Northwest Side Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to CA $1,096 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, 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.
Park Hyatt Chicago
Downtown Chicago
Price was CA $3,592, price is now CA $2,089 per person
CA $2,089
per person
Nov 17 - Nov 23
found 24 hours ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on Aug. 31, 2025
Arlo Chicago
Downtown Chicago
Price was CA $1,313, price is now CA $837 per person
CA $837
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,828 reviews)
Great staff and quality of service. Check in process a little confusing and stressful at first but location, amenities, and friendly team made our experience memorable.
Reviewed on Sep. 2, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,906, price is now CA $1,221 per person
CA $1,221
per person
Oct 7 - Oct 10
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
Best, very clean, best view, really enjoyed the stay!
Reviewed on Sep. 2, 2025
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
2 out of top 10 points of interest in this area
Appreciated for its restaurants and live music, you might consider exploring Irving Park. Check out the variety of things to see and do like Milwaukee Avenue, and jump on the metro at Irving Park Station (Blue Line) or Montrose Station (Blue Line) to get around the city.
Northwest Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $176 per night from Sep 4 to Sep 5
CA $176
CA $207 total
Sep 4 - Sep 5
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is CA $252 per night from Sep 22 to Sep 23
CA $252
CA $296 total
Sep 22 - Sep 23
includes taxes & fees
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $230 per night from Sep 22 to Sep 23
CA $230
CA $270 total
Sep 22 - Sep 23
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.
Discover the most popular places to visit in Northwest Side
Wrigley Field
4.5/5(158 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Michigan Avenue
4.5/5(19 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Navy Pier
4.5/5(459 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Northwest Side
Wendella's 90-min Chicago River Architecture Tour
CA $62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
CA $62
per adult
96% of travellers recommend
Other vacations you might like
- January Vacations and Deals
- February Vacations and Deals
- March Vacations and Deals
- April Vacations and Deals
- May Vacations and Deals
- June Vacations and Deals
- July Vacations and Deals
- August Vacations and Deals
- September Vacations and Deals
- October Vacations and Deals
- November Vacations and Deals
- December Vacations and Deals
Expedia's Latest Trends
Hotels
- Best Hotels in Winnipeg
- Best Hotels in Lagos
- Soldier Field hotels
- United Center hotels
- McCormick Place hotels
- Best Hotels in Calgary
- Wrigley Field hotels
- Lollapalooza hotels
- Best Hotels in Santa Monica
- Hilton Toronto Airport Hotel & Suites
- Best Hotels in Athens
- Michigan Avenue hotels
- Art Institute of Chicago hotels
- Millennium Park hotels
- Chicago Riverwalk hotels
- Vaughan Cheap Hotels
Flights
Cruises
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.