
Central Chicago Mountain Vacations
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Top Mountain vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥352,949, price is now ¥302,538 per person
¥302,538
per person
Sep 19 - Sep 22
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Would have liked coffeemaker in the room and some glasses or cups for water. The bathroom was nice, but for the price, we felt the room was cramped and the window small. Location was convenient.
Reviewed on Jun 26, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥690,245, price is now ¥564,212 per person
¥564,212
per person
Aug 14 - Aug 21
found 9 hours ago
Roundtrip non-stop flight included
Yamagata (GAJ) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
The hotel room cleanliness is of a very high standard. The complementary breakfast is extraordinary with a different majority of food and with a good procedure to take care of guests. The rooftop bar was sophisticated and attracts high class clientele. The room space is big enough to feel comfortable. There is individual Wi-Fi for each room that allows you to connect your phone to the TV. And the location downtown was excellent.
Reviewed on Jun 25, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥666,224, price is now ¥548,055 per person
¥548,055
per person
Aug 8 - Aug 14
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
It was everything I expected! The staff was amazing. Everything ran smoothly. I would say the pool could use a little updating. Everything was delightful. Definitely will be back.
Reviewed on Jun 24, 2026


Thompson Chicago, by Hyatt
Downtown Chicago
Price was ¥488,708, price is now ¥407,436 per person
¥407,436
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,399 reviews)
I truly enjoyed my stay at this hotel. From the moment I arrived, the staff made me feel welcome and valued. Everyone was so friendly, attentive, and genuinely eager to help, which made the experience even more enjoyable.
The hotel was clean, comfortable, and had everything I needed for a relaxing stay. I especially loved the location—it was convenient to restaurants, shopping, and local attractions, making it easy to get around and enjoy the area without any hassle.
Reviewed on Jun 21, 2026
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View all trips5* Mountain vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.

The Peninsula Chicago
Downtown Chicago
Price was ¥498,167, price is now ¥449,412 per person
¥449,412
per person
Sep 19 - Sep 22
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
We love the Peninsula! The staff, location, room, and the Shanghai restaurant top tier.
Reviewed on Jun 21, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥666,224, price is now ¥548,055 per person
¥548,055
per person
Aug 8 - Aug 14
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,893 reviews)
It was everything I expected! The staff was amazing. Everything ran smoothly. I would say the pool could use a little updating. Everything was delightful. Definitely will be back.
Reviewed on Jun 24, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips3 Night Mountain vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥352,949, price is now ¥302,538 per person
¥302,538
per person
Sep 19 - Sep 22
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Would have liked coffeemaker in the room and some glasses or cups for water. The bathroom was nice, but for the price, we felt the room was cramped and the window small. Location was convenient.
Reviewed on Jun 26, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥378,586, price is now ¥322,070 per person
¥322,070
per person
Sep 19 - Sep 22
found 8 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
The hotel room cleanliness is of a very high standard. The complementary breakfast is extraordinary with a different majority of food and with a good procedure to take care of guests. The rooftop bar was sophisticated and attracts high class clientele. The room space is big enough to feel comfortable. There is individual Wi-Fi for each room that allows you to connect your phone to the TV. And the location downtown was excellent.
Reviewed on Jun 25, 2026

Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all trips4 Night Mountain vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.


Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥460,246, price is now ¥373,894 per person
¥373,894
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Would have liked coffeemaker in the room and some glasses or cups for water. The bathroom was nice, but for the price, we felt the room was cramped and the window small. Location was convenient.
Reviewed on Jun 26, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥464,064, price is now ¥379,842 per person
¥379,842
per person
Sep 16 - Sep 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,756 reviews)
Excelente, ubicación perfecta cerca de todo
Reviewed on Jun 23, 2026
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See all available trips from Tokyo to Central Chicago
View all tripsThings to do

Chicago: Navy Pier Centennial Wheel Ticket
¥3,853
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


