Far Southeast Side All inclusive Vacations

Book a All inclusive 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 All inclusive vacation packages in Far Southeast Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
¥295,606
per person
Dec 26 - Dec 30
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥372,780
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

Downtown Chicago
¥369,477
per person
Nov 18 - Nov 24
found 12 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Room was dated and showed signs of hard wear; front desk staff unfriendly; door men never once open the door for us from the street; area around hotel dirty. Shay, the concierge was super nice though and the lobby was attractively decorated.

Reviewed on Oct 4, 2026

Arlo Chicago

Arlo Chicago

Downtown Chicago
¥336,010
per person
Nov 18 - Nov 24
found 12 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (2,384 reviews)
Nice room and staff . Resteraunt on site is good

Reviewed on Oct 5, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
¥333,768
per person
Nov 18 - Nov 24
found 12 hours ago
Roundtrip non-stop flight included
Fukuoka (FUK) to Chicago (ORD)
9.4/10 Exceptional! (3,877 reviews)
I enjoyed my stay at the LondonHouse. The property and room were very clean. The front desk staff was nice. Housekeeping was consistent. The bar staff were friendly but the staff at the rooftop bar could have been nicer. It was busy so I will give them grace but they were a little rude and I didn’t appreciate that considering I was staying at the property. I did not eat at the hotel to rate the food. The views from the vista room were amazing. I would stay again.

Reviewed on Oct 4, 2026

Don't see what you're looking for?
See all available trips from Tokyo to Far Southeast Side
View all trips

5* All inclusive 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
¥372,780
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
The Peninsula Chicago

The Peninsula Chicago

Downtown Chicago
¥510,908
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.8/10 Exceptional! (1,015 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
¥480,806
per person
Nov 9 - Nov 13
found 17 hours ago
Roundtrip 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 Osaka to Far Southeast Side
View all trips

3 Night All inclusive vacations in Far Southeast Side

Price found within the past 48 hours. Click for updated prices.
L7 Chicago by LOTTE

L7 Chicago by LOTTE

Downtown Chicago
¥504,466
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9.6/10 Exceptional! (4,918 reviews)
The best time and location

Reviewed on Oct 5, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
¥506,220
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Le Méridien Essex Chicago

Le Méridien Essex Chicago

Downtown Chicago
¥512,146
per person
Nov 29 - Dec 2
found 1 day ago
Roundtrip flight included
Kitakyushu (KKJ) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The rooms are very small ,the pictures and videos is what sells the hotel for sure. Disappointed with the stay and the amount I was charged

Reviewed on Oct 4, 2026

Don't see what you're looking for?
See all available trips from Kitakyushu to Far Southeast Side
View all trips

4 Night All inclusive vacations in Far Southeast Side

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

Hotel Riu Plaza Chicago

Downtown Chicago
¥284,348
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
¥372,780
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
¥306,844
per person
Nov 9 - Nov 13
found 1 day ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (3,877 reviews)
I enjoyed my stay at the LondonHouse. The property and room were very clean. The front desk staff was nice. Housekeeping was consistent. The bar staff were friendly but the staff at the rooftop bar could have been nicer. It was busy so I will give them grace but they were a little rude and I didn’t appreciate that considering I was staying at the property. I did not eat at the hotel to rate the food. The views from the vista room were amazing. I would stay again.

Reviewed on Oct 4, 2026

Don't see what you're looking for?
See all available trips from Osaka to Far Southeast 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 Southeast Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.