Chicago Vacation Rentals

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Vacation Rentals in Chicago

Level Chicago – Old Town
4 out of 5
1140 North Wells Street, Chicago, IL, 60610
Stay at this 4-star family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our ...
4.4/5 Excellent! (88 reviews)
"Great space and very friendly building. Particularly loved the gym/amenity area that also has steam and sauna."

Reviewed on Oct. 3, 2022

Sentral Michigan Avenue
3.5 out of 5
808 SOUTH MICHIGAN AVENUE, Chicago, IL, 60605
Fully refundableReserve now, pay when you stay
The price is CA $207 per night from Nov 1 to Nov 2
Stay at this 4-star aparthotel in Chicago. Enjoy free WiFi, valet parking, and dry cleaning or laundry services. Popular attractions Millennium Park and Navy ...
5/5 Exceptional! (2 reviews)
"Really enjoyed the stay and the staff was great"

Reviewed on Sep. 14, 2022

The Chicago Hotel Collection - Millennium Park
2.5 out of 5
55 E Washington St., Chicago, IL, 60602
Fully refundableReserve now, pay when you stay
The price is CA $150 per night from Nov 3 to Nov 4
Stay at this aparthotel in Chicago. Enjoy free WiFi, room service, and laundry facilities. Our guests praise the helpful staff and the quiet rooms in our reviews. ...
2.6/5 (82 reviews)
"I was nervous to book this property after reading the reviews, envisioning being stranded in the lobby with some weird check-in process and no room. As it turns out, check in could not have been easier. I simply entered my 4-digit confirmation code, sent to me by the hotel, and our keys were quickly ..."

Reviewed on Sep. 5, 2022

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Sonder South Wabash
3.5 out of 5
1419 South Wabash Avenue, Chicago, IL, 60605
Stay at this 3.5-star business-friendly aparthotel in Chicago. Enjoy free WiFi, a fitness center, and concierge services. Popular attractions Millennium Park ...
4.4/5 Excellent! (98 reviews)
"Great stay at this Sonder. A 10 minute Uber right to Field, Shedd, and Chicago Art Institute. There’s a nice grocery store a 5 minute walk up the street. The property itself was modern, clean and secure."

Reviewed on Oct. 2, 2022

WoodSpring Suites Chicago Addison
2.5 out of 5
991 E. Lake Street, Addison, IL, 60101
Fully refundableReserve now, pay when you stay
The price is CA $132 per night from Oct 11 to Oct 12
Stay at this business-friendly aparthotel in Addison. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. ...
3.1/5 (127 reviews)
A marvelous near-city stay!
"The hotel felt more like a nice studio apartment. Clean, spacious and well accomidated. The staff was extremely friendly and made sure I got checked in with everything I needed. The area around the hotel has plenty of beautiful nature trails as well as fountains and ponds that are very peaceful, ..."

Reviewed on Aug. 2, 2022

Sonder Jewelers Row
3.5 out of 5
19 South Wabash Avenue, Chicago, IL, 60603
Stay at this 3.5-star aparthotel in Chicago. Enjoy free WiFi, laundry facilities, and concierge services. Popular attractions Millennium Park and Navy Pier are ...
3.8/5 Good! (47 reviews)
"Excellent location!! Clean and pretty decor"

Reviewed on Aug. 14, 2022

Sonder The Plymouth
3.5 out of 5
South Dearborn Street, Van Buren, Chicago, IL, 60605
Stay at this 3.5-star business-friendly aparthotel in Chicago. Enjoy a rooftop terrace, barbecue grills, and a flat-screen TV. Popular attractions Millennium ...
4.2/5 Excellent! (37 reviews)
"It was clean, comfortable and quiet. Very nice rooftop lounge!"

Reviewed on Sep. 6, 2022

InTown Suites Extended Stay Chicago IL - Elk Grove/O'Hare
3 out of 5
2411 Landmeier Road, Elk Grove Village, IL, 60007
Stay at this 3-star business-friendly aparthotel in Elk Grove Village. Enjoy WiFi, laundry facilities, and a flat-screen TV. Popular attractions Rainbow Falls ...
1/5 (5 reviews)
"Booked a room through expedia, when I got there to check in place was closed. Never got my money back.."

Reviewed on Aug. 17, 2021

1BR Apartment - Walk to Shops - Downtown OAK PARK
The price is CA $115 per night from Nov 2 to Nov 3
Stay at this apartment in Oak Park. Enjoy WiFi, onsite parking, and 1 bedroom. Popular attractions Ernest Hemingway Museum and House and Garfield Park Conservatory ...
4.1/5 Very Good! (10 reviews)
Amazing location and great rental
"What a wonderful location and perfect little rental. We loved our weekend there. The neighborhood is wonderful, you really don’t need a vehicle. The unit was cozy and has everything we needed. Owner was great at communicating. Would stay again in a heartbeat."

Reviewed on Sep. 13, 2022

Trendy & Cozy Studio near Great Lakes | Six Flags
Stay at this apartment in North Chicago. Enjoy WiFi, 1 bedroom, and a shower/tub combo. Popular attractions Naval Base Great Lakes and Six Flags Great America ...
4/5 Very Good! (1 review)
Short review
"Quiet property, a little too hot in the room, everything we needed was available in the room."

Reviewed on Sep. 19, 2022

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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.

Other types of properties in Chicago you may be interested in

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL, 60605
Fully refundableReserve now, pay when you stay
The Whitehall Hotel

The Whitehall Hotel

4 out of 5
105 E Delaware Pl, Chicago, IL, 60611
Fully refundableReserve now, pay when you stay
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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chicago vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chicago vacation rentals we have selected for you start as low as CA $115 per night. Entering your travel dates in the search wizard 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?

Perfect for Navy Graduates, leisure, business: This highly rated vacation home rental in Chicago has air-conditioning and laundry facilities 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 New Your Home Away From Home! - Near Great Lakes Naval Base!! and King Bed, High-Speed WiFi, Large Deck & Playground.

How many vacation rentals are there in Chicago?

With 502 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 Symphony Center and Chicago Cultural Center, whereas Millennium Park and Chicago Riverwalk 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.

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