New Chicago Vacations from ￥370,900
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The Latest New Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Price was ￥451,386, price is now ￥370,900 per person
￥370,900
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,319 reviews)
2 blocks off Michigan ave, 1 block to the river, and great views of Lake Michigan. Staff was very helpful and kind.
Reviewed on May 15, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ￥488,788, price is now ￥389,378 per person
￥389,378
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
“Our stay was exceptional in every way. The hotel exceeded our expectations with its comfort, service, and overall atmosphere.”
Reviewed on May 15, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was ￥583,097, price is now ￥471,416 per person
￥471,416
per person
Jul 23 - Jul 27
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
I LOVE THIS HOTEL!!!
Reviewed on May 13, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
Price was ￥545,226, price is now ￥452,497 per person
￥452,497
per person
Aug 4 - Aug 9
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The morning coffee was excellent. We asked about tea in the evening and akettle and wonderful teas were brought to our room. We went to the bar for happy hour and the appetizers were great as were the prices. Nice location. Friendly staff.
Reviewed on May 12, 2026
Find the Best New Chicago Vacation Packages
New Chicago Hotel Deals
Fairfield Inn & Suites by Marriott Chicago Southeast/Hammond
7720 Corinne Dr Hammond IN
Fully refundableReserve now, pay when you stay
The price is ￥15,572 per night from May 28 to May 29
￥15,572
￥17,440 total
May 28 - May 29
includes taxes & fees
8/10 Very Good! (1,003 reviews)
Old, out dated
Reviewed on May 16, 2026
Econo Lodge South Holland - Chicago Southland
17301 S Halsted St, Building B South Holland IL
Fully refundableReserve now, pay when you stay
The price is ￥9,265 per night from Jun 1 to Jun 2
￥9,265
￥10,468 total
Jun 1 - Jun 2
includes taxes & fees
6/10 (784 reviews)
Everything was fine I’ll come back!! I enjoyed my time there.
Reviewed on May 13, 2026
Days Inn and Suites by Wyndham Hammond, IN
4000 Calumet Avenue Hammond IN
Fully refundableReserve now, pay when you stay
The price is ￥13,287 per night from May 28 to May 29
￥13,287
￥14,883 total
May 28 - May 29
includes taxes & fees
7.2/10 Good! (304 reviews)
Clean room good parking quiet atmosphere
Reviewed on May 15, 2026
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.
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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.
