Northwest Side Vacation Rentals

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Our top choices for Northwest Side vacation rentals

Pine Beam Sloth Apartment next to Blue Line

Pine Beam Sloth Apartment next to Blue Line
Irving Park
10.0 out of 10, Exceptional, (6 reviews)
"Beautifully decorated, spotless unit. Conveniently located."
United States
Holly G.
$263 nightly
The price is $269
May 11 - May 12
Total with taxes and fees
Pine Beam Sloth Apartment next to Blue Line

Chic 2BR Haven Near Irving Park

Chic 2BR Haven Near Irving Park
Irving Park
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful place. The host was awesome with communication and recommendations. Will definitely stay again when we come to the city"
United States
Katie L.
$241 nightly
The price is $269
May 26 - May 27
Total with taxes and fees
Chic 2BR Haven Near Irving Park

Charming Sunlit 1BR Apartment

Charming Sunlit 1BR Apartment
Irving Park
9.0 out of 10, Wonderful, (14 reviews)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
$181 nightly
The price is $201
May 11 - May 12
Total with taxes and fees
Charming Sunlit 1BR Apartment

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.
$234 nightly
The price is $261
May 19 - May 20
Total with taxes and fees
2BR Cozy & Functional Unit

Relaxing 3BR Getaway Close to Dining & Shopping

Relaxing 3BR Getaway Close to Dining & Shopping
Portage Park
9.4 out of 10, Exceptional, (3 reviews)
"Quick communication, great value, clean & bright."
United States
Barb S.
$288 nightly
The price is $322
May 12 - May 13
Total with taxes and fees
Relaxing 3BR Getaway Close to Dining & Shopping

Cozy 2BR Apartment w/ Washer & Dryer

Cozy 2BR Apartment w/ Washer & Dryer
Portage Park
10.0 out of 10, Exceptional, (1 review)
"Very clean and pet-friendly property—everything was neat, and the host was super responsive.The only drawback is that some furniture feels worn, so you need to be careful (the curtain in my mom’s room had loose pieces).Overall, we had a great stay!Thanks.Taisa."
United States
Taisa C.
$217 nightly
The price is $241
May 11 - May 12
Total with taxes and fees
Cozy 2BR Apartment w/ Washer & Dryer

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.
$228 nightly
The price is $254
May 11 - May 12
Total with taxes and fees
Cozy 2BR Apt for a Seamless Stay

2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit
Hermosa
8.8 out of 10, Excellent, (6 reviews)
"Comfortable beds, great location"
United States
Jason
$233 nightly
The price is $260
May 11 - May 12
Total with taxes and fees
2BR Chic & Comfortable Furnished Unit

Comfy Studio in Portage Park- Great Value!

Comfy Studio in Portage Park- Great Value!
Portage Park
10.0 out of 10, Exceptional, (1 review)
"The host was very friendly, helpful, and communicative. The apartment was clean and quiet. "
United States
Clifton C.
$160 nightly
The price is $178
May 12 - May 13
Total with taxes and fees
Comfy Studio in Portage Park- Great Value!

Trendy & Comfy Studio Unit

Trendy & Comfy Studio Unit
Portage Park
9.2 out of 10, Wonderful, (7 reviews)
"It was really a great place. Bb oo"
United States
Kate S.
$161 nightly
The price is $180
May 12 - May 13
Total with taxes and fees
Trendy & Comfy Studio Unit

1BR Apartment with a Warm & Welcoming Feel

1BR Apartment with a Warm & Welcoming Feel
Irving Park
9.0 out of 10, Wonderful, (4 reviews)
"It was wonderful and wil stay agian"
United States
Crystal P.
$209 nightly
The price is $234
May 25 - May 26
Total with taxes and fees
1BR Apartment with a Warm & Welcoming Feel

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

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (1 review)
$456 nightly
The price is $555
May 11 - May 12
Total with taxes and fees
Theater • Game Room • Gym • Firepit • 4BR Home

Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
$661 nightly
The price is $741
May 10 - May 11
Total with taxes and fees
Arcade • Theater • Gym • Office • Sleeps 15

1BR Retreat: Roomy & Well-Appointed

1BR Retreat: Roomy & Well-Appointed
Belmont Cragin
$176 nightly
The price is $195
May 11 - May 12
Total with taxes and fees
1BR Retreat: Roomy & Well-Appointed

2BR w/ Workspace - Coffee Bar - Near Transit

2BR w/ Workspace - Coffee Bar - Near Transit
Belmont Cragin
$323 nightly
The price is $399
May 11 - May 12
Total with taxes and fees
2BR w/ Workspace - Coffee Bar - Near Transit

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (1 review)
"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.
$699 nightly
The price is $851
May 10 - May 11
Total with taxes and fees
Sleeps 18 • 8BR • Game Room • Gym • Theater

Portage Park 1BR Retreat

Portage Park 1BR Retreat
Portage Park
8.8 out of 10, Excellent, (5 reviews)
"Great stay. Very good instructions along with video for entry. Clean and comfortable! Enjoyed our stay. Great Colombian coffee shop right downstairs to the right of the entrance."
United States
Ann F.
$176 nightly
The price is $195
May 11 - May 12
Total with taxes and fees
Portage Park 1BR Retreat

2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7
Irving Park
$262 nightly
The price is $310
May 17 - May 18
Total with taxes and fees
2BR Fitness Pad • Private Gym • Sleeps 7

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.
$180 nightly
The price is $200
May 11 - May 12
Total with taxes and fees
Ideal & Spacious 1BR Apt

Studio Near Wrigley • Sleeps 4 • Games + Fireplace

Studio Near Wrigley • Sleeps 4 • Games + Fireplace
Irving Park
$245 nightly
The price is $290
May 10 - May 11
Total with taxes and fees
Studio Near Wrigley • Sleeps 4 • Games + Fireplace
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

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 $154 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.