Chicago Vacations

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    Save up to NT$5,067 when you book a flight and hotel together*
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Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago

Find the Best Chicago Vacation Packages

Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$2,827 per night from Feb 9 to Feb 10
NT$2,827
NT$3,319 total
Feb 9 - Feb 10
includes taxes & fees
8/10 Very Good! (9,853 reviews)
Friendly staff. Clean room.

Reviewed on 2026/2/5

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,390 per night from Feb 21 to Feb 22
NT$4,390
NT$6,083 total
Feb 21 - Feb 22
includes taxes & fees
8.4/10 Very Good! (2,610 reviews)
Good

Reviewed on 2026/2/7

Hilton Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$3,247 per night from Feb 22 to Feb 23
NT$3,247
NT$3,812 total
Feb 22 - Feb 23
includes taxes & fees
8.4/10 Very Good! (5,637 reviews)
Yes room was spotless

Reviewed on 2026/2/4

Embassy Suites by Hilton Chicago Downtown River North
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.