
Southwest Side Vacations from ¥270,646
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The Latest Southwest Side Vacation Packages
Price found within the past 48 hours. Click for updated prices.


Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥548,432, price is now ¥396,654 per person
¥396,654
per person
May 14 - May 19
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
The view from our room was amazing. Everyone their is friendly and willing to help. The hotel is clean and inviting. Would recommend ten stars if I could.
Reviewed on Feb 22, 2026

Virgin Hotels Chicago
Downtown Chicago
Price was ¥386,440, price is now ¥294,140 per person
¥294,140
per person
May 14 - May 19
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) 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

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥436,495, price is now ¥348,258 per person
¥348,258
per person
May 14 - May 19
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,008 reviews)
Big rooms, great location, and the view was amazing! We truly enjoyed our stay overall and the space was perfect for our family.
However, we were a family of 5 staying for 3 days and only received towels for 3 people. We had to request the missing towels each day. The same happened with the sofa bed there were no sheets or bedding provided, and we had to contact the front desk at night for them to bring it.
Other than that, we loved our stay and would definitely come back!
Reviewed on Feb 21, 2026

River Hotel
Downtown Chicago
Price was ¥352,675, price is now ¥296,551 per person
¥296,551
per person
May 14 - May 19
found 18 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (4,800 reviews)
The room was exactly as advertised, efficient, clean , and priced right.
Reviewed on Feb 22, 2026
Where to stay in Southwest Side
Find the best Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Side

Back of the Yards
2 out of top 10 points of interest in this area
While Back of the Yards might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Bridgeport Art Center and Zhou B Art Center.
Find the Best Southwest Side Vacation Packages
Southwest Side Hotel Deals

Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥15,358 per night from Mar 4 to Mar 5
¥15,358
¥22,398 total
Mar 4 - Mar 5
includes taxes & fees
9.2/10 Wonderful! (3,388 reviews)
So clean, amazing breakfast - high quality rooms
Reviewed on Feb 22, 2026

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
8/10 Very Good! (9,926 reviews)
Great place
Reviewed on Feb 22, 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 ¥15,257 per night from Mar 4 to Mar 5
¥15,257
¥17,909 total
Mar 4 - Mar 5
includes taxes & fees
8.4/10 Very Good! (5,683 reviews)
Nice location, clean room, Happy Hour passes, and included breakfast.
Reviewed on Feb 22, 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.
Discover the most popular places to visit in Southwest Side

Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
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.

Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Southwest Side

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
Frequently asked questions
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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.





