North Side Vacation Packages
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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 $854, price is now CA $550 per person
CA $550
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
The staff were very friendly and helpful, and the location in the city is excellent. My only complaint is that the walls are quite thin, so you can easily hear noise from the surrounding rooms.
Reviewed on Sep. 8, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was CA $1,841, price is now CA $1,115 per person
CA $1,115
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,714 reviews)
Great location, service and facility. So glad we were able to experience this!
Reviewed on Sep. 8, 2025
Level Chicago - River North
Downtown Chicago
Price was CA $1,759, price is now CA $1,142 per person
CA $1,142
per person
Oct 24 - Oct 29
found 22 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (679 reviews)
Rooms could be updated. Staff was under trained. Amenities very nice, used family room daily with our toddler. Pool deck very modern and new
Reviewed on Sep. 8, 2025
The Langham, Chicago
Downtown Chicago
Price was CA $2,051, price is now CA $1,357 per person
CA $1,357
per person
Oct 19 - Oct 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug. 12, 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 $239 per night from Oct 6 to Oct 7
CA $239
CA $281 total
Oct 6 - Oct 7
includes taxes & fees
Hotel Lincoln
1816 N Clark Street, Chicago, IL
The price is CA $188 per night from Sep 23 to Sep 24
CA $188
CA $245 total
Sep 23 - Sep 24
includes taxes & fees
The Willows Hotel
555 W Surf St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $222 per night from Sep 29 to Sep 30
CA $222
CA $260 total
Sep 29 - Sep 30
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
4.5/5(158 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Lincoln Park Zoo
4.5/5(66 reviews)
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
4/5(5 reviews)
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
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Flights
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
