Itineraries for Your Trip to Chicago
1 Day in Chicago for First Timers
You could spend a lifetime getting to know Chicago and not seeing it all—I spent 10 years there and return regularly and still feel like I’ve barely scratched the surface. Though often overlooked compared to US coastal hubs, Chicago continues to thrive. There are top-notch museums like the Field Museum and Art Institute to discover, architecturally renowned skyscrapers like the Willis Tower and John Hancock Center to summit, classic bites from deep-dish pizza to Chicago hotdogs to savor, and some 77 community areas to explore.
Even if you only have one day in Chicago, you can still get a taste of all that makes this Midwestern metropolis so special—here’s your perfect itinerary.
If you only have time for one thing, make it summiting the Skydeck at the Willis Tower (or the Sears Tower, as locals continue to call it).
Expect intensely snowy winters and sweltering summers in Chicago, where seasons happen to their fullest—dress (and pack) accordingly.
To begin your morning in the Windy City, you could set off on foot or hop aboard a tour bus—but for the most authentically Chicago experience, there’s no better way to start than with a cruise along the Chicago River. With two branches that wend their way past many of the city’s top landmarks (and which eventually empty into Lake Michigan), the waterway offers first-hand views of the Chicago Riverwalk, Navy Pier, Marina City towers, and other iconic architectural gems. Get settled aboard the top deck and bring your camera for the ride.
If all that fresh air has worked up an appetite, you’re in luck—the Windy City is as celebrated for its food culture and classic dishes as for its architectural landmarks, and no trip is complete without a culinary excursion. Depending on the tour you pick, you can look forward to trying staples from deep-dish pizza and Chicago hotdogs to Italian beef sandwiches (which recently made a starring appearance on The Bear). In between, you stroll the vibrant Loop and look for highlights like Millennium Park and the Rookery Building.
To end your Chicago visit on a high note—quite literally—make your last stop of the day a trip to the tippy top of the Willis Tower. Skydeck Chicago, located 1,353 feet (412 meters) up, offers some of the best views of the city, Lake Michigan, and well beyond, and there’s no better time to visit than when the sun starts to go down. Watch the sea of skyscrapers begin to light up all around you—and even step out onto the glassed-in Ledge to feel like a true daredevil.
