Northwest Side Vacation Rentals

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Jan 13 - Jan 14
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Our top choices for Northwest Side vacation rentals

Interior
Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
2.0 star property
Irving Park
10.0 out of 10, Exceptional, (4 reviews)
"Amazing stay! So comfortable, clean, and the sushi underneath was the icing on the cake! We will definitely stay again when we come back! "
United States
Emily s.
$190 nightly
The price is $195
Jan 14 - Jan 15
Total with taxes and fees
Pine Beam Sloth Apartment next to Blue Line
TV, offices
Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.2 out of 10, Wonderful, (12 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
$154 nightly
The price is $170
Feb 2 - Feb 3
Total with taxes and fees
Charming Sunlit 1BR Apartment
TV, offices
1BR Homey Apt in Irving Park

1BR Homey Apt in Irving Park

1BR Homey Apt in Irving Park
Irving Park
9.0 out of 10, Wonderful, (4 reviews)
"It was wonderful and wil stay agian"
United States
Crystal P.
$158 nightly
The price is $174
Feb 2 - Feb 3
Total with taxes and fees
1BR Homey Apt in Irving Park
Iron/ironing board, travel crib, WiFi, bed sheets
Trendy & Comfy Studio Unit

Trendy & Comfy Studio Unit

Trendy & Comfy Studio Unit
Portage Park
9.6 out of 10, Exceptional, (4 reviews)
"Older property. Landlord special in the bathroom. Definitely needs better window coverings. Otherwise, comfortable, safe, and clean. "
United States
Courtney V.
$140 nightly
The price is $155
Feb 2 - Feb 3
Total with taxes and fees
Trendy & Comfy Studio Unit
TV, offices
Lovely 2BR with Parking Near United Center & Wrigley

Lovely 2BR with Parking Near United Center & Wrigley

Lovely 2BR with Parking Near United Center & Wrigley
Portage Park
9.0 out of 10, Wonderful, (4 reviews)
"The place was spacious and quiet at night. It was warm and cozy for a winter nights' stay. If you are a coffee person, bring your own! Host was responsive and helpful. "
United States
Kierstin A.
$183 nightly
The price is $200
Jan 19 - Jan 20
Total with taxes and fees
Lovely 2BR with Parking Near United Center & Wrigley
2 bedrooms, iron/ironing board, travel crib, WiFi
2BR Cozy & Functional Unit

2BR Cozy & Functional Unit

2BR Cozy & Functional Unit
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
"The host was available and helpful at check-in. The 2 bedroom apartment was clean and well stocked. We felt safe and at home. We slept well. We did not notice any street noise at night. We had more than we epected and everything we needed.It might be helpful to color code the keys with nail polish or something. The three locks to get into the unit felt like a struggle because we needed a quick turn around time between events. Otherwise, it was a great stay!!"
United States
Laura V.
$174 nightly
The price is $191
Feb 2 - Feb 3
Total with taxes and fees
2BR Cozy & Functional Unit
TV, offices
Cozy 1-Bedroom Apartment

Cozy 1-Bedroom Apartment

Cozy 1-Bedroom Apartment
Portage Park
10.0 out of 10, Exceptional, (1 review)
"The place was great! It's stocked with the basics, bed and couch are comfy, and everything is clean. There were only a handful of times when I heard the upstairs neighbor, but nothing too crazy. The neighborhood itself is very cute and quiet, with good food and stores within walking distance. Street parking was easy. Thank you! "
United States
Sarah M.
$153 nightly
The price is $168
Jan 15 - Jan 16
Total with taxes and fees
Cozy 1-Bedroom Apartment
Interior
2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit
Hermosa
10.0 out of 10, Exceptional, (4 reviews)
"Comfortable beds, great location"
United States
Jason
$174 nightly
The price is $191
Feb 2 - Feb 3
Total with taxes and fees
2BR Chic & Comfortable Furnished Unit
2 bedrooms, iron/ironing board, travel crib, WiFi
Homey 2BR Apt w/ Parking

Homey 2BR Apt w/ Parking

Homey 2BR Apt w/ Parking
Portage Park
9.4 out of 10, Exceptional, (9 reviews)
"It was clean and well maintained unit. It’s next to grocery store and pharmacy which was very convenient. It’s not too far from downtown. I would stay again here in future if available."
United States
Jatin
$174 nightly
The price is $191
Feb 2 - Feb 3
Total with taxes and fees
Homey 2BR Apt w/ Parking
3 bedrooms, WiFi
Bright Spaced 3BR Furnished Stay

