Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Mar 27 - Mar 29
In two months
May 8 - May 10
In three months
Jun 5 - Jun 7
In four months
Jul 3 - Jul 5

Our top choices for Chicago vacation rentals

Indoor pool

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,103 reviews)
"Best full kitchen multi-room family lodging"
United States
Lee
$143 nightly
The price is $168
Mar 19 - Mar 20
Total with taxes and fees
Sentral Michigan Avenue
TV, offices

Stylish Gold Coast 1BR with Vintage Flair

Stylish Gold Coast 1BR with Vintage Flair
Downtown Chicago
$207 nightly
The price is $232
Mar 24 - Mar 25
Total with taxes and fees
Stylish Gold Coast 1BR with Vintage Flair
Full-size fridge, microwave, oven, stovetop

Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.0 out of 10, Wonderful, (441 reviews)
"Clean, nice amenities and great staff."
United States
Sydnee
$176 nightly
The price is $207
Apr 5 - Apr 6
Total with taxes and fees
Level Chicago – Old Town
Lounge

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (186 reviews)
"Awesome stay "
United States
Sally
$251 nightly
The price is $295
Mar 22 - Mar 23
Total with taxes and fees
Kasa River North Chicago
1 bedroom, iron/ironing board, travel crib, WiFi

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (8 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
$208 nightly
The price is $233
Mar 15 - Mar 16
Total with taxes and fees
West Loop Living – Bright 1BR
TV, offices

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.
$206 nightly
The price is $231
Mar 11 - Mar 12
Total with taxes and fees
Sun-Drenched 1BR Apartment
TV, offices

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.
$208 nightly
The price is $233
Mar 12 - Mar 13
Total with taxes and fees
Modern Comfort: 1BR Unit w/ Laundry
Exterior

Spacious 4BR Central Apartment w/ Skyline Views

Spacious 4BR Central Apartment w/ Skyline Views
Near North Side
10.0 out of 10, Exceptional, (10 reviews)
"Great location, comfortable room, welcoming host."
United States
Treseanne A.
$911 nightly
The price is $1,124
Mar 11 - Mar 12
Total with taxes and fees
Spacious 4BR Central Apartment w/ Skyline Views
1 bedroom, WiFi, bed sheets

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
$209 nightly
The price is $234
Mar 17 - Mar 18
Total with taxes and fees
1BR Modern Luxe Apt with In-Unit Laundry
Interior

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.
$394 nightly
The price is $451
Mar 18 - Mar 19
Total with taxes and fees
River North Rooftop With In and Out Parking 3
Desk, iron/ironing board, travel crib, WiFi

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)
"We had a wonderful stay at this Vrbo! The home was spotless, cozy, and exactly as described. The host was friendly, responsive, and made everything easy from check-in to check-out. We would absolutely stay here again. Highly recommend!"
United States
Brianna K.
$195 nightly
The price is $220
Mar 11 - Mar 12
Total with taxes and fees
Chic Studio in the Heart of the Gold Coast
Outdoor dining

Relaxing Chicago Studio

Relaxing Chicago Studio
Edgewater
10.0 out of 10, Exceptional, (52 reviews)
"Easy to find, great location, very clean and cozy"
United States
Riley R.
$130 nightly
The price is $160
Apr 1 - Apr 2
Total with taxes and fees
Relaxing Chicago Studio
TV

Nice 1BR Spot, Unwind & Relax

Nice 1BR Spot, Unwind & Relax
Lincoln Square
9.8 out of 10, Exceptional, (27 reviews)
"Very clean & cozy! Conveniently located by great shopping & restaurants!"
United States
SHERI C.
$159 nightly
The price is $176
Mar 11 - Mar 12
Total with taxes and fees
Nice 1BR Spot, Unwind & Relax
Iron/ironing board, travel crib, WiFi, bed sheets

Sunny Studio in Heart of Ravenswood

Sunny Studio in Heart of Ravenswood
Uptown
9.4 out of 10, Exceptional, (6 reviews)
"Great neighborhood, easy check in/out. "
United States
Leah B.
$142 nightly
The price is $157
Mar 11 - Mar 12
Total with taxes and fees
Sunny Studio in Heart of Ravenswood
Iron/ironing board, travel crib, WiFi, bed sheets

Modern Studio Unit Near UChicago

Modern Studio Unit Near UChicago
Hyde Park
8.8 out of 10, Excellent, (15 reviews)
"Clean room and convenient location! "
United States
Gabriela
$162 nightly
The price is $181
Mar 11 - Mar 12
Total with taxes and fees
Modern Studio Unit Near UChicago
TV, offices

Bright & Modern 1BR in a Prime Area

Bright & Modern 1BR in a Prime Area
Hyde Park
8.8 out of 10, Excellent, (3 reviews)
"Property was very clean. We enjoyed ourselves, Thank you!"
United States
Charles S.
$178 nightly
The price is $198
Mar 11 - Mar 12
Total with taxes and fees
Bright & Modern 1BR in a Prime Area
TV, offices

Stylish 1BR Stay in Irving Vibes

Stylish 1BR Stay in Irving Vibes
Irving Park
9.0 out of 10, Wonderful, (4 reviews)
"The apartment was in a nice area. It was clean and included appropriate amenities. Bed was comfortable. Thanks!"
United States
Chris C.
$159 nightly
The price is $176
Mar 29 - Mar 30
Total with taxes and fees
Stylish 1BR Stay in Irving Vibes
Dining

Urban Comfort • 2BR in West Town

Urban Comfort • 2BR in West Town
West Town
9.6 out of 10, Exceptional, (7 reviews)
"The place was very clean and accommodating."
United States
Mark E.
$202 nightly
The price is $224
Mar 11 - Mar 12
Total with taxes and fees
Urban Comfort • 2BR in West Town
Game room

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade

W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
Brighton Park
9.4 out of 10, Exceptional, (9 reviews)
"Great location, spacious, and family friendly. Had cousins over and they had a blast playing the video games. "
United States
Jessica H.
$251 nightly
The price is $281
Mar 17 - Mar 18
Total with taxes and fees
W Pershing · Large Chicago Apt 3 Bed | 12 Min Downtown | Arcade
1 bedroom, iron/ironing board, travel crib, WiFi

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.2 out of 10, Wonderful, (12 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
$159 nightly
The price is $176
Mar 15 - Mar 16
Total with taxes and fees
Charming Sunlit 1BR Apartment
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

Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

10/10 Excellent
"This place was such a nice vibe! Had a lot of fun"
Jessica 7-night trip
Posted 1 hour ago
Aloft Chicago Mag Mile

Price trends for vacation rentals in Chicago

Less expensive
More expensive
This month
Next month
January
July
$295
$334
Month
Price
January
$267
February
$274
March
$295
April
$334
May
$366
June
$417
July
$468
August
$375
September
$324
October
$378
November
$379
December
$374
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 $106 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 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 art 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?

Wrigley Field/Lakeview -Entire Home- Large Groups!: This highly rated vacation home rental in Chicago is located on a lake and has a fireplace, a patio, 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. Kick off your shoes and enjoy yourself with a garden and a selection of games. Other favorite homes for rent in Chicago are A Home Away From Home! and Heart of the City Group Hub • Patio • Fireplace • Parking.

How many vacation rentals are there in Chicago?

With 945 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.