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How To Spend 3 days In Chicago

Welcome to the Windy City! Ready to spend 3 days in Chicago? Situated on the shores of Lake Michigan, this city is full of history, culture, and culinary delights. Join us for a descriptive adventure that takes you through the city’s most iconic landmarks, hidden gems, and delicious eats.

3 Days In Chicago

Day 1

9:00 AM – Rise and Shine at Lou Mitchell’s

Start your day at Lou Mitchell’s, a classic American breakfast joint that has been serving up delicious dishes since 1923. Fuel up with their famous “Airport” breakfast and chat with the friendly staff who have been there for decades.

10:00 AM – Millennium Park

Head to Millennium Park, a 24.5-acre public park that houses some of Chicago’s most famous landmarks, including the Cloud Gate sculpture, known as “The Bean.”

3 days in Chicago itinerary
The Chicago Bean
11:00 Am – Art Institute of Chicago

Explore one of the world’s great art museums, the Art Institute of Chicago. Home to over 300,000 works of art, this museum features an extensive collection of paintings, sculptures, and other artworks from around the world. Take a tour of the Impressionist galleries and see works by Monet, Renoir, and Degas.

1:00 PM – Lunch at Portillo’s

Grab lunch at Portillo’s, a Chicago staple known for its hot dogs, Italian beef sandwiches, and chocolate cake shakes.

2:00 Pm – Navy Pier

Head to Navy Pier, where you can take a ride on the Ferris wheel, enjoy a performance at the Chicago Shakespeare Theater, or simply take in the stunning views of Lake Michigan. If you’re feeling an adrenaline burst, take a boat tour from the pier and experience the skyline from a different perspective.

4:00 PM – Chicago Riverwalk

Take a leisurely stroll along the Chicago Riverwalk, a 1.25-mile pedestrian walkway that offers stunning views of the city’s impressive architecture.

6:00 PM – Dinner at Girl & The Goat

End your day at Girl & the Goat, a trendy restaurant that serves up innovative dishes made with fresh, locally sourced ingredients.

Day 2

9:00 AM – Breakfast at Wildberry Pancakes and Cafe

Start your day with a delicious breakfast at Wildberry Pancakes and Cafe, where you can enjoy fluffy pancakes and waffles made from scratch.

10:00 AM – The Field Museum

Explore the wonders of the natural world at The Field Museum. From dinosaurs to ancient civilizations, this museum has something for everyone.

12:00 PM – Lunch at the purple Pig

Indulge in Mediterranean-inspired small plates at The Purple Pig, a popular restaurant located in the River North neighborhood.

1:30 PM – Chicago Architecture Foundation Center River Cruise

Take a guided tour of Chicago’s stunning architecture on a Chicago Architecture Foundation Center River Cruise. Learn about the city’s famous buildings, including the Willis Tower and the John Hancock Center.

polar bear in body of water photography
Lincoln Park Zoo
3:30 PM – Lincoln Park Zoo

Visit the free-admission Lincoln Park Zoo, where you can see animals from around the world, including lions, tigers, and bears.

6:00 Pm – Dinner At Alinea

Experience culinary art at its finest at Alinea, a Michelin-starred restaurant that offers a multi-course tasting menu that is as visually stunning as it is delicious.

Day 3

9:00 AM – Breakfast at Cafe Robey

Start your day with breakfast at Cafe Robey, a rooftop restaurant that offers stunning views of the city.

10:00 AM – Willis Tower Skydeck

Step onto the Skydeck at Willis Tower, the tallest building in the Western Hemisphere. Enjoy 360-degree views of the city from the 103rd floor.

photo of city building
Willis Tower
12:00 PM – Lunch At Chicago Cut Steakhouse

Savor a delicious steak lunch at Chicago Cut Steakhouse, where you can enjoy some of the best cuts of meat in the city.

2:00 PM – The Magnificent Mile

Shop ’til you drop on the Magnificent Mile, a world-famous shopping district that offers high-end fashion, luxury brands, and department stores.

4:00 PM – The Second City Comedy Club

Laugh out loud at The Second City Comedy Club, a world-famous improv theater that has launched the careers of many famous comedians.

6:00 PM – Giordano’s

It’s time for deep-dish pizza! Head to Giordano’s for a cheesy, gooey pie that is sure to satisfy.

Giordano's store front
Giordano’s Deep Dish Pizza

Chicago, the city of broad shoulders, has a charm that captivates visitors from all around the world. We hope this three-day itinerary has given you a taste of the city’s rich history, world-class museums, delicious food, and stunning architecture. From the iconic Cloud Gate sculpture to the mouth-watering deep-dish pizza, Chicago has something for everyone. We hope you enjoyed your trip and created memories that will last a lifetime. Until next time, farewell from the Windy City!

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