Montgomery Vacations from ￥213,174
Book a 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
The Latest Montgomery Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ￥243,866, price is now ￥213,174 per person
￥213,174
per person
Apr 15 - Apr 18
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
The staff is incredible. We always enjoy staying here!
Reviewed on Feb 8, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥310,404, price is now ￥260,047 per person
￥260,047
per person
Apr 15 - Apr 18
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.
Reviewed on Feb 3, 2026
Waldorf Astoria Chicago
Downtown Chicago
Price was ￥315,934, price is now ￥266,546 per person
￥266,546
per person
Apr 15 - Apr 18
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026
Hyatt Regency Chicago
Downtown Chicago
Price was ￥270,720, price is now ￥235,223 per person
￥235,223
per person
Apr 15 - Apr 18
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (3,386 reviews)
Spacious and clean room but improvement points on amenities (missing tissue in tissue casing, need to call for amenities, nondairy milk available but not dairy milk, dirty coffee maker cannot make tea), dark, and separate towers inconvenient with friends & availability of lifts during conference season low. Road works and access by car/cab not warned
Reviewed on Feb 10, 2026
Find the Best Montgomery Vacation Packages
Montgomery Hotel Deals
SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street Lombard IL
Fully refundableReserve now, pay when you stay
The price is ￥11,944 per night from Feb 11 to Feb 12
￥11,944
￥13,256 total
Feb 11 - Feb 12
includes taxes & fees
9/10 Wonderful! (2,545 reviews)
The only complaint I have is the carpet was not cleanedcleaned vacuumed
Reviewed on Feb 4, 2026
The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd Willowbrook IL
The price is ￥15,740 per night from Feb 23 to Feb 24
￥15,740
￥20,585 total
Feb 23 - Feb 24
includes taxes & fees
8.4/10 Very Good! (1,397 reviews)
Estaba la habitación impecable y el personal parecía cortés
Reviewed on Feb 6, 2026
Motel 6 Naperville, IL
1585 Naperville Wheaton Road Naperville IL
Fully refundableReserve now, pay when you stay
The price is ￥7,298 per night from Feb 17 to Feb 18
￥7,298
￥8,137 total
Feb 17 - Feb 18
includes taxes & fees
7.8/10 Good! (1,225 reviews)
Staff was kind and helpful. The location was also amazing. It was a very restful stay. Thank you!
Reviewed on Feb 4, 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.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
