Northwest Side Vacation Packages 2026 from $385

The Latest Northwest Side vacation packages

Price found within the past 48 hours. Click for updated prices.

Sheraton Grand Chicago Riverwalk

Downtown Chicago

Save 100% on your flight

$385

per person

Dec 21 - Dec 24

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

8.6/10 Excellent! (1,841 reviews)

It took 55 minutes to check in and then when I was taking a shower, the showerhead fell off and the water pressure almost knocked me down, and you had to wiggle the toilet to get us to stop

Reviewed on Oct 19, 2026

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$462

per person

Jan 7 - Jan 13

found 24 hours ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (576 reviews)

Good locations

Reviewed on Oct 20, 2026

Four Seasons Hotel Chicago

Downtown Chicago

Save 100% on your flight

$885

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (1,002 reviews)

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

$483

per person

Jan 7 - Jan 11

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.2/10 Wonderful! (532 reviews)

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$458

per person

Dec 24 - Dec 27

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

9.4/10 Exceptional! (5,404 reviews)

Super clean, the waitstaff is amazing. The breakfast buffet is unreal.

Reviewed on Oct 20, 2026

Don't see what you're looking for?

See all available trips from Columbus to Northwest Side

View all trips

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.

A panoramic view of a city skyline with prominent skyscrapers, a river, and a bridge.

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

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

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 art 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

Live Wire Lounge

After visiting Live Wire Lounge, make a plan to see the other sights and activities in Chicago. Take in the live music while you're in the area.

See properties

Michella Terrace Banquet Rooms

Michella Terrace Banquet Rooms is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels?

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

What to do in Northwest Side

360 CHICAGO Observation Deck

$24

per adult

86% of travellers recommend

Wendella's 90-min Chicago River Architecture Tour

$41

per adult

94% of travellers recommend

cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$158

per adult

80% 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

$129 total

per night

Nov 11 - Nov 12

River Hotel

75 East Wacker Drive Chicago IL

Fully refundableReserve now, pay when you stay

$181 total

per night

Nov 1 - Nov 2

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

$143 total

per night

Nov 11 - Nov 12

8/10 Very Good! (2,538 reviews)

"Just mid for real over priced for what it is"

Reviewed on Oct 20, 2026

See all 5,072 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.