Plan Your Day at Leisure in the Windy City
We have compiled an extensive list of activities, shopping options, and restaurants for your time in Chicago. Browse the guide and the map to help you decide which activity you'd like to do. Be sure to reserve a time slot or book an activity for those that require planning ahead. We will not be arranging any of these activities for you, so you'll need to make your plans ahead of time! You will get a gift card at the Summit to cover the expense of an activity.
Unforgettable Activities for Your Chicago Visit
Admire the Chicago Skyline
Skydeck Chicago: Touch the Sky at Willis Tower
Skydeck Chicago, perched atop the Willis Tower (formerly known as the Sears Tower). Soaring 1,353 feet above the city, the Skydeck offers visitors a 360-degree panorama that stretches for up to 50 miles on a clear day.
Flyover Chicago: Soar Above the Sights
Flyover Chicago is a groundbreaking attraction that delivers the sensation of flight without ever leaving the city. Using advanced flight simulation technology, Flyover immerses guests in a multisensory journey through Chicago’s most iconic landmarks.
360 CHICAGO Observation Deck: Views from the John Hancock Center
Another must-see for those craving sky-high vistas is 360 CHICAGO, located on the 94th floor of the John Hancock Center. From this lofty perch, guests are treated to unobstructed views of Lake Michigan’s shimmering expanse, the city’s intricate grid, and the sprawling suburbs beyond.
Stroll through Millennium Park
No trip is complete without wandering Millennium Park. Snap a photo at Cloud Gate (“The Bean”), enjoy Lurie Garden, and explore public art and concerts at the Jay Pritzker Pavilion.
Explore the Museums of Chicago
This museum is particularly famous for its collection of Impressionist and Post-Impressionist paintings, including Georges Seurat’s “A Sunday on La Grande Jatte,” Grant Wood’s “American Gothic,” and works by Monet, Renoir, and Van Gogh. Don’t miss the Modern Wing, designed by Renzo Piano, which houses contemporary works and offers breathtaking views of Millennium Park.
The Field one of the largest natural history museums in the world, with over 24 million specimens and artifacts. The museum’s star attraction is Sue, the largest and most complete Tyrannosaurus rex fossil ever discovered. But there’s so much more: visitors can explore ancient Egyptian tombs, marvel at gemstones and rare minerals, walk through reconstructed habitats, and learn about cultures from around the globe.
The Museum of Science and Industry
If you’re fascinated by innovation and scientific discovery, the Museum of Science and Industry (MSI) is a must. Housed in the only remaining building from the 1893 World’s Fair, MSI is one of the largest science museums in the Western Hemisphere. Popular permanent exhibits include the Science Storms gallery, the Idea Factory for kids, and interactive displays about space, transportation, and the environment.
Highlights include artifacts from the city’s past, including Abraham Lincoln memorabilia, vintage fashion, and objects from the 1893 and 1933-34 World’s Fairs. Interactive displays and multimedia presentations bring Chicago’s history to life for visitors of all ages.
Space enthusiasts will find much to love at the Adler Planetarium, the first planetarium in the Western Hemisphere. Inside, visitors can explore the history and science of astronomy through exhibits on the solar system, space exploration, and the universe’s origins.
Visitors can journey from the Amazon rainforest to the Caribbean reef, encountering beluga whales, sea otters, sharks, and more. Interactive exhibits and daily animal presentations make the Shedd Aquarium a family favorite and a captivating stop on any Chicago itinerary
Cruise the Chicago River
Chicago Architecture Foundation Center River Cruise aboard Chicago’s First Lady
Passengers will marvel at the Tribune Tower, Willis Tower, the Wrigley Building, and other legendary structures, all while learning about the city’s rise from the ashes of the Great Chicago Fire to its status as a modern metropolis.
Wendella Architecture River Tours
Wendella, Chicago’s oldest family-owned boat tour company, has been navigating the city’s waterways since 1935. Their architecture tours are renowned for historical insights and striking views. The cruise takes guests along all three branches of the Chicago River, offering a comprehensive lesson on the styles and stories that shaped the city.
Shoreline Sightseeing Architecture River Tour
This lively and entertaining cruise is perfect for families and casual explorers alike. Shoreline’s guides are known for their engaging storytelling and detailed knowledge. In just over an hour, guests experience more than 40 of the city’s most significant buildings.
Kayak the River
For a unique perspective, paddle right through the heart of downtown with Urban Kayak. Join a guided tour on the Chicago River—choose from daytime, sunset, or even evening fireworks tours for stunning views of the city’s architecture and lively waterfront.
Enjoy Navy Pier
At Navy Pier you can ride the Centennial Wheel, visit the Chicago Children’s Museum, and take in festivals, performances, and fireworks along Lake Michigan’s edge.
Shop til You Drop
Indulge in luxury shopping, admire architectural gems, and enjoy vibrant street life along North Michigan Avenue.
