
Southmoor Vacations from ¥258,975
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 Southmoor Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥312,320, price is now ¥258,975 per person
¥258,975
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Our stay at the RIU exceeded our expectations within the hotel! Only downside was that it didn’t have a parking garage. Although the parking across the street wasn’t bad at all.
Reviewed on Jan 20, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥400,704, price is now ¥319,797 per person
¥319,797
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Exceptional service, great location, beautiful hotel
Reviewed on Jan 20, 2026

Level Chicago – Old Town
Downtown Chicago
Price was ¥337,890, price is now ¥285,200 per person
¥285,200
per person
Mar 15 - Mar 19
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly
Reviewed on Jan 18, 2026

Where to stay in Southmoor
Find the best Southmoor areas and neighborhoods for the activities you enjoy most. Learn more about Southmoor

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.
Southmoor Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥21,356 per night from Feb 14 to Feb 15
¥21,356
¥25,069 total
Feb 14 - Feb 15
includes taxes & fees
8/10 Very Good! (9,799 reviews)
Room was clean. Only interaction i had with staff is when i checked in and checked out. You should add on your advertisement, parking that you pay 62 a day for has no in and out privileges. No one rents a car to leave parked. How many times a day do i have to keep paying 62? I gave it a food rating ...
Reviewed on Jan 20, 2026

Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥20,625 per night from Feb 1 to Feb 2
¥20,625
¥28,855 total
Feb 1 - Feb 2
includes taxes & fees
8.4/10 Very Good! (2,555 reviews)
Did not have breakfast
Reviewed on Jan 19, 2026

Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥21,273 per night from Jan 28 to Jan 29
¥21,273
¥28,927 total
Jan 28 - Jan 29
includes taxes & fees
8.4/10 Very Good! (2,246 reviews)
Clean, attractive classic looking room and bathroom.
Reviewed on Jan 13, 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
Discover the most popular places to visit in Southmoor

Michigan Avenue
4.5/5(332 reviews)
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Things to do

Chicago: Navy Pier Centennial Wheel Ticket
¥3,883
per adult
88% of travellers recommend

Chicago Blackhawks Ice Hockey Game at United Center
¥10,515
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.