Bright Spaced 3BR Furnished Stay

Bright Spaced 3BR Furnished Stay
Portage Park
9.4 out of 10, Exceptional, (3 reviews)
"Quick communication, great value, clean & bright."
United States
Barb S.
$202 nightly
The price is $221
Jan 14 - Jan 15
Total with taxes and fees
Bright Spaced 3BR Furnished Stay
TV
Chic 2BR Haven Near Irving Park

Chic 2BR Haven Near Irving Park

Chic 2BR Haven Near Irving Park
Irving Park
9.8 out of 10, Exceptional, (9 reviews)
"Ample accommodations for two adults. Clean and in great condition!"
United States
Kathy D.
$174 nightly
The price is $191
Feb 2 - Feb 3
Total with taxes and fees
Chic 2BR Haven Near Irving Park
TV, offices
1BR Clean and Serene Apartment

1BR Clean and Serene Apartment

1BR Clean and Serene Apartment
2.0 star property
Belmont Cragin
$159 nightly
The price is $176
Jan 14 - Jan 15
Total with taxes and fees
1BR Clean and Serene Apartment
TV
Portage Park 1BR Retreat

Portage Park 1BR Retreat

Portage Park 1BR Retreat
Portage Park
8.8 out of 10, Excellent, (3 reviews)
"Clean comfortable space, friendly host, location was very convenient for our needs, with a short walk to the CTA. The only drawbacks were minor; there are no curtains-only blinds- which let in more morning light than we would have liked for sleeping in and there was minimal space in the bathroom for counter items and hanging up towels, travel kits ext."
United States
Brienne K.
$155 nightly
The price is $171
Feb 2 - Feb 3
Total with taxes and fees
Portage Park 1BR Retreat
Dining
2BR • Sleeps7 • Coffee Station • Backyard w/ Grill

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

2BR • Sleeps7 • Coffee Station • Backyard w/ Grill
2.0 star property
Belmont Cragin
$301 nightly
The price is $372
Jan 14 - Jan 15
Total with taxes and fees
2BR • Sleeps7 • Coffee Station • Backyard w/ Grill
TV
Cozy 2BR Apt for a Seamless Stay

Cozy 2BR Apt for a Seamless Stay

Cozy 2BR Apt for a Seamless Stay
Portage Park
8.0 out of 10, Very Good, (1 review)
"Everything as advertised. The only part that I was unsure of was what to do with the keys as this was not stated in any of the information provided. So I left them on the table. "
United States
Michael P.
$174 nightly
The price is $191
Feb 2 - Feb 3
Total with taxes and fees
Cozy 2BR Apt for a Seamless Stay
Interior
2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7
2.0 star property
Irving Park
$262 nightly
The price is $310
Jan 14 - Jan 15
Total with taxes and fees
2BR Fitness Pad • Private Gym • Sleeps 7
Dining
Sleeps 18 • 8BR • Game Room • Gym • Theater

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
2.0 star property
Portage Park
$611 nightly
The price is $744
Jan 14 - Jan 15
Total with taxes and fees
Sleeps 18 • 8BR • Game Room • Gym • Theater
Fridge, microwave, oven, stovetop
Cozy Studio in Jefferson Park

Cozy Studio in Jefferson Park

Cozy Studio in Jefferson Park
Portage Park
$144 nightly
The price is $160
Jan 19 - Jan 20
Total with taxes and fees
Cozy Studio in Jefferson Park
Fridge, microwave, oven, stovetop
Game Room • Fire-pit • Playground • Gym • Billiard

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

Game Room • Fire-pit • Playground • Gym • Billiard
2.0 star property
Belmont Cragin
$319 nightly
The price is $377
Jan 14 - Jan 15
Total with taxes and fees
Game Room • Fire-pit • Playground • Gym • Billiard
TV, offices
Ideal & Spacious 1BR Apt

Ideal & Spacious 1BR Apt

Ideal & Spacious 1BR Apt
Irving Park
8.0 out of 10, Very Good, (2 reviews)
"Excellent location. Clean. Quiet building. Host was incredibly responsive. There was a blizzard during our stay and the host graciously accomodated our request to extend our visit!"
United States
Jackie F.
$153 nightly
The price is $168
Feb 2 - Feb 3
Total with taxes and fees
Ideal & Spacious 1BR Apt
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

River Hotel

River Hotel

10/10 Excellent
"Great stay and superior room had a great river view!"
Austin 2-night trip
Posted 7 hours ago
River Hotel

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 $158 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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