
Southwest Side Vacations from ¥246,796
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The Latest Southwest Side Vacation Packages
Price found within the past 48 hours. Click for updated prices.

Eaglewood Resort and Spa
Price was ¥265,064, price is now ¥246,796 per person
¥246,796
per person
Jun 26 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (1,005 reviews)
Good hotel but to bad the hot tub is not hot enough and there's an another customer also complained about that
Reviewed on Apr 8, 2026

Palmer House a Hilton Hotel
Downtown Chicago
Price was ¥381,666, price is now ¥325,430 per person
¥325,430
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,344 reviews)
We had a wonderful stay. Enjoyed breakfast at the hotel, with wonderful, attentive staff.
Reviewed on Apr 8, 2026

Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Price was ¥324,456, price is now ¥294,628 per person
¥294,628
per person
Jun 25 - Jun 29
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (5,808 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly.
We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request so we hung out in the atrium for an hour and a half and it still wasn’t done, had to go down to the front desk again and ask which was very frustrating.
Reviewed on Apr 9, 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

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥18,247 per night from Apr 26 to Apr 27
¥18,247
¥21,420 total
Apr 26 - Apr 27
includes taxes & fees
8/10 Very Good! (10,073 reviews)
Room was clean, but cheaply remodeled and nothing really special.
Reviewed on Apr 9, 2026

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ¥21,735 per night from Apr 26 to Apr 27
¥21,735
¥25,516 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,085 reviews)
It was a pretty good hotel had a little hiccup, but overall we was able to work it out, but I will be coming back with my family.
Reviewed on Apr 9, 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 ¥24,653 per night from Apr 19 to Apr 20
¥24,653
¥28,940 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (5,828 reviews)
Perfect location for a family trip, the hotel amenities were amazing and the staff was very friendly. We did have an issue with having our room serviced during our stay, after a long day out we came back to it still not being serviced, after asking the front desk they said they would put in the request ...
Reviewed on Apr 9, 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
4.5/5(2,149 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Naval Base Great Lakes
4.5/5(461 reviews)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Navy Pier
4.5/5(4,923 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Southwest Side

Wendella's 90-min Chicago River Architecture Tour
¥6,427
per adult
94% of travellers recommend
Frequently asked questions
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