Far Southwest Side Beach Vacations

Book a Beach Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ¥109,000 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

Top Beach vacation packages in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥263,546
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Good location. Nice that breakfast was included but food was mediocre so most mornings we still went elsewhere to eat. Overall no big complaints. The room was clean and comfortable.

Reviewed on Oct 3, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
¥285,917
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥354,422
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago
¥374,218
per person
Nov 9 - Nov 16
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (3,324 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥386,152
per person
Dec 26 - Dec 30
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Don't see what you're looking for?
See all available trips from Osaka to Far Southwest Side
View all trips

5* Beach vacations in Far Southwest Side

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

Trump International Hotel & Tower Chicago

Downtown Chicago
¥386,152
per person
Dec 26 - Dec 30
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥506,288
per person
Nov 9 - Nov 13
found 6 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Perfect in all instances. Wish all the hotels would represent this class

Reviewed on Oct 1, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
¥431,458
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Don't see what you're looking for?
See all available trips from Tokyo to Far Southwest Side
View all trips

4 Night Beach vacations in Far Southwest Side

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥263,546
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Good location. Nice that breakfast was included but food was mediocre so most mornings we still went elsewhere to eat. Overall no big complaints. The room was clean and comfortable.

Reviewed on Oct 3, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
¥285,917
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
¥354,422
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
Don't see what you're looking for?
See all available trips from Osaka to Far Southwest Side
View all trips

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

¥3,812
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

¥6,275
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

¥6,642
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
See all activities in Far Southwest Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.