6 Days in Chicago: Deep-Dish Pizza and Lakefront Walks
Chicago is one of those cities that grabs you with its energy and never lets go. From its bold skyline to the smell of deep-dish pizza wafting through the streets, there’s something magnetic about the Windy City. If you’re craving a destination that blends big-city culture with relaxed lakeside vibes, Chicago is calling.
I spent six days in the heart of the city, wandering from historic neighborhoods to the edge of Lake Michigan, all while indulging in local eats and soaking up the city’s bold personality. Here’s how to make the most of your time—whether you’re a foodie, culture lover, or just here for those breezy lakefront walks.
Day 1: Strolling the Magnificent Mile and Chicago Riverwalk
Start your trip on Michigan Avenue’s Magnificent Mile, where upscale shops and architectural gems line the boulevard. Even if you’re not in the mood to shop, it’s the perfect way to get a feel for Chicago’s grandeur. Stop by The Wrigley Building and take in the historic charm before heading toward the Chicago River.
From there, walk down to the Chicago Riverwalk, a favorite spot for both locals and visitors. With café seating right by the water and art installations tucked along the path, it’s easy to spend hours here. If you’re up for it, hop on a river architecture cruise—a surprisingly fun and informative intro to the city’s skyline.
Day 2: Millennium Park and Art Institute of Chicago
No trip to Chicago is complete without seeing Cloud Gate, aka “The Bean.” Head to Millennium Park early to beat the crowds and get those reflective selfies. The park also has serene garden paths and public art that give you a quick escape from the city bustle.
Just next door is the Art Institute of Chicago, one of the best art museums in the world. You can easily spend half a day here exploring everything from Monet to modern installations. Don’t miss Grant Wood’s “American Gothic” or the stunning Impressionist collection on the second floor.
Day 3: Deep-Dish Pizza and the West Loop
Today’s all about flavor. Make your way to Lou Malnati’s, Giordano’s, or my personal favorite, Pequod’s, for a true taste of Chicago deep-dish pizza. The caramelized crust at Pequod’s is worth the hype—just make a reservation because the lines can be long.
In the afternoon, head to the West Loop, a trendy area packed with converted warehouses, high-end restaurants, and hidden cocktail bars. Fulton Market is ideal for wandering. Grab a coffee from Sawada Coffee or snag a table at Girl & the Goat for a memorable dinner.
Day 4: Lakefront Trail and Lincoln Park
One of the most beautiful parts of Chicago is its Lakefront Trail, a 18-mile path hugging Lake Michigan. Start around North Avenue Beach and walk north toward Lincoln Park for lake views and a skyline backdrop. Morning is best, especially if you enjoy a quieter walk with a gentle breeze off the water.
Lincoln Park is a lovely stop with gardens, ponds, and even a free Lincoln Park Zoo. It’s perfect for a slower-paced day. If you’re into photography, the Alfred Caldwell Lily Pool is a peaceful, lesser-known gem nearby.
Day 5: Museum Campus and Soldier Field
Dedicate today to the Museum Campus, home to three of Chicago’s top attractions: the Field Museum, the Shedd Aquarium, and the Adler Planetarium. You won’t have time to do them all in depth, so pick your favorite. I loved the Field Museum’s Sue the T. rex and the immersive Ancient Egypt exhibit.
After the museums, walk along the lake to Soldier Field. Even if you’re not a football fan, the view from the area near the Planetarium looking back at the skyline is stunning, especially around golden hour. Pack a light picnic and enjoy the wide green space by the water.
Day 6: Neighborhood Hopping – Wicker Park and Pilsen
Wrap up your trip by exploring two neighborhoods that offer a taste of local life. Start in Wicker Park, known for its indie boutiques, coffee shops, and street art. It’s a cool, walkable area where you can grab brunch at The Bongo Room or explore Myopic Books for hidden literary gems.
In the afternoon, head south to Pilsen, a vibrant neighborhood full of Mexican culture, murals, and incredible food. The National Museum of Mexican Art is free and well worth a visit. Don’t leave without trying tacos from Carnitas Uruapan—they’re legendary for a reason.
