Chicago Vacations from ₩481,712
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The Latest Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Downtown Chicago
Price was ₩606,585, price is now ₩481,712 per person
₩481,712
per person
Dec 23 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (1,852 reviews)
Great view of the park and easy to walk around to so many things. Loved the amenities and the shower was particularly nice for a hotel bathroom! Staff were nice and accommodating.
Reviewed on Nov 4, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was ₩1,216,372, price is now ₩830,252 per person
₩830,252
per person
Dec 23 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The Trump International Hotel was absolutely immaculate in appearance and the entire staff were fantastic in all aspects. The location is extremely desirable and within walking distance to numerous restaurants and attractions. However, my suite was somewhat underwhelming in regard to the bathroom. The deep soaking bathtub was smaller in scale than one would expect, and more specifically the shower head is set far too low for those of us who are six feet or taller. I would recommend this property.
Reviewed on Nov 3, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Price was ₩637,230, price is now ₩494,326 per person
₩494,326
per person
Dec 23 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Everything was wonderful and staff made the stay exceptional.
Reviewed on Nov 5, 2025
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Price was ₩666,955, price is now ₩530,934 per person
₩530,934
per person
Dec 23 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (303 reviews)
I love the decor and it was very clean. My only problem is they did not clean the room every day other than that is was very clean facility. Very safe location.
Reviewed on Oct 28, 2025
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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩160,454 per night from Dec 7 to Dec 8
₩160,454
₩188,346 total
Dec 7 - Dec 8
includes taxes & fees
8.4/10 Very Good! (5,197 reviews)
Our first time staying! Great location, lovee the free breakfast. Felt safe as well. We really enjoyed having the living room area too.
Reviewed on Nov 5, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩232,343 per night from Nov 7 to Nov 8
₩232,343
₩272,747 total
Nov 7 - Nov 8
includes taxes & fees
7.8/10 Good! (9,688 reviews)
Great stay comfortable bed and great location!
Reviewed on Nov 5, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩145,882 per night from Nov 17 to Nov 18
₩145,882
₩171,251 total
Nov 17 - Nov 18
includes taxes & fees
8.8/10 Excellent! (3,234 reviews)
Room clean and welcoming staff. The room has a great layout. perfect hotel to be downtown
Reviewed on Nov 6, 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.
Grant Park
4.5/5(3,318 reviews)
Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.
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