Northwest Side Holidays

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Where to stay in Northwest Side

Find the best Northwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Northwest Side
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Irving Park

2 out of top 10 points of interest in this area

Appreciated for its restaurants and live music, you might consider exploring Irving Park. Check out the variety of things to see and do like Milwaukee Avenue, and jump on the metro at Irving Park Station (Blue Line) or Addison Station (Blue Line) to get around the city.

Find hotels in Irving Park

Top hotels in Northwest Side

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is 3.639.942 ₫ per night from 17 Jan to 18 Jan
3.639.942 ₫
5.043.835 ₫ total
17 Jan - 18 Jan
includes taxes & fees
8.4/10 Very Good! (2,502 reviews)
Yes

Reviewed on 7 Jan 2026

Hilton Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is 3.747.633 ₫ per night from 17 Jan to 18 Jan
3.747.633 ₫
5.055.997 ₫ total
17 Jan - 18 Jan
includes taxes & fees
8.4/10 Very Good! (2,227 reviews)
Room was very clean and staff was great

Reviewed on 6 Jan 2026

Palmer House a Hilton Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is 2.347.655 ₫ per night from 18 Jan to 19 Jan
2.347.655 ₫
2.755.912 ₫ total
18 Jan - 19 Jan
includes taxes & fees
8.8/10 Excellent! (3,682 reviews)
Room and hotel overall very clean. Noted some things that could be updated in bathroom(stopper in sink didnt go all the way down, peeling caulk and some missing grout). Minor updates. Our sink was clogged when we checked in and I called the front desk, housekeeping and the hotel hotline 4 different ...

Reviewed on 7 Jan 2026

Hilton Chicago/Magnificent Mile Suites
See all 5,159 properties in Northwest Side
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.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

During your trip, find out what's happening in McCormick Place, a top convention centre in Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

McCormick Place
Soldier Field which includes a high-rise building, a city and modern architecture

Soldier Field

4/5(44 reviews)

Catch an event at Soldier Field during your trip to Chicago. Stroll along the lakeside or visit the notable monuments in this vibrant area.

Soldier Field

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