If you’re looking for high-end fashion, be sure to stop by the Gold Coast! Enjoy tree-lined streets in this historic neighborhood with luxury boutiques and couture showrooms.
Don’t miss out on speciality shops, modern malls, and historic department stores on State Street! You’ll also see some architectural highlights and enjoy delicious food as you walk down the street.
Discover Lincoln Park and the Zoo
Stroll through Lincoln Park’s gardens, visit the free Lincoln Park Zoo, and explore the conservatory’s lush flora.
Explore Chicago by Bike
Pedal your way through Chicago’s most iconic neighborhoods and lakefront with Bobby’s Bike Hike. These award-winning tours cater to all interests—whether you want to combine sightseeing with food tastings, dive into the city’s history, or just enjoy the fresh air and beautiful scenery. Family-friendly and fun for all fitness levels.
Sample Flavors at Local Markets
The Chicago French Market and Green City Market offer artisanal cheeses, global street food, and fresh pastries in a lively, local atmosphere.
Relax on Lake Michigan’s Beaches
Swim, sunbathe, and people-watch at North Avenue or Oak Street Beach, or bike along the scenic Lakefront Trail.
Explore Wicker Park and Bucktown
Sip coffee in indie cafés, browse art galleries, and enjoy local music in these hip, creative neighborhoods.
Take in Sports at Wrigley Field or United Center
Catch a Cubs game at historic Wrigley Field or see the Bulls or Blackhawks at United Center for a true Chicago sports experience.
Marvel at the Garfield Park Conservatory
At the Garfield Park Conservatory, you can wander through rooms of towering palms and vibrant flowers—truly a landscape art under glass.
Discover Street Art and Murals
Pilsen, Logan Square, and the West Loop boast vibrant murals and public art, perfect for a creative stroll.
Attend a Comedy Show
Experience the birthplace of improv at The Second City or iO Theater, where laughter and surprises abound.
Experience Chicago’s Music Scene
Catch jazz and blues at The Green Mill, Buddy Guy’s Legends, and Kingston Mines—or experience a major festival like Lollapalooza.
Chicago’s Essential Eats: A Culinary Adventure
Where to Get Classic Chicago-Style Hot Dogs
• Portillo’s – A Chicago institution, serving up classic dogs “dragged through the garden” for decades.
• Dave’s Red Hot
• The Weiner’s Club
• Jim’s Original
• Gene & Jude’s – Beloved for its old-school counter service and never any ketchup.
• Superdawg Drive-In – This retro spot features neon signs, carhop service, and a hot dog like no other.
• Byron’s Hot Dogs – A favorite for locals seeking a perfectly loaded Chicago dog.
Where to Try Italian Beef Sandwiches
• Al’s Beef – The original, still serving juicy, perfectly dipped beef sandwiches with sweet or hot peppers.
• Johnnie’s Beef – Known for their spicy giardiniera and long lines well worth the wait.
• Mr. Beef on Orleans – A downtown favorite with a cult-like following.
• Portillo’s – Also excels at hearty, flavorful Italian beef sandwiches.
Where to Eat Deep Dish Pizza
• Lou Malnati’s – Buttery crust, mountains of cheese, and a tangy tomato sauce make this a must-try.
• Giordano’s – Famous for its stuffed deep dish, with gooey cheese in every bite.
• Pequod’s Pizza – Known for its caramelized crust and robust toppings.
• Gino’s East – An iconic spot, with graffiti-lined walls and hearty slices.
• Uno Pizzeria –
• Chicago Pizza and Oven Grinder – Famous for the pizza pot pie
Steak Houses and Classic Chicago Steaks
• Gibsons Bar & Steakhouse – Legendary for aged steaks and old-school Chicago hospitality.
• Chicago Cut Steakhouse – Prime cuts and a view of the river make this a modern favorite.
• Gene & Georgetti – The city’s oldest steakhouse, blending tradition and quality since 1941.
• Bavette’s Bar & Boeuf – A stylish, speakeasy-inspired steakhouse with a decadent menu.
• Smith & Wollensky
• Mortons
Other Famous Chicago Foods and Eateries
• Garrett Popcorn Shops – The iconic “Chicago Mix” blends cheese and caramel popcorn for a sweet-savory snack.
• Mario’s Italian Lemonade – Italian Ices
• Margie’s Candies
• Fanny May Chocolates
• Original Rainbow Cone – A summer treat featuring five flavorful layers of ice cream.
• Harold’s Fried Chicken Fried chicken with Harold’s famous sauce
• The Berhoff – German
• Lou Mitchell Diner – Old School Diner
• Schneider’s Deli
• Billy Goat Tavern – Chicago Style “Cheezborger”
• Manny’s Cafeteria & Delicatessen – Corned Beef
• D’Amato’s Bakery and Subs
• Chicago-Style Cheesecake – Eli’s Cheesecake is rich, creamy, and world-famous.
• Palmer House Hotel – Birthplace of the Brownie!