Northwest Side Vacation Rentals

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Check prices for these dates

In two weeks
Jan 16 - Jan 18
In two months
Feb 27 - Mar 1
In three months
Mar 27 - Mar 29
In four months
Apr 24 - Apr 26

Our top choices for Northwest Side vacation rentals

Smart TV, stereo
Pine Beam Sloth Apartment next to Blue Line

Apartment in Irving Park

Pine Beam Sloth Apartment next to Blue Line
2.0 star property
10.0 out of 10, Exceptional, (4)
"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.
$196 nightly
The price is $200
Jan 8 - Jan 9
Total with taxes and fees
Pine Beam Sloth Apartment next to Blue Line
Fridge, oven, stovetop, toaster
Homey 2BR Apt w/ Parking

Apartment in Portage Park

Homey 2BR Apt w/ Parking
9.4 out of 10, Exceptional, (9)
"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
2 bedrooms, iron/ironing board, travel crib, WiFi
2BR Chic & Comfortable Furnished Unit

Apartment in Hermosa

2BR Chic & Comfortable Furnished Unit
10.0 out of 10, Exceptional, (4)
"Comfortable beds, great location"
United States
Jason
$178 nightly
The price is $195
Jan 4 - Jan 5
Total with taxes and fees
2BR Chic & Comfortable Furnished Unit
Fridge, microwave, oven, stovetop
1BR Homey Apt in Irving Park

Apartment in Irving Park

1BR Homey Apt in Irving Park
9.0 out of 10, Wonderful, (4)
"It was wonderful and wil stay agian"
United States
Crystal P.
$159 nightly
The price is $176
Jan 4 - Jan 5
Total with taxes and fees
1BR Homey Apt in Irving Park
Fridge, microwave, oven, stovetop
Lovely 2BR with Parking Near United Center & Wrigley

Apartment in Portage Park

Lovely 2BR with Parking Near United Center & Wrigley
9.0 out of 10, Wonderful, (4)
"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 5 - Jan 6
Total with taxes and fees
Lovely 2BR with Parking Near United Center & Wrigley
Fridge, oven, stovetop, coffee/tea maker
2BR Cozy & Functional Unit

Apartment in Belmont Cragin

2BR Cozy & Functional Unit
10.0 out of 10, Exceptional, (1)
"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.
$178 nightly
The price is $195
Jan 4 - Jan 5
Total with taxes and fees
2BR Cozy & Functional Unit
Interior
Trendy & Comfy Studio Unit

Apartment in Portage Park

Trendy & Comfy Studio Unit
9.6 out of 10, Exceptional, (4)
"Older property. Landlord special in the bathroom. Definitely needs better window coverings. Otherwise, comfortable, safe, and clean. "
United States
Courtney V.
$144 nightly
The price is $160
Jan 4 - Jan 5
Total with taxes and fees
Trendy & Comfy Studio Unit
Fridge, microwave, oven, stovetop
Cozy 1-Bedroom Apartment

Apartment in Portage Park

Cozy 1-Bedroom Apartment
10.0 out of 10, Exceptional, (1)
"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 4 - Jan 5
Total with taxes and fees
Cozy 1-Bedroom Apartment
Fridge, microwave, oven, stovetop
Cozy Studio in Jefferson Park

Apartment in Portage Park

Cozy Studio in Jefferson Park
$144 nightly
The price is $160
Jan 4 - Jan 5
Total with taxes and fees
Cozy Studio in Jefferson Park
1 bedroom, iron/ironing board, travel crib, WiFi
Prime City Stay in a 1BR Apt

Apartment in Irving Park

Prime City Stay in a 1BR Apt
9.2 out of 10, Wonderful, (12)
"Host was very attentive and answered all of our questions. It was very cozy and exactly as pictured."
United States
Brandon M.
$159 nightly
The price is $176
Jan 4 - Jan 5
Total with taxes and fees
Prime City Stay in a 1BR Apt
2 bedrooms, iron/ironing board, travel crib, WiFi
Chic 2BR Haven Near Irving Park

Apartment in Irving Park

Chic 2BR Haven Near Irving Park
9.8 out of 10, Exceptional, (9)
"Beautiful place. The host was awesome with communication and recommendations. Will definitely stay again when we come to the city"
United States
Katie L.
$174 nightly
The price is $191
Feb 2 - Feb 3
Total with taxes and fees
Chic 2BR Haven Near Irving Park
Microwave, oven, stovetop, coffee/tea maker
Bright Spaced 3BR Furnished Stay

Apartment in Portage Park

Bright Spaced 3BR Furnished Stay
9.4 out of 10, Exceptional, (3)
"Quick communication, great value, clean & bright."
United States
Barb S.
$202 nightly
The price is $221
Jan 4 - Jan 5
Total with taxes and fees
Bright Spaced 3BR Furnished Stay
2 bedrooms, WiFi, bed sheets
Cozy 2BR Apt for a Seamless Stay

Apartment in Portage Park

Cozy 2BR Apt for a Seamless Stay
8.0 out of 10, Very Good, (1)
"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
TV, offices
Ideal & Spacious 1BR Apt

Apartment in Irving Park

Ideal & Spacious 1BR Apt
8.0 out of 10, Very Good, (2)
"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.
$158 nightly
The price is $174
Feb 3 - Feb 4
Total with taxes and fees
Ideal & Spacious 1BR Apt
Fridge, microwave, oven, stovetop
2BR Traveler's Favorite • Modern and Clean

Apartment in Belmont Cragin

2BR Traveler's Favorite • Modern and Clean
2.0 star property
2BR Traveler's Favorite • Modern and Clean
1 bedroom, WiFi, bed sheets
Portage Park 1BR Retreat

Apartment in Portage Park

Portage Park 1BR Retreat
8.8 out of 10, Excellent, (3)
"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.
$159 nightly
The price is $176
Jan 5 - Jan 6
Total with taxes and fees
Portage Park 1BR Retreat
Iron/ironing board, travel crib, WiFi, bed sheets
1BR Clean and Serene Apartment

Apartment in Belmont Cragin

1BR Clean and Serene Apartment
2.0 star property
$159 nightly
The price is $176
Jan 4 - Jan 5
Total with taxes and fees
1BR Clean and Serene Apartment
Fridge, microwave, oven, stovetop
2BR Fitness Pad • Private Gym • Sleeps 7

Apartment in Irving Park

2BR Fitness Pad • Private Gym • Sleeps 7
2.0 star property
$252 nightly
The price is $298
Jan 4 - Jan 5
Total with taxes and fees
2BR Fitness Pad • Private Gym • Sleeps 7
Fridge, microwave, oven, stovetop
Private Workspace • Sleeps4 • Modern Stylish Stay

Apartment in Irving Park

Private Workspace • Sleeps4 • Modern Stylish Stay
2.0 star property
$227 nightly
The price is $268
Jan 7 - Jan 8
Total with taxes and fees
Private Workspace • Sleeps4 • Modern Stylish Stay
Iron/ironing board, travel crib, WiFi
Comfy Studio in Portage Park- Great Value!

Apartment in Portage Park

Comfy Studio in Portage Park- Great Value!
$144 nightly
The price is $160
Jan 4 - Jan 5
Total with taxes and fees
Comfy Studio in Portage Park- Great Value!
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

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

10/10 Excellent
"Got a great upgrade to the wellness room. The bathrooms are large and spacious. Mattress is on the softer side and the gym is small but has what you need. The staff is friendly as well. The best thing about this hotel is the location and I would stay here again! "
Jagbir 5-night trip
Posted 13 hours ago
LondonHouse Chicago, Curio Collection by Hilton

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 $106 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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