Chicago Vacations
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to ₩1,660,000 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
4 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
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩129,210 per night from May 25 to May 26
₩129,210
₩199,058 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,650 reviews)
Clean room
Reviewed on Apr 30, 2026
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩199,673 per night from May 26 to May 27
₩199,673
₩237,406 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (5,138 reviews)
Beautiful, clean room with an incredible downtown Chicago view. Totally worth it
Reviewed on Apr 29, 2026
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street Chicago IL
Fully refundable
The price is ₩161,999 per night from May 25 to May 26
₩161,999
₩192,611 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (3,463 reviews)
Great check in and check out experience
Reviewed on Apr 29, 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
4.5/5(4,925 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
4.5/5(7,309 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Grant Park
4.5/5(3,360 reviews)
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.
