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
EyeEm Custom Shoots Q4 2018

Irving Park

2 out of top 10 points of interest in this area

Irving Park is well liked for its restaurants and live music. If you're hoping to get in some sightseeing, Milwaukee Avenue and Irish American Heritage Center are top spots, and you can jump on the metro at Irving Park Station (Blue Line) or Addison Station (Blue Line) to get around.

Find hotels in Irving Park

Top hotels in Northwest Side

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is 3.030.402 ₫ per night from 26 Apr to 27 Apr
3.030.402 ₫
3.557.601 ₫ total
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,160 reviews)
Hotel has the markings of being grand, but needs a renovation in a lot of areas. The biggest issue we had is that the a/c is not adjustable in each room and the building was very warm on the 75 degree day in April. We called the front desk and they did bring us a fan that helped some and we realized ...

Reviewed on 20 Apr 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is 3.923.617 ₫ per night from 22 Apr to 23 Apr
3.923.617 ₫
4.606.210 ₫ total
22 Apr - 23 Apr
includes taxes & fees
8.8/10 Excellent! (5,114 reviews)
Really good location

Reviewed on 20 Apr 2026

River Hotel
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is 2.285.704 ₫ per night from 26 Apr to 27 Apr
2.285.704 ₫
3.487.031 ₫ total
26 Apr - 27 Apr
includes taxes & fees
8.2/10 Very Good! (2,636 reviews)
The room was actually pretty good and pretty good size for two people and a queen bed I really loved it and I would go back again.

Reviewed on 21 Apr 2026

Hotel Felix River North/Magnificent Mile
See all 5,118 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

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
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

5/5(1 review)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
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 fascinating museums and notable monuments in this vibrant area.

McCormick Place

Explore a world of travel with Expedia