
Central Chicago All inclusive Vacations
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Top All inclusive vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Fairmont Chicago at Millennium Park
Downtown Chicago
Price was ¥115,574, price is now ¥92,936 per person
¥92,936
per person
Jul 11 - Jul 13
found 22 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.8/10 Excellent! (2,176 reviews)
Clean room, overall nice hotel, restaurant was nice for happy hour. Lobby smelled like an old lady and peltons in gym were broken. Overall lovely stay.
Reviewed on Jun 9, 2026

Level Chicago Fulton Market
Downtown Chicago
Price was ¥508,926, price is now ¥399,982 per person
¥399,982
per person
Aug 12 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (491 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026

Thompson Chicago, by Hyatt
Downtown Chicago
Price was ¥393,374, price is now ¥343,296 per person
¥343,296
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,376 reviews)
We had requested for a 2pm checking but they gave us the room at 4pm and the normal checkin time is 3pm. Also the next day they did nit clean the room and we had requested that the beds and bathroom needs to be cleaned. They cleaned the room but left. Soaking wet towel on the bed. Little disappointed with our stay.
Reviewed on Jun 7, 2026


Nobu Hotel Chicago
Downtown Chicago
Price was ¥608,964, price is now ¥536,505 per person
¥536,505
per person
Aug 12 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (860 reviews)
Fabulous walkable neighborhood. Roo.s are spacious and very nicely designed
Reviewed on Jun 10, 2026
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View all trips5* All inclusive vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥536,366, price is now ¥531,124 per person
¥531,124
per person
Aug 12 - Aug 16
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Our third time at this hotel and still enjoying it.
Reviewed on May 30, 2026

Nobu Hotel Chicago
Downtown Chicago
Price was ¥608,964, price is now ¥536,505 per person
¥536,505
per person
Aug 12 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (860 reviews)
Fabulous walkable neighborhood. Roo.s are spacious and very nicely designed
Reviewed on Jun 10, 2026

The Langham, Chicago
Downtown Chicago
Price was ¥592,899, price is now ¥536,404 per person
¥536,404
per person
Aug 12 - Aug 16
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,002 reviews)
Incredible hotel and staff. The bar was great and the food was delicious. We would definitely stay here again.
Reviewed on Jun 10, 2026
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View all trips3 Night All inclusive vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.

citizenM Chicago Downtown
Downtown Chicago
Price was ¥377,108, price is now ¥355,367 per person
¥355,367
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (4,314 reviews)
ROOM LIGHTING CONTROLS: The wall mounted light switch for the vanity opened the window shades. I'm pretty sure this was a malfunction, as this hadn't happened during pasts stays here. WHY THIS MATTERS: When exiting the shower to use the lighted vanity mirror, flipping the switch opened the shades causing me to make a dash back to the protection of the shower. That switch same switch did not close the shades...something only done with tablet control.
Reviewed on Jun 10, 2026


LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥391,993, price is now ¥367,613 per person
¥367,613
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
We stayed in this hotel in our daughter's wedding weekend. It was wonderful, the river and city view from our 18th story room was spectacular. I recommend it to.all ages.
Reviewed on Jun 7, 2026
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View all trips4 Night All inclusive vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.


LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ¥499,468, price is now ¥404,625 per person
¥404,625
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
We stayed in this hotel in our daughter's wedding weekend. It was wonderful, the river and city view from our 18th story room was spectacular. I recommend it to.all ages.
Reviewed on Jun 7, 2026

The Emily Hotel
Downtown Chicago
Price was ¥422,324, price is now ¥352,472 per person
¥352,472
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,325 reviews)
Rooftop Movie theater looked fun during the daytime, but wasn’t committed enough to buy a ticket after sunset. Rooms were fine. Coffee shop was short-staffed the day I was there - to the point I gave up and moved on.
The staff I ran into in the hotel from housekeeping to front desk to bell staff were all universally pleasant and helpful.
Location was great - convenient to the show I was attending at the Cobra Lounge and to a pretty decent variety of decent looking food options. Don’t miss the Hubbard St viaducts on your morning walk.
Reviewed on Jun 8, 2026
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