Bloomingdale Vacations from ￥189,992
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- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
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The Latest Bloomingdale Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥298,767, price is now ￥224,794 per person
￥224,794
per person
Mar 13 - Mar 16
found 18 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It was like a Ritz Carlton like experience without the Ritz Carlton price tag.
Reviewed on Dec 31, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥253,246, price is now ￥194,618 per person
￥194,618
per person
Mar 13 - Mar 16
found 18 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Clean room
Clean bathroom
Friendly staff
Reviewed on Jan 1, 2026
The Peninsula Chicago
Downtown Chicago
Price was ￥306,118, price is now ￥244,084 per person
￥244,084
per person
Mar 13 - Mar 16
found 18 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Emil was a fabulous server at the Lobby Restaurant. I think that’s his name. Tall guy. Becca at front desk also fantastic. The lady who checked us in not so good.
Reviewed on Dec 29, 2025
The Emily Hotel
Downtown Chicago
Price was ￥240,948, price is now ￥197,552 per person
￥197,552
per person
Mar 13 - Mar 16
found 18 hours ago
Roundtrip non-stop flight included
Osaka (KIX) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Had a great dinner at Fora before a very short walk to the new years eve event we were headed to and then came back for a great night's sleep in a very comfortable room! All the staff we interacted with were great!
Reviewed on Jan 1, 2026
Find the Best Bloomingdale Vacation Packages
Bloomingdale Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥37,392 per night from Jan 3 to Jan 4
￥37,392
￥43,896 total
Jan 3 - Jan 4
includes taxes & fees
8.2/10 Very Good! (2,184 reviews)
Staff was excellent, roim was nice
Reviewed on Dec 30, 2025
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ￥18,485 per night from Jan 13 to Jan 14
￥18,485
￥21,069 total
Jan 13 - Jan 14
includes taxes & fees
8.6/10 Excellent! (2,264 reviews)
Room was nice, but beds were hard and pillows too soft. Barely slept. Doors are too loud and are constantly being slammed throughout day and night. Breakfast service was excellent. Wish there were more options for the price.
Reviewed on Dec 29, 2025
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
The price is ￥16,427 per night from Jan 20 to Jan 21
￥16,427
￥18,722 total
Jan 20 - Jan 21
includes taxes & fees
8.6/10 Excellent! (2,679 reviews)
Yes
Reviewed on Dec 29, 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Bloomingdale
Michigan Avenue
You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Bloomingdale
Chicago: Navy Pier Centennial Wheel Ticket
￥3,827
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
￥6,310
per adult
94% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
