Three Days in Chicago: Deep-Dish, Architecture & Jazz
Chicago is a city that grabs you from the moment you arrive. The towering skyline, the smell of buttery deep-dish pizza wafting through the streets, and the unmistakable sound of live jazz drifting from cozy bars—it’s a city that feels alive in every sense. Whether you’re here for the legendary food, stunning architecture, or vibrant music scene, Chicago delivers an unforgettable experience.
With just three days in Chicago, you’ll get a taste of its best. From a scenic river cruise and indulgent slices of deep-dish pizza to late-night jazz sessions in historic clubs, here’s the ultimate itinerary to make the most of your time in the Windy City.
Day 1: Deep-Dish Pizza & The Loop
Start your trip with a classic Chicago deep-dish pizza at Lou Malnati’s or Giordano’s—both serve up thick, buttery crusts loaded with layers of cheese and tangy tomato sauce. Order a small if you’re solo, but if you’re with friends, go all in on a large. It takes about 45 minutes to bake, so use the wait time to sip a local craft beer or plan your afternoon.
After lunch, head to Millennium Park to see the famous Cloud Gate (aka “The Bean”) and snap some photos. Then, take a short walk to the Art Institute of Chicago, home to Grant Wood’s “American Gothic” and Georges Seurat’s “A Sunday on La Grande Jatte.” If architecture fascinates you, consider an Architecture River Cruise for a breathtaking look at the city’s most famous skyscrapers.
Day 2: History, Museums & Skyline Views
Kick off your morning at the Field Museum, where you can meet SUE the T. rex and explore exhibits covering everything from ancient Egypt to deep-sea creatures. Right next door, the Shedd Aquarium is a must-visit, especially if you’re traveling with kids. The beluga whales and playful otters are crowd favorites.
For unbeatable views, head to Willis Tower’s Skydeck. Step onto the glass-bottomed Ledge, a clear box that extends 1,353 feet over the city. If heights aren’t your thing, opt for 360 CHICAGO at the John Hancock Center, where you can enjoy a cocktail at Bar 94 while watching the sunset over Lake Michigan.
Day 3: Jazz, Neighborhood Strolls & Hidden Gems
Spend your last day exploring one of Chicago’s vibrant neighborhoods. Head to Wicker Park for trendy coffee shops and vintage boutiques, or visit Pilsen, a cultural hub filled with stunning street art and authentic Mexican food. If you love history, check out the Chicago History Museum in Lincoln Park for a deep dive into the city’s past.
No trip to Chicago is complete without a night of live jazz. End your adventure at Green Mill Cocktail Lounge, a legendary Prohibition-era bar once frequented by Al Capone. The ambiance is intimate, the music is top-notch, and the experience is nothing short of magical. If you prefer a modern take on jazz, Andy’s Jazz Club offers a lively atmosphere with fantastic cocktails.
