Northwest Side Vacations from ￥93,126
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The Latest Northwest Side Vacation Packages
Price found within the past 48 hours. Click for updated prices.
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
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.
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.
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.
Find the Best Northwest Side Vacation Packages
Northwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
￥16,542
￥19,668 total
Nov 10 - Nov 11
includes taxes & fees
8/10 Very Good! (10,178 reviews)
"Old rooms and a lot carpets"
Reviewed on Oct 13, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
￥24,086
￥28,637 total
Nov 1 - Nov 2
includes taxes & fees
8.8/10 Excellent! (5,534 reviews)
"I absolutely loved this place. Close to everything and great view"
Reviewed on Oct 12, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
￥22,634
￥26,907 total
Nov 3 - Nov 4
includes taxes & fees
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.
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.
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.
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.
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.
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.
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?
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.
What to do in Northwest Side
Skydeck Chicago at Willis Tower
￥6,642
per adult
88% of travellers recommend
Frequently asked questions
How much does a Northwest Side vacation package cost?
Explore the best of Northwest Side from just ￥93,126. Choose from a great selection of rental cars, hotels and flights to suit every budget. Land even better deals when you add a few experiences or tours to your package.
How do I get a cheap travel package to Northwest Side?
Book everything all in one place with our Northwest Side vacation packages. We have deals on flights, hotels, tours and more that'll keep your pocketbook happy and your sense of adventure alive. And, with more than 550 air carriers and 1,000,000 hotel options globally to choose from, you'll have the flexibility to mix and match as you like.
How far in advance should I book my Northwest Side vacation?
Savvy travelers often reserve their seats early. You can generally look up international airfares on Expedia up to a year before your intended flight. If you're late to book, don't despair. Low prices occasionally become available just weeks prior to departure.
What does an Expedia Northwest Side travel package include?
Hotels, rental cars and flights, or any combination of the three — you decide! Whether you're headed to Northwest Side on a family road trip or traveling solo, there's a package to fit every budget and style. Once you've made your booking, why not add on some activities?
Can I choose my airline with a Northwest Side Expedia vacation package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our vacation packages give you the flexibility to pick from available flights, hotels and activities that suit you.
If I'm not able to travel, can I cancel my Northwest Side vacation package?
Because we understand life is full of surprises, the answer is yes. To find out more, head to our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to change or cancel it for no charge. Your airline, hotel or car rental company may impose a fee if your booking is older than that.
Explore a world of travel with Expedia
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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.
