Visiting Chicago in June (What to do in Chicago in June)

Aleena Mehmood2024-05-28

Table of Contents


Chicago, the "City of Big Shoulders," bursts with life in June. With warm days, clear skies, and a calendar brimming with events, it's no wonder June is a prime time to visit this dynamic metropolis. So, pack your bags, fellow travelers, and get ready to experience Chicago's vibrant energy firsthand with Tripshepherd!

Chicago Street

(Photo credit@BenjaminR./Unsplash)

Is June a Good Time to Visit Chicago?

Absolutely! June offers some of Chicago's most pleasant weather, with average highs in the low 80s Fahrenheit (around 27°C) and comfortable evenings. You'll escape the winter chill and the summer humidity, making it ideal for exploring the city on foot or enjoying outdoor activities. Plus, June explodes with festivals, concerts, and cultural events, offering something for every interest.

Reasons to Visit Chicago in June

Perfect Weather:

June provides a sweet spot between spring and summer, with comfortable temperatures and minimal rain.

Festival Frenzy:

Immerse yourself in Chicago's vibrant festival scene, from the world-renowned Chicago Blues Festival to the lively summer celebrations in Grant Park.

Outdoor Adventures:

June is prime time to explore Chicago's parks and waterfront. Kayak on Lake Michigan, have a picnic in Millennium Park or bike along the scenic lakefront path.

Cultural Gems:

Dive into Chicago's rich cultural tapestry with world-class museums like the Art Institute of Chicago or the Field Museum.

Baseball Fever:

Catch a game (or two!) at the iconic Wrigley Field and experience the electric atmosphere of Chicago Cubs baseball.

Discover Chicago's iconic sights on our Best of Chicago Tour!

Chicago June Weather

Pack for warm days and cool nights. Layers are your friend, with breathable fabrics ideal for exploring the city on foot. Don't forget sunglasses, sunscreen, and a hat for sunny days. Bring a light jacket for evenings, especially if you plan on enjoying outdoor activities or catching a late-night rooftop bar scene.

What to Wear in Chicago in June

Nothing makes the trip more satisfying than trip-friendly attire. Summer in Chicago is no joke and means you should pack while keeping in mind the warm weather. But don't worry, we have curated a list for you to make sure you pack all the essentials for the trip:

- Lightweight shirts and blouses

- Comfortable walking shoes

- Shorts or light pants

- A sundress or skirt

- Light sweater or jacket

- Sunglasses

- Sunscreen

- Hat

Things To Do In Chicago In June

Now that you're prepped for the weather, let's explore the exciting things to do in Chicago during June:

Immerse Yourself in Summer Festivals:

Chicago Blues Festival:

Immerse yourself in the rich history and soulful sounds of blues music at the world-famous Chicago Blues Festival. Held every June in Grant Park, this free event features legendary and up-and-coming blues artists on multiple stages.

Taste of Chicago:

Experience a culinary adventure at the iconic Taste of Chicago. Sample signature dishes from over 70 of the city's best restaurants, all while enjoying live music and entertainment in Grant Park. This ticketed event is a must for any foodie.

Windy City Smokeout:

Calling all BBQ lovers! The Windy City Smokeout transforms Grant Park into a haven for smoky goodness. Savor delicious barbecue from regional and national pitmasters, participate in grilling demonstrations, and enjoy live music.

Cloud Gate

(Photo credit@LanceAnderson/Unsplash)

Explore Chicago's Artistic Soul:

Art Institute of Chicago:

Delve into the world of art at the prestigious Art Institute of Chicago. Housing an impressive collection spanning centuries and continents, the museum is a wonderland for art enthusiasts. From iconic Impressionist masterpieces to contemporary installations, there's something for everyone.

Museum of Contemporary Art:

Immerse yourself in the cutting-edge of the art world at the Museum of Contemporary Art. Discover thought-provoking exhibits showcasing contemporary art, architecture, design, and photography. This museum is a must-visit for those seeking a taste of Chicago's vibrant art scene.

Millennium Park:

A must-visit for any Chicago itinerary, Millennium Park is a stunning blend of art, architecture, and nature. Snap a photo with the iconic Cloud Gate ("The Bean"), stroll through the Lurie Garden, or marvel at the Buckingham Fountain Chicago's playful water display.

Embrace the Great Outdoors:

Navy Pier:

Navy Pier is a lively waterfront destination offering something for everyone. Enjoy stunning views of Lake Michigan, indulge in delicious eats at various restaurants, or take a thrilling ride on the Centennial Wheel.

Lake Michigan:

Chicago's stunning shoreline beckons outdoor enthusiasts. Take a Shoreline Adventure Cruise on Lake Michigan, rent a kayak and explore the calm waters, or simply relax on the beach and soak up the sun.

Lincoln Park Zoo:

Home to over 2,000 animals from around the globe, Lincoln Park Zoo is a delightful place to spend an afternoon. Explore diverse exhibits, attend a feeding demonstration, or simply wander the lush grounds and learn about the incredible creatures that call Lincoln Park Zoo home. This free zoo is a perfect family-friendly activity.

Experience Chicago's Architectural Marvels:

Chicago Architecture Foundation River Cruise:

Embark on a captivating journey through time on the Chicago Architecture Foundation River Cruise. Learn about the city's rich architectural heritage as you glide past iconic landmarks like the Tribune Tower and the Wrigley Building.

