
Old Town Chicago Vacations from ¥279,560
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The Latest Old Town Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was ¥467,216, price is now ¥279,560 per person
¥279,560
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Nice and good variety breakfast. Room was nice and clean. Good shower with nice pressure. Complimentary bag storage after checking out.
Reviewed on Feb 24, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥647,042, price is now ¥463,177 per person
¥463,177
per person
Apr 14 - Apr 19
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
We had a great stay!
Reviewed on Feb 23, 2026

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥531,588, price is now ¥383,018 per person
¥383,018
per person
Apr 14 - Apr 19
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
From beginning to the end my stay was a 10/10. I only stayed one night but that one night was worth it.
Reviewed on Feb 24, 2026

LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥576,142, price is now ¥415,219 per person
¥415,219
per person
Apr 14 - Apr 19
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Everything was perfect!
Reviewed on Feb 23, 2026

Virgin Hotels Chicago
Downtown Chicago
Price was ¥538,122, price is now ¥391,416 per person
¥391,416
per person
Apr 14 - Apr 19
found 10 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,404 reviews)
Room was very clean, staff was very pleasant. Will definitely return
Reviewed on Feb 15, 2026
Where to stay in Old Town Chicago
Find the best Old Town Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Old Town Chicago

Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Old Town Chicago Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥13,801 per night from Feb 25 to Feb 26
¥13,801
¥16,201 total
Feb 25 - Feb 26
includes taxes & fees
8/10 Very Good! (9,931 reviews)
Overall we enjoy this hotel, some fixtures in the bathroom were missing. But on an important note, we were woken up by the front desk and by security at 3 AM regarding a noise and an assault above our room.
Reviewed on Feb 24, 2026

Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥15,317 per night from Mar 4 to Mar 5
¥15,317
¥22,340 total
Mar 4 - Mar 5
includes taxes & fees
9.4/10 Exceptional! (3,400 reviews)
The hotel was new and clean. The lobby is beautiful but the halls and the rooms feel a bit institutional. Also, only having two bottles of water provided for whatever your trip length is is very inconvenient. The only option is to buy $6-$8 water from the bar. 1 night = 2 bottles of water. 1 week, ...
Reviewed on Feb 24, 2026

Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥15,851 per night from Mar 4 to Mar 5
¥15,851
¥18,607 total
Mar 4 - Mar 5
includes taxes & fees
8.6/10 Excellent! (5,681 reviews)
Great location, room was spacious, checkin fast and seemless, breakfast was top notch!! By far one of the best we have had in our travels
Reviewed on Feb 24, 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.
Frequently asked questions
Things to do

Chicago River: 1.5-Hour Guided Architecture Cruise
¥6,810
per adult
98% of travellers recommend

Wendella's 90-min Chicago River Architecture Tour
¥6,269
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




