3-Day Chicago Itinerary: Iconic Sights, Culinary Delights & Cultural Gems

Day 1: Downtown Highlights

Chicago, USA on October 20, 2025

8:00am

Breakfast at Wildberry Pancakes and Cafe

Start your day with delicious pancakes and coffee at this popular downtown spot close to Millennium Park.
USD15, 1h

9:30am

Millennium Park

Explore this iconic park featuring Cloud Gate (‘The Bean’), Crown Fountain, and Lurie Garden, perfect for photos and a relaxing morning walk.
Free, 1h30m

11:30am

Art Institute of Chicago

Visit one of the oldest and largest art museums in the US, housing masterpieces from Impressionism to Modern Art, located just adjacent to Millennium Park.
USD25, 2h

1:30pm

Lunch at Giordano's

Enjoy Chicago’s famous deep-dish pizza at this classic pizzeria downtown; their stuffed pizza is a must-try.
USD20, 1h

3:00pm

Chicago Architecture River Cruise

Discover Chicago’s architectural history with a scenic 90-minute cruise along the Chicago River, covering notable buildings and stories.
USD50, 1h30m

5:00pm

Stroll along the Chicago Riverwalk

Relax and enjoy views of the river with dining and public art options, perfect for an early evening walk.
Free, 1h

7:00pm

Dinner at The Purple Pig

Savor Mediterranean-inspired small plates and charcuterie in a lively atmosphere near Michigan Avenue; great for sharing and variety.
USD35, 1h30m
View Hotels

Day 2: Museum Campus & Lakefront

Chicago, USA on October 21, 2025

8:30am

Breakfast at Yolk - Museum Campus Location

Fuel up with creative breakfast dishes in a bright setting near the lakefront to prepare for a day of cultural visits.
USD18, 1h

9:30am

Field Museum of Natural History

Explore vast natural history exhibits, including Sue the T-Rex and Ancient Egypt, offering a fascinating look at the natural world.
USD26, 2h30m

12:15pm

Lunch at Museum Campus Café or nearby

Grab a quick bite at the museum café or nearby eateries to maximize time for afternoon activities.
USD15, 45m

1:00pm

Shedd Aquarium

Visit this premier aquarium featuring thousands of aquatic animals and immersive exhibits like the Caribbean Reef and Wild Reef.
USD40, 2h

3:30pm

Adler Planetarium

Explore the universe with engaging exhibits and stunning skyline views from this historic planetarium.
USD19, 1h30m

5:30pm

Walk along Lake Michigan Shoreline

Enjoy fresh air and scenic views with a leisurely walk or bike ride along the lakefront path, absorbing the cityscape at sunset.
Free, 1h

7:30pm

Dinner at Cindy’s Rooftop

Dine with spectacular views over Millennium Park and the lake; the menu features seasonal American fare in a stylish setting.
USD50, 1h30m
View Hotels

Day 3: Lincoln Park & Shopping

Chicago, USA on October 22, 2025

8:00am

Breakfast at Batter & Berries

Indulge in creative breakfast options like stuffed French toast and fresh berries in the charming Lincoln Park neighborhood.
USD20, 1h

9:30am

Lincoln Park Zoo

Visit one of the nation’s oldest free zoos featuring animals from around the world in a beautiful park setting.
Free, 1h30m

11:15am

Lincoln Park Conservatory

Walk through lush greenhouses showcasing exotic plants and flowers, perfect for a peaceful mid-morning stop.
Free, 45m

12:15pm

Lunch at Cafe Ba-Ba-Reeba!

Enjoy lively tapas and Spanish-inspired dishes with a great ambiance in Lincoln Park.
USD25, 1h

1:30pm

Shopping on North Avenue and Armitage Avenue

Explore boutique shops, trendy apparel stores, and local crafts in a vibrant neighborhood setting before heading downtown.
Varies, 2h

4:00pm

Magnificent Mile Stroll

Walk the famous Michigan Avenue shopping district featuring flagship stores, luxury boutiques, and iconic landmarks.
Free, 1h30m

6:00pm

Early Dinner at Joe’s Seafood, Prime Steak & Stone Crab

Savor classic Chicago steakhouse fare with excellent seafood in an upscale, relaxed environment to close your trip.
USD60, 1h30m
View Hotels