Northwest Side Vacations from $406
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The Latest Northwest Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
$552
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (527 reviews)
The location is perfect and the building is quite nice. The rooms are also comfortable. This is not a hotel, but rather occupies several floors in a large apartment building. We had a couple issues with our room (malfunctioning, smoke alarm and empty body wash) and neither were dealt with despite a asking multiple times.
Reviewed on Sep 27, 2026
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See all available trips from Columbus to Northwest Side
View all tripsWhere to stay in Northwest Side
Find the best Northwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Northwest Side
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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?
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.
What to do in Northwest Side
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Northwest Side Hotel Deals
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$158 nightly
$188 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (5,462 reviews)
"The room and the facility were just right, and the location was lovely. But the best thing about the stay was the helpfulness and interest from the staff. From upgrading our room (to include the great view!), to helping us find one of the five Starbucks Roasterys in the world, and storing our luggage ..."
Reviewed on Oct 2, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$115 nightly
$136 total
Nov 2 - Nov 3
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
$143 nightly
$170 total
Nov 1 - Nov 2
Total with taxes and fees
8/10 Very Good! (2,391 reviews)
"Great experience on my first trip to Chicago"
Reviewed on Oct 2, 2026
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.
Find the Best Northwest Side Vacation Packages
Northwest Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
