Far Southeast Side Romantic Vacations

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Top Romantic vacation packages in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

Downtown Chicago
¥262,870
per person
Nov 9 - Nov 14
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (2,373 reviews)
We really like Silversmith. We've been there a couple of times. A smaller historical hotel and a bit more personal. We like the Loop! Staff was very good. Susan worked it all out for our group of 4 rooms. Good rooms. Try the "pure wellness" rooms. Quite nice. The attached Adamus restaurant, bar and lounge, was great; breakfast and dinner. The restaurant and bar staff were very attentive and personable! Renee was a fab bertender. Millennium Park and museums are a couple short blocks away. Very good home base to get something done or just explore Chicago.

Reviewed on Aug 29, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥354,762
per person
Nov 9 - Nov 14
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
隔音效果差

Reviewed on Aug 27, 2026

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥299,425
per person
Nov 9 - Nov 14
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
¥273,598
per person
Nov 9 - Nov 14
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,654 reviews)
Everything

Reviewed on Aug 29, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
¥274,777
per person
Nov 9 - Nov 14
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,314 reviews)
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5* Romantic vacations in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥354,762
per person
Nov 9 - Nov 14
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
隔音效果差

Reviewed on Aug 27, 2026

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4 Night Romantic vacations in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
¥276,589
per person
Nov 2 - Nov 6
found 15 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
8.2/10 Very Good! (2,960 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥292,324
per person
Nov 2 - Nov 6
found 15 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
The bed was really good. It was so comfortable that I slept like a baby. And the Breakfast was good also. All stuffs are nice , they always greet me with smil. I’ll recommend RIU Plaza Hotel to my friends if they go to Chicago.

Reviewed on Aug 29, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥304,695
per person
Nov 2 - Nov 6
found 15 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (159 reviews)
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥4,309
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

¥3,920
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

¥7,518
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Far Southeast Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.