Chicago is a city filled with iconic architecture, stunning waterfront views, world-class dining, and unforgettable experiences around every corner. Whether you're visiting for business, extending a conference stay, or planning a weekend getaway, the Windy City offers a perfect mix of culture, entertainment, and culinary excellence.
From river cruises and skyline views to deep-dish pizza and rooftop dining, here are some of the top attractions and food experiences to add to your Chicago itinerary.
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Chicago Architecture Center river cruise: One of the best ways to experience Chicago is from the water. This award-winning architecture cruise takes visitors along the Chicago River while expert guides share the stories behind the city’s legendary skyline and famous skyscrapers.
Millennium Park and Cloud Gate (“The Bean”): Millennium Park is home to Cloud Gate, a massive, mirrored sculpture nicknamed “The Bean” that reflects Chicago’s skyline and surrounding cityscape. (One of Chicago’s most photographed landmarks.) The park also features public art, gardens, fountains, and beautiful downtown views.
360 Chicago Observation Deck: Located on the 94th floor of the former John Hancock Center, 360 Chicago offers panoramic views of the city skyline and Lake Michigan. Visitors can also experience TILT, a thrilling moving platform that angles outward above Michigan Avenue.
Chicago Riverwalk: Stretching along the Chicago River through downtown, the Riverwalk is one of the city’s most vibrant gathering places. Visitors can enjoy scenic walking paths, waterfront dining, public art, and incredible architectural views.
Navy Pier: Navy Pier is one of Chicago’s most popular attractions, offering entertainment, restaurants, boat tours, and lakefront views. The iconic Centennial Wheel provides breathtaking views of the skyline and Lake Michigan.
The Magnificent Mile: Chicago’s famous Magnificent Mile combines luxury shopping, historic architecture, restaurants, and entertainment along Michigan Avenue. It’s a perfect destination for sightseeing, dining, and experiencing the energy of downtown Chicago.
Buckingham Fountain: Located in Grant Park, Buckingham Fountain is one of the largest fountains in the world and a classic Chicago landmark. The fountain’s water displays and evening light shows make it a favorite stop for visitors.
Oak Street Beach: Just steps from downtown, Oak Street Beach offers a unique combination of sandy shoreline and towering skyline views. It’s a great place to relax, walk along the lakefront, or enjoy summer in the city.
Lou Malnati’s Pizzeria: No visit to Chicago is complete without trying deep-dish pizza, and Lou Malnati’s is one of the city’s most iconic spots. Known for its buttery crust, rich tomato sauce, and layers of cheese, it delivers the quintessential Chicago pizza experience.
Portillo’s: Portillo’s is a Chicago institution famous for classic local favorites like Chicago-style hot dogs and Italian beef sandwiches. It’s a must-visit for travelers looking to experience authentic Chicago comfort food.
Cindy’s Rooftop: Located above the Chicago Athletic Association Hotel, Cindy’s Rooftop offers incredible views of Millennium Park and Lake Michigan. The restaurant is known for its elevated American cuisine, craft cocktails, and stylish rooftop atmosphere.
Girl & the Goat: One of Chicago’s most celebrated restaurants, Girl & the Goat is known for bold flavors and creative shared plates. Located in the trendy West Loop neighborhood, it’s a favorite for both locals and visitors.
Gibsons Bar & Steakhouse: Gibsons is one of Chicago’s legendary steakhouses, serving prime steaks, seafood, and classic cocktails in a lively atmosphere. It’s an excellent choice for business dinners or an upscale night out.
Pequod’s Pizza: Famous for its caramelized crust, Pequod’s offers a unique take on Chicago-style pizza. This beloved local favorite consistently ranks among the best pizza spots in the city.
The Purple Pig: Located along Michigan Avenue, The Purple Pig serves Mediterranean-inspired small plates with an emphasis on cheese, wine, and charcuterie. Its lively atmosphere and shareable menu make it a popular dining destination.
Garrett Popcorn shops: Garrett Popcorn has been a Chicago staple for decades and is famous for its signature Garrett Mix®, a combination of caramel and cheese popcorn. It’s the perfect snack to enjoy while exploring the city.
Chicago offers travelers a unique blend of architecture, culture, lakefront scenery, and unforgettable dining experiences. Whether you're taking in skyline views from the river, exploring Millennium Park, or enjoying deep-dish pizza at a local favorite, the city delivers memorable experiences for every type of traveler.
Planning your next business or leisure trip? Christopherson Business Travel helps travelers navigate every detail so they can experience the very best each destination has to offer.
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