Where to Experience the Best of Chicago

Famed for its bold architecture, iconic skyline, outdoor public art and never-ending list of activities for visitors and locals alike, Chicago is the Midwest's must-see city. From where to stay, what to do and where to eat, we've got you covered on how to make the most of your next visit to the Windy City.

Where to Stay

While accommodations are around every corner here, the InterContinental Chicago Magnificent Mile Hotel is in a prime location in the center of the fun, making it the perfect place to stay. As the only hotel with a front entrance on the Magnificent Mile, visitors can experience downtown Chicago in an up-close and personal type of way.

With 792 luxurious guestrooms, the oldest pool in Chicago, signature gold leaf molding, original family crests and hand-painted murals, you’ll find sophistication everywhere you look. Two on-site restaurants include Michael Jordan Steak House, serving modern American cuisine, and ENO, a wine lounge serving small bites, chocolate and cheese.

The hotel’s newest package, The Best of Chicago, allows guests to choose a pair of tickets for admission to one of Chicago’s top tourist destinations, including the Shedd Aquarium, the Field Museum, the Museum of Science and Industry, Chicago Children’s Museum and Navy Pier Ferris Wheel, the Art Institute of Chicago or The Ledge at Skydeck Chicago. In addition to their tickets, guests will also be treated to an in-room Chicago Truffle Skyline amenity that includes dessert truffles designed to resemble the downtown skyline.

What to Do

The Chicago Architecture River Cruise

Just last year, the Chicago Architecture Foundational Center River Cruise Aboard Chicago's First Lady was named as one of the seven most breathtaking river cruises around the world, so it's definitely a must-do while you’re in the area. Expertly trained volunteers lead the way as you cruise past more than 50 buildings along the Chicago River, learning the fascinating history behind them. Mid-May through mid-October offers an even better experience—the Twilight River Cruise. Watching the sunset along the Chicago skyline while sailing down the river is a serene moment you’re sure to remember.

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Chicago Trolley & Double Decker Co.

A fun and easy way to see the most popular sites of the city is a hop-on hop-off tour with Chicago Trolley & Double Decker Co. With 12 stops total—including the Skydeck, Navy Pier, the Chicago Art Institute and more—you can pick and choose where you start and where you end. Trolley’s run every 15-20 minutes, giving you enough time to explore a destination before hopping onboard a new trolley. The company also offers seasonal tours that include the Midnight Terror Tour, which takes you to the best haunted house in the city, and the Holiday Lights Tour, where you can experience the magic of the holidays in Chicago while sipping a complimentary cup of hot cocoa.

Skydeck Chicago

If you’re not a fan of heights, I’d recommend skipping this one. While museum-quality exhibits and ‘Reaching for the Sky,’ a theater presentation highlighting the best of Chicago, can be found on the lower floors of the Willis Tower, the 103rd floor is where it’s really at. The Ledge allows visitors the chance to step outside of the tallest building in the Western Hemisphere—at 1,353 feet in the air. Glass boxes extending more than 4 feet offer unparalleled views of the city that you won’t find elsewhere. On a clear day, if you look far enough, you’ll be rewarded with views of neighboring states Indiana, Wisconsin and Michigan.

The Art Institute of Chicago

Downtown Chicago is home to one of the greatest art museums in the world, the Art Institute of Chicago. Housing a collection spanning centuries from all parts of the globe, you could spend an entire day here. Popular pieces you cannot leave without seeing include the famous American Gothic painting by Grant Wood, depicting a father and daughter standing before a farmhouse in rural America; Stacks of Wheat (End of Summer) by Claude Monet, part of a series created between 1890 and 1891; and The Old Guitarist by Pablo Picasso, one of his most haunting images expressing human suffering.

Millennium Park

Cloud Gate, that bean-like sculpture often seen in movies and tv shows, can be found in one of Chicago’s top tourist destinations, Millennium Park. Free to the public, the park is a revolving door of concerts, exhibitions and year-round family activities. Millennium Park Ice Rink is set to open mid-November and will remain open until early March, providing some fun the whole family can enjoy. Lurie Garden is a 3.5-acre garden open year-round that pays homage to Chicago’s transformation from its flat and marshy origins to the beautiful city it has become today. Check out the park’s events calendar to see what’s happening during your visit.

What to Eat

Pequod’s Pizza

Did someone say Chicago-style pizza? If you’re looking for the best in the city, look no further than Pequod’s Pizza, Chicago’s most awarded and recognized pizza. Notorious for their pan-style pizza with a ‘caramelized crust’ edge, this hometown pizzeria offers soups, salads, sandwiches, pasta, multiple appetizers and, of course, mouth-watering, deep-dish pizza that’ll make you run back for more before heading home.

Al’s Italian Beef

A city staple, Al’s Italian Beef is home to the great Chicago sandwich. The history of the restaurant dates back to 1938, when Al Ferrari and his sister and brother-in-law, Frances and Chris Pacelli, Sr., created a recipe for an Italian beef sandwich. What started as a food stand in Chicago’s ‘Little Italy’ neighborhood has now become an iconic restaurant found at multiple locations throughout the city.

Al’s Big Beef is a must-try, obviously, but there’s also a secret menu (shhh) featuring sandwiches like The Italian Soaker, a French Bread sandwich dipped in gravy and topped with peppers and cheese, and Al’s Poor Boy, another French Bread sandwich dipped in gravy, but also filled with fries. If you’re feeling really brave, take the leap and add some cheese. You won't regret it.

Jim’s Original

Often imitated but never duplicated, Jim’s Original is a long-standing favorite of locals and visitors alike. Different from your typical sit-down restaurant, Jim’s is a food stand serving up the best Polish Sausage the city has to offer. What do you call a flat-grilled sausage placed inside of a bright yellow mustard smeared hot dog bun, topped with perfectly-caramelized sweet onions? Heaven on earth, that’s what you call it.