Chicago had been calling my name for a while. I’d seen the skyline in movies, dreamt of deep-dish pizza, and saved more Pinterest shots of The Bean than I’d care to admit. So when I finally planned a 4 day Chicago itinerary, I wanted to hit the perfect balance of iconic must-sees and slower, local discoveries.
Over four days, I walked through world-class museums, danced on rooftops, explored cozy neighborhoods, and yes—ate a ridiculous amount of food. Whether you’re a first-time visitor or a return traveler looking to go deeper, here’s exactly how I’d spend four days in Chicago.
🗓 Day 1: The Icons of Chicago – Downtown + Millennium Park
🏙️ Morning: The Loop + Millennium Park
I kicked things off with coffee near the Chicago Riverwalk, where the skyline views were instantly energizing. After a peaceful stroll, I made my way to Millennium Park—and yes, I finally saw The Bean in person! Touristy? Absolutely. But it’s worth seeing at least once.
- Don’t miss the Crown Fountain (especially in summer when kids play in it!)
- Snap skyline views from Pritzker Pavilion
🎨 Afternoon: Art Institute of Chicago
I spent nearly 3 hours inside the Art Institute, and it wasn’t enough. Monet, Seurat, Van Gogh—the Impressionist rooms alone could’ve taken up a whole afternoon.
- Tip: Enter from Monroe Street for shorter security lines
- Stop by the museum café for a recharge
🌃 Evening: Chicago River Architecture Cruise
One of my favorite experiences of the whole trip. The sunset cruise shows you just how magical the city’s architecture really is. It’s informative but relaxed—and nothing beats golden hour on the river.
- I booked with Chicago’s First Lady Cruises—they partner with the Chicago Architecture Center
- Bring a jacket even in summer—it gets breezy
🌭 Day 2: Food, Neighborhoods & Lakefront Views
🍩 Morning: Wicker Park + Breakfast at Mindy’s Bakery
Wicker Park surprised me—it felt hip without trying too hard. After wandering past colorful street art and boutiques, I grabbed a warm babka at Mindy’s Bakery and explored the quirky side streets.
🌮 Lunch: West Loop
Next stop: the West Loop’s Restaurant Row. I tried tacos at Bar Takito and couldn’t resist stopping by Do-Rite Donuts afterward.
- If you’re a foodie, block more time here—it’s a dream
🌊 Afternoon: Lakefront Trail + Lincoln Park
I rented a Divvy bike and cruised along the Lakefront Trail up to Lincoln Park. It’s the kind of route that makes you want to live in Chicago. Free attractions like the Lincoln Park Zoo and Conservatory made it even better.
🌆 Evening: Dinner + Drinks in Old Town
I ended the day in Old Town, one of the city’s most charming pockets. Dinner at Twin Anchors (famous for its ribs and Sinatra history) followed by cocktails at The VIG Chicago.
🎭 Day 3: Culture, Views & Rooftop Vibes
☕ Morning: Logan Square Coffee + Murals
Started with a slow morning in Logan Square, home to gorgeous homes and indie cafés. I grabbed a latte at Passion House Coffee and wandered through alleys of murals.
🏛️ Midday: Museum Campus
The trio of museums near the lake—Field Museum, Shedd Aquarium, and Adler Planetarium—are worth the hype. I only had energy for one, so I went with the Field Museum and stood in awe of Sue the T. Rex.
- Buy tickets online to skip lines
- Walk behind Adler Planetarium for a postcard view of the skyline
🌇 Sunset: 360 CHICAGO at the Hancock Center
Forget the Willis Tower. The 360 CHICAGO Observation Deck was quieter and had a bar with views. I watched the sun dip behind the city from 1,000 feet up—definitely a trip highlight.
🍸 Evening: Rooftop Bar + Late Dinner
Dinner at Etta in River North followed by drinks at LondonHouse Rooftop. Both places gave me that buzzy Chicago nightlife feel—upscale but not too buttoned-up.
🛍️ Day 4: Slow Morning + Shopping + Hidden Finds
🥐 Brunch in Andersonville
I wanted a slower final day, so I trained up to Andersonville, a Swedish-rooted neighborhood with charm for days. Brunch at Hopleaf was hearty and laid-back. Bonus: so many cute home stores and bookshops.
🛍️ Afternoon: Window Shopping on the Mag Mile
Even if you’re not a shopper, the Magnificent Mile is fun to stroll. I stopped into the Historic Water Tower, bought a couple souvenirs at Shinola, and people-watched like a local.
🖼️ Evening: Golden Hour at Promontory Point
For one last view, I Ubered down to Promontory Point in Hyde Park. It was calm, beautiful, and filled with locals walking dogs or just watching the skyline glow.
- Bring a picnic or grab snacks on the way
- The views here rival any rooftop
🧳 Final Thoughts:
Chicago has this way of feeling enormous yet totally accessible. In four days, I barely scratched the surface, but I walked away feeling full—in every sense of the word. If you love walkable cities, design, food, and friendly vibes, this 4 day Chicago itinerary is one I’d happily follow all over again.
FAQs: Chicago 4 Day Itinerary
Is 4 days enough to see Chicago?
Yes, four days is perfect for a first-timer! You’ll have time to cover downtown, a few neighborhoods, lakefront activities, and cultural spots.
What’s the best way to get around Chicago in 4 days?
Use the ‘L’ trains for quick hops across the city, walk as much as you can, and grab a Divvy bike for lakeside routes. Uber is handy for longer rides at night.
Where should I stay for this itinerary?
Stay in River North or the Loop for easy access to most sites. Wicker Park and Old Town are great for a more local vibe.
What’s the best season to visit Chicago?
Late spring to early fall (May to October) is ideal. The weather is walk-friendly, rooftops are open, and festivals bring the city to life.