Self-Guided Architecture Walk:

Lace up your walking shoes and explore Chicago's architectural wonders at your own pace. Download a self-guided walking tour app or grab a map and hit the streets. From the neoclassical grandeur of the Art Institute to the soaring skyscrapers of Michigan Avenue, Chicago is an architectural wonderland waiting to be discovered.

Indulge in Chicago's Culinary Delights:

Craft Beer Scene:

Chicago boasts a thriving craft beer scene, with breweries scattered throughout the city. Embark on a brewery tour, sample local brews at a gastropub, or head to a rooftop bar with stunning city views and a curated selection of craft beers.

Michelin-Starred Dining:

For a truly unforgettable culinary experience, treat yourself to a meal at one of Chicago's Michelin-starred restaurants. From innovative tasting menus to exquisite French fare, Chicago offers a diverse range of fine dining options.

Neighborhood Eats:

Venture beyond the tourist hotspots and explore Chicago's vibrant neighborhoods. Sample authentic Italian fare in Little Italy, savor delicious tacos in Pilsen or indulge in trendy brunch options in Wicker Park.

Experience the city's nightlife with our Scenic Chicago Night Tour!

Catch a Live Performance:

Chicago Symphony Orchestra:

Immerse yourself in the world of classical music with the Chicago Symphony Orchestra. Renowned for its virtuosity and artistic excellence, the orchestra offers a variety of concerts throughout the year.

Live Music Venues:

Chicago's vibrant music scene caters to all tastes. Catch an intimate jazz show in a cozy basement club, experience the electrifying energy of a rock concert, or enjoy a rooftop bar with live music under the stars.

Broadway in Chicago:

Catch the magic of Broadway in Chicago's historic theaters. From beloved classics to new musicals, there's always a captivating show to see.

Family-Friendly Fun:

Museum of Science and Industry:

Spark children's imaginations at the Museum of Science and Industry. Explore interactive exhibits, witness fascinating scientific phenomena, and learn about everything from space exploration to the human body. This museum is a guaranteed hit with kids of all ages.

Shedd Aquarium:

Dive into the underwater world at the renowned Shedd Aquarium. Encounter a dazzling array of aquatic life, from playful otters to majestic beluga whales. Interactive exhibits and educational programs make the Shedd Aquarium a perfect family activity.

Wrigley Field:

Experience the magic of baseball at the iconic Wrigley Field, home to the Chicago Cubs. Cheer on the home team, soak up the electric atmosphere, and enjoy a classic American ballpark experience.

Explore Beyond the City Limits:

Hyde Park:

Take a day trip to Hyde Park, the historic neighborhood that's also home to the prestigious University of Chicago. Explore the university campus, visit the Robie House (a Frank Lloyd Wright masterpiece), or stroll through the beautiful Jackson Park.

Day Trip to a Nearby Suburb:

Chicago's suburbs offer a variety of charming towns and attractions. Explore the quaint shops and restaurants in Oak Park, visit the stunning Morton Arboretum in Lisle, or take a boat tour through the historic canals of Des Plaines.

Visiting Chicago in June with Tripshepherd

With so much to see and do in Chicago during June, Tripshepherd is here to help you craft the perfect itinerary. Whether you're seeking a whirlwind adventure or a relaxed exploration, our local experts can design a tour that caters to your interests and preferences.


(Photo credit@TimGouw/Unsplash)


Is it expensive to visit Chicago in June?

Chicago can be visited on a budget or with a luxurious touch. Accommodation and flight prices tend to be higher in June due to peak season, but there are ways to save, such as booking in advance and exploring free activities. Tripshepherd offers tours for various budgets, and we can help you find ways to maximize your experience in Chicago.

How many days do I need in Chicago?

A minimum of 3-4 days is recommended to experience Chicago's highlights. However, with so much to see and do, you could easily spend a week or more exploring different neighborhoods and hidden gems. Tripshepherd can help you design an itinerary that fits your timeframe and interests.

What are some hidden gems in Chicago?

Chicago boasts a wealth of hidden treasures beyond the tourist hotspots. Explore the Garfield Park Conservatory for a stunning display of flowers and plants under glass. Catch a quirky independent film at the Music Box Theatre. Wander through the charming Lincoln Square neighborhood, known for its German heritage and lively cafes. Tripshepherd can introduce you to these hidden gems and create a unique Chicago experience for you.

Is Chicago safe to visit?

Chicago is generally a safe city for tourists. However, as with any major city, it's always wise to be aware of your surroundings and take precautions, such as avoiding deserted areas at night. Tripshepherd can provide guidance on safe neighborhoods and recommend areas to explore during your visit.

Customize your Chicago adventure with our Private Tour of Chicago!

How do I get around Chicago?

Chicago has a well-developed public transportation system, with buses and trains that can take you just about anywhere in the city. Taxis and ride-sharing services are also readily available. If you prefer to explore at your own pace, consider renting a bicycle or a car. Tripshepherd can advise you on the best transportation options based on your itinerary and preferences.


With its vibrant culture, stunning architecture, and endless entertainment options, Chicago is a city that never sleeps. June offers the perfect opportunity to experience Chicago at its finest, bathed in warm sunshine and buzzing with summer energy.

Trispehpherd offers the best tours in Chicago led by our fun and friendly local tour guides. Our itinerary for Chicago tours makes sure you enjoy the city to its fullest and don't miss out on any fun. Head over to our website and browse till you find the tour that's best for you.

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