Northwest Chicago Vacation Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Vacation Rentals in Northwest Chicago

Fridge, microwave, oven, stovetop
Game room/King Bed /Wi-Fi/Deck + Fire Pit
10.0 out of 10, Exceptional, (13)
"Relaxing, quiet and clean neighborhood. Love the retro decor. Kitchen is well equipped for those that might want to cook. A few branches were down in backyard, furniture wasn't set out yet such as outdoor dining table and chairs or gazebo, but overall property was in good condition. Thank you for a relaxing place to stay."
The price is $205
$425 total
includes taxes & fees
May 22 - May 23
Game room/King Bed /Wi-Fi/Deck + Fire Pit
Pool
Riverfront rental with fun activities
10.0 out of 10, Exceptional, (17)
"The house was clean, cozy, and comfortable. The downstairs area was the perfect size for me and my husband. We enjoyed the multiple options for sitting and watching the river (enclosed back porch, or back yard). Good birding, too. The neighborhood is quiet and we enjoyed walking across the nearby bridge to the greenway trail on the other side of the river. We hope to stay again next time we visit the area!"
The price is $175
$253 total
includes taxes & fees
May 22 - May 23
Riverfront rental with fun activities
Desk, iron/ironing board, WiFi, bed sheets
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
10.0 out of 10, Exceptional, (21)
"We were in town for our son’s wedding and this was the perfect location for our group. Apartment was as advertised and the host was very responsive and helpful. The rooftop provided a perfect place for some pre-wedding groom/best man photos as well."
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Exterior
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
10.0 out of 10, Exceptional, (176)
"Great stay! All of the rooms were wonderful! Really close to food! There are a lot of stairs so make sure you are able to walk up but really great place!"
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
Property grounds
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
10.0 out of 10, Exceptional, (40)
"Quaint and very clean."
Beautiful Cora Cottage on Fox Lake/Chain O'Lakes with 40 Ft. Private Boat Pier.
Exterior
Ground Floor Studios in Chicago by 747 Lofts
2.0 star property
10.0 out of 10, Exceptional, (7)
"Easy to check in, good information for parking in the area. The place was clean and nice."
The price is $101
$171 total
includes taxes & fees
May 27 - May 28
Ground Floor Studios in Chicago by 747 Lofts
Fridge, microwave, oven, stovetop
NEW LUXURY CONDO WITH PATIO DECK
10.0 out of 10, Exceptional, (124)
"This was our second time booking and our experience was as great as the first time. It is a convenient location to many areas around Ukraine Village. Love the space and immaculate condo. As a suggestion if you enjoy cooking bring your own spices and oil. They have everything in reference to dish ware, knives, pots/pans and glasses/cups. It was my birthday weekend and the host had a special gift for me. Very thoughtful!"
NEW LUXURY CONDO WITH PATIO DECK
Fridge, microwave, oven, stovetop
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
10.0 out of 10, Exceptional, (55)
"It was clean and nice."
3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY
Private kitchen | Fridge, microwave, oven, stovetop
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
10.0 out of 10, Exceptional, (145)
"Kim’s place is in a quiet neighborhood, just a couple blocks from the Roscoe Village shops and restaurants. It was also an easy 20 minute walk from shops and restaurants in the Southport area and a 30 minute walk from Wrigley Field. We had no problems parking on the street throughout our stay. If you enjoy Cubs games and a variety of restaurants and shops, all within walking distance…then this is the place for you!"
Roscoe Village Inn | Guesthouse | Walk to Chicago's Wrigley Field
50-inch Smart TV with satellite channels
The Neighborhood Hotel-Little Italy
2.0 star property
9.8 out of 10, Exceptional, (30)
"This is one of the best hotels I have ever stayed. Very clean, spacious, and everything is well-designed. Exceed my expectation in every aspect."
The Neighborhood Hotel-Little Italy
Exterior
Walking distance to restaurants, shops and Lake Michigan,
9.8 out of 10, Exceptional, (157)
"Great property and Ross is a wonderful host. Even recommended dinner spots Hope to stay here again"
Walking distance to restaurants, shops and Lake Michigan,
Property grounds
Wrigley/Southport Corridor Garden Oasis +parking!
9.8 out of 10, Exceptional, (38)
"The house was beautifully decorated, well-equipped with all necessary amenities, and perfectly located close to Wrigley Field and the local establishments. If available, I highly recommend upgrading to the garage option for parking, especially during Cubs home games. This worked out perfectly for us. Justin was very helpful and responsive to my questions. We would definitely stay here again."
Wrigley/Southport Corridor Garden Oasis +parking!
Fridge, microwave, oven, dishwasher
Stay in “STYLE” Apartment, close to CHI downtown
9.8 out of 10, Exceptional, (61)
"We booked this apartment for a quick trip and it is just as pictured. They had so many little extras in the bathroom, just in case you forgot something! I felt horrible for the tenant under due to our heavy footed children!"
Stay in “STYLE” Apartment, close to CHI downtown
A heated pool
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
9.8 out of 10, Exceptional, (24)
"The house is so big and beautiful, and we enjoyed our weekend staying there, thank you."
The price is $512
$1,398 total
includes taxes & fees
May 22 - May 23
HUGE Crystal Lake 7 Acre Ranch w/Pool & Hot Tub
Smart TV, books
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
9.6 out of 10, Exceptional, (7)
"Great unit! Spacious and clean. We were able to have the best family mini vacay sharing tons of laughs and memories. I believe it is family owned, which is a bonus for us. We even crossed paths with the grandmother who was very kind and accommodating. The only downside was that the neighborhood looked a bit rough in the harsh light of day. However, we only encountered polite neighbors and an adorable doggo next door."
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
Exterior
Cozy modern unit w/ easy access to downtown Chi
9.6 out of 10, Exceptional, (18)
"It’s really confortable clean and accesible easy"
Cozy modern unit w/ easy access to downtown Chi
Property grounds
Hidden East Village Gem
9.6 out of 10, Exceptional, (20)
"This was a great place in a great neighborhood. A little problem with the locks but handyman was called and problem resolved in about an hour and a half."
Hidden East Village Gem
Outdoor dining
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
"Had a great time used space for birthday event!!"
The price is $300
$345 total
includes taxes & fees
May 22 - May 23
national historic home near downtown airports no parties no events
Exterior
Chic Suite/Mins to L Train /Laundry/Free Parking
9.4 out of 10, Exceptional, (18)
"The manager had unbelievable communication. He has his phone with him constantly and responds immediately. It's a good walking neighborhood lots of sidewalks and pleasant surroundings. The condo itself is exceptionally clean. For the price in that neighborhood it is a very good value."
The price is $80
$187 total
includes taxes & fees
May 22 - May 23
Chic Suite/Mins to L Train /Laundry/Free Parking
Property grounds
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
9.2 out of 10, Wonderful, (9)
"Great location with two master suites with king beds. Breakfast buffet was good. Next time I will request first floor as there is no elevator."
The price is $164
$209 total
includes taxes & fees
May 28 - May 29
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Don't see what you're looking for?
See all available properties in Northwest 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.

