3 Days in Chicago: Discovering the Best of the Windy City
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Chicago is such an incredible city, packed with energy and endless things to do! I know 3 days in Chicago might sound like barely enough time to soak it all in, but trust me—you can fit in so much during a long weekend here.
When we visited, let’s just say the universe threw us a few curveballs. From hazy skies caused by Canada’s wildfires to surprise rain showers, and even a holiday weekend plus a NASCAR event shutting down streets (hello, no Bean access!), it was a wild ride.
Thankfully, growing up in the Midwest means I’ve been to Chicago more times than I can count (and I’ll definitely be back!), so I’m here to help you craft an epic 3-day itinerary, no matter what surprises the Windy City throws your way!
When is the best time to visit Chicago?
Chicago truly shines in the summer (June to August), buzzing with festivals, outdoor concerts, and endless fun—just be ready for some crowds! If you prefer a quieter vibe, spring (April to May) and fall (September to October) are your sweet spots, with mild weather, blooming flowers or colorful leaves, and fewer tourists.
Winter might be chilly, but it turns the city into a festive wonderland with ice skating, holiday markets, and stunning snowy views (plus budget-friendly hotel deals!). Whether you’re chasing sunshine or snowy magic, there’s a perfect time for everyone to fall in love with Chicago!
Chicago CityPASS
If you only have 3 days in Chicago and want to see some of the city’s top attractions, check out the Chicago CityPASS. It includes admission to some of the most popular Chicago activities at a discounted price, saving up to 48% off regular admission fees. We used this for our trip, and it was perfect!
The CityPASS includes admission to the Shedd Aquarium and Skydeck Chicago, plus three of the following attractions:
- Field Museum
- Art Institute of Chicago
- Shoreline Sightseeing Architecture River Tour
- Museum of Science and Industry
- Adler Planetarium
- 360 CHICAGO Observation Deck
17+ Best Things to Do with 3 Days in Chicago
1. Chicago Architecture River Cruise
The Chicago Architecture River Tour comes highly recommended by both locals and visitors, and for good reason! It’s a must-do experience that showcases the city’s stunning architecture and captivating skyline from a unique perspective.
Sit back and relax on the cruise while knowledgeable guides share truly fascinating historical and architectural insights about the iconic buildings that line the Chicago River.
2. Riverwalk
The Riverwalk is where the magic of Chicago really shines! This 1.25-mile pedestrian-friendly path winds along the river, offering iconic views of the city skyline. It’s dotted with charming cafes, restaurants, and outdoor seating areas, making it the perfect place to grab a bite, sip on a drink, or just soak up the city’s energy.
3. The Bean
This one is a must for your 3 days in Chicago, especially if it’s your first time! Located in Millennium Park, the Cloud Gate sculpture, affectionately known as “The Bean,” is a beloved Chicago landmark.
Reflecting the city’s skyline in its polished, mirrored surface, this unique art installation offers a playful and interactive experience and fun photo op!
4. 360 Chicago
For views that will take your breath away, head to 360 Chicago in the John Hancock Building. From 1,000 feet above the ground, you’ll be treated to panoramic scenes of the city and Lake Michigan. It’s a perspective of Chicago you’ll never forget, so don’t forget your camera!
5. Shedd Aquarium
The Shedd Aquarium is an aquatic wonderland! Dive into the fascinating world of marine life and explore a variety of interesting exhibits.
Get up close and personal with dolphins, otters, and beluga whales. This educational and entertaining experience will leave you with a greater appreciation for the wonders of the ocean. It’s the perfect family-friendly Chicago activity!
6. Dine at Some of the Best Restaurants in the Country
Chicago is internationally renowned for its culinary scene, with everything from trendy gastropubs to world-class fine dining! One standout from our trip was Sunda New Asian, where every dish was an explosion of flavor. From fresh sushi rolls to creative fusion dishes, we couldn’t get enough!
From the moment we took our first bite at Sunda New Asian’s Chicago location, it captured our hearts, so we were thrilled when we got a location in Midtown Tampa!
7. Grant Park
Right in the heart of downtown Chicago, Grant Park is the city’s gorgeous “Front Yard”! This urban oasis is packed with iconic landmarks, but the star of the show is Buckingham Fountain. Inspired by the Latona Fountain at Versailles, it’s one of the largest fountains in the world—pretty impressive, right?
If you love big cities, check out my NYC guide, 3-day LA itinerary, and fun Miami restaurants guide!
The Fountain puts on a major water display for 20 minutes every hour starting at 9 AM. Beginning at dusk, a special light and music display accompanies the major display, with the final major display beginning at 10:35 PM.
8. Skydeck Chicago
Even with some smoggy weather and wildfire haze during our visit, the views from Skydeck Chicago were still incredible! Hop in the elevator and zoom up to the 103rd floor of the Willis Tower.
Once you’re there, step onto The Ledge—a glass-floored platform that lets you look straight down. Gulp! Feeling extra brave? Try the Tilt experience for $10 and lean out over the city for a thrill you won’t forget.
9. Magnificent Mile
Calling all shopaholics—Chicago’s Magnificent Mile is your dream come true! This buzzing stretch of retail heaven is packed with luxury boutiques, flagship stores, and big-name department stores.
But wait, it’s not just about shopping! The architecture here is a sight to see, with towering skyscrapers and historic gems that make the whole street feel, well, magnificent.
10. Adler Planetarium
Take yourself on a celestial journey at the Adler Planetarium! This cosmic wonderland lets you explore the mysteries of space with hands-on exhibits and fascinating shows. From black holes to the history of space travel, Adler will have you dreaming of the stars. It’s an out-of-this-world experience you won’t want to miss!
