Northwest Side Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Northwest Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,436
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (5,106 reviews)
Overall, Hotel Riu Plaza Chicago exceeded my expectations. Great location, great staff, good food, amazing views, and an unforgettable rooftop experience. I would definitely stay here again and recommend it to anyone visiting Chicago.
Reviewed on Sep 2, 2026
The Emily Hotel
Downtown Chicago
CA $1,633
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,339 reviews)
Love staying at the Emily! Everyone is always so friendly and helpful and the loft style rooms are super comfortable and spacious. The neighborhood has the best food and coffee of every type within walking distance and many clubs as well including Garcia's and Broken Hearts.
Reviewed on Aug 31, 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
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
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 $142
CA $169 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,253 reviews)
"It was great! We arrived early and the front desk was able to check us in early and our room and view was just amazing! Loved how clean everything was."
Reviewed on Sep 2, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $158
CA $188 total
Sep 7 - Sep 8
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 Sep 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.
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.
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
Wendella's Lake and River Architecture Tour
CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
CA $56
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 $1,080. 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
- Downtown Chicago Hotels
- Hotels with Free Airport Shuttle in Chicago
- Chicago Hotels
- Pet-Friendly Hotels in Chicago
- Hotels with Free Breakfast in Chicago
- Hotels near Soldier Field
- River North Hotels
- All Inclusive Resorts and in Chicago
- Hotels with Free Parking in Chicago
- Motels in Chicago
- The Loop Hotels
- Marriott Hotels & Resorts in Chicago
- West Loop Hotels
- Cheap Hotels in Chicago
- Lincoln Park Hotels
- Hotels near Wrigley Field
- Rosemont Hotels
- Hotels near Navy Pier
- Fulton Market Hotels
- Cheap Hotels in Downtown Chicago
- Hotels near O'Hare Intl.
- Hotels near McCormick Place
- Hotels near United Center
- Hotels near Millennium Park
- Magnificent Mile Hotels
- Flights from Windsor (YQG) to Chicago (ORD)
- Flights to Chicago
- Flights from Washington (DCA) to Chicago (ORD)
- Flights from Kelowna (YLW) to Chicago (ORD)
- Flights from Thunder Bay (YQT) to Chicago (ORD)
- Flights from Waterloo (ALO) to Chicago (ORD)
- Flights from Hamilton (YHM) to Chicago (ORD)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from Edmonton (YEG) to Chicago (ORD)
- Flights from Seattle (SEA) to Chicago (ORD)
- Flights from Minneapolis (MSP) to Chicago (ORD)
- Flights from Delhi (DEL) to Chicago (ORD)
- Flights from Midway Intl.
- Flights from Saskatoon (YXE) to Chicago (ORD)
- Flights from Buffalo (BUF) to Chicago (ORD)
- Flights from London (YXU) to Chicago (ORD)
- Flights from Indianapolis (IND) to Chicago (ORD)
- Flights from Winnipeg (YWG) to Chicago (ORD)
- Flights from Kitchener (YKF) to Chicago (ORD)
- Flights from Los Angeles (LAX) to Chicago (ORD)
- Flights from Halifax (YHZ) to Chicago (ORD)
- Flights from Toronto (YYZ) to Chicago (MDW)
- Flights from O'Hare Intl.
- Flights from Chicago
- Flights from Detroit (DTW) to Chicago (ORD)
- Flights from Québec (YQB) to Chicago (ORD)
- Flights from Victoria (YYJ) to Chicago (ORD)
- Flights from Montreal (YUL) to Chicago (ORD)
- Flights from Toronto (YTZ) to Chicago (MDW)
- Flights from Syracuse (SYR) to Chicago (ORD)
- Flights from Calgary (YYC) to Chicago (ORD)
- Flights from San Francisco (SFO) to Chicago (ORD)
- Flights from Toronto (YYZ) to Chicago (ORD)
- Flights from Fargo (FAR) to Chicago (ORD)
- Flights from Regina (YQR) to Chicago (ORD)
- Flights from Vancouver (YVR) to Chicago (ORD)
- Flights from Dallas (DFW) to Chicago (ORD)
- Flights from Ottawa (YOW) to Chicago (ORD)
- 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
- Chicago Vacations
- Unity Temple
- Ernest Hemingway Museum and House
- Frank Lloyd Wright Historic District
- United Center
- Golf Vacations
- 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.
