Compare Chicago Vacation Rentals

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Chicago Rentals

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
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
$174 nightly
The price is $204 total per night
$204 total
Nov 10 - Nov 11
Total with taxes and fees
Guests staying at Sentral Michigan Avenue enjoy an indoor pool, a 24-hour 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 dry cleaning/laundry and luggage storage. Additional amenities include meeting rooms, a 24-hour business center, and a meeting room.
Pool
Kitchen
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
$222 nightly
The price is $261 total per night
$261 total
Nov 11 - Nov 12
Total with 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 concierge services, dry cleaning/laundry, 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
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
$110 nightly
The price is $129 total per night
$129 total
Nov 9 - Nov 10
Total with 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
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
$135 nightly
The price is $159 total per night
$159 total
Nov 10 - Nov 11
Total with 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
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
0.74 mi from city center
$135 nightly
The price is $159 total per night
$159 total
Nov 9 - Nov 10
Total with 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
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 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 The Opal Apartments River North

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 out of 5
61 West Erie Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
0.91 mi from city center
$118 nightly
The price is $139 total per night
$139 total
Nov 9 - Nov 10
Total with taxes and fees
Guests of Sonder by Marriott Bonvoy The Opal Apartments River North enjoy features like free WiFi in public areas. Helpful staff is there to provide concierge services, as well as offer insight about the area.
Kitchen
Free WiFi
Kasa River North Chicago

Kasa River North Chicago

4 out of 5
808 N Wells St, Chicago, IL
1.16 mi from city center
$231 nightly
The price is $272 total per night
$272 total
Nov 12 - Nov 13
Total with taxes and fees
Guests of Kasa River North Chicago enjoy a gym, a rooftop terrace, and a business center. Staff members can help with accommodation requests, and provide concierge services. Additional amenities include a seasonal outdoor pool, express check-out, and a communal living room.
Pool
Kitchen
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
0.13 mi from city center
$110 nightly
The price is $129 total per night
$129 total
Nov 24 - Nov 25
Total with 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
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
$187 nightly
The price is $214 total per night
$214 total
Nov 12 - Nov 13
Total with 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
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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 $129 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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