Downtown Holidays from AU$3,261
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Top Holiday Package Deals in Downtown
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 Downtown
Find the best Downtown areas and neighborhoods for the activities you enjoy most. Learn more about Downtown
North Side
1 out of top 10 points of interest in this area
While visiting North Side, you might make a stop by sights like North Beach and Michigan Maritime Museum.
Our pick of the best Downtown Hotel Deals
Old Harbor Inn
515 Williams Street, South Haven, MI
Fully refundableReserve now, pay when you stay
The price is AU$220 per night from 19 Nov to 20 Nov
AU$220
19 Nov - 20 Nov
includes taxes & fees
9.4/10 Exceptional! (675 reviews)
Easy to find. Walkable to town. Nice place to stay. Fresh coffee in the morning.
Reviewed on 10 Nov 2025
Historic Hotel Nichols
201 Center St South Haven MI
The price is AU$239 per night from 30 Nov to 1 Dec
AU$239
30 Nov - 1 Dec
includes taxes & fees
9.6/10 Exceptional! (123 reviews)
AMAZING PLACE TO STAY!!
Reviewed on 4 Nov 2025
New Home with swim spa, theatre & game room. 1 block to town & close to beach.
South Haven
10/10 Exceptional! (193 reviews)
We had a great stay! The house was clean and comfortable. The host was friendly and accommodating. The swim spa was amazing. Perfect location for our annual Mom’s Weekend Away!
Reviewed on 23 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.