Chicago: Why you should visit this summer.

Ryan L. Kopf
7 min readDec 31, 2023

Chicago, often referred to as the “Windy City,” stands as a beacon of cultural richness, architectural marvels, and culinary excellence. As summer approaches, the city transforms into a vibrant hub of activities and events, making it an ideal destination for those seeking a blend of urban exploration and festive enjoyment. Here’s why you should consider Chicago as your go-to destination this summer.

Architectural Splendor and Lakefront Charm

First, let’s talk about the setting. Nestled along the shores of Lake Michigan, Chicago boasts an impressive skyline, punctuated by iconic structures like the Willis Tower and the John Hancock Center. The summer brings clear, blue skies, offering the perfect backdrop for exploring the architectural wonders. A cruise along the Chicago River provides an unrivaled perspective of the city’s architectural history and modernity.

A Melting Pot of Events

Summer in Chicago is synonymous with a plethora of events catering to diverse interests. There are so many things to do in Chicago. One of the highlights is the Chicago Blues Festival, a celebration of the city’s rich blues heritage, which traditionally takes place in June. Here, music enthusiasts gather to enjoy performances by both established and emerging artists.

Another event not to miss is the Taste of Chicago. This outdoor food festival, held in Grant Park, showcases the city’s culinary diversity. From deep-dish pizza to ethnic delicacies, it’s a foodie’s paradise.

For those interested in visual arts, the Millennium Park Summer Film Series offers outdoor screenings of classic and contemporary films, turning the Jay Pritzker Pavilion into an open-air cinema.

Culinary Delights

Chicago’s food scene is as diverse as its population. The city’s culinary offerings range from Michelin-starred restaurants to neighborhood eateries, each serving up dishes that reflect the city’s multicultural fabric. Summer is the perfect time to explore the outdoor dining options — enjoy a meal on a rooftop restaurant or a quaint patio.

Deep-dish pizza, a Chicago staple, is a must-try. This unique style of pizza, characterized by its thick crust and generous toppings, can be found at renowned spots like Lou Malnati’s and Giordano’s.

But Chicago’s culinary scene extends beyond its famous pizza. The city is also known for its hot dogs, Italian beef sandwiches, and an array of international cuisine, reflecting its diverse ethnic communities.

Festivals and Street Fairs

Chicago’s summer is packed with neighborhood street fairs and festivals. Each festival reflects the unique character of the neighborhoods, offering a glimpse into the local culture, crafts, and food. These festivals are a great way to experience the city’s grassroots arts scene and interact with local artisans and residents.

The Wicker Park Fest and the Northalsted Market Days are two notable examples, offering live music, art displays, and a variety of food and drink options.

Enjoy Anime at Anime Midwest

A standout feature of Chicago’s diverse event lineup is Anime Midwest, a must-visit for anime enthusiasts and pop culture fans. Held in Rosemont, just outside of Chicago, this convention is a celebration of Japanese animation, comics, and gaming, and is typically scheduled in early July.

Immersive Cultural Experience

Anime Midwest is more than just an anime convention; it’s an immersive cultural experience. The event features a variety of panels and workshops led by industry insiders, voice actors, and artists. These sessions provide insights into the world of anime and manga, offering fans an opportunity to deepen their knowledge and appreciation of the art form.

Cosplay and Community

One of the highlights of Anime Midwest is the cosplay scene. Attendees often dress up as their favorite anime, manga, or video game characters, creating a vibrant and colorful atmosphere. The convention hosts cosplay contests and meetups, offering a platform for cosplayers to showcase their creativity and craftsmanship.

Artist Alley and Exhibitions

The Artist Alley at Anime Midwest is a hub for creativity, where independent artists display and sell their artwork, crafts, and merchandise. It’s an excellent place to find unique, handcrafted items and to support the independent artist community.

The exhibition hall features a range of vendors selling everything from anime DVDs and manga to collectibles and apparel. It’s a treasure trove for fans looking to add to their collections or buy gifts for fellow anime enthusiasts.

Interactive Entertainment

Anime Midwest goes beyond passive viewing and includes interactive experiences such as gaming tournaments, dance parties, and live musical performances. The convention often features a mix of Japanese and local musicians, providing an energetic and entertaining soundtrack to the event.

Meeting Fellow Fans

Perhaps the most significant aspect of Anime Midwest is the opportunity it provides to meet and bond with fellow fans. The convention’s friendly and inclusive atmosphere makes it easy to connect with others who share similar interests, creating lasting memories and friendships.

