Chicago Adventure Vacations
Book a Adventure 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
Top Adventure vacation packages in Chicago
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was ￥748,800, price is now ￥672,508 per person
￥672,508
per person
Apr 29 - May 5
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
Reviewed on Mar 27, 2026
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Price was ￥665,902, price is now ￥600,634 per person
￥600,634
per person
Apr 29 - May 5
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,858 reviews)
The pool is spectacular - but deep! Kids should bring floats - it's an 19th century pool redone for today so ladders only. LOVED the location and very nice staff. Very helpful. Breakfast on site was pricey was excellent. All meals are pricey in Chicago so to be expected I suppose.
Reviewed on Mar 26, 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
Price was ￥448,796, price is now ￥405,562 per person
￥405,562
per person
Apr 29 - May 5
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (2,245 reviews)
Excellent room, well designed and spacious
Reviewed on Mar 26, 2026
5* Adventure vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥387,162, price is now ￥369,124 per person
￥369,124
per person
Jun 11 - Jun 14
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (999 reviews)
Service was wonderful! Hotel is very well located close to shops, restaurants and coffee shops. Lots to see and do around and hotel itself is pure luxury. We had a wonderful stay!
Reviewed on Mar 27, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥748,800, price is now ￥672,508 per person
￥672,508
per person
Apr 29 - May 5
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Excellent room and facilities. Helpfull staff and amazing locstion.
Reviewed on Mar 27, 2026
3 Night Adventure vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Warwick Allerton - Chicago
Downtown Chicago
Price was ￥313,202, price is now ￥276,068 per person
￥276,068
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (3,039 reviews)
Requested additional towels, never came. Luggage racks were difficult to obtain. Rooms are small. Bring your own hairdryer. Water pressure in shower is minimal.
Reviewed on Mar 27, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥331,952, price is now ￥300,328 per person
￥300,328
per person
Jun 11 - Jun 14
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,646 reviews)
Hotel is beautiful and located in an excellent area. Everything is around you
Reviewed on Mar 28, 2026
4 Night Adventure vacations in Chicago
Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown Magnificent Mile
Downtown Chicago
Price was ￥398,072, price is now ￥364,765 per person
￥364,765
per person
Jun 12 - Jun 16
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,828 reviews)
Great omelette station
Reviewed on Mar 27, 2026
Top Adventure Chicago Hotels
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,335 reviews)
All in all, it was an excellent experience with the exception of the water pressure. The hot water pressure was absolutely horrible.
Reviewed on Mar 27, 2026
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 4 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
9.4/10 Exceptional! (3,462 reviews)
Increíble hotel súper friendly staff!
Reviewed on Mar 27, 2026
Swissotel - Chicago
323 E Wacker Dr Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the ...
9/10 Wonderful! (3,227 reviews)
Some issues with the room and internet, had to switch rooms. The second room had a malfunctioning toilet fill valve, it would shut off due to friction, requiring me to pull the lid and jiggle it to fill. Some outlet's didn't work. Low hanging fruit that can be attended to can go a long way. Staff ...
Reviewed on Mar 27, 2026
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
