Chicago Holidays from AU$6,234
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The Latest Chicago Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Price was AU$7,067, price is now AU$6,234 per person
AU$6,234
per person
2 Jan - 8 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Its room was perfect the only bad part was their was a couple stains in the bathroom wall
Reviewed on 1 Dec 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was AU$7,947, price is now AU$6,774 per person
AU$6,774
per person
2 Jan - 8 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The property was beautiful. The holiday decorations were magical. The staff was friendly and helpful.
Reviewed on 1 Dec 2025
The Emily Hotel
Downtown Chicago
Price was AU$7,246, price is now AU$6,354 per person
AU$6,354
per person
2 Jan - 8 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.
Reviewed on 26 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
Fully refundableReserve now, pay when you stay
The price is AU$169 per night from 18 Dec to 19 Dec
AU$169
18 Dec - 19 Dec
includes taxes & fees
8.4/10 Very Good! (5,333 reviews)
The location is great! We had to leave a couple hours into our stay due to a major snowstorm so my feedback is limited. We weren’t able to enjoy the breakfast this time but it was fantastic last time we were there. The room was very clean and staff were extremely helpful. I received a text asking ...
Reviewed on 30 Nov 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 7 Dec to 8 Dec
AU$149
7 Dec - 8 Dec
includes taxes & fees
8.8/10 Excellent! (3,402 reviews)
Loved it!
Reviewed on 29 Nov 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 28 Dec to 29 Dec
AU$225
28 Dec - 29 Dec
includes taxes & fees
8.4/10 Very Good! (2,099 reviews)
Great atmosphere and friendly staff.
Reviewed on 26 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
4.5/5(64 reviews)
A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.
Millennium Park
4.5/5(73 reviews)
One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.
United Center
5/5(8 reviews)
Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
What to do in Chicago
Wendella's 90-min Chicago River Architecture Tour
AU$69
per adult
94% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
AU$38
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.