Northwest Chicago Vacation Rental Travel Info

Popular accommodation
Northwest Chicago private vacation homes
International airports
Chicago, IL (ORD-O'Hare Intl.) and Chicago, IL (MDW-Midway Intl.)

Other types of properties in Northwest Chicago you may be interested in

Lobby
SureStay Plus Hotel by Best Western Chicago Lombard
2.5 star property
8.6 out of 10, Excellent, (1526)
"Perfect "
The price is $85
$95 total
includes taxes & fees
May 22 - May 23
SureStay Plus Hotel by Best Western Chicago Lombard
Front of property - evening/night
Eaglewood Resort and Spa
4.0 star property
8.4 out of 10, Very Good, (1003)
"This was a little getaway for me. A tranquil and luxurious stay just outside of Chicago."
The price is $119
$152 total
includes taxes & fees
Jun 2 - Jun 3
Eaglewood Resort and Spa
Indoor pool, outdoor pool
Marriott Chicago O'Hare
3.5 star property
8.2 out of 10, Very Good, (1002)
"The staff were so helpful and friendly, makes me want to come back. Great customer service. "
The price is $169
$198 total
includes taxes & fees
May 23 - May 24
Marriott Chicago O'Hare
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 Northwest 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 Northwest 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 Northwest Chicago vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Northwest Chicago vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Northwest 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 Northwest 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 $80 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 Northwest Chicago rentals

At Expedia, we put the best Northwest 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 Northwest 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 Northwest 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 Northwest 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.

Recent reviews of Northwest Chicago properties
Expedia verified reviews

Sonesta Simply Suites Chicago O'Hare Airport

Sonesta Simply Suites Chicago O'Hare Airport

5/5 Excellent
"Very efficient and professional front desk."
A verified traveler stayed at Sonesta Simply Suites Chicago O'Hare Airport
Posted 11 hours ago
Sonesta Simply Suites Chicago O'Hare Airport