Chicago Holidays from AU$3,261
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to AU$703 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Chicago Holiday Deals
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)
The room had no soundproofing. Every night a car was revving loudly across Michigan Ave around midnight, making it impossible to sleep without noise-cancelling AirPods.
Reviewed on 18 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 Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Chicago Holiday
Chicago Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
Population | 2,720,500 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Chicago Riverwalk, Shedd Aquarium and Art Institute of Chicago |
Our pick of the best Chicago Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
The price is AU$158 per night from 8 Dec to 9 Dec
AU$158
8 Dec - 9 Dec
includes taxes & fees
8.4/10 Very Good! (5,271 reviews)
Great location. Fantastic staff. Breakfast was absolutely amazing. Only issue we had was insufficient bath towels and front desk resolved this quickly. I would gladly stay here again without a doubt
Reviewed on 18 Nov 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$230 per night from 25 Nov to 26 Nov
AU$230
25 Nov - 26 Nov
includes taxes & fees
8.4/10 Very Good! (2,057 reviews)
Excellent!
Reviewed on 13 Nov 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$162 per night from 14 Dec to 15 Dec
AU$162
14 Dec - 15 Dec
includes taxes & fees
8.8/10 Excellent! (3,284 reviews)
Amazing
Reviewed on 14 Nov 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.
Discover the most popular places to visit in Chicago
Navy Pier
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
Millennium Park
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
Chicago Riverwalk
Stroll along the waterfront of the Chicago River to pass some of the city’s most appealing attractions and appreciate how a once grim area has been successfully revamped.
What to do in Chicago
Skydeck - Willis Tower Admission
AU$67
per adult
98% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
AU$37
per adult
84% of travellers recommend
Explore a world of travel with Expedia
Lodging
- Hotels near Aon Center
- Hotels near Art Institute of Chicago
- Hotels near Auditorium Building and Theatre
- Hotels near Buckingham Fountain
- Hotels near Cadillac Palace Theatre
- Apartments in Central Chicago
- B&B in Central Chicago
- Luxury Hotels in Central Chicago
- Hotels near Chicago Cultural Center
- Hotels near Chicago Museum Campus-11th Street Station
- Hotels near Chicago Riverwalk
- Hotels near Chicago Symphony Orchestra
- Hotels near Chicago Theatre
- Hotels near Chicago Union Station
- Resort in Clark-Lake Station
- Hotels near Cloud Gate
- Hotels near Daley Plaza
- Beach Hotels in Downtown Chicago
- Boutique Hotels in Downtown Chicago
- Cheap Hotels in Downtown Chicago
- Hilton Hotels in Downtown Chicago
- Historic Hotels in Downtown Chicago
- Hotels with Parking in Downtown Chicago
- Lgbt Welcoming Hotels in Downtown Chicago
- Luxury Hotels in Downtown Chicago
- Spa Hotels in Downtown Chicago
- Downtown Chicago Hotels
- Four Seasons Hotels in Gold Coast
- Hotels near Goodman Theater
- Hotels near Grant Park
- Hotels near House of Blues Chicago
- Hotels near James M. Nederlander Theatre
- Hotels near LaSalle Street Station
- Hotels near Lollapalooza
- Hotels near Madison-Wabash Station
- Magnificent Mile Hotels
- Hotels near Michigan Avenue Bridge
- Hotels near Michigan Avenue
- Hotels near Millennium Park
- Printers Row Hotels
- Hotels near Randolph-Wabash Station
- All Inclusive Hotels in River North
- Boutique Hotels in River North
- Cheap Hotels in River North
- Hotels with Parking in River North
- Luxury Hotels in River North
- River North Hotels
- Hotels near Ronald McDonald House near Lurie Children’s
- Hotels near Roosevelt University
- Hotels near State Street
- Historic Hotels in Streeterville
- Streeterville Hotels
- Boutique Hotels in The Loop
- Luxury Hotels in The Loop
- Ski Hotels in The Loop
- The Loop Hotels
- Theatre District Hotels
- Hotels near Willis Tower
Flights
Packages
- 360 CHICAGO
- Art Institute of Chicago
- Austin Holidays
- Buckingham Fountain
- Busy Beaver Button Museum
- Visit Downtown Chicago
- Visit Magnificent Mile
- Chicago Museum of Science and Industry
- Visit River North
- Visit The Loop
- Cloud Gate
- Daley Plaza
- Downtown Chicago Holidays
- Garfield Park Conservatory
- Gold Coast Holidays
- Grace Abbott Homes Holidays
- Grant Park
- Hyde Park Hair Salon
- Lincoln Hall
- Lincoln Park Conservatory
- Lincoln Park
- Lincoln Park Zoo
- Millennium Park
- Montrose Beach
- Navy Pier
- Oak Street Beach
- Robie House
- Rookery
- South Loop Holidays
- United Center
- University of Illinois Chicago
- Water Tower Place
- Wicker Park Holidays
- Willis Tower
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
