Chicago Vacations from ￥200,594
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 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 Vacation Packages
Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ￥256,630, price is now ￥200,594 per person
￥200,594
per person
Mar 15 - Mar 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Amazing room view great service just no microwave that’s all they need
Reviewed on Dec 27, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥385,898, price is now ￥274,520 per person
￥274,520
per person
Mar 15 - Mar 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Excellent! Everything was perfect, beautiful and the staff are amazing!
Reviewed on Dec 27, 2025
The Peninsula Chicago
Downtown Chicago
Price was ￥399,685, price is now ￥297,235 per person
￥297,235
per person
Mar 15 - Mar 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Beautifully decorated for Christmas. Spotless as always.
Reviewed on Dec 27, 2025
Hilton Chicago O'Hare Airport
O'Hare
Price was ￥271,780, price is now ￥207,398 per person
￥207,398
per person
Feb 11 - Feb 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Early check in available for $25, worth it for getting rest between flights. Very friendly staff
Reviewed on Dec 27, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ￥285,935, price is now ￥221,613 per person
￥221,613
per person
Mar 15 - Mar 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
Room was very spacious and clean. The location was perfect walking distance from a lot great eating and tourists spots.
Reviewed on Dec 18, 2025
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.
Find the Best Chicago Vacation Packages
Chicago Hotel Deals
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥13,994 per night from Jan 5 to Jan 6
￥13,994
￥16,426 total
Jan 5 - Jan 6, 2026
includes taxes & fees
8.8/10 Excellent! (3,549 reviews)
Room was warm Recommend softer toilet paper please
Reviewed on Dec 23, 2025
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥20,542 per night from Jan 2 to Jan 3
￥20,542
￥28,030 total
Jan 2 - Jan 3, 2026
includes taxes & fees
8.4/10 Very Good! (2,170 reviews)
Clean rooms, extremely friendly staff, onsite Starbucks, Lockwood restaurant was amazing, beautiful gathering area in the lounge. Close to all the Christmas must do’s. Decorated so so beautifully for Christmas!
Reviewed on Dec 24, 2025
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥12,776 per night from Jan 9 to Jan 10
￥12,776
￥14,998 total
Jan 9 - Jan 10, 2026
includes taxes & fees
8.6/10 Excellent! (2,014 reviews)
Easy check in. Ready to upgrade. I love how central it is and the water stations on each floor. This is our second time to stay here and will do it again!
Reviewed on Dec 23, 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
Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Chicago
Wendella's 90-min Chicago River Architecture Tour
￥6,310
per adult
94% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
￥3,827
per adult
88% of travellers recommend
Explore a world of travel with Expedia
- Gay friendly Hotels in Downtown Chicago
- Capsule Hotels in Chicago
- Aparthotels in Rush Street
- Luxury Hotels in Theatre District
- Hotels near Chicago Architecture Foundation
- Adults Only Resorts & in The Loop
- Condo Rentals in Clark-Lake Station
- Hotels near DePaul University-Loop Campus
- Hotels near Aon Center
- Apartments in Chicago
- Hotels with Hot Tubs in Chicago
- Near South Side Hotels
- Business Hotels in Chicago
- Luxury Hotels in Central Chicago
- River North Hotels
- Streeterville Hotels
- Hotels near Civic Opera House
- Town Houses in Chicago
- Pet-Friendly Hotels in Chicago
- Chinatown Hotels
- Hotels near Chase Tower
- Boutique Hotels in Chicago
- Hotels near Union Park
- Golf Hotels in Chicago
- B&B in Chicago
- Luxury Hotels in Downtown Chicago
- Hotels near Goodman Theater
- Shopping Hotels in Magnificent Mile
- Cheap Hotels in Downtown Chicago
- Hotels near 360 CHICAGO
- Cheap Hotels in Chicago
- Ryokans in Chicago
- Shopping Hotels in Downtown Chicago
- Chicago Hotels
- Business Hotels in Old Town Chicago
- Romantic Hotels in Downtown Chicago
- Adventure Hotels in Chicago
- Green Hotels in The Loop
- Hotels near Grand Station
- Hotels near Cadillac Palace Theatre
- Downtown Chicago Hotels
- Hostels in Chicago
- Hotels near Northwestern Memorial Hospital
- Hotels with an Indoor Pool in Gold Coast
- Aparthotels in Chicago Station
- Gay friendly Hotels in Chicago
- Family Hotels in The Loop
- Adults Only Resorts & in Downtown Chicago
- South Loop Hotels
- Hotels near Adler Planetarium and Astronomy Museum
- Beach Hotels in Chicago
- Boutique Hotels in Downtown Chicago
- Green Hotels in Downtown Chicago
- Hotels near Grant Park
- Resorts in Chicago McCormick Place Station
- Hotels near Columbia College Chicago
- Theatre District Hotels
- Hotels near Art Institute of Chicago
- Resorts & Hotels with Spas in Downtown Chicago
- Hotels with Bars in Chicago
- Hotels near Chicago Station
- Hotels near 333 West Wacker Drive
- The Loop Hotels
- Hotels near Michigan Avenue
- Hotels near Millennium Station
- Aparthotels in Chicago Station
- Hotels near Chicago Theatre
- Central Station Hotels
- Cheap Hotels in Theatre District
- Hotels with smoking rooms in Chicago
- All-Inclusive Hotel Hotels in Downtown Chicago
- Pet-Friendly Hotels in Downtown Chicago
- Houseboats in Chicago Station
- Apartments in Central Chicago
- West Loop Hotels
- Rv Parks in Chicago
- Luxury Hotels in The Loop
- Aparthotels in Chicago
- Hotels near Harris Theater
- Motels in Chicago
- Hotels near James M. Nederlander Theatre
- Hotels near Richard J. Daley Center
- Hotels with an Indoor Pool in Rush and Division
- Hotels near Washington Square
- Rush and Division Hotels
- Hotels near Chicago Union Station
- Hotels near Carbide and Carbon Building
- Hotels near Chicago Board of Trade Building
- Hotels near Chicago Cultural Center
- Family Hotels in Chicago
- Hotels with an Indoor Pool in Chicago
- Hotels with Hot Tubs in Downtown Chicago
- 5 Star Hotels in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
