Central Chicago Mountain Vacations
Book a Mountain Hotel + Flight or Car together to unlock savings
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- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
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Top Mountain vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
￥379,826
per person
Oct 1 - Oct 8
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
My go to place to stay. Luxurious, travel-friendly rooms, excellent pool/hot tub area outside, and great workout facilities. Fantastic location next to Fulton Market. The desk staff is always exceptional and helpful.
Reviewed on Aug 12, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
￥405,665
per person
Oct 1 - Oct 8
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
I had an amazing time at the hotel. The employees were helpful and the rooftop view is amazing.
Reviewed on Aug 17, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
￥523,290
per person
Oct 1 - Oct 8
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.
Reviewed on Aug 16, 2026
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View all trips5* Mountain vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥523,290
per person
Oct 1 - Oct 8
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
This is an excellent 5 star hotel. So accommodating in every way possible. This is the second time I have stayed at this Chicago property.
Reviewed on Aug 16, 2026
Nobu Hotel Chicago
Downtown Chicago
￥582,604
per person
Oct 9 - Oct 12
found 18 hours ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9.4/10 Exceptional! (897 reviews)
Rooms and beds are always so nice. Very calming and always get a good night’s sleep. I’ve always had a great experience. One detail which falls short is the toilet paper is very rough. Aside from this detail everything else surpasses my expectations.
Reviewed on Aug 16, 2026
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View all trips3 Night Mountain vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
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View all tripsThings to do
Chicago: Navy Pier Centennial Wheel Ticket
￥3,920
per adult
90% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,518
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.
