Central Chicago Vacations from ￥335,878
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The Latest Central Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥472,308, price is now ￥335,878 per person
￥335,878
per person
Oct 6 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,096 reviews)
Quick and easy check in and check out, friendly and helpful staff
Reviewed on Aug 29, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ￥778,928, price is now ￥543,686 per person
￥543,686
per person
Oct 6 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump
Reviewed on Aug 29, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was ￥609,956, price is now ￥430,196 per person
￥430,196
per person
Oct 6 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,100 reviews)
The best hotel for Navy Pier
Reviewed on Aug 28, 2025
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥501,303, price is now ￥354,314 per person
￥354,314
per person
Oct 6 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (3,067 reviews)
The staff was helpful &’ nice. The hotel itself was clean
Reviewed on Aug 24, 2025
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ￥487,238, price is now ￥354,164 per person
￥354,164
per person
Oct 6 - Oct 13
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,975 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.
Reviewed on Aug 25, 2025
Where to stay in Central Chicago
Find the best Central Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Central Chicago
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
Find the Best Central Chicago Vacation Packages
Central Chicago Hotel Deals
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥22,202 per night from Sep 3 to Sep 4
￥22,202
￥26,063 total
Sep 3 - Sep 4
includes taxes & fees
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥28,980 per night from Sep 15 to Sep 16
￥28,980
￥34,020 total
Sep 15 - Sep 16
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is ￥24,739 per night from Sep 3 to Sep 4
￥24,739
￥29,040 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (4,802 reviews)
"Very nice,everything is around.Highly recommend."
Reviewed on Aug 27, 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 Central Chicago
Michigan Avenue
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.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
What to do in Central Chicago
Chicago By Night River & Lake Cruise
￥6,651
per adult
96% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
￥5,986
per adult
94% of travellers recommend
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Activities
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.