Compare Northwest Chicago Vacation Rentals

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Northwest Chicago Rentals

Barrington Meadows Wedding Venue & Farm: Where Dreams Come True

Barrington Meadows Wedding Venue & Farm: Where Dreams Come True

Barrington IL
6.37 mi from city center
$6,255 nightly
The price is $6,692 total per night
$6,692 total
Dec 22 - Dec 23
Total with taxes and fees
This campground is a smoke-free campground.
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Maywood IL
19.75 mi from city center
$222 nightly
The price is $237 total per night
$237 total
Dec 22 - Dec 23
Total with taxes and fees
At this vacation home, guests have access to features like laundry facilities. This smoke-free vacation home also has barbecue grills.
NEW LUXURY PENTHOUSE CONDO

NEW LUXURY PENTHOUSE CONDO

Chicago IL
25.72 mi from city center
At this condo, guests have access to a rooftop terrace, a terrace, and laundry facilities. This condo building also has a garden.
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
24.14 mi from city center
$169 nightly
The price is $194 total per night
$194 total
Dec 21 - Dec 22
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 garden, and a banquet hall.
Relaxing Chicago Studio

Relaxing Chicago Studio

Chicago IL
25.33 mi from city center
$130 nightly
The price is $160 total per night
$160 total
Jan 12 - Jan 13, 2026
Total with taxes and fees
At this apartment, guests have access to features like laundry facilities.
Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago

Chicago IL
25.33 mi from city center
$120 nightly
The price is $148 total per night
$148 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
At this apartment, guests have access to features like laundry facilities.
Luxurious 3 Bedroom Apartment in Chicago

Luxurious 3 Bedroom Apartment in Chicago

Chicago IL
25.33 mi from city center
At this apartment, guests have access to features like laundry facilities.
Wrigleyville Suites

Wrigleyville Suites

2 out of 5
3727 N Clifton Ave Chicago IL
26.27 mi from city center
$136 nightly
The price is $160 total per night
$160 total
Dec 21 - Dec 22
Total with taxes and fees
Guests staying at Wrigleyville Suites enjoy free WiFi in public areas, laundry facilities, and a garden.
3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

3F Vintage Graystone in Little Italy near loop UIC United Ct & McCormick Place

Chicago IL
27.61 mi from city center
At this apartment, guests have access to features like laundry facilities.
The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4 out of 5
1431 W Taylor St Chicago IL
27.77 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.
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Chicago IL
27.91 mi from city center
$184 nightly
The price is $202 total per night
$202 total
Dec 21 - Dec 22
Total with taxes and fees
At this apartment, guests have access to features like laundry facilities.
Stylish Apartment near Chicago Downtown

Stylish Apartment near Chicago Downtown

2 out of 5
3030 S Lyman St Chicago IL
28.94 mi from city center
Stay at this aparthotel in Chicago. Enjoy free WiFi and air conditioning. Popular attractions Soldier Field and United Center are located nearby.
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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.

Northwest Chicago Large Group Rentals

How to Book Vacation Rentals in Northwest Chicago



🏠 What is the best price for Northwest Chicago vacation rentals?

Northwest Chicago vacation rentals range in price, starting at $148 per night.


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

Orbitz offers a wide range of Northwest 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 Northwest Chicago condo rentals.


🏠 Is it free to cancel my Northwest 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 Northwest 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 Northwest 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 Northwest 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 Northwest Chicago apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Northwest 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 Northwest Chicago package deals will get you even more savings.

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