
Bloomingdale Vacations from ¥291,128
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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 ¥351,120, price is now ¥291,128 per person
¥291,128
per person
Jan 17 - Jan 21
found 7 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
Room exceptional well kept, staff extremely nice Ms Diana in the front desk and Luis in the concierge were superb
Reviewed on Nov 10, 2025

Pendry Chicago
Downtown Chicago
Price was ¥478,928, price is now ¥418,007 per person
¥418,007
per person
Jan 2 - Jan 8
found 3 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
A great location, a fabulous building, and a delightful room. The one mystery was a background thumping noise that persisted throughout the stay. Fortunately, didn't disturb sleep. The reception staff sloughed off any knowledge or interest in the cause, but we couldn't imagine that the source was an unknown to hotel staff, and potentially fixable.
Reviewed on Nov 12, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ¥466,364, price is now ¥410,922 per person
¥410,922
per person
Jan 2 - Jan 8
found 3 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on Oct 28, 2025

Hotel Riu Plaza Chicago
Downtown Chicago
Price was ¥464,252, price is now ¥415,319 per person
¥415,319
per person
Jan 2 - Jan 8
found 3 hours ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Room was spotless on arrival and through our stay. Housekeeping Staff were all diligent and courteous. When our TV / internet connection stopped working, Jordan from maintenance solve the issue within minutes and took the time to explain the steps involved in case it happened again(it didn't). Room was spacious. Member services, concierge and reception staff were good. Overall a great experience. Only drawback was that one of the reasons we picked the hotel was to enjoy the rooftop patio views which were advertised as one of the best in the city... Unfortunately it was closed the entire length of our stay. I understand rooftop bar/food service was unavailable but access should have at least been granted, especially on the sunnier days.
Reviewed on Nov 12, 2025
Find the Best Bloomingdale Vacation Packages
Bloomingdale Hotel Deals

DoubleTree by Hilton Hotel Chicago Wood Dale - Elk Grove
1200 N Mittel Blvd, Wood Dale, IL
Fully refundableReserve now, pay when you stay
The price is ¥13,770 per night from Nov 23 to Nov 24
¥13,770
¥15,281 total
Nov 23 - Nov 24
includes taxes & fees
8/10 Very Good! (1,011 reviews)
Very quick checkin efficient and faat
Reviewed on Nov 9, 2025

SureStay Plus Hotel by Best Western Chicago Lombard
222 E 22nd Street, Lombard, IL
Fully refundableReserve now, pay when you stay
The price is ¥11,430 per night from Nov 13 to Nov 14
¥11,430
¥12,686 total
Nov 13 - Nov 14
includes taxes & fees
8.8/10 Excellent! (2,363 reviews)
We entire stay was wonderful. From checking in to sleeping to breakfast and checking out.
Reviewed on Nov 11, 2025

Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is ¥15,452 per night from Nov 24 to Nov 25
¥15,452
¥17,613 total
Nov 24 - Nov 25
includes taxes & fees
8.6/10 Excellent! (2,115 reviews)
Really good experience! Really nice and clean
Reviewed on Nov 12, 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

Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Michigan Avenue
4.5/5(332 reviews)
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.

Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Bloomingdale

Skydeck - Willis Tower Admission
¥6,717
per adult
96% of travellers recommend

Chicago: Navy Pier Centennial Wheel Ticket
¥3,749
per adult
84% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.


