Northwest Side Holidays from AU$2,345
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$2,500 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
The Latest Northwest Side Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
AU$3,791
per person
11 Nov - 18 Nov
found 1 day ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
Pablo was amazing and he made my 50th birthday experience amazing . Thank you for the champagne and cake surprise . Super recommended .
Reviewed on 1 Sept 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
AU$3,051
per person
11 Nov - 18 Nov
found 1 day ago
Return flight included
Brisbane (BNE) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
The room was very clean and spacious. Staff was very informative about what was accessible during our stay. I would definitely stay here again if I come back to visit Chicago.
Reviewed on 1 Sept 2026
Our guide on 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
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.
Northwest Side Holiday
Northwest Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Our pick of the best Northwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
AU$169
7 Sept - 8 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
AU$202
7 Sept - 8 Sept
includes taxes & fees
8/10 Very good! (2,142 reviews)
"Coming back for sure!"
Reviewed on 1 Sept 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (884 reviews)
"More cutlery more awalible front desk"
Reviewed on 31 Aug 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.
The Gift Theatre
You can make plans for a show at The Gift Theatre during your stay in Chicago. Discover the top-notch restaurants and acclaimed theatre scene in this vibrant 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.
What to do in Northwest Side
Wendella's 90-min Chicago River Architecture Tour
AU$56
per adult
94% of travellers recommend
Chicago White Sox Baseball Game at Guaranteed Rate Field
AU$55
per adult
Frequently asked questions
How much does a Northwest Side holiday package cost?
Explore the best of Northwest Side from just AU$2,345. 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.
Explore a world of travel with Expedia
- Albany Park Hotels
- Hotels near Athenaeum Theatre
- Hotels near Busy Beaver Button Museum
- Apartments in Chicago
- Accor Hotels in Chicago
- Cheap Hotels in Chicago
- Experience Forest Park living near Top Places like downtown Chicago
- Chicago Hotels
- Serviced Apartments in Chicago
- Downtown Chicago Hotels
- Edison Park Hotels
- Four Seasons Hotels in Gold Coast
- Lakeview Hotels
- Logan Square Hotels
- Cheap Hotels in Melrose Park
- Norwood Park Hotels
- Oak Park Hotels
- O'hare Hotels
- Hotels near O'Hare Intl.
- The Loop Hotels
- United Center Hotels
- Wicker Park Hotels
- Hotels near Wrigley Field
- Flights to Chicago
- Flights to Oak Park
- Flights from O'Hare Intl.
- Flights from Chicago
- Flights from Adelaide (ADL) to Chicago (ORD)
- Flights from Atlanta (ATL) to Chicago (ORD)
- Flights from Austin (AUS) to Chicago (ORD)
- Flights from Brisbane (BNE) to Chicago (ORD)
- Flights from Paris (CDG) to Chicago (ORD)
- Flights from Washington (DCA) to Chicago (ORD)
- Flights from Dallas (DFW) to Chicago (ORD)
- Flights from Detroit (DTW) to Chicago (ORD)
- Flights from Hobart (HBA) to Chicago (ORD)
- Flights from Honolulu (HNL) to Chicago (ORD)
- Flights from Houston (HOU) to Chicago (ORD)
- Flights from New York (JFK) to Chicago (ORD)
- Flights from Las Vegas (LAS) to Chicago (ORD)
- Flights from Los Angeles (LAX) to Chicago (ORD)
- Flights from New York (LGA) to Chicago (ORD)
- Flights from London (LHR) to Chicago (ORD)
- Flights from Orlando (MCO) to Chicago (ORD)
- Flights from Melbourne (MEL) to Chicago (ORD)
- Flights from Miami (MIA) to Chicago (ORD)
- Flights from Minneapolis (MSP) to Chicago (ORD)
- Flights from Perth (PER) to Chicago (ORD)
- Flights from Philadelphia (PHL) to Chicago (ORD)
- Flights from San Diego (SAN) to Chicago (ORD)
- Flights from Seattle (SEA) to Chicago (ORD)
- Flights from San Francisco (SFO) to Chicago (ORD)
- Flights from Sydney (SYD) to Chicago (ORD)
- Flights from Vancouver (YVR) to Chicago (ORD)
- Flights from Toronto (YYZ) to Chicago (ORD)
- Abbott Park
- Apache Park
- Art Institute of Chicago
- Buckingham Fountain
- Visit Downtown Chicago
- Visit Edison Park
- Chicago Riverwalk
- Visit The Loop
- Visit West Loop
- Chicago Holidays
- Visit Chicago
- Cloud Gate
- Downtown Chicago Holidays
- Elk Grove Village Holidays
- Visit Elk Grove Village
- Frank Lloyd Wright Historic District
- Visit Franklin Park
- Garfield Park Conservatory
- Gold Coast Holidays
- Golf Holidays
- Grant Park
- Griffin Museum of Science and Industry
- Kathy Osterman Beach
- Legoland® Discovery Center
- Lincoln Hall
- Lincoln Park Zoo
- Lombard Holidays
- Millennium Park
- Montrose Beach
- Navy Pier
- Norma Holidays
- Oak Street Beach
- Pullman Holidays
- Six Flags Great America
- University of Illinois Chicago
- Waukegan BMX Track
- Willis Tower
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
