Northwest Side Packages (Flight + Hotel)
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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
Irving Park
5 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
3 out of top 10 points of interest in this area
If you're spending some time in Portage Park, Milwaukee Avenue and Six Corners are top sights worth seeing.
Dunning
Restaurants and parks are just a few things travellers like about Dunning. A stop by Schiller Woods is also recommended if you've got time to explore the area.
Belmont Cragin
1 out of top 10 points of interest in this area
Belmont Cragin is well liked for its restaurants and live music. If you're hoping to see more of the larger area, Walt Disney House and Frank Lloyd Wright Historic District are some interesting sights nearby to check out.
Hermosa
1 out of top 10 points of interest in this area
Travellers like the historical sites in Hermosa, and Walt Disney House is a top attraction you might want to visit.
Top hotels in Northwest Side
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
฿3,819
฿4,541 total
7 Sept - 8 Sept
includes taxes & fees
8/10 Very good! (10,249 reviews)
"The only issue my husband and I have was the bathroom. Ever since our stay, the toilet has been making loud noise and kept running like it was still filling the tank even when we’re not using it. It could be probably cause the old building or old water pipes?? The room we were staying was 1204. But ..."
Reviewed on 2 Sept 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
฿3,776
฿4,490 total
7 Sept - 8 Sept
includes taxes & fees
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (886 reviews)
"I felt comfortable during my stay at Kasa. There was a lot of room space and having a balcony was great"
Reviewed on 2 Sept 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.
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 with a stop at Walt Disney House. Experience the entertainment choices and acclaimed theatre scene in this vibrant area.
Six Corners
You can browse for the perfect souvenirs at Six Corners during your visit to Chicago. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.
Avondale Music Hall
You can make plans for 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 exploring the galleries in Irish American Heritage Center in 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.
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.
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
Chicago: Willis Tower Skydeck and The Ledge Ticket
฿1,559
per adult
88% of travellers recommend
Frequently asked questions
How much does a Northwest Side holiday package cost?
Explore the best of Northwest Side from just . 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 holiday 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 holiday?
Savvy travellers 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 travelling 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 holiday package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines worldwide. Our holiday 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 holiday 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
