Chicago Vacation Rentals

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Vacation Rentals in Chicago

Interior
Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (395)
"It was amazing to have a whole apartment for the price of a hotel room... less actually. Their system is simple and painless. I will book here again!"
The price is $159
$216 total
includes taxes & fees
May 27 - May 28
Sentral Michigan Avenue
Apartment, 1 Bedroom, City View | Living area | Flat-screen TV, streaming services
Sonder Market Hall
3.5 star property
8.2 out of 10, Very Good, (77)
"It was an excellent stay. I didn’t understand the Sonder model—no front desk and electronic check in. However once I got beyond that shock I didn’t mind it. I know some folks would find the setup disconcerting. I would stay in a Sonder hotel again."
The price is $118
$138 total
includes taxes & fees
May 27 - May 28
Sonder Market Hall
49-inch Smart TV with digital channels, TV, streaming services
Kasa Magnificent Mile Chicago
4.0 star property
9.2 out of 10, Wonderful, (221)
"Nice location and nice property. We enjoyed our visit there."
Kasa Magnificent Mile Chicago
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City view from property
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (295)
"Overall the stay was amazing. We will definitely be booking here again."
The price is $194
$228 total
includes taxes & fees
May 28 - May 29
Sonder South Wabash
Exterior
Sonder The Burnham
3.5 star property
8.8 out of 10, Excellent, (51)
"We loved the space, very clean, great amenities, looks like a perfect combo of a cozy apartment and a hotel room. The only problem is that it’s not very soundproof, and you can hear people using restrooms or showering in the neighboring rooms. But would definitely stay again!"
The price is $203
$238 total
includes taxes & fees
May 28 - May 29
Sonder The Burnham
Interior
Found Chicago powered by Sonder
3.5 star property
7.6 out of 10, Good, (125)
"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 $207
$244 total
includes taxes & fees
Jun 6 - Jun 7
Found Chicago powered by Sonder
Front of property - evening/night
Level Chicago – Old Town
4.0 star property
8.8 out of 10, Excellent, (207)
"Nice"
The price is $285
$351 total
includes taxes & fees
May 13 - May 14
Level Chicago – Old Town
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, (28)
"Great location, Great Neighborhood, plenty of dining options within walking distance. You can park by the hotel to unload and load and there is limited time meter parking or late night early am free parking streetside... When you can find it. There is a parking garage at the corner of Taylor and Paulina that is only $9 if in after 3p and out before 8a... Which is a steal by Chicago parking costs. It's a short 3 block walk to the hotel... Well lit and sidewalks. The only nitpick I can even...
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)
"Very nice property "
The price is $72
$76 total
includes taxes & fees
May 13 - May 14
WoodSpring Suites Chicago Addison
Exterior
Sonder Jewelers Row
3.5 star property
8.2 out of 10, Very Good, (99)
"This is an overall very convenient, clean and well maintained apartment hotel. Transportation is convenient, there are restaurants and other amenities nearby, and the facilities within the hotel are also good. However, the only downside is that it is close to the station and there is construction nearby, so it is very noisy. However, if I had the chance to choose again, I would choose this hotel. I am satisfied."
The price is $212
$248 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, (65)
"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, (66)
"Great place to stay and visit Chicago on foot. The property was exactly what we hoped for. "
The price is $263
$309 total
includes taxes & fees
May 13 - May 14
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 13 - May 14
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,
9.6 out of 10, Exceptional, (155)
"This is a fantastic location just outside of the city on a quiet street but close to everything. The Property Manager (Ross) is fantastic with communication and even after our flight was delayed three times, he met us at the door, gave us a thorough tour of where everything is located, and some great tips on where to eat. It's a $20 UBER to the heart of the city (Millenium Park) and the place is spotless! Highly recommend if you're looking for a place to hang your hat for a few days!"
Walking distance to restaurants, shops and Lake Michigan,
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.0 out of 10, Wonderful, (8)
"Excellent"
The price is $151
$194 total
includes taxes & fees
May 13 - May 14
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, (36)
"Great access to Wrigley/ South Port & Lake view neighborhoods. Very Clean and laid out space that maximizes the space in this unit. Will be back soon!"
Wrigley/Southport Corridor Garden Oasis +parking!
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
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
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.)

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, (6717)
"The Congress is a short wall to the Symphony, and the art museum. It's an old hotel but clean and everything worked. Mattresses were a little too firm for me. "
The price is $175
per night
May 14 - May 15
Congress Plaza Hotel
Front of property
Warwick Allerton - Chicago
4.0 star property
7.8 out of 10, Good, (2577)
"Great location near shops, food outlet’s, etc"
The price is $115
per night
May 27 - May 28
Warwick Allerton - Chicago
Exterior
The Westin Michigan Avenue Chicago
4.5 star property
8.6 out of 10, Excellent, (1008)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"
The price is $188
per night
May 28 - May 29
The Westin Michigan Avenue 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 $72 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 fascinating museums. The array of shops and acclaimed art scene are some other things you might want to check out while you're here.

What are some of the best vacation rentals in Chicago?

Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking: Visitors give good reviews to this Chicago vacation home rental, which is located in the city center and offers a barbecue grill, air-conditioning, and cable TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Chicago?

With 1366 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 Grant Park and Millennium 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

Eurostars Magnificent Mile

Eurostars Magnificent Mile

5/5 Excellent
"Nice place and good service. "
A verified traveler stayed at Eurostars Magnificent Mile
Posted 15 hours ago
Eurostars Magnificent Mile