Northwest Side Adults Only Holidays
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Top flight + Adults Only hotel deals in Northwest Side
Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was AU$3,484, price is now AU$3,201 per person
AU$3,201
per person
8 Jan - 15 Jan
found 7 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (3,388 reviews)
Great location, very central. Clean rooms, lovely staff
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 7 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (1,771 reviews)
It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively setting. Welcome champagne upon check in was a nice touch. The Terrace 16 restaurant/bar also served scrumptious choices on the menu. Overall, very satisfied with our stay.
Reviewed on 14 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 7 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (1,131 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 7 hours 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
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 7 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (2,226 reviews)
Room was super clean. Awesome view and the staff was great!
Reviewed on 16 Nov 2025
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Price found within the past 48 hours. Click for updated prices.
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 7 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
18.8/10 Exceptional! (1,771 reviews)
It was absolutely wonderful. We were upgraded to a suite which was pretty sweet (no pun intended)! At night the surrounding view of the lake along the lakeside of the hotel was spectacular. The Rebar on the mezzanine floor with a live musician playing a saxophone on a Saturday, was a cozy and lively setting. Welcome champagne upon check in was a nice touch. The Terrace 16 restaurant/bar also served scrumptious choices on the menu. Overall, very satisfied with our stay.
Reviewed on 14 Nov 2025
The Peninsula Chicago
Downtown Chicago
Price was AU$5,936, price is now AU$5,681 per person
AU$5,681
per person
8 Jan - 15 Jan
found 7 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
19.6/10 Exceptional! (1,002 reviews)
Historic hotel, located in a quiet neighborhood in the heart of the city, within walking distance of everything.
Reviewed on 14 Nov 2025
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
