North 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 North Side Vacation Deals
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was CA $1,018, price is now CA $551 per person
CA $551
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Everything was very good; however, the soundproofing could be improved as we could clearly hear what was happening in the neighboring rooms
Reviewed on Sep 9, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $2,194, price is now CA $1,304 per person
CA $1,304
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
We picked the Trump Hotel-Chicago to celebrate our 35th Wedding Anniversary mainly for the location and the amenities. The hotel EXCEEDED our expectations in every way. (1) The staff is so warm, kind, compassionate and extremely professional in such a friendly down-to-earth way. (2) The property itself is immaculate. (3) The amenities: Terrace 16- the view will take your breath away! The food/cocktails were fabulous as was the service. (3) Pablo - Director of Rooms, Curtis -Concierge were off the charts fabulous. I wish I could remember all the staff names that went out of their way to make our weekend so special. I cannot wait to stay here again. As another reviewer said: put any political opinions aside and treat yourself to a stay here. YOU WILL LOVE IT. (There is no political aura here...only a fantastic team that wants you to enjoy your stay and they go out of their way to make sure you do).
Reviewed on Sep 8, 2025
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was CA $1,124, price is now CA $694 per person
CA $694
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,014 reviews)
First time but won’t be the last. Very nice place with lots to do right around there.
Reviewed on Sep 9, 2025
The Royal Sonesta Chicago River North
Downtown Chicago
Price was CA $955, price is now CA $609 per person
CA $609
per person
Nov 12 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (2,078 reviews)
TV didn’t work correctly(Guide kept sticking). Need microwaves and better iron in rooms.
Reviewed on Sep 8, 2025
Where to stay in North Side
Find the best North Side areas and neighborhoods for the activities you enjoy most. Learn more about North Side
Lincoln Park
5 out of top 10 points of interest in this area
5/5(20 area reviews)
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
North Side Hotel Deals
The Majestic Hotel
528 W Brompton Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Oct 5 to Oct 6
CA $217
CA $255 total
Oct 5 - Oct 6
includes taxes & fees
Hotel Lincoln
1816 N Clark Street, Chicago, IL
The price is CA $186 per night from Sep 29 to Sep 30
CA $186
CA $243 total
Sep 29 - Sep 30
includes taxes & fees
The Willows Hotel
555 W Surf St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Oct 5 to Oct 6
CA $217
CA $255 total
Oct 5 - Oct 6
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 North Side
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Lincoln Park Zoo
This small zoo in the center of Chicago is perfect for small children and parents looking for a quiet, leisurely stroll — and some impressive animals!
Chicago History Museum
Take a stroll through time, with historical artifacts that explore the city’s rich and colorful history.
What to do in North Side
Wendella's 90-min Chicago River Architecture Tour
CA $62
per adult
94% of travellers recommend
Chicago: Architecture Boat Tour with Drinks
CA $58
per adult
88% 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
- The Simon Hotel Sydney
- Best Hotels in Washington
- Ramada by Wyndham Cornwall
- Soldier Field hotels
- Best Hotels in Kingston
- United Center hotels
- McCormick Place hotels
- Best Hotels in Calgary
- The Royal Park Hotel Tokyo Haneda Airport Terminal 3
- Wrigley Field hotels
- Lollapalooza hotels
- Hotel Vallea Bromont, Tapestry Collection by Hilton
- Michigan Avenue hotels
- Art Institute of Chicago hotels
- B&B Elora
- Millennium Park hotels
- Chicago Riverwalk hotels
- Club Wyndham Grand Desert
Flights
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
