A nighttime city skyline reflected in a calm body of water, with illuminated buildings and a bridge.

North Side Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for North Side holiday rentals

A modern living room with a fireplace, a dining area with a wooden table and chairs, and a kitchen with a white railing.

1. Wrigleyville Suites

Wrigleyville Suites
2.0 star property
Lakeview
8.2 out of 10, 54, (54 reviews)
"We had a great stay! Perfect location for cubs games and hanging out in wrigleyville."
United States
Kate
The price is S$343
includes taxes & fees
22 Sept - 23 Sept
Wrigleyville Suites
A modern building with the name 'SENIORAL' prominently displayed on the facade.

2. Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.0 out of 10, 1317, (1,317 reviews)
"clean property, amazing staff, in-unit laundry machines, awesome location"
United States
Allison
The price is S$263
includes taxes & fees
21 Sept - 22 Sept
Sentral Michigan Avenue
A modern kitchen with a large island, bar stools, and a city view.

3. Level Chicago – Old Town

Level Chicago – Old Town
4.0 star property
Downtown Chicago
9.2 out of 10, 524, (524 reviews)
"Location and facility was very nice"
United States
Brian
The price is S$482
includes taxes & fees
29 Sept - 30 Sept
Level Chicago – Old Town

4. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
4.0 star property
Downtown Chicago
8.2 out of 10, 30, (30 reviews)
"Location is perfect to visit Chicago for the weekend. The unit is clean and size is perfect for the family."
United States
Xiaoyu
The price is S$369
includes taxes & fees
20 Sept - 21 Sept
Kasa Lake Shore Chicago
A spacious hotel lobby with a high ceiling, chandeliers, and a bar area.

5. The Gem Museum Suites

The Gem Museum Suites
3.5 star property
Downtown Evanston
9.4 out of 10, 256, (256 reviews)
"Really helpful staff, really nice rooms."
United States
Archita
The price is S$277
includes taxes & fees
5 Oct - 6 Oct
The Gem Museum Suites
A living room with a sofa, armchair, dining table, and a TV.

6. At Home in Oak Park

At Home in Oak Park
3.5 star property
Oak Park
9.6 out of 10, 12, (12 reviews)
"Great place, clean, and very accommodating! "
United States
Theresa
The price is S$432
includes taxes & fees
13 Oct - 14 Oct
At Home in Oak Park
A spacious living room with a grand piano, a comfortable sofa, and a dining area with a chandelier.

7. Historic Oak Park Home

Historic Oak Park Home
2.0 star property
Oak Park
10.0 out of 10, 5, (5 reviews)
"The owner was awesome. Convenient parking and beautiful area! Will definitely make a reservation again."
United States
Janette
The price is S$458
includes taxes & fees
14 Oct - 15 Oct
Historic Oak Park Home
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

8. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is S$602
includes taxes & fees
22 Sept - 23 Sept
Classic Forest Park Foursquare < 1 Mi to Blue Line
A building with a white exterior and a tree with white blossoms in front.

9. Historic Oak Park Residence

Historic Oak Park Residence
2.0 star property
Oak Park
9.6 out of 10, 12, (12 reviews)
"The house is in an amazing neighborhood, easy access to subway, extremely clean and great follow-up and follow through communication with owner!"
United States
Ann-Marie
The price is S$489
includes taxes & fees
30 Sept - 1 Oct
Historic Oak Park Residence
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top North Side Hotel Reviews

City Suites Hotel

City Suites Hotel

10/10 Excellent
"Convenient historical hotel close to everything Uptown. Hoai at front desk was super helpful and went above and beyond to assist us!"
James 2-night trip
Posted 15 hours ago
City Suites Hotel

Explore a world of travel with Expedia