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.
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
¥319,194
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (550 reviews)
Great staff and amenities. Beautiful pool, bbq area and more. Terrific room Only issues was parking was $68 a day, plus incidental holds of $200 per day. Security is strong and is close to Fulton Market and we would walk over to the RiverWalk every day As the hotel is permanent residents and renters security is job 1. Problems you have to go to the third floor to get a baggage cart and you have to leave your drivers license, which I didn’t care for and to get into the garage you have to call security and more than once no one answered and you had to go into the building and find them. For the money your room key or a key pad should allow you in.

Reviewed on Aug 21, 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
¥387,570
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,335 reviews)
Lovely place in Westloop, close to everything, quiet, clean and efficient. I would stay there again.

Reviewed on Aug 20, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥461,172
per person
Nov 15 - Nov 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
It’s amazing view from the window! All my family love it! Clean and cozy !

Reviewed on Aug 21, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago
¥586,192
per person
Oct 9 - Oct 16
found 3 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Pendry Chicago

Pendry Chicago

Downtown Chicago
¥416,680
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,145 reviews)
Very crowded with tourist bus guests

Reviewed on Aug 21, 2026

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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
¥461,172
per person
Nov 15 - Nov 20
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
It’s amazing view from the window! All my family love it! Clean and cozy !

Reviewed on Aug 21, 2026

The Langham, Chicago

The Langham, Chicago

Downtown Chicago
¥562,640
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Waldorf Astoria Chicago

Waldorf Astoria Chicago

Downtown Chicago
¥736,678
per person
Nov 4 - Nov 11
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Had the best time ,Staff was excellent! Accommodating and friendly!

Reviewed on Aug 21, 2026

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3 Night Romantic vacations in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥274,372
per person
Sep 26 - Sep 29
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥308,025
per person
Oct 1 - Oct 4
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
L7 Chicago by LOTTE

L7 Chicago by LOTTE

Downtown Chicago
¥287,923
per person
Oct 3 - Oct 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (4,495 reviews)
Muy atentos desde que llegamos hasta que partimos. Ofrecen servicio de café y agua todo el día, y lo surten en la habitación cuando se necesita . Muy limpia y cómoda la habitación. Eduardo muy atento cada vez que lo veíamos y nos ayudó con la reserva del perilla para cenar, cuando al principio se nos negó para desayunar.

Reviewed on Aug 22, 2026

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4 Night Romantic vacations in Far Southeast Side

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Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
¥314,018
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.4/10 Very Good! (2,128 reviews)
The location could not be better--close to Michigan Avenue and the Red Line L--and the property is clean, quiet, and safe. The only thing that rankled were the elevators, for which one typically has to wait years for: ended up taking the stairs often, and I was staying on the 9th floor.

Reviewed on Aug 21, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥369,916
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
¥319,909
per person
Sep 21 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
8.2/10 Very Good! (2,899 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.