Whether you’re a Windy City local or a first-time visitor, this dynamic metropolis has something for everyone for an unforgettable 3-day adventure in Chicago. From iconic landmarks like Navy Pier and Millenium Park to deep-dish pizza and trendy neighborhoods, Chi-town is brimming with endless sights, bites, and fun. With just 72 hours to explore the city, let’s dive into the perfect itinerary to visit world-class museums, indulge your inner foodie, and soak in the stunning skyline to make every moment count in a city that deserves a spot on your travel bucket list.
Best Time to Spend 3 Days in Chicago
The best time of year to visit depends on what type of weather you like but typically the temperatures are mildest from April-June and September-November with a daily average of about 60 degrees. The summer months like most areas, are more crowded and more pricey than other times and sometimes brutally hot. Chicago winters call for the quietest time of the year to visit because well-its freezing! Take these things into consideration when planning your trip.
Adventure, Food, and Fun in Chicago-Day 1
When you arrive in Chicago, spend a little time familiarizing yourself with the city and take a walk through Grant Park, perhaps ride the L, or explore the banks of Lake Michigan. After your stroll, you will most likely have worked up an appetite. Be prepared for choices and more choices! With a reputation as one of the country’s top culinary capitals, Chicago is known for its restaurants and people take their food seriously! From classic hidden gems, and trendy spots, to Michelin-star restaurants, Chicago offers a diverse and amazing breadth of choices in the city for an incredible dining experience. One thing is for sure when in town, you are guaranteed to have a great meal whether it’s your first time or one-hundredth time in the Windy City.
You can’t think of Chicago without thinking about pizza. Although there is much debate about more sauce or more cheese, or deep-dish or thin crust-both sides are fiercely loyal to their preference. There is no shortage of choices when looking for a pie. First on your bucket list should be Forno Rosso. They take their pizza seriously and, in a world, where take-out is often encouraged, that’s a no-go here. They believe that during transportation, the quality will suffer, and they won’t allow this to happen. All ingredients are imported from Italy, and this restaurant keeps people coming back for more on repeat. Check it out for the city’s best thin-crust pizzas.
Now that you’ve enjoyed a delicious lunch, take a scenic stroll along the Chicago Riverwalk. There are four areas to explore: The Arcade, The Confluence, The Civic, and The Esplanade. If the weather is nice, there are restaurants and bars with outdoor dining on the river to enjoy.
Once known as the Sears Tower, Willis Tower is one of the largest skyscrapers in the world at 110 stories and worth a visit. It’s an event space, tourist attraction, office building, and more with plenty to see. Check out the Skydeck which is open year-round, seven days a week. You will need tickets, and it’s a popular attraction so get them in advance. It takes about 30 minutes to enjoy the exhibits and spend as much time as you’d like at the top. Visit The Ledge, a glass balcony that extends four feet outside Willis Tower’s 103rd floor. If you’re afraid of heights this may not be for you! At 1,353 feet in the air, it’s quite a
thrill, and an Instagram-worthy moment so snap a picture here.
Head over to one of Chicago’s most popular attractions, Navy Pier for endless activities, restaurants, and more. Home to the Centennial Wheel, an iconic Ferris wheel that is the unofficial symbol of the Navy Pier, it’s a must-do if you’re heading there. It rises nearly 200 feet in the air and features remarkable views of the Chicago skyline and Lake Michigan. It’s surrounded by fantastic rides and games perfect for the kids too. You could spend hours wandering around here and never get bored.
Buckle up for Lake Michigan’s most iconic thrill ride to wrap up the day! Take a Seadog Lakefront Speedboat Tour with stunning panoramic views of Chicago at top speed. Race across the shoreline while an entertaining and informative narrator shares fun facts about the history of the city skyline. Departing from Navy Pier, this exciting experience combines sightseeing with an exhilarating speedboat ride perfect for your whole crew.
Enjoy a fabulous dinner at Navy Pier at one of the many dining options from quick bites to fine dining. There is something for every tastebud and style (you may want to wait until after your speedboat ride).
Unforgettable Sights-Day 2
Rise and shine grab a quick breakfast and/or coffee, and head over to Millenium Park to beat the crowds. This public park is located within the Loop, and
you will find the world-famous sculpture, “The Bean.” This is a great spot for a photo along with Crown Fountain and Lurie Garden. There are also events throughout the year held here, and the best part is-they’re free so check out the pavilion during your 3 days in Chicago.
It’s off to the Chicago Theater, located just a few blocks from Millenium Park. This theater offers Broadway in Chicago performances if you’re able to catch a show.
Time to get off those feet and get on board a Premier Plus Architectural Lunch Cruise on the Chicago River. Cruise down the Chicago River and enjoy the spectacular skyline from the best vantage point. You will enjoy a delectable plated lunch and craft cocktails while marveling at captivating panoramas of Chicago’s iconic architecture from our glass-enclosed vessel. Breathtaking views of landmarks such as the Willis Tower, Navy Pier, and the Old Chicago Post Office can be admired from the comfortable interior or the open-air spaces. This upscale experience on the Chicago River is complete with light narration, masterful DJ entertainment, and top-notch service.
Head uptown to catch a jazz show at the Green Mill which Al Capone once frequented (his favorite booth is still standing). This has been featured in both movies and television shows. If time allows, you’re smack dab in the middle of one of the most diverse neighborhoods in Chicago, and there’s plenty to eat and drink around. A great option is Ba Le Sandwiches, especially after a long day. With a menu offering more than a dozen sandwiches, there are tons of options for everyone, including vegetarian and vegan. Each one is served on crusty French bread with mayo, pickled daikon, carrots, cilantro, onions, and jalapenos. You can grab a sweet treat to go for the hotel room too.
A Day of Art and Culture- Day 3
Start your day by visiting the Art Institute of Chicago which is home to a collection of art that spans centuries and the globe. There are many exhibitions and 
free daily tours that will intrigue and excite you. There is a wide range of exhibits and various programs to explore for all ages.
In keeping with the arts and culture theme, visit the Field Museum with over 40 million specimens and artifacts in its collection connecting all of us to the natural world and the human story. You won’t want to miss SUE, the world’s most complete Tyrannosaurus Rex.
When you think of Chicago, you think of one of its specialties, a Chicago-style hot dog. No one does it better than Portillo’s They’ll load it up the right way with all the goodies like mustard, relish, onions, tomatoes, peppers, and a kosher pickle.
Head over to Shedd Aquarium on the shore of Lake Michigan and discover the wonder of the aquatic animal world. Your whole family will love playful penguins, colorful coral, and beautiful belugas as you journey through oceans, lakes, rivers, and reefs.
Cap off your third day in Chicago with a dinner experience on Lake Michigan that will make your final day a special occasion. Dine on a chef-prepared plated meal and enjoy craft cocktails and exceptional service. You will soak in sweeping views of Chicago’s iconic landmarks, such as Willis Tower and Navy Pier from comfortable indoor areas and open-air decks while our DJ plays all your favorite hits. This will make for an unforgettable last night in the city.
Eat, Explore, Repeat: 3 Epic Days in Chicago
There are so many reasons to visit Chicago. With an award-winning food scene, amazing attractions, stunning shorelines, dining and sightseeing cruises, and gorgeous green spaces, you will never run out of things to see and do. With only 3 days to spend in the city, you will be hard-pressed to see it all but it’s a great start. Whether you’re a Chicagoan or a first-timer, this vibrant urban oasis is truly a year-round destination in the heart of the United States. Friendly locals, soaring skyscrapers, and pristine shorelines are calling you to visit to begin your fun-filled windy city getaway.
