Chicago Vacations
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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$4,214 per night from May 27 to May 28
NT$4,214
NT$5,010 total
May 27 - May 28
includes taxes & fees
8/10 Very Good! (10,140 reviews)
"tiniest room i’ve ever stayed in and shower leaked all over the floor and"
Reviewed on 2026/5/25
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$7,542 per night from Jun 16 to Jun 17
NT$7,542
NT$9,866 total
Jun 16 - Jun 17
includes taxes & fees
9.4/10 Exceptional! (4,247 reviews)
"We had a very nice stay"
Reviewed on 2026/5/25
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is NT$4,796 per night from May 27 to May 28
NT$4,796
NT$5,702 total
May 27 - May 28
includes taxes & fees
7.8/10 Good! (1,472 reviews)
"Staff was extremely helpful!"
Reviewed on 2026/5/25
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
4.5/5(2,149 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(461 reviews)
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
4.5/5(4,925 reviews)
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.
