Montgomery Vacations from ￥302,538
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The Latest Montgomery Vacation Packages
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 11 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Great location, we were able to walk everywhere we wanted to see. The red line is about a 10 minute walk if you are heading to Wrigley.
Reviewed on Jun 26, 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 8 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
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥471,278, price is now ￥399,099 per person
￥399,099
per person
Aug 9 - Aug 14
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
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 ￥14,882 per night from Jun 29 to Jun 30
￥14,882
￥16,516 total
Jun 29 - Jun 30
includes taxes & fees
9/10 Wonderful! (2,818 reviews)
"Nice stay, breakfast was yummy, rooms were clean."
Reviewed on Jun 26, 2026
Chicago Club Inn & Suites
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is ￥11,274 per night from Jul 26 to Jul 27
￥11,274
￥12,512 total
Jul 26 - Jul 27
includes taxes & fees
7.2/10 Good! (1,604 reviews)
"Simple and relaxing resort with serene garden courtyard. Hubby and I enjoyed the 2 person whirlpool tub. The room could use a refresh but served our purpose of staycation. Hot breakfast was fresh."
Reviewed on Jun 25, 2026
Red Roof Inn PLUS+ Chicago - Willowbrook
7535 Kingery Highway Willowbrook IL
Fully refundableReserve now, pay when you stay
The price is ￥11,939 per night from Jul 12 to Jul 13
￥11,939
￥13,369 total
Jul 12 - Jul 13
includes taxes & fees
6.4/10 (1,160 reviews)
"The room was disgusting and unsat. critters and other things. The smell was atrocious upon entering the room. On the site the photos were deceptive and misleading. The comforters were stained and had smells in them. in the long run look at all sites and and reviews better"
Reviewed on Jun 23, 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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
