Looking for the Best 4 Day Chicago Itinerary? I have got the guide for you!
Dramatic skyscrapers above deep blue water paint the backdrop for America’s Windy City, Chicago.
Located in the midwestern United States, Chicago is sometimes overshadowed by bustling New York City and dreamy Los Angeles- but it’s no less iconic.
Chicago has made a name for itself as the third-largest city in the United States.
Featuring famous festivals, delicious food, and Broadway shows, there is a little something for everyone in Chicago.
Come for the Chicago Cubs and stay for historical architecture, free beaches, unique neighborhoods, and hidden pockets to explore.
No matter your travel style, Chicago has something to show off to everyone.
4 Day Chicago Itinerary
Day 1: Museums, Millennium Park, Grant Park
Field Museum
Begin your first day at Chicago’s Field Museum.
Explore ancient history through the extensive dinosaur exhibits, including Sue, the largest and most complete T. rex ever discovered.
Visit the Ancient Egypt exhibit to see real mummies.
Dive into the Grainger Hall of Gems featuring dazzling gemstones from around the globe.
Don’t miss the Evolving Planet exhibit, which takes you on a journey through 4 billion years of life on Earth.
Its central location makes The Field Museum an ideal starting point for exploring the city.
Lunch at Relish Hot Dog
Grab a Chicago-style hot dog from Relish Hot Dog stands outside of the museums. (Vegetarians- they got you covered!)
Enjoying a Chicago hot dog is part of the city’s unique culture!
A classic Chicago Hotdog is served on a poppy seed bun and topped with yellow mustard, bright green relish, chopped onions, tomato wedges, a pickle spear, sport peppers, and a dash of celery salt.
Local tradition strictly forbids ketchup!
Millennium Park
Walk to Millennium Park to enjoy your hot dog lunch!
Millennium Park is one of Chicago’s most visited destinations housing its iconic “Bean” or Cloud Gate sculpture.
Walk to Lurie Garden and check out flower blooms in the summer while admiring skyscrapers- got it all!
Grant Park
Grant Park is located just one block away from Millennium Park.
It is famous for its huge Buckingham Fountain and stunning views of Lake Michigan.
The park hosts outdoor events all year such as concerts and festivals like the Chicago Jazz Festival.
Deep Dish Pizza Dinner
Deep dish pizza is a Chicago staple! It’s characterized by its thick crust and generous layers of cheese, sauce, and stuffed toppings.
Some of the best places to experience authentic deep dish pizza include Lou Malnati’s, Giordano’s, and Pequod’s.
More time? Day 1 Add-Ons:
- Chicago Museum of Culture (Free)- across from Millennium Park.
- Maggie Daley Park
Day 2: Skyscrapers, Chicago River, Navy Pier
Skydeck Chicago
Skydeck Chicago provides one of the most iconic views of the city!
From a glass box high in the sky, enjoy this exhilarating experience.
Tip: If you’re looking to save money, I recommend the Signature Lounge at the John Hancock Building. There’s no skybox, but the views are incredible.
Chicago Riverwalk
The Chicago Riverwalk is a vibrant waterfront pathway with scenic views.
It’s one of my favorite outdoor activities in Chicago! I love it during all seasons, but especially in summer.
It’s a perfect spot to watch boats pass, enjoy a riverside coffee, or simply soak in the beauty of Chicago’s urban landscape!
Tip: Check out the fall party if you visit Chicago in October!
Architecture Cruise
Taking a Chicago architecture cruise is one of the most popular tours to take in Chicago!
It’s a relaxing and unique way to learn about the hidden gems and landmarks of the city.
The tour runs year-round. It’s a favorite among both locals and tourists.
Popular Chicago Tours:
Navy Pier
Navy Pier is a dynamic entertainment destination spanning over 3,000 feet along Lake Michigan!
It’s known for its famous Centennial Ferris wheel, offering panoramas of the city skyline and lake.
Its lively atmosphere and family-friendly attractions make Navy Pier a must-visit for anyone in Chicago.
Tip: I recommend taking public transportation or Uber to Navy Pier.
Parking at the on-site garage is convenient but expensive.
More time? Day 2 Add-On:
- Color Factory after the Skydeck. (Both are located in the same building).
Day 3: Lincoln Park
Lincoln Park Conservatory
The Lincoln Park Conservatory is a hidden treasure.
It’s one of my favorite non-touristy things to do in Chicago!
This lush greenhouse showcases exotic plants, vibrant flowers, and seasonal displays.
Visitors are drawn to its Victorian architecture and its tranquil escape.
The Lincoln Park Conservatory is free of charge.
Secure your free timed-entry reservation on the conservatory website.
Nature Boardwalk and Picnic Lunch
The Nature Boardwalk in Lincoln Park is one of my favorite places to walk in the city.
This winding, mile-long pathway offers stunning views of the Chicago skyline.
Settle in under a tree or on a bench to enjoy a picnic lunch.
Lakefront Trail
The Lakefront Trail in Chicago is an 18-mile-long multi-use path that runs along the scenic shoreline of Lake Michigan.
This trail offers breathtaking views of the lake, downtown skyline, and vibrant city neighborhoods.
The path is dotted with beaches, parks, and attractions.
North Avenue Beach
North Avenue Beach is a prime Chicago summer activity.
It’s known for its sandy shoreline, lively atmosphere, and stunning views of the city skyline.
The beach offers facilities such as restrooms, showers, and concessions, ensuring a comfortable experience for visitors.
Popular beachside spots like Castaways provide refreshing drinks and snacks.
It’s also a great spot to capture some photos on a Chicago girls weekend!
⭐Seasonal Things To Do in Chicago
- Winter
- Spring
- Summer
- Fall
Day 4: State Street, Magnificent Mile, Broadway
State Street
State Street in Chicago is an iconic street in the windy city.
Known for its historic theaters, shopping venues, and cultural landmarks, it’s an ideal place to begin your last day in Chicago.
One of the best photo spots in Chicago is here- The Chicago Theatre!
Nearby shopping spots like Macy’s on State Street are famous for holiday festivities beginning Thanksgiving Weekend in Chicago.
Magnificent Mile
The Magnificent Mile is a premier commercial district of Chicago.
It’s known for its upscale shops, world-class dining options, and cultural attractions.
Architectural landmarks, such as the Tribune Tower and the historic Wrigley Building, make for some great Chicago Instagram spots.
Broadway Show
Your 4 Day Chicago Itinerary ends with a Broadway show on State Street.
Watching a Broadway show in Chicago is a dazzling experience part of the city’s culture.
Top Broadway shows that have been featured in Chicago include Hamilton, The Lion King, Wicked, and Les Misérables.
Famous theaters include Nederlander and the Cadillac Palace.
⭐Midwest Planning Guides
Conclusion
This 4-day Chicago itinerary is packed with exciting activities, from exploring the Lincoln Park Conservatory to enjoying a Broadway show.
You’ll experience the city’s rich culture, beautiful architecture, and delicious food, like deep dish pizza.
Each day offers something new and memorable. There are so many amazing ways to experience the windy city!
It’s easy to combine Chicago with longer itineraries on a Midwest Road Trip or as a weekend getaway for couples.
Now, it’s your turn to enjoy the Windy City and share your own Chicago adventure!
