Holiday rentals in Northwest Side

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Top-rated holiday rentals in Northwest Side

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Flat in Avondale
Lovely, bright, 3-bedroom Avondale flat. Private.
3 bedroom apartment perfect for families or groups of 3-5 people. Transportation is accessible with many CTA bus stops nearby, the Kennedy expressway only minutes away, and two Blue line stations less than a 15 minutes walk. The newly redecorated apartment is located on a quiet street in the up-and-coming Avondale neighborhood with free street parking (parking permit will be provided). Only a few minutes away from Logan Square, amazing restaurants, nightlife, and entertainment are easy to find.
8–15 AprIndividual Host,
£149 per night
4.96 out of 5 average rating, 337 reviews
Guest favourite
Guest suite in Portage Park
Peaceful Portage Park Apartment
You have the entire apartment all to yourself (kitchen, bathroom, 2 bedrooms and an office). Shared backyard. Portage park is located about halfway between O’hare airport and downtown. It is one of the safest neighborhoods in Chicago. Parking is easy! We’re 2 blocks away from a park (dog park, playground, walking/running path, tennis courts, indoor and Olympic sized outdoor pool). Fairly close to coffee shops and good places to eat We are family friendly House trained dogs are ok : $10/night
19–26 Jan
£114 per night
4.93 out of 5 average rating, 344 reviews
Guest favourite
Flat in Avondale
Designer Avondale Attic
Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.
2–9 MayIndividual Host,
£101 per night
4.97 out of 5 average rating, 115 reviews

Popular amenities for Northwest Side holiday rentals

Other great holiday rentals in Northwest Side

Superhost
Flat in Portage Park
Classic Chicago Bungalow Garden Unit
15–22 Apr
£93 per night
4.84 out of 5 average rating, 69 reviews
Superhost
Flat in Belmont Cragin
Spacious Comfy Apartment Fast Wi-Fi Selfcheck-in
9–16 FebIndividual Host,
£74 per night
4.87 out of 5 average rating, 15 reviews
Guest favourite
Guest suite in Chicago
The Abode Chicago - Portage Park- 20min> O'Hare
4.92 out of 5 average rating, 50 reviews
Guest favourite
Flat in Portage Park
Comfortable, modern apartment 20 Min from Downtown
26 Feb – 5 Mar
£122 per night
4.95 out of 5 average rating, 97 reviews
Guest favourite
Flat in Chicago
King Size Sleep Number Bed in Cozy Home w/ No fees
25 Dec – 1 Jan
£107 per night
4.96 out of 5 average rating, 25 reviews
Guest favourite
Guest suite in Irving Park
Entire 1-bedroom Apartment in Vintage Bungalow
8–15 Aug
£96 per night
4.93 out of 5 average rating, 41 reviews
Guest favourite
Flat in Chicago
Comfy & Private Chicago Studio
26 Sept – 3 OctIndividual Host,
£92 per night
5.0 out of 5 average rating, 41 reviews
Guest favourite
Guest suite in Jefferson Park
The Vanderpool House
30 Apr – 7 May
£102 per night
4.94 out of 5 average rating, 94 reviews
Guest favourite
Flat in Portage Park
Top Floor Portage Park Lookout
8–15 May
£109 per night
4.94 out of 5 average rating, 16 reviews
Guest favourite
Guest suite in Portage Park
Eddy Street Upstairs Apartment
1–8 May
£86 per night
4.93 out of 5 average rating, 75 reviews
Guest favourite
Guest suite in Chicago
Logan Square Garden Suite
27 Mar – 3 Apr
£97 per night
4.93 out of 5 average rating, 42 reviews
Guest favourite
Guest suite in Portage Park
Portage Park Entire 3BR Garden Unit
13–20 May
£152 per night
5.0 out of 5 average rating, 6 reviews

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