A curved pathway with a metal fence, flowering trees, and a street lamp.

Northwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Northwest Side vacation rentals

A round table with a wooden board holding cheese, crackers, and grapes, a bottle of wine, and two glasses.

1. Sleeps 7 • Huge Projector • Designated Workspace

Sleeps 7 • Huge Projector • Designated Workspace
Irving Park
9.0 out of 10, Wonderful, (9 reviews)
"Great location and easy on street parking. "
United States
Lori A.
$264 nightly
The price is $313
Oct 27 - Oct 28
Total with taxes and fees
Sleeps 7 • Huge Projector • Designated Workspace
A modern dining area with a white table, chairs, and a chandelier. There is a painting on the wall and a plant on the sideboard.

2. 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
$336 nightly
The price is $415
Oct 19 - Oct 20
Total with taxes and fees
Sleeps7 • 2BR • Coffee Station • Backyard w/ Grill
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"
United States
Ashley Y.
$868 nightly
The price is $1,057
Oct 22 - Oct 23
Total with taxes and fees
Sleeps 18 • 8BR • Game Room • Gym • Theater
A bedroom with a large mirror, a potted plant, a neatly made bed, and a white wall with a power outlet.

4. Sleeps 4 • New Modern 1BR • Private Workspace

Sleeps 4 • New Modern 1BR • Private Workspace
Irving Park
9.4 out of 10, Exceptional, (3 reviews)
"Really nice apartment with ample street parking. Depending on what time you get there it might be harder to find a spot but we got there around 8pm and found a spot very close to the apartment. Host was very responsive, only thing is i wish they would have sent the check in codes to my phone as a text rather than as a message through the app since it didn’t load all the way and it took some time to receive it. Spacious, Great amenities, perfect for multiple guests. Walls are a bit thin as I...
United States
Mia S.
$255 nightly
The price is $301
Oct 14 - Oct 15
Total with taxes and fees
Sleeps 4 • New Modern 1BR • Private Workspace
A neatly made bed with a folded white towel, a potted plant, a wall-mounted abstract painting, and a nightstand with a lamp.

5. Relaxing 3BR Getaway Close to Dining & Shopping

Relaxing 3BR Getaway Close to Dining & Shopping
Portage Park
9.8 out of 10, Exceptional, (8 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.
$235 nightly
The price is $260
Oct 14 - Oct 15
Total with taxes and fees
Relaxing 3BR Getaway Close to Dining & Shopping
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

6. 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
$478 nightly
The price is $581
Oct 15 - Oct 16
Total with taxes and fees
Theater • Game Room • Gym • Firepit • 4BR Home
A kitchen with wooden cabinets, a microwave, stove, oven, and a refrigerator.

7. 1BR Retreat: Roomy & Well-Appointed

1BR Retreat: Roomy & Well-Appointed
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
$219 nightly
The price is $238
Oct 21 - Oct 22
Total with taxes and fees
1BR Retreat: Roomy & Well-Appointed
Room

8. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (4 reviews)
"Good place for a large group or family."
United States
Daniel J.
$723 nightly
The price is $809
Oct 14 - Oct 15
Total with taxes and fees
Arcade • Theater • Gym • Office • Sleeps 15
A compact kitchen with wooden cabinets, a microwave, a stove, and a dining table with chairs.

9. 2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit
Hermosa
$239 nightly
The price is $267
Oct 19 - Oct 20
Total with taxes and fees
2BR Chic & Comfortable Furnished Unit
A modern living room with a blue sofa, a white armchair, a round coffee table with a plant, a flat-screen TV, and abstract wall art.

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

Lovely 2BR w/ Parking Near United Center & Wrigley
Portage Park
$225 nightly
The price is $250
Oct 25 - Oct 26
Total with taxes and fees
Lovely 2BR w/ Parking Near United Center & Wrigley
A kitchen with a wooden countertop, a sink, and a knife block.

