Bloomingdale Trail, The 606, is an elevated pedestrian trail that travels through the Bucktown and Humboldt Park neighborhoods on Chicago's northwest side. Streets of Chicago.

Holiday Rentals in Northwest Side

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Our top choices for Northwest Side holiday rentals

2BR Fitness Pad • Private Gym • Sleeps 7

2BR Fitness Pad • Private Gym • Sleeps 7
Irving Park
The price is €273
includes taxes & fees
21 Jun - 22 Jun
2BR Fitness Pad • Private Gym • Sleeps 7

Trendy & Comfy Studio Unit

Trendy & Comfy Studio Unit
Portage Park
9.4 out of 10, Exceptional, (8 reviews)
"Nice clean space"
United States
Griffin
The price is €158
includes taxes & fees
14 Jun - 15 Jun
Trendy & Comfy Studio Unit

Portage Park 1BR Retreat

Portage Park 1BR Retreat
Portage Park
9.0 out of 10, Wonderful, (6 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.
The price is €172
includes taxes & fees
15 Jun - 16 Jun
Portage Park 1BR Retreat

1BR 1BA Windy City Hideout

1BR 1BA Windy City Hideout
Belmont Cragin
1BR 1BA Windy City Hideout

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.
The price is €159
includes taxes & fees
21 Jun - 22 Jun
Comfy Studio in Portage Park- Great Value!

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.
The price is €185
includes taxes & fees
23 Jun - 24 Jun
Cozy 1-Bedroom Apartment

Sleeps 4 • New Modern 1BR • Private Workspace

Sleeps 4 • New Modern 1BR • Private Workspace
Irving Park
10.0 out of 10, Exceptional, (1 review)
"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.
Sleeps 4 • New Modern 1BR • Private Workspace

1BR Retreat: Roomy & Well-Appointed

1BR Retreat: Roomy & Well-Appointed
Belmont Cragin
1BR Retreat: Roomy & Well-Appointed

Stylish 1BR Stay in Irving Vibes

Stylish 1BR Stay in Irving Vibes
Irving Park
8.4 out of 10, Very good, (5 reviews)
"Great place to stay Comfy bed and setting"
United States
Steven
The price is €162
includes taxes & fees
16 Jun - 17 Jun
Stylish 1BR Stay in Irving Vibes

2BR w/ Workspace - Coffee Bar - Near Transit

2BR w/ Workspace - Coffee Bar - Near Transit
Belmont Cragin
The price is €360
includes taxes & fees
17 Jun - 18 Jun
2BR w/ Workspace - Coffee Bar - Near Transit

Ideal & Spacious 1BR Apt

Ideal & Spacious 1BR Apt
Irving Park
8.8 out of 10, Excellent, (3 reviews)
"The apartment was perfect for our visit. The host was extremely responsive and helpful throught the process. We especially appreciated the clear check-in instructions and simple check-out process (aka, we weren't asked to do a deep cleaning before the next arrival). We'll definitely stay here again!"
United States
Lilia T.
Ideal & Spacious 1BR Apt

1BR Gem by Shops & Dining

1BR Gem by Shops & Dining
Portage Park
6.0 out of 10, (2 reviews)
"The location was great for us as we were visiting family in the area. Everything worked well for us although more loghting in the bathroom would be a helpful."
United States
Matt E.
1BR Gem by Shops & Dining

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.
1BR Apartment with a Warm & Welcoming Feel

Charming 1BR in Old Irving

Charming 1BR in Old Irving
Irving Park
7.0 out of 10, Good, (2 reviews)
"Despite how cute the apartment was, the radiators are not on a thermostat in the unit and the house was very hot. Whatever timer they used kicked on around 4 am and the radiators all released steam for 2-3 hours straight. It was so loud they left earplugs by the bed. The couch in the living room is so bad it should be replaced ASAP. They need one table or dresser in the bedroom for clothes. There are a good amount of hangers in the closet, but no drawers or shelves anymore so you can't unpack a...
United States
David C.
Charming 1BR in Old Irving

2BR Chic & Comfortable Furnished Unit

2BR Chic & Comfortable Furnished Unit
Hermosa
9.0 out of 10, Wonderful, (7 reviews)
"Comfortable beds, great location"
United States
Jason
2BR Chic & Comfortable Furnished Unit

Cozy 2BR with King Beds + Full Kitchen

Cozy 2BR with King Beds + Full Kitchen
Portage Park
2.0 out of 10, (1 review)
The price is €234
includes taxes & fees
22 Jun - 23 Jun
Cozy 2BR with King Beds + Full Kitchen

Cozy 2BR Apt for a Seamless Stay

Cozy 2BR Apt for a Seamless Stay
Portage Park
9.0 out of 10, Wonderful, (2 reviews)
"The apt was exactly how it is described online. Clean and tucked in a neighborhood. The location is 5 miles away by car from Wringley Field. We found a breakfast place within walking distance called Portage Park breakfast. Good food. Liquor store nearby too."
United States
Tania
The price is €205
includes taxes & fees
17 Jun - 18 Jun
Cozy 2BR Apt for a Seamless Stay

Relaxing 3BR Getaway Close to Dining & Shopping

Relaxing 3BR Getaway Close to Dining & Shopping
Portage Park
9.4 out of 10, Exceptional, (3 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.
Relaxing 3BR Getaway Close to Dining & Shopping

Cozy Studio in Jefferson Park

Cozy Studio in Jefferson Park
Portage Park
2.0 out of 10, (1 review)
"There was no heat so I left after an hour. The host said I should wait for the radiators to cycle in to heat up. There were 3 radiators and two of them were ice cold. The one that did get a little warm was hissing steam and leaking ion the floor. I’m 71 years old and wasn’t planning on a camping trip. So I left and found another place. I will insist on nothing but a full refund and in fact should be compensated for the inconvenience and hardship. "
United States
Victoria A.
The price is €164
includes taxes & fees
22 Jun - 23 Jun
Cozy Studio in Jefferson Park

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.
The price is €762
includes taxes & fees
17 Jun - 18 Jun
Sleeps 18 • 8BR • Game Room • Gym • Theater
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 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, apart-hotels, 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 €81 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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