Chicago Through the Seasons: Must-Try Experiences Year-Round

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Chicago is a city that offers up a delightful smorgasbord no matter the time of year. From singing spring blossoms to the dead winter charm of a white wonderland, there are things to do in Chicago year-round. Whether you live in the city or visit its splendors from time to time, Chicago experiences can be found around every seasonal corner.

Spring Awakening: Embrace the Freshness

Spring in Chicago is soul-reviving. Clear your head by walking through Millennium Park, where the new green leaves and flowers of spring will be reflected in the Cloud Gate (aka “The Bean”). Engage your nose at Garfield Park Conservatory, where the flower shows in the conservatory should put a spring in your step, sending you outside to enjoy some fresh air surrounded by what nature has to offer.

When spring rolls around, it’s the perfect time to buckle in for a helicopter tour. Soar over the city and take in life from above while you observe the stunning skyline and Lake Michigan. It’s a completely unique way to watch the city buzz with the energy of a new season.

Summer Vibes: Dive into the Energy

When the weather is warm, Chicago is teeming with summer festivals, music in every corner of the city, and fun along the waterfront. For starters, you’ll want to be sure to stop by Navy Pier, where you can ride the famous Ferris wheel, enjoy free music or performance, and, of course, indulge in classic Chicago-style deep-dish pizza. To get active outside while in the city, rent kayaks and explore the Chicago River — taking in the incredible views along the iconic waterway.

When the summer heat is still on, it’s time to dance in the streets as Lollapalooza, the Chicago Blues Festival, and more arrive in time to lend their melodies to this already incredible season.

Fall Adventures: Relish the Beauty

Fall in Chicago brings turning leaves, beautiful shades of red and gold, and its very own scenic escape. For starters, head to the Lakefront Trail, the perfect place for a leisurely bike/lakefront ride where fall’s beauty surrounds you and illuminates your senses. The glistening waters of Lake Michigan glimmer as it comes to life. Another great way to enjoy the autumn air is to visit the Chicago Botanic Garden, where you can get lost among the flowers of the season.

For more fall fun (and possibly more fright), head out on a ghost tour in the city. These guided walks make you learn about the haunted history of the Windy City and get into the spooky spirit of the season.

Winter Wonderland: Revel in the Festivities

To truly experience the city captivated by winter, start at McCormick Tribune Ice Rink in Millennium Park, where you can ice skate with the city skyscraper’s lights and the starlit sky all around you. It isn’t hard to close your eyes and picture memories just like this in the Windy City.

Once you find yourself looking for a warmer indoor activity, Chicago offers plenty of fun for the artsy! The Art Institute of Chicago has a proud art history. The Institute is a museum with pieces that breathe engineering excellence displayed in their breathtaking collections. Chicago’s art culture on display is a great indoor aesthetic of Chicago architecture to witness. 

Year-Round Delights: Embrace the Extraordinary

Beloved amongst residents and visitors, the Architecture River tours are a way to witness the windy city from a new angle. While the river can be toured year-round, there is something memorable about snuggling up indoors in the glass room of the tour boat, driving through the city as an expert anthropologist shares tales of the engineering marvel that remains otherworldly.

When it comes to culture in Chicago, there’s creativity around every corner in the Windy City. Steppenwolf Theatre Company and Goodman Theatre are just two of Chicago’s powerhouses for renowned plays and captivating shows any month of the year. Sitting in the front row for Broadway shows in Chicago, with performances at theaters in the Downtown Theatre District and nowhere else in the world, performing arts are celebrated and innovated 24/7.

If you’re a sports lover, Chicago has something in store for you as well. Experience the lively spirit of Chicago Cubs at Wrigley Field in the summer, and see the fans come together in the United Center to support the Chicago Bulls and Blackhawks throughout the basketball and hockey seasons. The city’s love of sports creates an experience you’ll never forget. One thing is for sure: winter, spring, summer, or fall — Chicago is one destination that never goes out of style, and the experiences you share here with someone you love will remain lifetime memories.