11. 1BR 1BA Windy City Hideout

1BR 1BA Windy City Hideout
Belmont Cragin
$159 nightly
The price is $176
Oct 14 - Oct 15
Total with taxes and fees
1BR 1BA Windy City Hideout
A modern living room with a green sofa, a black leather chair, and a coffee table. There are abstract wall art pieces and a wall-mounted lamp.

12. Smart & Stylish 2-Bedroom Unit

Smart & Stylish 2-Bedroom Unit
Irving Park
$246 nightly
The price is $276
Nov 11 - Nov 12
Total with taxes and fees
Smart & Stylish 2-Bedroom Unit
A modern living room with a white coffee table, a vase with flowers, a bottle of wine, and a cheese board with snacks.

13. 2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7
Irving Park
9.4 out of 10, Exceptional, (8 reviews)
"Great property in a central location. Neighborhood was quiet and safe with good parks nearby. Apartment had good amenities and perfect for our stay. Communication with host was excellent"
United States
Carey M.
$307 nightly
The price is $363
Oct 22 - Oct 23
Total with taxes and fees
2BR Fitness Pad • Private Gym • Sleeps 7
Exterior

14. Stylish 1BR Stay in Irving Vibes

Stylish 1BR Stay in Irving Vibes
Irving Park
$180 nightly
The price is $200
Oct 26 - Oct 27
Total with taxes and fees
Stylish 1BR Stay in Irving Vibes
A modern living room with a grey sofa, a small side table, a coffee table, and a large window with blinds.

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

Chic, Quiet 1BR Near Dining Options– Perfect for 2
Belmont Cragin
$213 nightly
The price is $231
Oct 27 - Oct 28
Total with taxes and fees
Chic, Quiet 1BR Near Dining Options– Perfect for 2
A bathroom with a toilet, sink, and bathtub.

16. 1BR Apartment with a Warm & Welcoming Feel

1BR Apartment with a Warm & Welcoming Feel
Irving Park
$230 nightly
The price is $251
Oct 19 - Oct 20
Total with taxes and fees
1BR Apartment with a Warm & Welcoming Feel
A modern living room with a sectional sofa, a glass coffee table, and a dining area in the background.

17. Cozy 2BR Apartment w/ Washer & Dryer

Cozy 2BR Apartment w/ Washer & Dryer
Portage Park
$216 nightly
The price is $240
Nov 1 - Nov 2
Total with taxes and fees
Cozy 2BR Apartment w/ Washer & Dryer
A wooden dining table with four chairs, a small potted plant, and a lamp on a side table.

18. Portage Park 1BR Retreat

Portage Park 1BR Retreat
Portage Park
$236 nightly
The price is $258
Nov 1 - Nov 2
Total with taxes and fees
Portage Park 1BR Retreat
Interior

19. Cozy Studio in Portage Park

Cozy Studio in Portage Park
Portage Park
$143 nightly
The price is $158
Oct 14 - Oct 15
Total with taxes and fees
Cozy Studio in Portage Park
A modern living room with a sofa, a coffee table with a plant, a flat-screen TV, and a radiator.

20. Chic 2BR Haven Near Irving Park

Chic 2BR Haven Near Irving Park
Irving Park
$219 nightly
The price is $244
Oct 21 - Oct 22
Total with taxes and fees
Chic 2BR Haven Near Irving Park
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.
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Top Northwest Side Hotel Reviews

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

10/10 Excellent
"The staff at Gold Club. Mandan geninely treats you like your guest at her own home. We were at the hotel for Chicago Marathon; and their soecial athlete breakfast and attention to details were very helpful."
Ahmad reza 4-night trip
Posted 10 hours ago
Fairmont Chicago at Millennium Park

Find out more about Northwest Side

Everything you need to know about Northwest Side 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 Side 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 Side vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Northwest Side vacation 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 low season months. For more hustle and bustle, you may prefer to visit Northwest Side 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 $81 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 Side rentals

At Expedia, we put the best Northwest Side 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 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 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 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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