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

Level Chicago Fulton Market
Downtown Chicago
Price was ¥399,936, price is now ¥293,079 per person
¥293,079
per person
May 1 - May 6
found 14 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (347 reviews)
Room smelled like food but overall very clean, very great service and staff both night and morning shift.
Reviewed on Feb 16, 2026

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥573,400, price is now ¥427,516 per person
¥427,516
per person
Apr 30 - May 6
found 14 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great hotel, plus excellent service me and my wife like it we definitely coming back thanks
Reviewed on Feb 17, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥573,705, price is now ¥431,470 per person
¥431,470
per person
Apr 30 - May 6
found 14 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026

Viceroy Chicago
Downtown Chicago
Price was ¥489,058, price is now ¥391,456 per person
¥391,456
per person
Apr 30 - May 6
found 14 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.4/10 Exceptional! (1,129 reviews)
The room was so beautiful and spotless. We got housekeeping the whole stay. The staffs were so great and kind to us. Will definitely stay in another Viceroy.
Reviewed on Feb 20, 2026

Stay One Chicago
Downtown Chicago
Price was ¥473,903, price is now ¥388,238 per person
¥388,238
per person
May 1 - May 6
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
No reviews
The property was great, the room was awesome! The "Stay One Chicago" is really just a name on paper, and maybe one employee who is physically at the property. I am pretty sure that he wasn't even directly employed by the "hotel".
So in a nutshell, the organization has not worked out any kind of structure for checking in other than the guy that told us to download the Door, OR the Latch app. He said that the app is very difficult to get logged into.
Long story made short, we wasted the 1st 2 hours in the hotel trying to get the app (both my wife and I).
The app never worked, and we finally got physical key cards from the guy working for the building.
There was one small piece of paper with scan codes for restaurants, but zero property maps, rules, room cleaning, and nothing explaining how to get to, or use any of the amenities. It was the worst 1st 3 hours of a vacation that we have experienced.
I still gave it a 4-star because the local people were so nice and helpful, even though helping us wasn't part of their job. The valet guys were the best, super nice, and helpful.
Reviewed on Feb 10, 2026
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View all trips5* All inclusive vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.

Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ¥573,400, price is now ¥427,516 per person
¥427,516
per person
Apr 30 - May 6
found 14 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Great hotel, plus excellent service me and my wife like it we definitely coming back thanks
Reviewed on Feb 17, 2026

Waldorf Astoria Chicago
Downtown Chicago
Price was ¥573,705, price is now ¥431,470 per person
¥431,470
per person
Apr 30 - May 6
found 14 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
Completely loved our stay. Probably the best hotel in all Chicago. Amenities are great and the staff are even better.
Reviewed on Jan 26, 2026

The Peninsula Chicago
Downtown Chicago
Price was ¥1,117,442, price is now ¥984,472 per person
¥984,472
per person
May 1 - May 6
found 14 hours ago
Roundtrip flight included
Osaka (ITM) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The room was comfortable and beautiful design. Comfortable bed and bedding. Large desk. Good walkable location. But we could hear sirens at night
Reviewed on Feb 16, 2026
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View all trips3 Night All inclusive vacations in Northwest Side
Price found within the past 48 hours. Click for updated prices.


Level Chicago – Old Town
Downtown Chicago
Price was ¥346,104, price is now ¥295,819 per person
¥295,819
per person
May 13 - May 16
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
First off I want to give a special shout out to Eric! He assisted us so well in every way possible. I also didn’t expect it to be such a nice condo complex but I was so impressed by the rooms, amenities and the workers. Will definitely be coming back very soon!
Reviewed on Feb 19, 2026

Arlo Chicago
Downtown Chicago
Price was ¥348,052, price is now ¥299,496 per person
¥299,496
per person
May 13 - May 16
found 22 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Chicago (ORD)
9.2/10 Wonderful! (1,862 reviews)
Updated, modern clean hotel that smelled good! Great service!
Reviewed on Feb 20, 2026
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View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
