
Far Southeast Side Adventure Vacations
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Top Adventure vacation packages in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.

Level Chicago Fulton Market
Downtown Chicago
Price was ¥399,936, price is now ¥293,079 per person
¥293,079
per person
May 1 - May 6
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥573,705, price is now ¥431,470 per person
¥431,470
per person
Apr 30 - May 6
found 2 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026

Viceroy Chicago
Downtown Chicago
Price was ¥489,058, price is now ¥391,456 per person
¥391,456
per person
Apr 30 - May 6
found 2 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.4/10 Exceptional! (1,129 reviews)
We stayed at the Viceroy Chicago last night and had a wonderful experience. The hotel is stylish, comfortable, and feels thoughtfully designed in every detail. The staff was warm and welcoming from the moment we arrived, and the service throughout our stay was excellent. Our room was spotless with a great layout, and the overall atmosphere of the hotel made it easy to relax and enjoy the night. A really lovely stay—highly recommend.
Reviewed on Feb 15, 2026

Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was ¥401,074, price is now ¥335,386 per person
¥335,386
per person
Apr 30 - May 6
found 2 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.4/10 Exceptional! (1,003 reviews)
The room was clean, the staff at check in was great. The lobby amenities were good. Having a water refill station with still and sparkling water was clutch. Location is amazing! Will return.
Reviewed on Feb 17, 2026

DoubleTree by Hilton Chicago - Magnificent Mile
Downtown Chicago
Price was ¥395,874, price is now ¥347,374 per person
¥347,374
per person
Apr 30 - May 6
found 2 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
8.8/10 Excellent! (2,140 reviews)
Staff was very friendly, great location!
Reviewed on Feb 19, 2026
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View all trips5* Adventure vacations in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥494,822, price is now ¥365,182 per person
¥365,182
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great hotel, plus excellent service me and my wife like it we definitely coming back thanks
Reviewed on Feb 17, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥573,705, price is now ¥431,470 per person
¥431,470
per person
Apr 30 - May 6
found 2 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026

The Peninsula Chicago
Downtown Chicago
Price was ¥587,878, price is now ¥471,300 per person
¥471,300
per person
May 1 - May 6
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The room was comfortable and beautiful design. Comfortable bed and bedding. Large desk. Good walkable location. But we could hear sirens at night
Reviewed on Feb 16, 2026
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View all trips3 Night Adventure vacations in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥373,341, price is now ¥278,734 per person
¥278,734
per person
May 13 - May 16
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
The service was excellent, the rooms were clean and comfortable, and the breakfast buffet was also good. The bar in the lobby also served the best cocktails we had on the entire trip. The location was AMAZING, right off of Magnificent Mile! We were within 12 minutes walking time to 95% of the places we wanted to go. This hotel is great value for money.
Reviewed on Feb 20, 2026

Level Chicago – Old Town
Downtown Chicago
Price was ¥346,104, price is now ¥295,819 per person
¥295,819
per person
May 13 - May 16
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon!
Reviewed on Feb 19, 2026

Arlo Chicago
Downtown Chicago
Price was ¥348,052, price is now ¥299,496 per person
¥299,496
per person
May 13 - May 16
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Excellent customer service from Security to Front Desk ,Restaurant,cleanliness ,best amenities
Reviewed on Feb 16, 2026
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See all available trips from Tokyo to Far Southeast Side
View all trips4 Night Adventure vacations in Far Southeast Side
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ¥320,896, price is now ¥263,220 per person
¥263,220
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,365 reviews)
Room neat, clean and cozy. Check in was easy. Small and intimate for quick weekend getaway.
Reviewed on Feb 16, 2026

Arlo Chicago
Downtown Chicago
Price was ¥363,925, price is now ¥295,364 per person
¥295,364
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Excellent customer service from Security to Front Desk ,Restaurant,cleanliness ,best amenities
Reviewed on Feb 16, 2026

Level Chicago – Old Town
Downtown Chicago
Price was ¥322,658, price is now ¥265,831 per person
¥265,831
per person
May 15 - May 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon!
Reviewed on Feb 19, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
