Chicago Vacation Rentals

Vacation Rentals in Chicago

Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (406)
"Great find!"
The price is $159
$216 total
includes taxes & fees
May 27 - May 28
Sentral Michigan Avenue
Interior
Sonder Market Hall
3.5 star property
8.2 out of 10, Very Good, (83)
"I loved having the whole space to ourselves. Felt the privacy of the entire building, more than a hotel. It was great. Would probably book again!"
The price is $99
$116 total
includes taxes & fees
May 27 - May 28
Sonder Market Hall
City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (298)
"What a nice surprise. First time I have used Sonder. But will not be the last. Great value for the money. "
The price is $192
$226 total
includes taxes & fees
May 27 - May 28
Sonder South Wabash
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49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (233)
"The room was very clean and nice. A great option for downtown Chicago"
Kasa Magnificent Mile Chicago
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (129)
"I enjoyed the fact that everything was close. The hotel was cleaned but I never saw a personal member. The code to enter didn't work and people inside had to help fellow clients to enter."
The price is $206
$242 total
includes taxes & fees
Jun 18 - Jun 19
Found Chicago powered by Sonder
Front of property - evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (208)
"Nice"
The price is $205
$258 total
includes taxes & fees
May 27 - May 28
Level Chicago – Old Town
Exterior
Sonder The Burnham
3.5 star property
8.8 out of 10, Excellent, (59)
"Other than the stairs going up from the entrance door, everything is perfect. "
The price is $194
$228 total
includes taxes & fees
May 28 - May 29
Sonder The Burnham
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
10.0 out of 10, Exceptional, (31)
"This is one of the best hotels I have ever stayed. Very clean, spacious, and everything is well-designed. Exceed my expectation in every aspect."
The Neighborhood Hotel-Little Italy
1 bedroom, premium bedding, pillowtop beds, desk
WoodSpring Suites Chicago Addison
2.5 star property
6.0 out of 10, (184)
"ITS A VERY NICE AND UPBEAT ESTABLISHMENT.......I ENJOYED THE STAY ONLY THING I DIDNT LIKE WAS THERE HOUSE KEEPING SCHEDULE BUT OTHER THAN THAT ITS A NICE QUIET LOCATION WITH NICE PEOPLE"
The price is $90
$95 total
includes taxes & fees
May 26 - May 27
WoodSpring Suites Chicago Addison
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very Good, (101)
"The entire experience was fantastic. Clear instructions in how to get into the building and the apartment, fully stocked kitchen and extremely comfortable bed"
The price is $196
$230 total
includes taxes & fees
May 28 - May 29
Sonder Jewelers Row
Exterior
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (66)
"Very clean and comfortable. Great location very close to an L stop. Walkable to shopping and the lake front and river walk"
Kasa River North Chicago
Family Apartment, 3 Bedrooms, Non Smoking, Balcony | Living area | Smart TV, streaming services
Kasa South Loop Chicago
4.0 star property
9.4 out of 10, Exceptional, (161)
"Highly recommend! Amazing view of the city and the lake, clean and quiet yet close to everything. Thoughtfully furnished with nice surprises like power strips, white noise machine in bedroom, electric kettle etc. It was ideal and we’d stay there again. "
Kasa South Loop Chicago
City view from property
Sonder The Plymouth
3.5 star property
8.4 out of 10, Very Good, (67)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is $237
$278 total
includes taxes & fees
Jun 19 - Jun 20
Sonder The Plymouth
3 bedrooms, WiFi, bed sheets
Your Home Away From Home
2.0 out of 10, (1)
"No me agradó"
The price is $150
$173 total
includes taxes & fees
May 24 - May 25
Your Home Away From Home
Private kitchen | Fridge, microwave, oven, stovetop
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (106)
"The host communicated well. The area was busy but felt safe. I felt it was expensive for the location. Very clean."
Luxury Home Away From Your Home
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is $150
$193 total
includes taxes & fees
May 27 - May 28
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (38)
"The house was beautifully decorated, well-equipped with all necessary amenities, and perfectly located close to Wrigley Field and the local establishments. If available, I highly recommend upgrading to the garage option for parking, especially during Cubs home games. This worked out perfectly for us. Justin was very helpful and responsive to my questions. We would definitely stay here again."
Wrigley/Southport Corridor Garden Oasis +parking!
Outdoor pool
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
10.0 out of 10, Exceptional, (198)
"This was an amazing place, in a great location, the view was unbelievable, and there was lots of things to do in the area our host, we’re great to work with, they had great insight, and information to share with us to make our stay even more enjoyable. we would definitely use their property again"
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
Fridge, microwave, oven, stovetop
LakeHouse
10.0 out of 10, Exceptional, (6)
"I loved this house. It was clean, spacious, the piano made it that much better. I will definitely be back again."
LakeHouse
Don't see what you're looking for?
See all available properties in Chicago
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.

Chicago Vacation Rental Travel Info

Number of vacation rentals
8
Popular accommodation
Chicago apartments
Known landmarks
Art Institute of Chicago, Chicago Riverwalk and Chicago Theatre
International airports
Chicago, IL (ORD-O'Hare Intl.) and Chicago, IL (MDW-Midway Intl.)

Price trends for vacation rentals in Chicago

Less expensive
More expensive
Next month
April
June
$275
Month
Price
January
$115
February
$114
March
$115
April
$113
May
$215
June
$275
July
$275
August
$240
September
$179
October
$184
November
$170
December
$141
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.

Other types of properties in Chicago you may be interested in

Lobby
Congress Plaza Hotel
3.5 star property
7.6 out of 10, Good, (6789)
"I enjoyed staying at the historical hotel but definitely the room could use a refresher."
The price is $167
$196 total
includes taxes & fees
May 27 - May 28
Congress Plaza Hotel
View from property
River Hotel
4.0 star property
8.8 out of 10, Excellent, (2892)
"Absolutely loved our one night stay here! The building is beautiful, the room was so clean and modern, the view of the river was spectacular and the check in/out process was as easy and fast as can be! Super close to all restaurants, bars, and stores. Definitely will be staying here again!"
The price is $149
$175 total
includes taxes & fees
May 27 - May 28
River Hotel
Front of property
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2608)
"I don’t really write reviews for places I stay at but this one impressed me beyond my expectations. I planned this trip for my fiancé’s 30th birthday and the location and price of this hotel is the best you will find. Not too far away from everything, conveniently located transportation and so many food choices! My fiancé never shuts up about NYC but Chicago has definitely taken a place in his heart. He even asked to come back. Highly recommend this hotel for everything and beyond."
The price is $125
$162 total
includes taxes & fees
May 27 - May 28
Warwick Allerton - Chicago
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.

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 $90 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.

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?

Luxury Home Away From Your Home: This highly rated vacation home rental in Chicago has air-conditioning and cable TV to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a fridge, a stovetop, and a microwave, so you can cook with friends or family. Other favorite homes for rent in Chicago are Lincoln Park Living - Suite 2! and Your Home Away From Home.

How many vacation rentals are there in Chicago?

With 1359 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 Art Institute of Chicago and CIBC Theatre, 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.

Recent reviews of Chicago properties
Expedia verified reviews

Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

5/5 Excellent
"Hundreds of restaurants within walking distance."
A verified traveler stayed at Hilton Garden Inn Chicago Downtown/Magnificent Mile
Posted 22 hours ago
Hilton Garden Inn Chicago Downtown/Magnificent Mile