Central Chicago Vacations from ￥313,970
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The Latest Central Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Price was ￥384,375, price is now ￥313,970 per person
￥313,970
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,653 reviews)
The views were spectacular
Reviewed on Sep 4, 2025
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Price was ￥500,885, price is now ￥391,596 per person
￥391,596
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,028 reviews)
It was great for a short stay with my family. We enjoyed the location and proximity to public transportation.
Reviewed on Sep 4, 2025
Virgin Hotels Chicago
Downtown Chicago
Price was ￥444,359, price is now ￥357,198 per person
￥357,198
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Great modern location. The fee onsite was different that the fee told but it was a great stay. I would stay here again.
Reviewed on Sep 1, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥440,848, price is now ￥357,674 per person
￥357,674
per person
Oct 5 - Oct 10
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,129 reviews)
The Lake was beautiful.
Reviewed on Sep 5, 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
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥21,886 per night from Sep 22 to Sep 23
￥21,886
￥25,692 total
Sep 22 - Sep 23
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥26,376 per night from Sep 14 to Sep 15
￥26,376
￥30,962 total
Sep 14 - Sep 15
includes taxes & fees
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ￥24,724 per night from Sep 22 to Sep 23
￥24,724
￥29,024 total
Sep 22 - Sep 23
includes taxes & fees
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
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.
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
4.5/5(7,198 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
What to do in Central Chicago
Wendella's 90-min Chicago River Architecture Tour
￥5,986
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
￥6,651
per adult
96% of travellers recommend
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Flights
Activities
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
