A river with a yellow boat, surrounded by tall buildings and a bridge.

Chicago Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

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, (1,199 reviews)
"Great location"
United States
JAVIER
$177 nightly
The price is $208
Jul 1 - Jul 2
Total with taxes and fees
Sentral Michigan Avenue
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, (497 reviews)
"Very clean and loved the location and amenities with the store on the first floor was fantastic"
United States
Kimberly
$273 nightly
The price is $320
Jun 30 - Jul 1
Total with taxes and fees
Level Chicago – Old Town
TV, offices

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, (24 reviews)
"Great location. "
United States
Tom S.
$961 nightly
The price is $1,116
Jul 23 - Jul 24
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 6
TV, offices

River North Rooftop With In and Out Parking 1

River North Rooftop With In and Out Parking 1
Downtown Chicago
9.8 out of 10, Exceptional, (6 reviews)
"Awesome location, great place would definitely recommend will hopefully return"
United States
lucas c.
$433 nightly
The price is $499
Jul 26 - Jul 27
Total with taxes and fees
River North Rooftop With In and Out Parking 1
TV, offices

River North Rooftop With In and Out Parking 6

River North Rooftop With In and Out Parking 6
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"Host was amazing, very responsive. VRBO was spotless! Great location! Would definitely stay here again."
United States
Amy L.
$458 nightly
The price is $518
Jul 19 - Jul 20
Total with taxes and fees
River North Rooftop With In and Out Parking 6
TV, offices

LIVN Millennium Park Downtown Chicago 2BR

LIVN Millennium Park Downtown Chicago 2BR
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Excellent location... Very cleaned....it is perfect"
United States
Granada
$226 nightly
The price is $267
Jul 1 - Jul 2
Total with taxes and fees
LIVN Millennium Park Downtown Chicago 2BR
TV, offices

South Loop Rooftop With In and Out Parking 3

South Loop Rooftop With In and Out Parking 3
Downtown Chicago
8.8 out of 10, Excellent, (5 reviews)
"Clean place. Family friendly. Location was great. A lot of restaurants close by. Great communication from the host."
United States
jaspreet
$521 nightly
The price is $596
Jul 19 - Jul 20
Total with taxes and fees
South Loop Rooftop With In and Out Parking 3
Fridge, microwave, oven, stovetop

Beautiful Unit CHI in Prime River North - 1

Beautiful Unit CHI in Prime River North - 1
Downtown Chicago
9.2 out of 10, Wonderful, (23 reviews)
"Location was fun"
United States
Robert L.
Beautiful Unit CHI in Prime River North - 1
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
9.2 out of 10, Wonderful, (9 reviews)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
$178 nightly
The price is $210
Jun 30 - Jul 1
Total with taxes and fees
LIVN West Loop Chicago Queen Superior Studio
TV, offices

Modern West Loop Gem-City Views & Prime Location 4

Modern West Loop Gem-City Views & Prime Location 4
Downtown Chicago
10.0 out of 10, Exceptional, (9 reviews)
"Amazing accommodation"
United States
Jiri N.
$898 nightly
The price is $1,038
Jul 2 - Jul 3
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 4
Interior

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.8 out of 10, Exceptional, (7 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.
$525 nightly
The price is $601
Jul 1 - Jul 2
Total with taxes and fees
River North Rooftop With In and Out Parking 3
TV, offices

Modern West Loop Gem-City Views & Prime Location 2

Modern West Loop Gem-City Views & Prime Location 2
Downtown Chicago
9.4 out of 10, Exceptional, (9 reviews)
"Excellent location, very clean & comfortable. West Loop is an awesome area to stay in Chicago. Seamless check in process."
United States
Dean R.
$846 nightly
The price is $974
Jul 26 - Jul 27
Total with taxes and fees
Modern West Loop Gem-City Views & Prime Location 2
TV, offices

