Chicago Illinois 7 Day Itinerary
Chicago, Illinois 7-Day Itinerary
Day 1: Explore The Loop & Millennium Park
- Start your day with breakfast at Amy’s Café & Bookstore.
- Visit iconic landmarks like Willis (Sears) Tower, Cloudgate (The Bean), and the Art Institute of Chicago.
- Lunch at Lou Malnati’s Pizzeria for a famous Chicago-style deep dish pizza.
- Spend the afternoon in Millennium Park, enjoy the Crown Fountain, Lurie Garden, and Frank Gehry’s Jay Pritzker Pavilion.
- Dinner at Girl & The Goat, one of Chicago’s top restaurants.
- Evening stroll along Michigan Avenue and The Magnificent Mile.
Day 2: Museum Campus & Navy Pier
- Breakfast at Wayfarer Cafe.
- Head to Museum Campus: Shedd Aquarium, Adler Planetarium, and the Field Museum.
- Lunch at Museum Café in Shedd Aquarium or nearby food trucks.
- Afternoon at Navy Pier: Centennial Wheel, Chicago Shakespeare Theater, and the Smith Museum of Stained Glass Windows.
- Dinner at River North Seafood.
Day 3: Lincoln Park & Wrigley Field
- Breakfast at Pastoral Artisan Bakery & Cafe.
- Explore Lincoln Park: Lincoln Park Zoo, Lincoln Park Conservatory, and the Alfred Caldwell Lily Pool.
- Lunch at The Purple Pig or nearby food trucks in Lincoln Park.
- Afternoon game at Wrigley Field (if available during your visit).
- Dinner at Gibsons Bar & Steakhouse.
Day 4: The 606 & Wicker Park
- Breakfast at The Bongo Room.
- Walk or bike along The 606 elevated park.
- Explore Wicker Park neighborhood: Wicker Park Bucktown Chamber of Commerce, Flaming Saddles Saloon, and the Chicago Murals.
- Lunch at Big Star for tacos and margaritas.
- Afternoon shopping on Division Street and Milwaukee Avenue.
- Dinner at Avec, an upscale Mediterranean restaurant.
Day 5: River North & Michigan Ave Shops
- Breakfast at Eggsperience.
- Visit the Chicago Cultural Center, The Art of Chocolate Museum, and the Chicago Architecture Center.
- Lunch at The Purple Pig or nearby food trucks.
- Afternoon shopping on Michigan Avenue.
- Dinner at Girl & The Goat (if not visited earlier) or try a new restaurant in River North.
Day 6: Lincoln Square & Andersonville
- Breakfast at Sweet Maple.
- Explore Lincoln Square: Old Town School of Folk Music, the historic Ravenswood Castle, and Katherine Dock.
- Lunch at Andersonville Gyro Corner or Ann Sather’s.
- Afternoon in Andersonville: Hansa Teckel Brewery, Swedish American Museum, and Andersonville Antiques District.
- Dinner at Frankie’s Italian American Kitchen.
Day 7: Chicago Riverwalk & Departure Preparation
- Breakfast at The Bagel Hole or Ann Sather’s (if not visited earlier).
- Visit the Chicago Riverwalk, Navy Pier Festival Hall (if not visited earlier), and take a River Architecture Cruise.
- Lunch at Frontera Fresco.
- Spend the rest of your day doing last-minute shopping or sightseeing before preparing for departure.
Transportation: Chicago Transit Authority (CTA) operates an extensive bus and train system, including the “L” trains. Taxis and ride-sharing services like Uber and Lyft are also available. For exploring neighborhoods like Wicker Park, Lincoln Square, and Andersonville, consider biking or walking.
Tips:
- Chicago weather can be unpredictable; pack layers.
- Purchase a Go Chicago Card for discounted admission to many attractions.
- Visit during summer for outdoor activities and events like Taste of Chicago, Lollapalooza, and the Air & Water Show.
- Enjoy Chicago’s vibrant nightlife with live music venues, comedy clubs, and rooftop bars.