Downtown Chicago Holidays from AU$963
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Your Downtown Chicago Holiday
Reserving a Downtown Chicago holiday package is a great way to get to know this unique neighbourhood. From its must-visit places to its lesser-known delights, you'll be sure to uncover something new. Some leading nearby attractions to see during your trip to Downtown Chicago include Millennium Park, Willis Tower and Art Institute of Chicago. Whatever your travel plans or the size of your budget, booking your dream Downtown Chicago holiday is a cinch with Expedia.
Top Holiday Package Deals in Downtown Chicago
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was AU$1,181, price is now AU$963 per person
AU$963
per person
23 Dec - 26 Dec
found 22 hours ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
Clean room, friendly staff, great location and within walking distance from all shops!
Reviewed on 7 Oct 2025
Pendry Chicago
Downtown Chicago
Price was AU$1,361, price is now AU$1,027 per person
AU$1,027
per person
23 Dec - 26 Dec
found 22 hours ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.
Reviewed on 11 Oct 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was AU$1,295, price is now AU$977 per person
AU$977
per person
23 Dec - 26 Dec
found 22 hours ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine
Reviewed on 4 Oct 2025
Swissotel - Chicago
Downtown Chicago
Price was AU$1,263, price is now AU$971 per person
AU$971
per person
23 Dec - 26 Dec
found 22 hours ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
The view from the panoramic view was amazing. The gym was comfortable and the credit to amuse was nice
Reviewed on 9 Oct 2025
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was AU$1,290, price is now AU$1,062 per person
AU$1,062
per person
23 Dec - 26 Dec
found 22 hours ago
Return direct flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,920 reviews)
Fabulous suite overlooking Millenium Park and Lake Michigan. Clean, attentive staff, and good amenities. Walk to everything.
Reviewed on 10 Oct 2025
Our guide on where to stay in Downtown Chicago
Find the best Downtown Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Downtown Chicago
Magnificent Mile
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
Our pick of the best Downtown Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$305 per night from 26 Oct to 27 Oct
AU$305
26 Oct - 27 Oct
includes taxes & fees
8/10 Very Good! (9,333 reviews)
"Very clean"
Reviewed on 7 Oct 2025
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$276 per night from 9 Nov to 10 Nov
AU$276
9 Nov - 10 Nov
includes taxes & fees
8.4/10 Very Good! (5,052 reviews)
"good"
Reviewed on 7 Oct 2025
Freehand Chicago
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$149 per night from 12 Nov to 13 Nov
AU$149
12 Nov - 13 Nov
includes taxes & fees
7.8/10 Good! (2,425 reviews)
"Excellent location, clean and good room partners"
Reviewed on 6 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.
Discover the most popular places to visit in Downtown 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.
Grant Park
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
Activities
Skydeck - Willis Tower Admission
AU$67
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
AU$37
per adult
84% of travellers recommend
Explore a world of travel with Expedia
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- 360 CHICAGO
- Art Institute of Chicago
- Buckingham Fountain
- Busy Beaver Button Museum
- Visit Magnificent Mile
- Chicago Museum of Science and Industry
- Visit The Loop
- Chicago Holidays
- Visit Chicago
- Cloud Gate
- Daley Plaza
- Garfield Park Conservatory
- Gold Coast Holidays
- Grace Abbott Homes Holidays
- Grant Park
- Hyde Park Hair Salon
- Kathy Osterman Beach
- 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
- Car hire near Chicago
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- Car hire near Magnificent Mile
- Compact Car Hire in Chicago
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- Economy Car Hire in Chicago
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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.