5 Days in Chicago: Deep-Dish Pizza, Jazz & Architectural Wonders
Chicago is a city that knows how to make an impression. With its stunning skyline, world-class museums, deep-rooted music scene, and legendary food, the Windy City is a playground for culture lovers and adventure seekers alike. Whether you’re here for the iconic deep-dish pizza, the birthplace of modern jazz, or the architectural marvels that define the skyline, five days is just enough time to soak it all in.
This itinerary takes you through the best of Chicago, balancing must-see attractions with local favorites. From the depths of historic speakeasies to the heights of the Willis Tower Skydeck, get ready for an unforgettable trip.
Day 1: Exploring the Loop & A Classic Deep-Dish Experience
Start your trip in Chicago’s Loop, the vibrant downtown district filled with towering skyscrapers, famous theaters, and public art. Take a morning stroll along Millennium Park, where you’ll find Cloud Gate—better known as “The Bean.” Snap a few photos before heading to the Art Institute of Chicago, home to masterpieces like Van Gogh’s The Bedroom and Seurat’s A Sunday on La Grande Jatte.
For lunch, it’s time for a Chicago rite of passage—deep-dish pizza. Head to Lou Malnati’s, Giordano’s, or Pequod’s for a slice of cheesy, buttery heaven. Walk it off with a scenic stroll along the Chicago Riverwalk, where you can admire the city’s breathtaking architecture up close. In the evening, catch a Broadway show at the Chicago Theatre or explore the bar scene in The West Loop, a hotspot for craft cocktails.
Day 2: Architecture & The Magnificent Mile
Chicago is known as the birthplace of the modern skyscraper, so an architecture tour is a must. The best way to see it all? A Chicago River architecture cruise. These guided boat tours offer fascinating stories about the city’s most famous buildings, including the Willis Tower, Tribune Tower, and Wrigley Building.
After your cruise, head to The Magnificent Mile, a shopper’s paradise lined with luxury brands, historic landmarks, and stylish cafés. Make a stop at Water Tower Place for unique finds, then grab lunch at Eataly Chicago for a break from deep-dish. If you’re up for more exploring, take the elevator up to 360 Chicago Observation Deck at the John Hancock Center for sweeping views of Lake Michigan and the city skyline.
Day 3: A Day at the Museums & Evening Jazz
Spend the morning at Museum Campus, home to three of the city’s top attractions. The Field Museum houses Sue, the world’s most complete Tyrannosaurus rex skeleton, while the Shedd Aquarium offers an up-close look at marine life from around the world. Science lovers shouldn’t miss the Adler Planetarium, where space exhibits and stargazing experiences await.
As night falls, immerse yourself in Chicago’s legendary jazz scene. Head to The Green Mill Cocktail Lounge, a speakeasy-style club once frequented by Al Capone, or check out Andy’s Jazz Club for a mix of classic and contemporary performances. Pair the music with a classic Chicago-style cocktail for the perfect night out.
Day 4: Hyde Park & South Side Gems
Venture south to Hyde Park, one of Chicago’s most historic and charming neighborhoods. Start at the Museum of Science and Industry, where interactive exhibits let you walk through a German U-boat, experience a simulated tornado, and explore a massive model railroad.
After the museum, take a walk through Jackson Park, designed by landscape architect Frederick Law Olmsted. This green oasis is home to the Garden of the Phoenix, a hidden Japanese garden that feels like a secret retreat. Wrap up your day with a meal at Virtue, a celebrated Southern-inspired restaurant known for its fried green tomatoes and buttermilk-fried chicken.
Day 5: Neighborhoods, Street Art & Skyline Views
Your last day is all about experiencing Chicago’s unique neighborhoods. Start in Wicker Park, a hip district filled with indie boutiques, record stores, and top-tier coffee shops like La Colombe. Walk along Damen Avenue and admire the street art murals, then grab brunch at The Bongo Room for their famous chocolate tower French toast.
In the afternoon, explore Pilsen, an artsy neighborhood known for its vibrant Mexican heritage and colorful murals. Stop by the National Museum of Mexican Art, then try authentic tacos at Carnitas Uruapan. End your trip with one last panoramic view of the city at the Skydeck Chicago, located in the Willis Tower. If you’re feeling brave, step onto The Ledge, a glass box that extends 1,353 feet above the ground—one last unforgettable moment before you say goodbye to Chicago.
