Northwest Side Vacation Packages
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Top Northwest Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
CA $6,031
per person
Oct 7 - Oct 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around
Reviewed on Aug 16, 2026
Level Chicago Fulton Market
Downtown Chicago
CA $1,393
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.
Reviewed on Aug 17, 2026
Level Chicago – Old Town
Downtown Chicago
CA $1,152
per person
Oct 23 - Oct 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (512 reviews)
Beautiful property in great location! Would have definitely been a 5 but rooms facing the pool was very noisy
Reviewed on Aug 19, 2026
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
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.
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.
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.
Ready to book your vacation to Northwest Side?
Northwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $168
CA $199 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very good! (10,271 reviews)
"Room 406: Clean and quiet."
Reviewed on Aug 20, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $197
CA $235 total
Aug 30 - Aug 31
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.
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.
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.
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.
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: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Northwest Side vacation package cost?
Explore the best of Northwest Side from just CA $790. 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.
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- Chicago Theatre
- Grant Park
- Visit Chicago
- Montrose Beach
- Northwestern University
- Water Tower Place
- Garfield Park Conservatory
- Lincoln Park Zoo
- Lakeview Vacations
- Chicago Riverwalk
- Buckingham Fountain
- Downtown Chicago Vacations
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- Unity Temple
- Ernest Hemingway Museum and House
- Frank Lloyd Wright Historic District
- United Center
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- Willis Tower
- Legoland® Discovery Center
- Wrigley Field
- 875 North Michigan Avenue
- Art Institute of Chicago
- Ann and Robert H. Lurie Children's Hospital
- Visit Downtown Chicago
- Rosemont Vacations
- Navy Pier
- Marina City
- Visit The Loop
- International Museum of Surgical Science
- The Loop Vacations
- Millennium Park
- Robie House
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
