How to Spend One Day in Chicago: The Ultimate 24-Hour Itinerary

Chicago is known for its stunning skyline, deep-dish pizza, and iconic attractions. Spending a weekend or more here is ideal, but what if you only have one day in Chicago? This 24-hour itinerary is designed to help you make the most out of a day in the city, with a focus on downtown gems. From landmarks and local eats to breathtaking views, here’s how to make the most of your downtown day in Chicago.

Morning: Start with Iconic Chicago Landmarks

Breakfast at the Loop

Start the day off with breakfast in downtown Chicago, often referred to as “The Loop”. Wildberry Pancakes & Cafe is a locally known favorite that serves a variety of unique specialty pancakes, fresh berries, and rich coffee.

If you’re in the mood for a classic retro diner vibe, Eleven City Diner is the perfect choice. It offers a nostalgic atmosphere, serving classic hearty American breakfast options like bagels, omelets, and waffles.

Millennium Park: A Can’t-Miss Attraction

After breakfast, take a stroll over to Millennium Park, one of the city’s most famous attractions. It is home to the Cloud Gate statue, also known as “The Bean”. As you explore the park, you will see interactive fountains, beautiful gardens, and free events. The Lurie Garden is located on the southern end of the park and consists of a combination of different flowers, shrubs, and trees. Take a moment to enjoy the serene beauty of the garden on your own, or choose to participate in a guided walk, lecture, or interactive demonstration. Afterwards, cool off by the interactive Crown Fountain, a one of a kind public art and video sculpture. This unique sculpture allows you to interact with the water, providing the perfect way to cool off on a sunny day. It makes for a great photo opportunity as well!

Art Institute of Chicago

A short walk from Millennium Park will bring you to the world-renowned Art Institute of Chicago. This iconic museum features a variety of artwork and was one of Trip Advisor’s “Best of the Best” U.S. attractions. They offer free 45-minute tours where an experienced guide will show you all of the museum’s iconic artwork, as well as some lesser-known treasures. Take your time admiring these exquisite pieces of art and soaking in the culture before heading to the next destination.

Midday: Experience Chicago’s Culinary Scene and Skyline Views

Lunch: Classic Chicago Deep-Dish Pizza

You can’t spend a day in Chicago without indulging in its famous deep-dish pizza. Head over to Lou Malnati’s or Giordano’s, both known for their gooey, cheesy pizzas. Lou Malnati’s pizza tends to have a crispier crust, while Giordano’s has a softer, doughy crust. If you prefer a classic Chicago deep dish with lighter sauce, Lou Malnati’s might be the choice for you. On the other hand, Giordano’s tends to appeal to those who like a thicker sauce and cheese ratio, leading to a richer pizza. No matter what you choose, both options are sure to give you the ultimate Chicago deep-dish experience.

Chicago River Architecture Tour

After lunch, sit back, relax, and embark on a cruise through the Chicago River. Here at Tours and Boats, our 90-minute architecture boat tours are the perfect way to delve into Chicago’s history and experience architectural marvels such as the Willis Tower, Tribune Tower, and Wrigley Building. Our ship’s 360-degree viewing capabilities allow you to see the city from every angle. Gain a deeper appreciation for the city’s unique artistic architectural styles while capturing amazing skyline photos. This is an activity you won’t want to miss!

Afternoon: Stroll Through Downtown Chicago

Magnificent Mile

If you only have 24 hours in Chicago, you need to add The Magnificent Mile on your list of things to do. Located in a section of Michigan Avenue, The Mag Mile is one of Chicago’s most iconic shopping districts. Here you will find luxury brands, deluxe fashion outlets, fine dining restaurants, and exciting events. Shopping is not the only thing this area has to offer. While strolling down the avenue, you’ll see examples of stunning architecture, experience beautiful gardens, and pass by many breathtaking butterfly sculptures created by local artists. Whether you’re an avid shopper or just want to feel the pulse of the city, walking through this premier commercial district is a great way to take in Chicago’s dynamic energy.

Navy Pier

After the Magnificent Mile, head to the Navy Pier, the top visited destination in the Midwest. Enjoy scenic views of Lake Michigan, take a ride on the Centennial Wheel, and participate in your pick of events and attractions. The vibrant atmosphere of this historic pier is sure to add some fun and excitement to your day. If you’re feeling peckish, grab some Chicago-style popcorn at Garrett Popcorn Shops.

Evening: End Your One Day in Chicago with the Best of Chicago’s Nightlife

Dinner with a View

For a memorable dinner, reserve a table at Cindy’s Rooftop, located at the Chicago Athletic Association Hotel. This stylish rooftop eatery offers stunning views of Millennium Park and Lake Michigan. Their menu features fresh seafood and crafted cocktails.

If you prefer a riverside experience, head to River Roast, an upscale restaurant with stunning views of downtown Chicago. Their menu features American tavern fare, such as roasted meats, fresh seafood, and delicious sides. Enjoy your meal right on the Chicago River.

Willis Tower Skydeck

As the sun sets, head over to the Willis Tower Skydeck for an unforgettable experience. The Skydeck’s glass observation boxes extend out from the building, giving you the feeling of standing right above the city. Watching the sun set behind the city skyline is the perfect way to end your downtown day in Chicago.

Catch a Show at The Chicago Theatre

If you’re a night owl with a love of live shows and performances, consider ending the night with a show at The Chicago Theatre. This historic venue not only has a stunning marquee and beautiful antique architecture, it also hosts a variety of performances, from Broadway shows and comedy acts to concerts and live events. There’s a show for everyone. Just the ambiance alone makes for a magical experience. Be sure to check the show schedule in advance and grab tickets at a time that works for you.

Making the Most of Your 24 Hours in Chicago

With just one day in Chicago, you can experience the highlights of this vibrant city through these iconic and timeless activities and landmarks. Whether you’re taking in the skyline on a river cruise, enjoying the famous Chicago deep-dish pizza, or taking in the art and history, this 24-hour itinerary ensures you’ll make the most out of a downtown day in Chicago, with unforgettable memories that will last a lifetime.

Don’t forget to book your architectural tour through Tours and Boats. We offer 90-minute tours as well as private tours and cruises. Whether you’re a first-time visitor or a seasoned traveler, Chicago is bound to capture your heart in just one day.