Northwest Side Vacation Packages 2026

Plan, book, travel with confidence
Better together
Save up to $2,000 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

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

A city skyline with illuminated buildings, a river, and a bridge.

Irving Park

4 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 Avondale Music Hall are top spots, and you can jump on the metro at Irving Park Station (Blue Line) or Addison Station (Blue Line) to get around.

A city skyline with several high-rise buildings, including a prominent glass skyscraper and a building with a spire.

Portage Park

4 out of top 10 points of interest in this area

While visiting Portage Park, you might make a stop by sights like Milwaukee Avenue and Six Corners.

Belmont Cragin

1 out of top 10 points of interest in this area

The restaurants and live music are a few reasons travelers visit Belmont Cragin. Want to see more of the surrounding area? Walt Disney House and Frank Lloyd Wright Historic District are a few top sights nearby.

A city skyline with modern skyscrapers, a river, and a marina.

Dunning

Restaurants and parks are just a few things travelers like about Dunning. A stop by Schiller Woods is also recommended if you've got time to explore the area.

The Chicago Theatre with a prominent marquee displaying movie titles.

Hermosa

1 out of top 10 points of interest in this area

Travelers like the historic sites in Hermosa, and Walt Disney House is a top attraction you might want to visit.

Stay near popular Northwest Side attractions

Portage Park

After visiting Portage Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

See properties

Walt Disney House

Learn about the local history of Chicago when you take a trip to Walt Disney House. Experience the entertainment choices and acclaimed theater scene in this vibrant area.

See properties

Six Corners

You can browse for the perfect souvenirs at Six Corners during your stay in Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

See properties

Avondale Music Hall

You can enjoy a show at Avondale Music Hall on your trip to Chicago. Take in the live music while you're in the area.

See properties

Irish American Heritage Center

You can spend an afternoon browsing the exhibits at Irish American Heritage Center in Chicago. Take in the live music while you're in the area.

See properties

Hanson Park

After visiting Hanson Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

See properties

The Gift Theatre

You can make plans for a show at The Gift Theatre on your trip to Chicago. Discover the top-notch restaurants and acclaimed theater scene in this vibrant area.

See properties

COLOR CLUB

COLOR CLUB is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Take in the live music while you're in the area.

See properties

What to do in Northwest Side

360 CHICAGO Observation Deck

$27

per adult

86% of travellers recommend

Chicago: Willis Tower Skydeck and The Ledge Ticket

$47

per adult

88% of travellers recommend

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25

per adult

90% of travellers recommend

See all activities in Northwest Side

Northwest Side Hotel Deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

$109 nightly

$130 total

Sep 8 - Sep 9

Total with taxes and fees

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$132 nightly

$157 total

Sep 7 - Sep 8

Total with taxes and fees

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL

9.4/10 Exceptional! (857 reviews)

"Muy práctico todo solo que si es necesario que le digan a uno que tienen el inventario del apartamento para que no vayan a cobrar por algo que falte dentro del hotel. No todos los implementos estaban completos"

Reviewed on Aug 15, 2026

Get rates

See all 4,897 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.