North Side Vacation Packages
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Top Holiday Package Deals in North Side
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
Price was CA $913, price is now CA $671 per person
CA $671
per person
Jan 21 - Jan 24
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.
Reviewed on Nov 3, 2026
Pendry Chicago
Downtown Chicago
Price was CA $1,344, price is now CA $983 per person
CA $983
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
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
Downtown
3 out of top 10 points of interest in this area
If you're spending some time in Downtown, Warner Vineyards and South Haven Center for the Arts are top sights worth seeing.
North Side Hotel Deals
Yelton Manor Bed & Breakfast
140 North Shore Drive South Haven MI
The price is CA $200 per night from Nov 18 to Nov 19
CA $200
CA $222 total
Nov 18 - Nov 19
includes taxes & fees
9.2/10 Wonderful! (176 reviews)
"It was an amazing place… so beautiful and north beach is literally right across the street!! Will definitely be renting again!! Staff were amazing. Had the whole place to our selves that night."
Reviewed on Nov 3, 2026
Beachfront Condo on Lake Michigan with heated pool.
South Haven MI
10/10 Exceptional! (83 reviews)
"Super clean condo was perfect for a beach getaway! Well appointed with all of the utensils, dishes, cookware, glassware you need! Fantastic private beach with patio overlooking the lake. Close walk to the pier and riverfront. We’ve already booked for next year."
Reviewed on Sep 16, 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 North Side attractions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.