Central Chicago Cheap Vacations
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Top Cheap vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥436,728, price is now ￥354,310 per person
￥354,310
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,464 reviews)
The staff was wonderful. The room was beautiful. I really enjoyed myself.
Reviewed on Jun 25, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥460,246, price is now ￥373,894 per person
￥373,894
per person
Sep 16 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Terrible attitude of the front desk clerk.
Room smelled bad, dirty carpet.
Reviewed on Jun 24, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥464,064, price is now ￥379,842 per person
￥379,842
per person
Sep 16 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,744 reviews)
Excelente, ubicación perfecta cerca de todo
Reviewed on Jun 23, 2026
Thompson Chicago, by Hyatt
Downtown Chicago
Price was ￥488,708, price is now ￥407,436 per person
￥407,436
per person
Sep 16 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,399 reviews)
I truly enjoyed my stay at this hotel. From the moment I arrived, the staff made me feel welcome and valued. Everyone was so friendly, attentive, and genuinely eager to help, which made the experience even more enjoyable.
The hotel was clean, comfortable, and had everything I needed for a relaxing stay. I especially loved the location—it was convenient to restaurants, shopping, and local attractions, making it easy to get around and enjoy the area without any hassle.
Reviewed on Jun 21, 2026
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View all trips5* Cheap vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
The Peninsula Chicago
Downtown Chicago
Price was ￥636,708, price is now ￥545,340 per person
￥545,340
per person
Sep 16 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,009 reviews)
We love the Peninsula! The staff, location, room, and the Shanghai restaurant top tier.
Reviewed on Jun 21, 2026
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See all available trips from Tokyo to Central Chicago
View all trips3 Night Cheap vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Omni Chicago Hotel
Downtown Chicago
Price was ￥557,828, price is now ￥527,178 per person
￥527,178
per person
Aug 18 - Aug 21
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,813 reviews)
Located in a walkable area near many Chicago attractions. We had a delicious breakfast in the hotel restaurant and the bar is nice. Room was large and comfortable
Reviewed on Jun 23, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥571,986, price is now ￥534,238 per person
￥534,238
per person
Aug 18 - Aug 21
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,464 reviews)
The staff was wonderful. The room was beautiful. I really enjoyed myself.
Reviewed on Jun 25, 2026
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
Price was ￥565,475, price is now ￥534,254 per person
￥534,254
per person
Aug 18 - Aug 21
found 11 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,993 reviews)
Older hotel in River North. Microscopic lobby. Occasionally disinterested desk staff. Immaculate room, great a/c, good shower and good water pressure, comfortable bed, and quiet. "Amenities" weren't exactly visible but, to a fair extent, that reflects the small footprint of the hotel. I'd stay there again.
Reviewed on Jun 23, 2026
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See all available trips from Tokyo to Central Chicago
View all trips4 Night Cheap vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥436,728, price is now ￥354,310 per person
￥354,310
per person
Jul 27 - Jul 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,464 reviews)
The staff was wonderful. The room was beautiful. I really enjoyed myself.
Reviewed on Jun 25, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was ￥460,246, price is now ￥373,894 per person
￥373,894
per person
Sep 16 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,767 reviews)
Terrible attitude of the front desk clerk.
Room smelled bad, dirty carpet.
Reviewed on Jun 24, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was ￥464,064, price is now ￥379,842 per person
￥379,842
per person
Sep 16 - Sep 20
found 16 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,744 reviews)
Excelente, ubicación perfecta cerca de todo
Reviewed on Jun 23, 2026
Don't see what you're looking for?
See all available trips from Tokyo to Central Chicago
View all tripsThings to do
Wendella's 90-min Chicago River Architecture Tour
￥6,478
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
