Northwest Chicago All inclusive Vacations
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Top All inclusive vacation packages in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥393,950, price is now ￥308,172 per person
￥308,172
per person
Jun 8 - Jun 12
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Service was terrific in every way! Warm and helpful staff. Fantastic breakfast included!
Reviewed on Mar 25, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥619,115, price is now ￥437,907 per person
￥437,907
per person
May 28 - Jun 2
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Everything was perfect
Reviewed on Mar 25, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was ￥495,778, price is now ￥352,488 per person
￥352,488
per person
May 28 - Jun 2
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (421 reviews)
10/10 makes you feel at home. One of the best hotels I’ve ever stayed in.
Reviewed on Mar 23, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥541,318, price is now ￥398,727 per person
￥398,727
per person
May 28 - Jun 2
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
I went and checked in but when I got to the room it had a broken nightstand. Everything else was nice and clean!
Reviewed on Mar 25, 2026
Hilton Chicago
Downtown Chicago
Price was ￥658,325, price is now ￥510,528 per person
￥510,528
per person
May 28 - Jun 2
found 23 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.6/10 Excellent! (2,675 reviews)
We loved our stay. Two adults and our eight-year-old son took a weekend trip to Chicago. This hotel was very close to the field museum and walking distance to magnificent mile. Short Uber ride to nearby shopping and Willis Tower.
The staff were awesome and upgraded our room at a low price. We felt very safe and staff were very helpful. The eighth floor had a beautiful pool, spa and sauna, great view of lake mi, open late too. We dined for breakfast at yoke and Niu B for dinner. Delicious. At checkout we purchased a future Hilton grand vacation at a great discount too. Let’s go. :)
Reviewed on Mar 25, 2026
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View all trips5* All inclusive vacations in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥487,896, price is now ￥398,236 per person
￥398,236
per person
Jun 8 - Jun 12
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Perfect room size for 2+1. The river view was breathtaking especially in the late evening while serenade of colors highlighted other buildings surrounding the Trump Tower hotel. Good food at the restaurant and nice staff helping you to enjoy the memorable time during the visit.
We will be back in near future for surr!
Reviewed on Mar 24, 2026
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View all trips3 Night All inclusive vacations in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North
Downtown Chicago
Price was ￥353,290, price is now ￥298,874 per person
￥298,874
per person
May 13 - May 16
found 8 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (2,465 reviews)
Great Staff ! Stay was very comfortable and the hotel has a great location near plenty of restaurants
Reviewed on Mar 25, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥430,412, price is now ￥342,638 per person
￥342,638
per person
Jun 6 - Jun 9
found 10 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Service was terrific in every way! Warm and helpful staff. Fantastic breakfast included!
Reviewed on Mar 25, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was ￥367,785, price is now ￥325,429 per person
￥325,429
per person
May 13 - May 16
found 8 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
I went and checked in but when I got to the room it had a broken nightstand. Everything else was nice and clean!
Reviewed on Mar 25, 2026
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See all available trips from Osaka to Northwest Chicago
View all trips4 Night All inclusive vacations in Northwest Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥455,255, price is now ￥339,702 per person
￥339,702
per person
May 13 - May 17
found 5 hours ago
Roundtrip flight included
Osaka (OSA) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Service was terrific in every way! Warm and helpful staff. Fantastic breakfast included!
Reviewed on Mar 25, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥487,896, price is now ￥398,236 per person
￥398,236
per person
Jun 8 - Jun 12
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Perfect room size for 2+1. The river view was breathtaking especially in the late evening while serenade of colors highlighted other buildings surrounding the Trump Tower hotel. Good food at the restaurant and nice staff helping you to enjoy the memorable time during the visit.
We will be back in near future for surr!
Reviewed on Mar 24, 2026
Level Chicago - River North
Downtown Chicago
Price was ￥427,132, price is now ￥350,566 per person
￥350,566
per person
Jun 8 - Jun 12
found 20 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (876 reviews)
Clean room, Great amenities and super helpful and accommodating staff
Reviewed on Mar 15, 2026
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See all available trips from Osaka to Northwest Chicago
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
