How to Spend Three Days in Chicago: A Perfect Itinerary for First-Time Visitors
If you truly want to experience the real Chicago, following our three-day itinerary is the perfect way to do it. Instead of just snapping photos at tourist hotspots, you'll dive into the city's soul—marveling at hidden architectural gems with Inside Chicago Walking Tours, cruising the river to uncover the stories behind the skyline, and exploring neighborhoods bursting with character beyond the Loop. Whether you're soaking in jazz at the legendary Green Mill Cocktail Lounge, savoring deep-dish pizza at Pequod’s, or discovering the street art of the West Loop, you'll see a side of Chicago that most visitors miss. Trust us—this isn’t just a trip; it’s a deep dive into what makes Chicago truly unforgettable.
Day 1: Architecture & History Crash Course
Chicago is a city of stunning architecture, and there’s no better way to start your trip than by exploring its famous buildings and historical landmarks.
Morning: Take an Award-Winning Interior Architecture Tour with Inside Chicago Walking Tours!
Kick off your trip with Chicago’s original and best interior architecture tours from Inside Chicago Walking Tours.
Discover hidden gems inside Chicago’s most impressive buildings, including stunning Art Deco lobbies, historic skyscrapers, and modern masterpieces.
Learn about the city’s architectural evolution from the Great Chicago Fire of 1871 to today’s skyline.
Afternoon: Visit the Chicago History Museum in Lincoln Park.
Head to the Chicago History Museum in Lincoln Park to dive deeper into the city's rich past.
Explore exhibits on Chicago’s role in shaping American history, from the Great Fire to the rise of blues and jazz.
Check out the interactive features, including a vintage ‘L’ car and a large-scale diorama of the city.
Evening: Architecture Boat Tour & Dinner
Take a relaxing 90-minute architecture cruise with Tours and Boats on the Chicago River.
Admire the breathtaking skyline as expert guides explain the stories behind world-renowned buildings by architects like Mies van der Rohe and Bruce Graham.
Enjoy dinner at River Roast, a riverfront restaurant, known for its fall-apart roasted meat dishes.
After Dinner: Stroll & Nightcap
Admire the views from all along the Chicago Riverwalk, with buildings lit up beautifully at night.
Enjoy any of our exclusive rooftop bars for a late-night cocktail — we recommend the rooftop of the Virgin Hotel!
If you’re visiting on a Wednesday or Saturday in the summer, catch the free fireworks from Navy Pier!
Day 2: Neighborhoods, Local Culture, and Jazz Music
Chicago’s charm extends far beyond the downtown Loop. Today, venture into diverse neighborhoods and immerse yourself in local culture.
Morning: Exploring Neighborhoods Outside the Loop — like Wicker Park, Hyde Park, and Andersonville
Ride the ‘L’ train to Wicker Park/Bucktown, Hyde Park, Andersonville, or any of Chicago’s nearly 200 neighborhoods to see where most of Chicago lives.
Stroll along Milwaukee Avenue and Division Street, or Clark Street near Foster, or the University of Chicago campus, stopping at unique boutiques, record stores, and local coffee shops.
Enjoy a delicious lunch at a neighborhood restaurant — with so many neighborhoods, the restaurant options are endless!
Afternoon: Lakefront & Lincoln Park
Take a scenic walk along the Lakefront Trail, soaking in views of Lake Michigan and the skyline.
Visit the Lincoln Park Conservatory and Lincoln Park Zoo — both free year-round!
Enjoy the many restaurants and shops of Lincoln Park — and the gigantic park itself!
Evening: Jazz Night in Uptown
Head to the Green Mill Cocktail Lounge, one of the oldest jazz clubs in the country, once frequented by Al Capone.
Enjoy live jazz performances while sipping classic cocktails in this historic, speakeasy-style venue. Cash only!
If you’re taking an Uber, have them take you for a quick view from the Adler Planetarium before dropping you off at your downtown hotel. The views at night are amazing!
Day 3: Food, Art, and Comedy
On your final day, savor the best of Chicago’s culinary scene, discover street art, and explore a few last iconic spots and hidden gems.
Morning: Chinatown to West Loop
Start with a cafe and pastry at Tous Les Jours in Chinatown.
Walk around both Chinatown’s old and new sections, browsing souvenir shops for Chicago souvenirs on a budget.
Ride the Green Line “L” from Chinatown to the West Loop, a vibrant neighborhood of old factories, new skyscrapers, and amazing food.
Afternoon: West Loop Food Crawl
Explore the West Loop, Chicago’s hottest food neighborhood, peppered with creative street art.
Sample bites from famous spots like Au Cheval (burgers), Girl & the Goat (small plates), or The Publican.
Walk through Fulton Market, once a meatpacking district, now home to company headquarters, trendy restaurants, and cute cafes.
Evening: Local Improv Comedy & Deep-Dish Pizza Finale
End your trip with a classic deep-dish pizza at Lou Malnati’s or Pequod’s, two of Chicago’s most beloved pizzerias.
Make sure to sample our local beers and spirits — Chicago is a huge beer town!
Catch the best of improv comedy at the iO (formerly ImprovOlympic), especially their “Improvised Shakespeare” show.
Final Tips for Visiting Chicago
Chicago, the Windy City, is an incredible destination for tourists looking to experience world-class architecture, deep history, vibrant jazz music, and an unbeatable food scene. Whether you’re a first-time visitor or a returning traveler, we hope you are inspired by our three-day itinerary! We hope that it will help you make the most of your trip while covering Chicago’s most iconic attractions and some hidden gems beyond the Loop. Just a few final tips for your Chicago trip:
Getting Around: Use the ‘L’ train and buses for convenient and affordable transportation, with late-night rides from Uber/Lyft and taxis.
Weather: Dress in layers—Chicago’s weather can be unpredictable!
Don’t limit yourself to just “the Loop,” our downtown area. It’s a wonderful, history-and-architecture-packed neighborhood, but there are 199 more to explore!
Don’t waste your time with hokey tours that tell you false and silly stories in gangster accents. Chicago is famous for its architecture and music: get to know the real heart of the city by exploring those instead!
See both the OUTSIDE of our world-famous architecture on a boat tour, and the INSIDE of our world-famous architecture with Inside Chicago Walking Tours — even locals don’t go where we go!