River North Private Balcony With In and Out Parking

River North Private Balcony With In and Out Parking
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Place was easily accessible- very clean and an amazing alternative to hotel living for 2 colleagues. Coffee was available and all the basics of a hotel. "
United States
Rae M.
$463 nightly
The price is $536
Jul 9 - Jul 10
Total with taxes and fees
River North Private Balcony With In and Out Parking
TV, offices

LIVN Millennium Park Downtown Chicago Superior 2 BR

LIVN Millennium Park Downtown Chicago Superior 2 BR
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We loved the location."
United States
Nicoll M.
$253 nightly
The price is $299
Jul 1 - Jul 2
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Superior 2 BR
Pool

South Loop Rooftop With In and Out Parking 2

South Loop Rooftop With In and Out Parking 2
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Great place to stay! Parking was easy and secure. The building was super clean and had lots of amenities. Host was very responsive to messages and very accommodating to our last minute schedule changes. "
United States
Kara V.
$548 nightly
The price is $629
Jul 21 - Jul 22
Total with taxes and fees
South Loop Rooftop With In and Out Parking 2
2 bedrooms, desk, iron/ironing board, travel crib

South Loop Rooftop With In & Out Parking 1

South Loop Rooftop With In & Out Parking 1
Downtown Chicago
9.0 out of 10, Wonderful, (2 reviews)
"We loved the property! It was well kept, clean, with a seamless check in and check out process! I wish the parking garage would have been closer but otherwise everything was great! Shout out to the host for his promptness with all my questions! I would recommend this place if they are looking for a place to stay! "
United States
Bridney K.
$600 nightly
The price is $694
Jul 2 - Jul 3
Total with taxes and fees
South Loop Rooftop With In & Out Parking 1
Dining

LIVN Millennium Park Downtown Chicago Studio

LIVN Millennium Park Downtown Chicago Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"Great location, lovely furnishings and amenities."
United States
Georgina E.
$171 nightly
The price is $202
Jun 30 - Jul 1
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Studio
Dining

LIVN Millennium Park Downtown Chicago Prem Studio

LIVN Millennium Park Downtown Chicago Prem Studio
Downtown Chicago
10.0 out of 10, Exceptional, (3 reviews)
"The check in and out process was very quick. Communication with the host was great. "
United States
Raquel W.
$180 nightly
The price is $213
Jun 30 - Jul 1
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Prem Studio
TV, offices

LIVN Millennium Park Downtown Chicago Superior 1BR

LIVN Millennium Park Downtown Chicago Superior 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Excelente, well located. Recommended."
United States
Sandra S.
$204 nightly
The price is $241
Jul 1 - Jul 2
Total with taxes and fees
LIVN Millennium Park Downtown Chicago Superior 1BR
1 bedroom, iron/ironing board, travel crib, WiFi

LIVN West Loop Chicago King Studio

LIVN West Loop Chicago King Studio
Downtown Chicago
10.0 out of 10, Exceptional, (4 reviews)
"Amazing studio apartment style room, super clean, very helpful staff, and great location."
United States
William
$186 nightly
The price is $220
Jul 1 - Jul 2
Total with taxes and fees
LIVN West Loop Chicago King Studio
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

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"Good and clean.... Staff were nice and acted quickly with my requests... No complaints"
Dalvonte 2-night trip
Posted 1 hour ago
Congress Plaza Hotel

Price trends for vacation rentals in Chicago

Less expensive
More expensive
Next month
May
July
$444
Month
Price
January
$297
February
$251
March
$291
April
$251
May
$249
June
$400
July
$444
August
$396
September
$367
October
$323
November
$318
December
$347
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 $181 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This highly rated vacation home rental in Chicago is located in the city center and has a balcony, a barbecue grill, and air-conditioning to put you at ease 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 ENVITAE Hotel, 4BR Luxury Modern Apartments and King Comfort apartment, Quiet, Clean, AC & WiFi.

How many vacation rentals are there in Chicago?

With 889 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 Wrigley Field and Michigan Avenue.

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.