I’ll be honest—when I first planned a week in Chicago, I wasn’t sure how much I’d be able to fill. Turns out, seven days barely scratch the surface. From world-class art and deep-dish pizza to jazz bars and lakeside strolls, the Windy City completely swept me off my feet.
Whether it’s your first time in town or your third, this Chicago 7 day itinerary will help you explore it all: the must-see highlights, a few low-key local spots, and even some personal favorites I stumbled on along the way.
📍 Day 1: Downtown Highlights & Riverwalk Vibes
Start with:
- Millennium Park: Yes, The Bean. But also Crown Fountain and those surprisingly serene gardens.
- Art Institute of Chicago: One of my favorite museums in the country. Don’t miss the Impressionists section.
Afternoon stroll:
- Walk along Chicago Riverwalk. Grab a coffee, admire the architecture, and just soak it in.
Dinner:
- Lou Malnati’s or Giordano’s for deep-dish. Touristy? Sure. Worth it? Absolutely.
Evening:
- If you’re not wiped, catch views from the Chicago Observation Deck at 360 CHICAGO (John Hancock).
🏙 Day 2: Architecture Cruise + Magnificent Mile
Morning:
- Chicago Architecture Foundation River Cruise: Genuinely one of the best things I did all week.
Lunch:
- Try Eataly or Purple Pig for a quick but elevated meal near the Magnificent Mile.
Afternoon:
- Explore Magnificent Mile. Even if you’re not shopping, the historic buildings and bridges are gorgeous.
Evening:
- Walk up to Navy Pier. The sunset from the pier is worth the crowds.
🎨 Day 3: Museums + Hyde Park Day
Morning:
- Head to Museum Campus. My pick: Field Museum or Shedd Aquarium.
Afternoon adventure:
- Take a ride to Hyde Park. Stroll around the University of Chicago campus and stop by Frank Lloyd Wright’s Robie House.
Dinner:
- I grabbed a hearty sandwich at Valois Restaurant, a local classic where even Obama used to eat.
🌮 Day 4: Food Tour + West Loop Dining
Morning:
- Sleep in or grab a late brunch at Wildberry Pancakes.
Midday:
- Book a Chicago Food Planet or Secret Food Tour through River North or Wicker Park. You’ll try everything from Chicago dogs to Polish pastries.
Evening:
- Head to Fulton Market District in the West Loop. So many incredible restaurants—I went with Girl & The Goat (book ahead!).
🖼️ Day 5: Lincoln Park + Hidden Gems
Morning in nature:
- Explore Lincoln Park Conservatory and Lincoln Park Zoo (free and adorable).
Afternoon gems:
- Walk through Old Town or the Chicago History Museum. Quiet, pretty, and full of character.
Evening drink:
- Have a rooftop cocktail at Z Bar or The J. Parker.
🎷 Day 6: Neighborhoods + Live Music
Morning:
- Ride the ‘L’ to Logan Square or Wicker Park. Browse indie shops, vintage stores, and quirky cafes.
Afternoon:
- Stop by Reckless Records, sip a drink at Ipsento 606, and enjoy the 606 Trail walk.
Evening:
- Catch a jazz set at Green Mill Cocktail Lounge in Uptown. Old-school, vibey, unforgettable.
🌅 Day 7: Lakefront + Farewell Views
Start your morning early:
- Walk or bike along Lakefront Trail from Oak Street Beach to Museum Campus. The skyline views here? Unreal.
Brunch treat:
- Go big on your last day—try Beatrix or 3 Arts Club Cafe (inside a dreamy Restoration Hardware).
Final stop:
- If you’ve got time before your flight, unwind at AIRE Ancient Baths in River West. A spa day before a flight? Chef’s kiss.
🧳 Travel Tips for One Week in Chicago
- Getting Around: Buy a CTA 7-day Ventra pass. Super easy for buses and trains.
- Best Time to Visit: Late spring to early fall. I went in early September and it was dreamy.
- Where I Stayed: I split between The Robey (great for West Side exploring) and LondonHouse for river views.
✨ Final Thoughts
Seven days in Chicago gave me everything I wanted—art, food, lake breezes, and late-night music—and still left me wanting more. If you’re dreaming of a city that blends grit with grace, skyscrapers with soul, you’ll feel right at home here too.
Let me know if you try this itinerary—or better yet, if you discover your own favorites. I’d love to hear about them.