Northwest Side Holiday Rentals

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Our top choices for Northwest Side holiday rentals

1. Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
Belmont Cragin
9.6 out of 10, Exceptional, (7 reviews)
"Room was nice and in a safe location."
United States
Jacob
The price is NZ$658
includes taxes & fees
12 Nov - 13 Nov
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill

2. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.2 out of 10, Wonderful, (12 reviews)
"Truly wonderful experience and amazing hosts that are responsive!"
United States
Dev J.
The price is NZ$585
includes taxes & fees
17 Nov - 18 Nov
Sleeps 7 • Huge Projector • Designated Workspace

3. Relaxing 3BR Getaway Close to Dining & Shopping

Relaxing 3BR Getaway Close to Dining & Shopping
Portage Park
9.8 out of 10, Exceptional, (10 reviews)
"Great stay for a family weekend - we were within easy uber distance of our family and downtown - where we went to watch the Chicago marathon."
United States
Surya B.
The price is NZ$389
includes taxes & fees
17 Nov - 18 Nov
Relaxing 3BR Getaway Close to Dining & Shopping

4. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is NZ$975
includes taxes & fees
12 Nov - 13 Nov
Theater • Game Room • Gym • Firepit • 4BR Home

5. 1BR Retreat: Roomy & Well-Appointed

1BR Retreat: Roomy & Well-Appointed
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"Perfect but be ready for parking"
United States
Sylvia B.
The price is NZ$393
includes taxes & fees
16 Nov - 17 Nov
1BR Retreat: Roomy & Well-Appointed

6. Studio Near Wrigley • Sleeps 4 • Games • Fireplace

Studio Near Wrigley • Sleeps 4 • Games • Fireplace
Irving Park
10.0 out of 10, Exceptional, (7 reviews)
"Clean, comfortable bed, plenty of amenities. Steps and entry were a little awkward. Street parking only unless you paid extra for their garage which was a very tight fit for my sedan. Note older building so could hear neighbors but it wasn’t intrusive. Also note 3.6 miles to Wrigley was a 25 minute drive. Overall great place and would stay again."
United States
Meagan C.
The price is NZ$479
includes taxes & fees
17 Nov - 18 Nov
Studio Near Wrigley • Sleeps 4 • Games • Fireplace

7. Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveller
The price is NZ$1,566
includes taxes & fees
17 Nov - 18 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater

8. Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
Irving Park
10.0 out of 10, Exceptional, (8 reviews)
"Very clean and comfortable, and great location right next to the blue line."
United States
Jen H.
Pine Beam Sloth Apartment next to Blue Line

9. Cozy 2BR Apartment w/ Washer & Dryer

Cozy 2BR Apartment w/ Washer & Dryer
Portage Park
10.0 out of 10, Exceptional, (1 review)
"Overall experience was wonderful. I would stay again and definitely recommend to anyone traveling to the area 5 stars all around! "
United States
Cristy D.
The price is NZ$387
includes taxes & fees
16 Nov - 17 Nov
Cozy 2BR Apartment w/ Washer & Dryer

10. Sleeps 26 • Modern Multi-Unit • Gym • Workspaces

Sleeps 26 • Modern Multi-Unit • Gym • Workspaces
Irving Park
10.0 out of 10, Exceptional, (1 review)
"Nice and spacious thanks again for good commuincation"
United States
Sasha H.
The price is NZ$3,361
includes taxes & fees
4 Dec - 5 Dec
Sleeps 26 • Modern Multi-Unit • Gym • Workspaces

11. Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.6 out of 10, Exceptional, (5 reviews)
"Everyone was super happy with the house and the location."
United States
Rhiannon
The price is NZ$918
includes taxes & fees
17 Nov - 18 Nov
Game Room • Fire-pit • Playground • Gym • Billiard

12. Chic, Quiet 1BR Near Dining Options– Perfect for 2

Chic, Quiet 1BR Near Dining Options– Perfect for 2
Belmont Cragin
2.0 out of 10, (1 review)
"This whole experience of this was the worst possible way to get embarrassed humiliated disrespectful and unprofessional things to happen on your birthday I mean I hope that no one has to endure this"
United States
Durente
The price is NZ$414
includes taxes & fees
30 Nov - 1 Dec
Chic, Quiet 1BR Near Dining Options– Perfect for 2

13. 2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit
Hermosa
4.0 out of 10, (1 review)
"Unlisted expenses and check in process, stopped responding after I checked in. Asks unnecessary information about my personal life"
United States
Edward
The price is NZ$379
includes taxes & fees
16 Nov - 17 Nov
2BR Chic & Comfortable Furnished Unit

14. 1BR 1BA Windy City Hideout

1BR 1BA Windy City Hideout
Belmont Cragin
The price is NZ$300
includes taxes & fees
30 Nov - 1 Dec
1BR 1BA Windy City Hideout

15. Cozy Studio in Portage Park

Cozy Studio in Portage Park
Portage Park
The price is NZ$280
includes taxes & fees
19 Nov - 20 Nov
Cozy Studio in Portage Park

16. Homey 2BR Apt w/ Parking

Homey 2BR Apt w/ Parking
Portage Park
The price is NZ$397
includes taxes & fees
9 Dec - 10 Dec
Homey 2BR Apt w/ Parking

17. Lovely 2BR w/ Parking Near United Center & Wrigley

Lovely 2BR w/ Parking Near United Center & Wrigley
Portage Park
The price is NZ$357
includes taxes & fees
18 Nov - 19 Nov
Lovely 2BR w/ Parking Near United Center & Wrigley

18. Luxury Home, 7 miles to Downtown Chicago, 5 Beds, Near O'Hare Airport

Luxury Home, 7 miles to Downtown Chicago, 5 Beds, Near O'Hare Airport
Belmont Cragin
The price is NZ$1,300
includes taxes & fees
12 Nov - 13 Nov
Luxury Home, 7 miles to Downtown Chicago, 5 Beds, Near O'Hare Airport

19. Smart & Stylish 2-Bedroom Unit

Smart & Stylish 2-Bedroom Unit
Irving Park
The price is NZ$421
includes taxes & fees
12 Nov - 13 Nov
Smart & Stylish 2-Bedroom Unit

20. Well-Laid-Out 1BR Apt Near Transit

Well-Laid-Out 1BR Apt Near Transit
Portage Park
The price is NZ$419
includes taxes & fees
17 Nov - 18 Nov
Well-Laid-Out 1BR Apt Near Transit
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.

Find holiday rentals that suit your style

Top Northwest Side Hotel Reviews

Find out more about Northwest Side

Everything you need to know about Northwest Side holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Northwest Side holiday rental for you. At Expedia, you can take your pick from private holiday 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 Northwest Side holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Northwest Side holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Northwest Side. 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 Northwest Side holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Northwest Side holiday rentals we have selected for you start as low as NZ$280 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Northwest Side rentals

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

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 Side. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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