Chicago Holidays from AU$2,013
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The Latest Chicago Holiday Deals
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was AU$3,201, price is now AU$2,822 per person
AU$2,822
per person
26 Feb - 1 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.
Reviewed on 11 Jan 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was AU$2,960, price is now AU$2,612 per person
AU$2,612
per person
26 Feb - 1 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
First time there. Staff was helpful and they provided excellent memorable service
Reviewed on 20 Jan 2026
The Emily Hotel
Downtown Chicago
Price was AU$2,389, price is now AU$2,110 per person
AU$2,110
per person
26 Feb - 1 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Everything about this hotel is special. Great staff- awesome restaurant/bar. Location is perfect. This hotel is my destination every time I come to the city. Which is quite often.
Reviewed on 20 Jan 2026
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
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$166 per night from 23 Feb to 24 Feb
AU$166
23 Feb - 24 Feb
includes taxes & fees
8/10 Very Good! (9,790 reviews)
Really interesting place, great price for the location too. Staff was very friendly.
Reviewed on 19 Jan 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$267 per night from 1 Feb to 2 Feb
AU$267
1 Feb - 2 Feb
includes taxes & fees
8.4/10 Very Good! (2,541 reviews)
Great staff, good location .
Reviewed on 14 Jan 2026
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$277 per night from 30 Jan to 31 Jan
AU$277
30 Jan - 31 Jan
includes taxes & fees
9.2/10 Wonderful! (3,260 reviews)
GREAT HOTEL
Reviewed on 22 Jan 2026
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
Chicago: Navy Pier Centennial Wheel Ticket
AU$37
per adult
88% of travellers recommend
Chicago Crime and Mob Bus Tour
AU$73
per adult
92% of travellers recommend
Explore a world of travel with Expedia
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- 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.