11. Field Museum
Ready to time travel? Head to The Field Museum, where history comes to life! From ancient Egyptian mummies to the star of the show—Sue, the biggest and most complete T-Rex skeleton ever discovered—you’ll be blown away by the incredible stories waiting to be uncovered.
It’s a must for anyone curious about the world’s fascinating past!
12. Blue Man Group
Get ready for a show like no other! The Blue Man Group is one of Chicago’s longest-running performances, and it’s easy to see why. This vibrant blend of comedy, music, and mind-bending visuals is pure entertainment gold.
From their rhythmic drumming to their hilarious interactive antics, these blue-faced performers will have you laughing, gasping, and completely captivated. If you’re looking for a unique night out in Chicago, this is it!
13. Check Out a Speakeasy
Chicago has so many speakeasies! With only 3 days in Chicago, we didn’t get to hit nearly as many as I would’ve liked, but what we lacked in quantity we made up for in quality.
Three Dots and a Dash stole the show with its tropical tiki vibes, expertly crafted cocktails, and an ambiance that felt like an island getaway. Plus, it’s just a short walk from Sunda New Asian—making it the perfect stop for pre-dinner drinks or a fun nightcap after your meal.
14. Have a Chicago-Style Hot Dog
When in Chicago, you have to try a classic Chicago-style hot dog! This isn’t your average dog—it’s an all-beef hot dog on a poppy seed bun, piled high with mustard, onions, neon-green sweet pickle relish, tomatoes, a dill pickle spear, sport peppers, and a sprinkle of celery salt.
We grabbed ours from a stand right outside The Field Museum, and let me tell you—it hit the spot! It’s the perfect fuel for exploring more of the city and an absolute must for your Chicago adventure.
15. Visit the Largest Starbucks in the World
Coffee lovers, brace yourselves—you’re about to enter caffeinated paradise! The Starbucks Reserve Roastery in Chicago is the largest Starbucks in the world, and it’s truly next-level.
Spread across five incredible floors, this coffee wonderland has rare and small-batch brews from around the globe, along with menu items you won’t find at your regular Starbucks.
Each floor offers something unique, from cocktails to artisanal baked goods, and the whole experience feels like a love letter to coffee!
16. Boat Day
If you’re visiting Chicago in the summer, a boat day is non-negotiable! There’s just something magical about cruising on the sparkling waters of Lake Michigan with the city’s stunning skyline as your backdrop. Whether you opt for a relaxing sunset cruise or go all out with a private boat rental for you and your crew, nothing beats a day out on the water!
17. Navy Pier
Navy Pier is one of the best things to do in Chicago! This iconic Chicago hotspot has exciting rides and attractions plus sweeping views of Lake Michigan and the city skyline. It’s a sensory overload in the best way possible!
Visiting during the summer? Don’t miss the fireworks displays every Wednesday and Saturday night. They light up the night sky, creating the perfect romantic or family-friendly ambiance.
And if you’re looking to shop or grab a bite, Navy Pier’s got you covered with countless restaurants, shops, and entertainment options!
Bonus Activities for Your 3 Days in Chicago
- Lincoln Park Conservatory— A stunning botanical haven that showcases a variety of plant species, from towering palms to rare orchids. It’s a great free thing to do in Chicago!
- Jackson Park— An expansive park with lush greenery, scenic trails, and picturesque lagoons. Check out The Garden of the Phoenix, an exquisite Japanese garden within the park.
- WNDR Museum— A fun museum full of multi-sensory, contemporary art installations.
- Ice Cream Museum— Another fun museum! It’s immersive, interactive, and full of fun photo ops!
- Lincoln Park Zoo— This free-admission zoo is the perfect family fun activity if you still have time to spare during your 3 days in Chicago.
- Bike along the Lakefront trail— This scenic 18-mile trail offers stunning views of the lake and city skyline! Get a bike rental here.
Where to Stay in Chicago
Chicago is a city brimming with diverse neighborhoods and plenty of accommodation options. As you plan your Chicago itinerary, keep in mind the proximity of your chosen hotel to your planned activities and attractions. Here are some top picks for where to stay in Chicago in the Loop area:
- The Blackstone Autograph Collection— The Blackstone offers a blend of historic charm and modern luxury. With stunning views of Lake Michigan and proximity to iconic landmarks like Millennium Park and Grant Park, this hotel is the perfect base for exploring the city.
- Sentral Michigan Avenue— Situated along the vibrant Magnificent Mile, Sentral Michigan Avenue provides easy access to world-class shopping, dining, and entertainment. The hotel’s contemporary design, upscale amenities, and central location make it a popular choice for both leisure and business travelers.
- Bluegreen Vacations Hotel Blake, Ascend Resort Collection— Experience boutique elegance at Hotel Blake. The hotel’s stylish rooms, personalized service, and convenient location make it a standout option if you’re seeking a memorable stay in Chicago.
For availability and rates for your specific dates check out available accommodation options here.
Are you ready for an epic 3 days in Chicago?!
I hope you’ve enjoyed this whirlwind tour of the city for your 3 days in Chicago! From exploring iconic landmarks to enjoying delicious food and soaking in the vibrant atmosphere, Chicago has so much to offer in a short time. Whether you’re a first-time visitor or a returning traveler, there’s always something new to discover in this city. Here’s to more amazing travels and unforgettable experiences!
Before you go, be sure to follow me on Insta @guidedbydestiny and check out some of my other Midwest blog posts:
Fun things to do in the Twin Cities
Perfect weekend in Chattanooga
