Compare Chicago Vacation Rentals

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Chicago Rentals

Sentral Michigan Avenue

Sentral Michigan Avenue

4 out of 5
808 SOUTH MICHIGAN AVENUE, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.67 mi from city center
$194 nightly
The price is $228 total per night
$228 total
Sep 2 - Sep 3
Total includes taxes and fees
Guests staying at Sentral Michigan Avenue enjoy an indoor pool, a gym, and free WiFi in public areas. Valet parking is offered for USD 75 per night. The 24-hour front desk has staff standing by to help with luggage storage and dry cleaning/laundry. Additional amenities include a business center, an arcade/game room, and express check-in.
Pool
Kitchen
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 out of 5
1436 West Randolph Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.84 mi from city center
$127 nightly
The price is $149 total per night
$149 total
Aug 24 - Aug 25
Total includes taxes and fees
At Sonder by Marriott Bonvoy Market Hall Apartments West Loop, guests enjoy features like a nightclub, a gym, and free WiFi in public areas. Friendly staff can provide concierge services, and also offer advice about sightseeing.
Kitchen
Free WiFi
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
1140 North Wells Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.59 mi from city center
$218 nightly
The price is $256 total per night
$256 total
Sep 2 - Sep 3
Total includes taxes and fees
At Level Chicago – Old Town, guests have access to a 24-hour gym, a sauna, and a rooftop terrace. Self parking is offered for USD 68.30 per night. The front desk is staffed 24/7 to help with dry cleaning/laundry, concierge services, and luggage storage. Other amenities at this family-friendly aparthotel include free WiFi in public areas, a 24-hour business center, and a seasonal outdoor pool.
Pool
Kitchen
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

4 out of 5
One Superior Place, Chicago, IL
1 mi from city center
Guests of Kasa Magnificent Mile Chicago enjoy features like a gym, free WiFi in public areas, and express check-out. Self parking is available for USD 51.00 per day.
Kitchen
Washer
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4 out of 5
1431 W Taylor St, Chicago, IL
1.95 mi from city center
The Neighborhood Hotel-Little Italy features free WiFi in public areas and laundry facilities. Staff members can answer questions about accommodations, and also provide luggage storage.
Kitchen
Pet friendly
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 out of 5
1419 South Wabash Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
1.2 mi from city center
$143 nightly
The price is $168 total per night
$168 total
Aug 25 - Aug 26
Total includes taxes and fees
Guests staying at Sonder by Marriott Bonvoy South Wabash Apartments South Loop enjoy features like a gym. Staff members are on hand to provide concierge services, luggage storage, and access to locker space.
Kitchen
Washer
Kasa South Loop Chicago

Kasa South Loop Chicago

4 out of 5
900 S Clark Street, Chicago, IL
0.7 mi from city center
At Kasa South Loop Chicago, guests have access to a gym, a rooftop terrace, and free WiFi in public areas. Self parking is available for USD 32 per night. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include a business center, an arcade/game room, and express check-out.
Kitchen
Washer
The Gem Museum Suites

The Gem Museum Suites

3.5 out of 5
1555 Oak Avenue, Evanston, IL
Free Cancellation
Reserve now, pay when you stay
11.79 mi from city center
$219 nightly
The price is $250 total per night
$250 total
Aug 14 - Aug 15
Total includes taxes and fees
Guests of The Gem Museum Suites enjoy features like a 24-hour gym, free WiFi in public areas, and a terrace. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area. Additional amenities include laundry facilities, a banquet hall, and a garden.
Breakfast included
Kitchen
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 out of 5
South Dearborn Street, Van Buren, Chicago, IL
0.31 mi from city center
$178 nightly
The price is $209 total per night
$209 total
Aug 25 - Aug 26
Total includes taxes and fees
At Sonder by Marriott Bonvoy The Plymouth Apartments Loop, guests have access to a rooftop terrace. Staff members can help with accommodation requests, and provide luggage storage.
Kitchen
Washer
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 out of 5
555 West Jackson Boulevard, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.74 mi from city center
$169 nightly
The price is $199 total per night
$199 total
Aug 24 - Aug 25
Total includes taxes and fees
A gym and free WiFi in public areas are features at Sonder by Marriott Bonvoy The Burnham Apartments Loop. Staff members are on hand to provide concierge services, luggage storage, and access to locker space.
Kitchen
Free WiFi
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 out of 5
19 South Wabash Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.13 mi from city center
$152 nightly
The price is $179 total per night
$179 total
Aug 21 - Aug 22
Total includes taxes and fees
At Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park, guests have access to free WiFi in public areas. Staff members are on hand to provide concierge services, luggage storage, and access to locker space.
Kitchen
Washer
Wrigleyville Suites

Wrigleyville Suites

2 out of 5
3727 N Clifton Ave, Chicago, IL
5 mi from city center
Guests staying at Wrigleyville Suites enjoy free WiFi in public areas, laundry facilities, and a garden.
Free WiFi
Air conditioning
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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.

Chicago Large Group Rentals

How to Book Vacation Rentals in Chicago



🏠 What is the best price for Chicago vacation rentals?

Chicago vacation rentals range in price, starting at $149 per night.


🏠 What types of vacation rentals in Chicago can I rent?

Orbitz offers a wide range of Chicago rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Chicago condo rentals.


🏠 Is it free to cancel my Chicago vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Chicago vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Chicago. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Chicago?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Chicago apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Chicago?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Chicago package deals will get you even more savings.

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