Chicago Vacations from NT$29,422
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The Latest Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was NT$43,745, price is now NT$29,422 per person
NT$29,422
per person
May 15 - May 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
The bar was fine we got 2 free drinks.
Reviewed on 2026/4/1
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was NT$60,227, price is now NT$35,716 per person
NT$35,716
per person
May 15 - May 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great breakfast. Comfortable beds. Rooftop bar was not open. The resort fee at check in was a surprise. A great location and nice place.
Reviewed on 2026/4/1
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was NT$72,381, price is now NT$50,602 per person
NT$50,602
per person
May 15 - May 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
The staff were great. Amenities were also wonderful. Will come back.
Reviewed on 2026/3/31
Arlo Chicago
Downtown Chicago
Save 100% on your flight
Price was NT$60,844, price is now NT$43,198 per person
NT$43,198
per person
May 15 - May 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.4/10 Exceptional! (2,019 reviews)
Wonderful location Nicely updated and appointed rooms. Quiet. Quick elevator. Excellent restaurant on site. Great value for money. Very helpful staff.
Reviewed on 2026/3/29
Sports Illustrated Resorts Chicago
Downtown Chicago
Save 100% on your flight
Price was NT$49,006, price is now NT$34,831 per person
NT$34,831
per person
May 15 - May 19
found 1 day ago
Roundtrip non-stop flight included
Pittsburgh (PIT) to Chicago (ORD)
9.2/10 Wonderful! (1,414 reviews)
Check in was quick and easy, room was clean and spacious
Reviewed on 2026/3/9
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 NT$3,473 per night from Apr 5 to Apr 6
NT$3,473
NT$4,077 total
Apr 5 - Apr 6
includes taxes & fees
8/10 Very Good! (10,029 reviews)
very old and grand hotel. felt like i was in the titanic but a hotel. Was very eerie and felt haunted. if you are in to ghost wonderful place to stay. the stairs alone are just breath taking.
Reviewed on 2026/3/31
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,394 per night from Apr 12 to Apr 13
NT$4,394
NT$5,158 total
Apr 12 - Apr 13
includes taxes & fees
9/10 Wonderful! (4,023 reviews)
Very nice
Reviewed on 2026/4/1
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,570 per night from Apr 12 to Apr 13
NT$4,570
NT$5,365 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (5,796 reviews)
The location is great. A great coffee shop across the street, quick walk to a number of things (or a quick ride). It’s a great price for the amount of space. We had a corner suite, which did not have a window into the hall, so that was a plus. The omelette station was good at breakfast. However, ...
Reviewed on 2026/4/1
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
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Explore a world of travel with Expedia
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- Merchandise Mart
- Chicago Theatre
- Prentice Women's Hospital
- Willis Tower
- Art Institute of Chicago
- Chicago Children's Museum
- Water Tower Place
- Cooking & Hospitality Institute of Chicago
- Oak Street Beach
- Shops at North Bridge
- Crown Fountain
- Visit Greektown
- Northwestern Memorial Hospital
- Visit Chicago
- Buckingham Fountain
- Gold Coast Vacations
- Afrocentric Bookstore
- Navy Pier
- Chicago Riverwalk
- Museum of Contemporary Art Chicago
- 333 West Wacker Drive
- State Street
- Harold Washington Library Center
- Millennium Park
- Bridgehouse and Chicago River Museum
- Newberry Library
- The East Bank Club
- 311 S Wacker Dr
- Visit Downtown Chicago
- Grant Park
- Chicago City Hall
- Vietnam Veterans Memorial
- Film Row Cinema
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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.
