3 days you’ll remember in Chicago, Illinois.
Chicago is a city that doesn’t just show up—it shows off. From deep-dish pizza and jaw-dropping architecture to lakefront strolls and skyline views from the Willis Tower, the Windy City knows how to charm. Whether you’re snapping pics at The Bean or vibing to blues in a tucked-away club, every block has a rhythm of its own.
This Foresyte itinerary was built for three unforgettable days in Chicago—layered with flavor, grit, and skyline magic that lingers long after you’ve left.
Let’s take it from the top.
Itinerary inspired by the Foresyte community.
📍 Wind at my Back
Day 1: Architecture River Cruise
“Glide beneath century-old bridges as glass towers stretch above. This is Chicago from the water… bold, breathtaking, unforgettable.”
Day 1: Dinner @ Swift and Sons
“Classic chophouse elegance with perfectly seared steaks and a side of old-school charm. Come hungry, leave changed.”
Day 2: Chicago Pizza
“Deep dish that defies physics. Golden crust, molten cheese, and enough swagger to fuel a layover romance.”
Day 2: Lunch @ Ciccio Mio
“Tucked away and candlelit, this Italian hideaway flirts with velvet booths and truffle butter.”
Day 2: Art Institute
“A world of expression beneath grand columns. Lose track of time in Monet, Warhol, and whispers of genius.”
Day 2: Dinner @ Pistores Cuisine
“A warm welcome in the form of handmade pastas and bold Italian traditions. Date night approved.”
Day 3: Brunch @ Quartino Wine Bar
“Bustling, boisterous, and deliciously chaotic. Small plates and bold pours in an all-day Euro-style affair.”
Day 3: Iconic Bites Walk
“A walking tour of edible icons. Think Italian beef, hot dogs with everything, and plenty of napkins.”
Day 3: Bites @ Violet Hour
“Low-lit and effortlessly cool. The kind of cocktail bar where your drink has a backstory.”
Day 3: Field Museum
“Where dinosaurs roam and ancient worlds come alive. It’s not just a museum, it’s a time machine!”
Day 3: Dinner @ Lena Brava
“Wood-fired seafood and Baja soul in the heart of the city. Smoke, spice, and sunset vibes.”
New York Itinerary FAQ.
What are the best things to do in Chicago for a weekend trip?
Top things to do in Chicago include visiting Millennium Park, exploring the Art Institute of Chicago, cruising the Chicago River, catching a show at Second City, and enjoying deep-dish pizza.
When is the best time to visit Chicago for a weekend getaway?
The best time to visit Chicago is from late spring through early fall (May to October) when the weather is warm and the city’s outdoor festivals are in full swing.
Where should I stay in Chicago for a weekend trip?
The best neighborhoods to stay in Chicago for a weekend are The Loop, River North, and the Magnificent Mile—all close to top attractions, restaurants, and nightlife.
What food is a must-try in Chicago during a weekend visit?
Don’t miss Chicago-style deep-dish pizza, Italian beef sandwiches, Garrett popcorn, Chicago-style hot dogs, and iconic steakhouse dinners.
Is Chicago walkable for a weekend trip?
Yes, downtown Chicago is very walkable with most major attractions located within a few miles. The city is also well-connected by public transportation.
How do I get around Chicago for a weekend trip?
Use the “L” trains, buses, rideshare, or simply walk. The CTA system is reliable and ideal for exploring neighborhoods beyond downtown.
Where meaningful travel begins.
Start your journey with Foresyte, where the planning is part of the magic.
Discover the experiences that matter most.
