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
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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩140,028 per night from Nov 25 to Nov 26
₩140,028
₩164,380 total
Nov 25 - Nov 26
includes taxes & fees
8.4/10 Very Good! (5,235 reviews)
Clean room; kind and courteous staff; excellent breakfast and happy hour included
Reviewed on Nov 10, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩143,324 per night from Dec 7 to Dec 8
₩143,324
₩168,248 total
Dec 7 - Dec 8
includes taxes & fees
8.8/10 Excellent! (3,280 reviews)
Room was clean, bell staff and front desk were very helpful and accommodating. The restaurant staff were very friendly and accommodating!
Reviewed on Nov 13, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩151,578 per night from Nov 16 to Nov 17
₩151,578
₩177,928 total
Nov 16 - Nov 17
includes taxes & fees
8/10 Very Good! (9,549 reviews)
The check in was quick and I was able to receive a view of the lake which was wonderful. The location was easily walkable to the magnificent mile and soldier field. Staff was friendly and helpful. I was not aware or notified of any breakfast for the hotel so I have no comment. Location is fantastic. ...
Reviewed on Nov 13, 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 Chicago
Navy Pier
4.5/5(4,870 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
4.5/5(7,198 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
University of Chicago
4.5/5(1,167 reviews)
Take a campus tour or just explore the area around University of Chicago, a top university in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
Other vacations you might like
Expedia's Latest Trends
Hotels
Cars
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
