Windy City Wonders: A 3-Day Chicago Itinerary
- Stuart Sokoloff
- Apr 6
- 3 min read
Updated: Apr 8
Get ready to experience the very best of Chicago in just three unforgettable days. From iconic sights like Millennium Park and the Chicago Riverwalk to world-class museums, buzzing neighborhoods, and a deep dive into the city’s legendary food scene, this itinerary blends culture, cuisine, and stunning skyline views. Whether it’s your first visit or your first time really exploring, you’re in for a true Windy City adventure.
Day 1: Architecture, Art, and the Riverfront
Morning
Coffee & Breakfast Kick off your Chicago adventure with a latte and pastry from Oromo Café in Lincoln Square or Sawada Coffee in the West Loop. Both are stylish spots serving delicious drinks in Insta-worthy spaces.
Chicago Architecture Boat Tour Head downtown to the Chicago River for the Chicago Architecture Center River Cruise. It’s the best intro to the Windy City — you’ll cruise past iconic skyscrapers and learn the fascinating stories behind the skyline.
Lunch
Lou Malnati’s or Giordano’s Try Chicago’s famous deep-dish pizza at one of its legendary spots. Lou Malnati’s has a buttery crust, while Giordano’s is known for its cheesy stuffed pie. You can’t go wrong with either.
Afternoon
Millennium Park Take a stroll to Millennium Park and snap a photo with “The Bean” (Cloud Gate). Walk through the serene Lurie Garden and check out the Crown Fountain’s interactive video towers.
Art Institute of Chicago Just a few steps away is the Art Institute of Chicago, one of the top art museums in the world. Don’t miss Grant Wood’s American Gothic, Seurat’s A Sunday Afternoon on the Island of La Grande Jatte, and the museum’s impressive collection of Impressionist and modern art.
Dinner & Drinks
The Purple Pig Dine on inventive Mediterranean small plates at The Purple Pig, right on Michigan Avenue. The bone marrow, pork shoulder, and house charcuterie are standout dishes.
Three Dots and a Dash For drinks, head to Three Dots and a Dash, a secret tiki bar tucked down an alley. With fun, tropical cocktails served in funky mugs, it’s a perfect way to end your first night in the city.
Day 2: Neighborhood Vibes, Views & Live Entertainment
Morning
Coffee & Breakfast Grab a croissant and espresso at La Colombe or Floriole Café & Bakery in Lincoln Park for a charming local feel.
Lincoln Park Exploration Stroll through Lincoln Park, visit the Lincoln Park Zoo (free admission!), and check out the Lincoln Park Conservatory with its lush greenhouse.
Lunch
Small Cheval or Portillo’s Craving a burger? Small Cheval offers one of the best in the city. If you want something more Chicago-style, go for a hot dog and Italian beef sandwich from Portillo’s.
Afternoon
360 Chicago Observation Deck Head to 360 Chicago in the John Hancock building for panoramic city views from 1,000 feet up. Daredevils can try TILT, a glass enclosure that tilts you over the edge!
Shopping & Wandering the Magnificent Mile Take a leisurely walk along the Magnificent Mile, Chicago’s premier shopping district. Browse designer shops, iconic department stores, and local boutiques.
Dinner & Drinks
Girl & the Goat Book ahead for dinner at Girl & the Goat in the West Loop, a buzzy hotspot with globally inspired small plates by Chef Stephanie Izard. The roasted pig face and green beans are must-tries.
Live Music or a Comedy Show Catch some live entertainment:
Green Mill Cocktail Lounge – historic jazz club with a speakeasy vibe
The Second City – legendary improv comedy
Chicago Theatre – iconic venue for concerts, comedy, and more
Day 3: Museums, Beaches & Wrigleyville Fun
Morning
Coffee & Breakfast Start your day at Do-Rite Donuts & Coffee or Intelligentsia Coffee for something sweet and caffeinated.
Museum Campus Adventure Head to Chicago’s Museum Campus, home to three of the city’s best:
Field Museum – home of Sue the T. rex
Shedd Aquarium – massive aquatic exhibits
Adler Planetarium – space lovers, this one's for youTake a lakeside walk along the shore for beautiful skyline views.
Lunch
Chicago French Market or Revival Food Hall Grab lunch at Chicago French Market (near Ogilvie Station) or Revival Food Hall (near the Loop) for a diverse array of local vendors and quick bites.
Afternoon
Lakefront Chill or Wrigleyville Vibes
Weather nice? Relax at North Avenue Beach or Oak Street Beach.
Baseball fan? Head up to Wrigleyville, even if it’s not game day. Walk around the iconic Wrigley Field, grab a beer, and soak in the neighborhood’s festive feel.
Dinner & Drinks
Au Cheval or RPM Italian
Au Cheval – Known for arguably the best burger in America (expect a wait).
RPM Italian – Sleek, upscale spot perfect for a final night out.
Nightcap Options
Cindy’s Rooftop – Cocktails with a view over Millennium Park
The Aviary – High-end cocktail experience in the West Loop
Revolución Steakhouse – Latin-inspired cocktails and a cozy setting
