Northwest Side Holidays

Book a Hotel + Flight or Car together to unlock savings

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
Default Image

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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is 2.425.580 ₫ per night from 7 Dec to 8 Dec
2.425.580 ₫
2.847.388 ₫ total
7 Dec - 8 Dec
includes taxes & fees
8.4/10 Very Good! (5,331 reviews)
Very nice hotel

Reviewed on 29 Nov 2025

Embassy Suites by Hilton Chicago Downtown River North
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 2.196.204 ₫ per night from 7 Dec to 8 Dec
2.196.204 ₫
2.578.125 ₫ total
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (3,372 reviews)
Rooms are spotless and front desk service amazing. Cleaning room service very kind and friendly.

Reviewed on 25 Nov 2025

Hilton Chicago/Magnificent Mile Suites
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 2.810.509 ₫ per night from 28 Dec to 29 Dec
2.810.509 ₫
3.958.383 ₫ total
28 Dec - 29 Dec
includes taxes & fees
8.4/10 Very Good! (2,102 reviews)
Excellent check in experience and follow up from Ella. The lobby bar area was beautiful with the Christmas trees and other decorations.

Reviewed on 27 Nov 2025

Palmer House a Hilton Hotel
See all 5,124 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 art galleries and notable monuments in this vibrant area.

McCormick Place
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

4.5/5(147 reviews)

After visiting Millennium Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.

Millennium Park