Chicago Holidays
- Plan, book, travel with confidence
- Better togetherSave up to HK$1,282 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
Top Chicago Flight + Hotel Deals
Price found within the past 48 hours. Click for updated prices.
Hilton Orrington / Evanston
Downtown Evanston
Price was HK$3,649, price is now HK$2,769 per person
HK$2,769
per person
7 Mar - 10 Mar
found 14 hours ago
Return direct flight included
Toronto (YTO) to Chicago (ORD)
7.6/10 Good! (1,002 reviews)
Courteous staff, good breakfast selection,
Reviewed on 23 Jan 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was HK$5,281, price is now HK$3,547 per person
HK$3,547
per person
7 Mar - 10 Mar
found 14 hours ago
Return direct flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Beautiful room, great location. Will definitely stay there again.
Reviewed on 28 Jan 2026
Arlo Chicago
Downtown Chicago
Price was HK$4,547, price is now HK$3,453 per person
HK$3,453
per person
7 Mar - 10 Mar
found 14 hours ago
Return direct flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
The hotel itself was really nice, but we had to move rooms because the adjoining room was being really loud at 10 AM on a Saturday.
Very hard to find parking, but it’s an alright spot.
Reviewed on 27 Jan 2026
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.
Top hotels in Chicago
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is HK$1,053 per night from 14 Feb to 15 Feb
HK$1,053
HK$1,236 total
14 Feb - 15 Feb
includes taxes & fees
8/10 Very Good! (9,821 reviews)
Yes perfectly clean
Reviewed on 24 Jan 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is HK$825 per night from 5 Feb to 6 Feb
HK$825
HK$969 total
5 Feb - 6 Feb
includes taxes & fees
8.4/10 Very Good! (5,594 reviews)
AC kept the room warm, staff was nice and helpful with travel accommodations
Reviewed on 24 Jan 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is HK$1,528 per night from 27 Feb to 28 Feb
HK$1,528
HK$1,794 total
27 Feb - 28 Feb
includes taxes & fees
8.2/10 Very Good! (2,202 reviews)
Room was great and so was the service.
Reviewed on 25 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.
Popular places to visit
Soldier Field
4/5(44 reviews)
Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.
Grant Park
4.5/5(96 reviews)
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
Six Flags Great America
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
What to do in Chicago
Chicago: Navy Pier Centennial Wheel Ticket
HK$191
per adult
88% of travellers recommend
Chicago Crime and Mob Bus Tour
HK$382
per adult
92% of travellers recommend
Explore a world of travel with Expedia
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- Ping Tom Memorial Park
- Bridgehouse and Chicago River Museum
- Monadnock Building
- Downtown Chicago Holidays
- Montrose Beach
- Chicago History Museum
- Hyde Park Hair Salon
- Greater Salem Baptist Church
- Peggy Notebaert Nature Museum
- Grace Abbott Homes Holidays
- Wintrust Arena
- Aon Center
- Water Tower Place
- Lincoln Park Zoo
- Prentice Women's Hospital
- Chicago Museum Campus Holidays
- Frank Lloyd Wright Historic District
- Lincoln Park Conservatory
- Gold Coast Holidays
- United Center
- North Avenue Beach
- Holy Name Cathedral
- Art Institute of Chicago
- Loyola University Chicago
- Willis Tower
- Kathy Osterman Beach
- Buckingham Fountain
- Crown Fountain
- Soldier Field
- Grant Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
