Chicago Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩234,741 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Where to stay in Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Find the Best Chicago Vacation Packages
Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩131,094 per night from Feb 3 to Feb 4
₩131,094
₩153,892 total
Feb 3 - Feb 4
includes taxes & fees
8/10 Very Good! (9,839 reviews)
Great a+++
Reviewed on Feb 1, 2026
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩148,067 per night from Feb 8 to Feb 9
₩148,067
₩173,816 total
Feb 8 - Feb 9
includes taxes & fees
8.4/10 Very Good! (5,617 reviews)
Friendly desk staff, clean room. Fridge didn't have temp adjuster and contents froze, bottles broke.
Reviewed on Jan 28, 2026
DoubleTree by Hilton Chicago - Magnificent Mile
300 E Ohio St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩129,115 per night from Feb 10 to Feb 11
₩129,115
₩151,569 total
Feb 10 - Feb 11
includes taxes & fees
8.6/10 Excellent! (2,280 reviews)
Close to everything!! The staff were super friendly. I would book again when in Chicago.
Reviewed on Feb 2, 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.
Discover the most popular places to visit in Chicago
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Grant Park
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
Explore a world of travel with Expedia
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
