Imagine sipping coffee by Lake Michigan, standing beneath the giant Bean, and watching the skyline glow at sunset—all in just three days. I recently spent a long weekend in Chicago and was surprised by how much I could experience without feeling rushed. Whether you’re into food, art, city walks, or skyline views, this Chicago 3 day itinerary balances the must-sees with local favorites I genuinely loved. Here’s exactly how I planned it—plus tips I’d definitely recommend.
📍 Day 1: Iconic Chicago + River Vibes
🖼️ Morning: Millennium Park & The Art Institute
I started my trip in the heart of downtown. Millennium Park felt like the perfect intro—The Bean (aka Cloud Gate) was even shinier than I expected. Right nearby, I wandered into the Art Institute of Chicago. I could’ve spent all day there, but even an hour lets you see classics like Monet’s Water Lilies and Grant Wood’s American Gothic.
- 📸 Tip: The Lurie Garden next to the Bean is peaceful and usually crowd-free.
- 🎟️ Admission: Book Art Institute tickets online to skip the line.
🍕 Afternoon: Deep-Dish + Riverwalk Stroll
Giordano’s was my go-to for deep-dish pizza—it’s a heavy meal, but a must-try. Afterward, I walked along the Chicago Riverwalk. It’s one of the city’s best features: skyline views, pop-up cafes, and murals under every bridge.
- 🍺 Stop for a drink at Tiny Tapp right on the water.
🌆 Evening: Architecture River Cruise at Sunset
This was a highlight. The 90-minute cruise gave such a unique view of the city’s architecture and felt surprisingly relaxing. Watching the sun go down behind the skyscrapers was magic.
- 🛳️ I booked the 7PM tour with Chicago’s First Lady Cruises and would 100% do it again.
🌇 Day 2: Museums, Neighborhoods & Night Views
🏛️ Morning: Field Museum or Shedd Aquarium
I opted for the Field Museum (Sue the T-Rex was the star), but if you’re traveling with kids or love sea life, Shedd Aquarium is right next door. Both are part of the Museum Campus with lake views you won’t forget.
- ☕ Grab coffee beforehand at Hero Coffee Bar—a tiny spot with a cute alley setup.
🌮 Afternoon: Wicker Park Wandering & Lunch
I love exploring neighborhoods, and Wicker Park delivered. Think artsy boutiques, vintage shops, and tacos at Big Star. It felt way more local than downtown.
- 🛍️ Don’t miss Myopic Books and Reckless Records if you’re into hidden finds.
🌃 Evening: 360 CHICAGO or Skydeck at Night
I ended the day with city views from above. Skydeck at Willis Tower is more famous (yes, the glass ledge!), but I personally preferred 360 CHICAGO for fewer crowds and a view of Lake Michigan.
- 📷 Tip: Go right before sunset for golden hour photos, then watch the city lights turn on.
🌳 Day 3: Parks, Cafes & Local Vibes
🌅 Morning: Sunrise at North Avenue Beach
I’m not a morning person, but watching the sunrise behind the skyline from North Avenue Beach was worth the early alarm. It’s peaceful, and locals are out jogging or walking dogs—very Chicago.
- 🥐 I warmed up afterward with pastries from La Fournette in Old Town.
🎨 Late Morning: Lincoln Park & Free Zoo
Lincoln Park felt like a breath of fresh air. The Conservatory is gorgeous and free, and the Lincoln Park Zoo is perfect if you’re traveling with little ones—or just want a cute animal fix.
- 🌿 The Nature Boardwalk behind the zoo has a photogenic honeycomb pavilion.
🍽️ Afternoon: Brunch in Lakeview + Andersonville
I had brunch at Southport Grocery (get the grown-up pop tart) in Lakeview, then headed to Andersonville—a historic Swedish neighborhood with charming shops, bookstores, and cafés.
- 🛍️ Women & Children First bookstore is a gem.
🎭 Evening: Comedy or Jazz Night
For my last night, I chose a classic: live comedy at The Second City. If that’s not your vibe, Green Mill Cocktail Lounge has jazz history dating back to Al Capone days.
- 🍸 Either way, end the night with a cocktail and some laughs or tunes.
🌟 Chicago Travel Tips
- 🚇 Getting Around: The CTA “L” trains are easy to use. I got a 3-day Ventra pass and it saved time and money.
- 👜 Packing Tip: Chicago weather changes fast—bring layers and comfy shoes.
- 📅 Best Time to Visit: Late spring and early fall are perfect. Summer is vibrant but crowded, winter is icy (and beautiful, if you’re brave).
✨ Where to Stay in Chicago
I stayed near River North—it was central and walkable to most sights. Some top picks:
- The Hoxton (trendy, rooftop pool, great breakfast)
- LondonHouse Chicago (epic views from the rooftop)
- Freehand Chicago (budget-friendly boutique feel)
📌 Conclusion
Chicago surprised me. It felt like a perfect mix of iconic and intimate—with skyline views one moment and cozy neighborhoods the next. If you’re visiting for a long weekend, this Chicago 3 day itinerary will help you soak in the best of the city without burning out. Let me know if you try any of these spots—or if you discover a new favorite!
🙋♀️ FAQs
What’s the best time to visit Chicago?
Late May to early October offers the best weather. Fall is crisp and colorful, while summer is ideal for festivals.
Is 3 days enough to explore Chicago?
Yes! You won’t see everything, but three days is perfect for hitting major sights and exploring local spots.
How do I get around Chicago?
Use the CTA trains and buses. A 3-day Ventra pass is convenient and covers most areas.
What should I wear in Chicago?
Comfortable shoes, layers, and a light jacket. Weather changes quickly—even in summer.
Which river cruise is best in Chicago?
I recommend the architecture cruise with Chicago’s First Lady—it’s informative and perfectly timed for golden hour.