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 Homes in Northwest Side

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Our top choices for Northwest Side holiday homes

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
The price is €475
includes taxes & fees
9 Jul - 10 Jul
Game Room • Fire-pit • Playground • Gym • Billiard

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 €764
includes taxes & fees
17 Jun - 18 Jun
Sleeps 18 • 8BR • Game Room • Gym • Theater

Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (2 reviews)
"Great home, clean ample space. Host was responsive and helpful. I would certainly stay again."
United States
Latasha C.
Arcade • Theater • Gym • Office • Sleeps 15

Sleeps 26 • Modern Multi-Unit • Gym • Workspaces

Sleeps 26 • Modern Multi-Unit • Gym • Workspaces
Irving Park
Sleeps 26 • Modern Multi-Unit • Gym • Workspaces

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"Un superbe building avec des prestations sympas, un chouette appartement avec tout ce qu’il faut pour être confortable et les petits détails qui font la différence, notamment pour un court séjour car cela évite de voyager avec ou de courir en acheter: savon pour les mains, shampooing, gel douche, lessive, café etc il est très proche de la ligne rouge du métro et d’un arrêt de bus. "
United States
Emeline B.
The price is €820
includes taxes & fees
25 Jun - 26 Jun
ENVITAE Hotel, 4BR Luxury Modern Apartments

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is €486
includes taxes & fees
6 Jul - 7 Jul
Near Lake and Museum • Modern • Game Area

Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
10.0 out of 10, Exceptional, (1 review)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is €184
includes taxes & fees
15 Jun - 16 Jun
Attractive Coach House Apartment for rent in Oak Park.

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (83 reviews)
"nice little place! quiet area "
United States
Nayeli A.
The price is €194
includes taxes & fees
28 Jun - 29 Jun
Master qtr close to nature & easy urban facilities

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very good, (28 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is €261
includes taxes & fees
16 Jun - 17 Jun
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.6 out of 10, Exceptional, (61 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is €345
includes taxes & fees
9 Jul - 10 Jul
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (68 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is €277
includes taxes & fees
24 Jun - 25 Jun
✽ Charming Cottage ✽ close to College/Town/Station

Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
10.0 out of 10, Exceptional, (1 review)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Lovely 3-bedroom house in Villa Park with WiFi and AC

Lovely 3-bedroom house in Villa Park with WiFi and AC
Villa Park
9.0 out of 10, Wonderful, (2 reviews)
"Location was great."
United States
Jessica F.
The price is €421
includes taxes & fees
15 Jun - 16 Jun
Lovely 3-bedroom house in Villa Park with WiFi and AC

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.6 out of 10, Exceptional, (29 reviews)
"Clean house, Nice amenities, roomy and Close to the city! We very much enjoyed our stay here. "
United States
Ella A.
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Game Room

Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Game Room
Brookfield
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Crimson Manor. The property was super clean and well furnished, and kitchen was well-appointed. Stacey was a very responsive and attentive host. Even when we had difficulty getting into the garage, she had it resolved in 10 minutes. The basement game room is awesome - especially if you have a family! We recommend this property!"
United States
Steve H.
The price is €515
includes taxes & fees
28 Jun - 29 Jun
Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Game Room

Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!

Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!
Villa Park
8.4 out of 10, Very good, (5 reviews)
"Great location and perfect set up for a family size Vaca!! Loved it!"
United States
Robin C.
The price is €434
includes taxes & fees
15 Jun - 16 Jun
Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (50 reviews)
"Great stay"
United States
Steve T.
The price is €321
includes taxes & fees
24 Jun - 25 Jun
LUXE 3 BR, 2 BA + Hot Tub

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
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Top Northwest Side Hotel Reviews

Find out more about Northwest Side

Northwest Side Holiday Homes information

Number of reviews
360
Accommodation
332 Holiday Homes
Lowest Price
€184
Highest Price
€820

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