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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
¥286,880
per person
Nov 17 - Nov 22
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.4/10 Exceptional! (157 reviews)
Great stay

Reviewed on Aug 23, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥357,160
per person
Nov 17 - Nov 22
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Everything was outstanding!

Reviewed on Aug 23, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥326,482
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Rooms are extremely cold. Glass/ mirrors & table dirty with fingerprints & crumbs still on table. Shower leaked water all over floor. Toilet had hair on it. Not informed about hidden $30 feet a day. Did not sleep comfortably during stay due to room temperature

Reviewed on Aug 23, 2026

Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
¥310,036
per person
Nov 4 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (518 reviews)
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 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 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
¥357,160
per person
Nov 17 - Nov 22
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.6/10 Exceptional! (1,960 reviews)
Everything was outstanding!

Reviewed on Aug 23, 2026

The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥462,080
per person
Nov 17 - Nov 22
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
First time staying at this Property and we absolutely loved it! Will definitely go back and recommend

Reviewed on Aug 23, 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

Downtown Chicago
¥736,678
per person
Nov 4 - Nov 11
found 1 day 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.
Level Chicago - River North

Level Chicago - River North

Downtown Chicago
¥269,536
per person
Sep 26 - Sep 29
found 19 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,055 reviews)
Front desk staff where very unprofessional - friends of theirs hanging out at the desk and when asked for assistance it was as if we were bothering them. housekeeping staff was excellent and attentive when we had to ask for extra bedding and towels since we were 4 not 2pp - these extra items should have been in the room at check in. Pool deck, hot tub, exercise room and sauna/steam area are all top notch. We really loved the concept but would have liked more of a customer service oriented stay.

Reviewed on Aug 23, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥312,929
per person
Oct 3 - Oct 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Beautiful new LEED hotel. Staff were exceptional. Unique part of the room was that you had to place your room key in reader inside your room in order to activate electricity ( room Lights,TV, etc.). I suggest they make visitors aware when they check in. Liked the safety features with the elevator too.

Reviewed on Aug 24, 2026

Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥284,169
per person
Oct 3 - Oct 6
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Rooms are extremely cold. Glass/ mirrors & table dirty with fingerprints & crumbs still on table. Shower leaked water all over floor. Toilet had hair on it. Not informed about hidden $30 feet a day. Did not sleep comfortably during stay due to room temperature

Reviewed on Aug 23, 2026

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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.