North Side Holidays from AU$3,261
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Top Holiday Package Deals in North Side
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was AU$3,574, price is now AU$3,261 per person
AU$3,261
per person
8 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (2,229 reviews)
Room was super clean. Awesome view and the staff was great!
Reviewed on 16 Nov 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was AU$5,281, price is now AU$4,263 per person
AU$4,263
per person
8 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (1,773 reviews)
Political stigma aside, I must say, this property is stunning across the board. From the moment you enter the building you're met with this amazingly inviting fragrance.
The Room was spotless. All the staff was sincere, kind, hospitable, and surprisingly diverse. Also, The front desk was exceptionally accommodating while I (minimally) "stress tested" the room service. 10/10 would and Will return.
Mr. & Mrs.S
Reviewed on 17 Nov 2025
Pendry Chicago
Downtown Chicago
Price was AU$3,863, price is now AU$3,404 per person
AU$3,404
per person
8 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (1,130 reviews)
Staff was our favorite part! Very very professional and friendly
Reviewed on 14 Nov 2025
Hilton Chicago O'Hare Airport
O'Hare
Price was AU$4,436, price is now AU$3,975 per person
AU$3,975
per person
8 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
16.4/10 Exceptional! (2,158 reviews)
Not having coffee available until 6 AM (at an airport!) is just so wrong.
Reviewed on 15 Nov 2025
Aloft Chicago Downtown River North
Downtown Chicago
Price was AU$3,611, price is now AU$3,276 per person
AU$3,276
per person
8 Jan - 15 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (1,161 reviews)
Staff was nice and helpful. I guess the only thing that I was a bit disappointed was the rooms, you can hear EVERYTHING.
Reviewed on 18 Nov 2025
Our guide on 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
South Side
While South Side isn't home to many top sights, South Beach and South Haven Lighthouse are some notable places to visit nearby.
Our pick of the best North Side Hotel Deals
Luxury Home on North Beach-NEW Heated Pool & Hot Tub, Firepit, Game Room & More!
South Haven MI
9.6/10 Exceptional! (48 reviews)
The house was awesome. Nice and really close to the beach. The backyard was really nice. The pool was heated which was nice. Overall just a great place to stay.
Reviewed on 28 Sept 2025
Yelton Manor Bed & Breakfast
140 North Shore Drive South Haven MI
Fully refundableReserve now, pay when you stay
The price is AU$282 per night from 19 Nov to 20 Nov
AU$282
19 Nov - 20 Nov
includes taxes & fees
9.2/10 Wonderful! (120 reviews)
Good time enjoying the weekend here!
Reviewed on 19 Oct 2025
Beachfront Luxury Home-NEW Private Heated Pool, Lake View, Firepit, Game Room
South Haven MI
9.8/10 Exceptional! (48 reviews)
Wonderful location, just 200 ft walk to the beach. The owners were very responsive and caring. Wonderful space.
Reviewed on 24 Oct 2025
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.