
Montgomery Vacations from ¥210,174
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The Latest Montgomery Vacation Packages
Price found within the past 48 hours. Click for updated prices.

The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Price was ¥265,634, price is now ¥210,174 per person
¥210,174
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (2,027 reviews)
The property is Great I got married there!
Reviewed on Sep 24, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥343,518, price is now ¥246,906 per person
¥246,906
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Clean rooms and friendly staff. Centrally located. Breakfast is a feast. One of the best hotel breakfasts I have experienced. Roof top bar has a terrific view of the City and perfect for an evening cocktail. They don't have their own parking. I think this is typical for downtown so I recommend figuring that out before you arrive.
Reviewed on Sep 24, 2025

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥399,230, price is now ¥289,662 per person
¥289,662
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
The hotel was above the expectations and river view was fabulous also staff were incredibly awesome specially the front dest employee Natalia she was helpful, smiling and welcoming.
Reviewed on Sep 24, 2025

theWit Chicago, a Hilton Hotel
Downtown Chicago
Price was ¥326,194, price is now ¥242,014 per person
¥242,014
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!
Reviewed on Sep 21, 2025

The Emily Hotel
Downtown Chicago
Price was ¥304,646, price is now ¥239,497 per person
¥239,497
per person
Nov 29 - Dec 3
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,222 reviews)
I was so disappointed in my stay at the Emily. For almost $500/night I was expecting nice, spacious rooms. The room was so small, the sink was in the hallway, the bed was so uncomfortable, dingy design. I’ve stayed at better Aloft or Moxy rooms. The food at Fora, the hotel restaurant, is uninspired and unseasoned. The brunch chiliques were bland. Skip this hotel in west loop and stay at the hoxton instead
Reviewed on Sep 22, 2025
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 ¥12,339 per night from Oct 2 to Oct 3
¥12,339
¥13,694 total
Oct 2 - Oct 3
includes taxes & fees
8.8/10 Excellent! (2,269 reviews)
"I don’t really have any complaints. I thought it was pretty nice. The only issue I can see is if somebody wasn’t able to stand very well. The bathtubs are really tight. It’s almost like you can’t stand flat on the ground."
Reviewed on Sep 19, 2025

The Champagne Lodge & Luxury Suites
16 W 621 S. Frontage Rd, Willowbrook, IL
The price is ¥13,126 per night from Sep 29 to Sep 30
¥13,126
¥17,632 total
Sep 29 - Sep 30
includes taxes & fees
8.4/10 Very Good! (1,257 reviews)
Just Relaxing
"I had a wonderful time and was able to relax."
Reviewed on Sep 23, 2025

Motel 6 Naperville, IL
1585 Naperville Wheaton Road, Naperville, IL
Fully refundableReserve now, pay when you stay
The price is ¥7,774 per night from Oct 14 to Oct 15
¥7,774
¥8,665 total
Oct 14 - Oct 15
includes taxes & fees
7.8/10 Good! (1,076 reviews)
"The property was super clean and the staff was nice and knowledgeable"
Reviewed on Sep 16, 2025
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.