXURY PENTHOUSE CONDO
Classic Apartment | Private kitchen
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2.0 star property
Bridgeport
$331 nightly
The price is $389
Dec 8 - Dec 9
Total with taxes and fees
Stylish Apartment near Chicago Downtown
Microwave, oven, stovetop, coffee/tea maker
Cozy Studio in Hyde Park-Walk to Lake & University

Cozy Studio in Hyde Park-Walk to Lake & University

Hyde Park
8.8 out of 10, Excellent, (15)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
United States
Nancy
$140 nightly
The price is $155
Dec 8 - Dec 9
Total with taxes and fees
Cozy Studio in Hyde Park-Walk to Lake & University
Fridge, microwave, oven, stovetop
Lakeview 2BR Apartment

Lakeview 2BR Apartment

Lakeview
9.2 out of 10, Wonderful, (27)
"The apartment was as described and the customer service was amazing! "
United States
Michael M.
$166 nightly
The price is $181
Dec 8 - Dec 9
Total with taxes and fees
Lakeview 2BR Apartment
Interior
Art Villa

Art Villa

5.0 star property
West Town
10.0 out of 10, Exceptional, (2)
" "
United States
tomonobu
Art Villa
Fridge, microwave, oven, stovetop
LakeHouse

LakeHouse

South Shore
9.4 out of 10, Exceptional, (24)
"This was a cute place with a lot of space. Nice backyard with areas to chill. The grand piano is beautiful and in tune!"
United States
Kenna C.
LakeHouse
Interior
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, (14)
"Host was easy to communicate with and very thoughtful. We were in town for a concert and they gifted us with ear protection for us all. Location was great too "
United States
Tiffany N.
$187 nightly
The price is $206
Dec 11 - Dec 12
Total with taxes and fees
Twice as Nice: Chic 2BR Stay with Style & Space
Outdoor dining
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Near West Side
10.0 out of 10, Exceptional, (269)
"Beautiful property fully loaded with amenities."
United States
Allie P.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place
TV, offices
Modern West Loop Gem-City Views & Prime Location 6

Modern West Loop Gem-City Views & Prime Location 6

2.0 star property
Downtown Chicago
10.0 out of 10, Exceptional, (4)
"Great place"
United States
Daniel L.
Modern West Loop Gem-City Views & Prime Location 6
Terrace/patio
Chicago Luxury Penthouse Gold Coast Best Location

Chicago Luxury Penthouse Gold Coast Best Location

Downtown Chicago
10.0 out of 10, Exceptional, (3)
"I used to live in Chicago and have a short term rental in Ohio myself. This place is legit. This property is in the best location close to beach restaurants and bars. Perfect for college reunion. Rooftop was awesome place for us to catch up over coffee and plan the day. The kitchen has everything we needed. Speakers throughout was a nice touch. I can’t be more complementary of the hosts responsiveness and helpfulness. We would definitely stay here again."
United States
Justin F.
Chicago Luxury Penthouse Gold Coast Best Location
Dining
55-56 Mag Mile Penthouse

55-56 Mag Mile Penthouse

Downtown Chicago
10.0 out of 10, Exceptional, (300)
"Great location, great property, great views. "
United States
Mark D.
55-56 Mag Mile Penthouse
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

Homewood Suites by Hilton Chicago Downtown South Loop

Homewood Suites by Hilton Chicago Downtown South Loop

10/10 Excellent
"Great experience "
Duronda 1-night trip
Posted 13 hours ago
Homewood Suites by Hilton Chicago Downtown South Loop

Price trends for vacation rentals in Chicago

Less expensive
More expensive
This month
Next month
November
October
$308
$276
Month
Price
January
$276
February
$270
March
$271
April
$297
May
$351
June
$380
July
$349
August
$313
September
$281
October
$419
November
$236
December
$308
Price trend information excludes taxes and fees and is based on base rates for a nightly stay for 2 adults found in the last 7 days on our site and averaged for commonly viewed vacation rentals in Chicago. Select dates and complete search for nightly totals inclusive of taxes and fees.

Find out more about Chicago

Everything you need to know about Chicago vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chicago vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chicago vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chicago vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chicago. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chicago in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $103 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chicago rentals

At Expedia, we put the best Chicago vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chicago rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chicago vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chicago. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

LakeHouse: This highly rated vacation home rental in Chicago is located on the beach and has a fireplace, a balcony, 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. You and your friends and family can relax into your vacation with amenities like a selection of games. Other favorite homes for rent in Chicago are AeroStay Retreat – 4BR Home Near O’Hare Airport! and NEW to the market! Relax with family in a super Lux Custom SFH. West town..

How many vacation rentals are there in Chicago?

With 922 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 Lake Michigan 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.