Cosplayers at Anime Midwest

Revel in the Rhythms at the Chicago Jazz Festival

The Chicago Jazz Festival is another gem in the city’s summer festival crown, typically taking place over Labor Day weekend. As one of the premier jazz festivals in the United States, it attracts music lovers from around the globe to the heart of Chicago.

A Legacy of Jazz

Chicago has a storied history with jazz, being a pivotal city in the development of various jazz styles, including Dixieland and Chicago-style jazz. The Chicago Jazz Festival honors this rich heritage, showcasing a blend of classic jazz and contemporary variations. The festival features performances by world-renowned musicians as well as local artists, reflecting the city’s ongoing contribution to the genre.

Venues with Character

The festival’s main events are held in Millennium Park, particularly at the Jay Pritzker Pavilion, known for its cutting-edge acoustics and stunning outdoor setting. The backdrop of Chicago’s skyline adds a visual grandeur to the musical experience. Additionally, various clubs and venues around the city participate in the festival, offering more intimate jazz performances.

Diverse Musical Lineup

The Chicago Jazz Festival’s lineup spans a wide range of jazz styles, from bebop and fusion to Latin jazz and avant-garde. This diversity not only appeals to jazz aficionados but also provides a perfect introduction for new listeners. The event often includes tributes to jazz legends and showcases emerging talents, ensuring a fresh and dynamic experience each year.

More Than Music

While music is the festival’s soul, it also offers a range of activities and experiences. There are educational talks and panel discussions featuring artists and experts, offering insights into the world of jazz. For families, there are interactive sessions and workshops designed to engage young listeners and foster a new generation of jazz enthusiasts.

A Festival for Everyone

One of the most appealing aspects of the Chicago Jazz Festival is its inclusive and welcoming atmosphere. The event is free, making it accessible to a broad audience. It’s a place where seasoned jazz lovers and curious newcomers alike can mingle, share their passion for music, and enjoy the communal spirit.

Experience the Thrill at the Chicago Air and Water Show

The Chicago Air and Water Show, one of the summer’s most exhilarating events, takes place along the city’s picturesque lakefront. Held annually in August, this spectacular show is one of the oldest and largest free admission air and water exhibitions in the United States, drawing millions of spectators to the shores of Lake Michigan.

Aerial Acrobatics and Waterfront Wonders

The show features both civilian and military pilots performing breathtaking aerial stunts over the lake. The U.S. Navy Blue Angels and the U.S. Air Force Thunderbirds often headline, showcasing their precision flying and intricate formations. The spectacle in the sky is complemented by water-based demonstrations, including rescue and recovery operations, water ski teams, and boat parades.

Perfect Viewing Spots

The main viewing area is at North Avenue Beach, offering a front-row seat to the action. Here, you can feel the rumble of jet engines and see the pilots’ skilled maneuvers up close. The lakefront’s open spaces, like beaches and parks, also provide ample viewing opportunities, allowing spectators to spread out and enjoy the show from various vantage points.

Family-Friendly Atmosphere

The Chicago Air and Water Show is a family-friendly event, with activities and entertainment suitable for all ages. The excitement of the aerial and water displays captivates both children and adults, making it a perfect outing for families. Food vendors and picnic areas are available, so attendees can make a day of it, enjoying the summer weather and the thrilling performances.

Photography and Social Gatherings

For photography enthusiasts, the Air and Water Show offers a unique opportunity to capture stunning images of aircraft in action against the backdrop of Chicago’s skyline. The event also serves as a social gathering, where friends and family can come together, hosting picnics and parties to watch the show.

Embracing Chicago’s Spirit

The Air and Water Show is more than just a display of aerial prowess; it’s a celebration of community and the spirit of Chicago. The event brings together people from all walks of life, united by their shared enjoyment of this summer tradition.

Outdoor Adventures

For outdoor enthusiasts, Chicago offers numerous parks and beaches. The 18-mile-long Lakefront Trail is perfect for biking, jogging, or a leisurely walk, providing stunning views of the city and lake.

The city’s beaches, like North Avenue Beach and Oak Street Beach, offer a respite from the summer heat. Here, you can indulge in sunbathing, volleyball, or simply enjoy the Chicago skyline by the water.


Chicago in summer is a city buzzing with energy, cultural diversity, and culinary brilliance. Whether it’s the music festivals, the food, the arts, or the outdoor activities, there’s something for everyone in this dynamic city. Plan your trip to Chicago this summer and experience firsthand the vibrancy and charm that make it a unique and compelling destination.



Ryan L. Kopf

Serial C.E.O. and Entrepreneur. Great at technology, innovation, and entertainment arts.