Northwest Side Holidays
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Northwest Side Flight & Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
S$885
per person
4 Dec - 8 Dec
found 1 day ago
Return flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (3,512 reviews)
The staff was genuinely helpful and made us feel welcome throughout our stay. The views from our room were beautiful, and it was nice to have a comfortable place to return to after each day. The hotel was immaculate and comfortable.
The location worked really well for our family. Everything we wanted to see was nearby, so we didn't waste time getting around the city. We were able to visit the places we came for without any hassle.
We had a great time and would definitely come back here on our next trip to Chicago. I'd recommend the Swisshotel without hesitation.
Reviewed on 20 Sept, 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 COLOR CLUB 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
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
S$283
27 Sept - 28 Sept
includes taxes & fees
8.8/10 Excellent! (5,448 reviews)
"The elevator system needs to be updated."
Reviewed on 19 Sept, 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
S$271
7 Oct - 8 Oct
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
S$272
13 Oct - 14 Oct
includes taxes & fees
8/10 Very good! (2,282 reviews)
"Cons: Bathroom was a bit outdated. Tub difficult to get in and out of. Elevators are tiny. Pros: Friendly staff, easy to check in and out, valet parking easy to use, great breakfast buffet, used a second party vendor and had no complications, decent price, nice ambience, food hours went well beyond ..."
Reviewed on 20 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 art galleries 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.
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.
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.
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.
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.
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
Frequently asked questions
How much does a Northwest Side holiday package cost?
Explore the best of Northwest Side from just S$854. 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.
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- Visit Edison Park
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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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
