South Suburbs All inclusive Vacations
Book a All inclusive Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ￥109,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top All inclusive vacation packages in South Suburbs
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Downtown Chicago
Price was ￥1,144,238, price is now ￥883,210 per person
￥883,210
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,141 reviews)
The only thing that could have been better was the number of outlets by the beds to charge electronics. Nick at the front desk was very helpful & amazing!
Reviewed on Jun 30, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥1,189,232, price is now ￥893,911 per person
￥893,911
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,756 reviews)
Our stay at the Londonhouse was excellent. The location is superb right by the riverwalk and across from the Hop On Hop Off bus and the boat rides. The staff was great and very helpful. A special shout out to Juan Carlos at the restaurant and Luke at the Rooftop, where the view is amazing.
Reviewed on Jun 30, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥1,182,134, price is now ￥889,270 per person
￥889,270
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.
Reviewed on Jun 30, 2026
The Godfrey Hotel Chicago
Downtown Chicago
Price was ￥1,181,084, price is now ￥913,977 per person
￥913,977
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,283 reviews)
I mean….loved this place! It was clean, the staff were very helpful, the rooftop bar is to die for.
Reviewed on Jul 1, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥1,169,453, price is now ￥906,070 per person
￥906,070
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,392 reviews)
Gorgeous property, excellent view and room was very clean. Staff were friendly and helpful.
Reviewed on Jun 21, 2026
5* All inclusive vacations in South Suburbs
Price found within the past 48 hours. Click for updated prices.
Four Seasons Hotel Chicago
Downtown Chicago
Price was ￥895,568, price is now ￥768,496 per person
￥768,496
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
The hotel is very clean
Good air conditioning
The staff is great
The bar at the restaurant is very good
The location is the best in Chicago
Fancy neighborhood
Reviewed on Jun 30, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥1,505,726, price is now ￥1,322,488 per person
￥1,322,488
per person
Jul 31 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The very best hotel I’ve ever experienced! The customer service and their willingness to go far above and beyond any expectation was remarkable! This may have ruined all other hotel stays because of the bar that was set after this trip!
Reviewed on Jun 30, 2026
4 Night All inclusive vacations in South Suburbs
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥709,500, price is now ￥599,950 per person
￥599,950
per person
Sep 14 - Sep 18
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Great stay; fabulous location, amazing views and access to so much; friendly staff. Super friendly and accommodating housekeeping! Food/bar service took a long long time, every time..long wait to order…long wait to get drinks…long wait to pay bill. Not enough staff behind the bar.
Reviewed on Jun 30, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
