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TO DO LIST📍10 Kitschy Things to Do in Chicago this Summer


10 Kitschy Things to Do in Chicago this Summer

OFFBEAT & TOTALLY FUN THINGS TO DO IN CHICAGO

Spring & Summer in Chicago are more than just Lake Michigan swims and Millennium Park picnics. The weather gets warmer, and the city comes alive with a vibrant scene that celebrates the quirks and charms that make it truly unique. Whether you’re a visitor looking to escape the ordinary or a local resident seeking new adventures, Chicago’s offbeat activities promise memorable experiences. This feature is your ticket to discovering 10 kitschy things to do in the Windy City this summer. From untold stories in hidden speakeasies to quirky air shows, these activities are sure to offer a fresh perspective on Chitown.


10 Offbeat Chicago Experiences You Can't Miss


Relive the Rat Pack Era at Green Mill Cocktail Lounge


1. Relive the Rat Pack Era at Green Mill Cocktail Lounge

Escape into the jazz age at the legendary Green Mill Cocktail Lounge, a favorite haunt of the Rat Pack. The ambient lighting, velvet furniture, and the original bar set the perfect stage for live jazz performances. It’s not just a step into the past, but a cultural delight that still thrives in the present. Best time to visit: evenings for live music or mid-afternoon for the historic atmosphere.



Have a Zany-Good Time at Kitsch'n in Rosco Village


2. Have a Zany-Good Time at Kitsch'n in Rosco Village

One kitschy restaurant in Chicago that's fun for a weekend visit is Kitsch'n On Roscoe. Located in Chicago's charming Roscoe Village Neighborhood, Kitsch'n has been serving up new takes on breakfast, lunch, and brunch favorites daily since 1998. It offers a zany-fun theme with a delightful ambiance perfect for a leisurely weekend meal experience. Customers praise the delicious food, lovely hidden patio, fabulous bloody marys, and unique dishes like green eggs and ham. It's a great spot to enjoy a quirky dining experience while exploring the vibrant culinary scene of Chicago. Best time to visit: Sunday brunch



. Head to the Garfield Park Conservatory for a Palm House Party


3. Head to the Garfield Park Conservatory for a Palm House Party

The Garfield Park Conservatory’s historic Palm House is more than a hotbed of tropical plants; it’s a relic from the 19th century. An architectural gem complete with a collection of palms and ferns, its striking dome and ornate ironwork evoke the feeling of an exotic garden party straight from the days of Gilded Age Chicago. At 65 ft high and 90 ft wide, this is the largest room in the Conservatory. Best time to visit: weekdays to avoid weekend crowds.



4. Discover Forgotten Speakeasies on a Prohibition-Era Walking Tour


4. Discover Forgotten Speakeasies on a Prohibition-Era Walking Tour

Uncover Chicago’s covert history with a Prohibition-Era Walking Tour. Led by historians, these tours take you down alleyways to former speakeasies that now live hidden in plain sight. Each tour weaves a tale of secret passwords, mobster lore, and architectural remnants that tell a rich story of the Roaring Twenties. Best time to visit: late afternoon for mild weather and better storytelling acoustics.



Meet the 'Czars' of Chicago's Scene at the Money Museum


5. Meet the 'Czars' of Chicago's Scene at the Money Museum

The Federal Reserve Bank of Chicago’s Money Museum offers a behind-the-scenes look at the world of currency, where you can see rare bills, historical coins, and the production process in action. Engage with interactive exhibits, and even take home your own bag of money shredded for souvenirs. Best time to visit: check for guided tours that offer additional insights.





6. Get Insta-Famous at the Colorful Chicago Murals

Chicago is a canvas for vibrant street art, and these larger-than-life murals have taken over social media feeds. From the iconic ‘Greetings from Chicago’ mural in Logan Square to the colorful explosion on Hubbard Street, these murals are not only artistic but are an ode to the city’s diverse culture and history. Check them out on your own or schedule a fun and unique tour. Best time to visit: during the golden hour for the best lighting and fewer people.



7. Witness the Air and Water Show from a Secret Spot


7. Witness the Air and Water Show from a Secret Spot

Every August, the Air and Water Show wows millions with aerobatic stunts on the lakefront. Instead of battling the crowds at Navy Pier, opt for a unique view at one of the city's lesser-known vantage points. Local favorites include the breakwater at Fullerton Beach or the Adler Planetarium lawn. Best time to visit: early morning for the Parade of Ships or late afternoon for twilight stunts.



8. Absorb the Atmosphere at the International Museum of Surgical Science


8. Absorb the Atmosphere at the International Museum of Surgical Science

Nestled in a historic mansion overlooking Lake Michigan, the International Museum of Surgical Science offers a wide-eyed look into the history of surgery, medicine, and anatomy. With ancient artifacts, interactive exhibits, and rotating contemporary art installations, it’s a one-of-a-kind museum, perfect for those fascinated by science and history. Best time to visit: for a different perspective, in the evening during special After Dark events.



9. Stargaze in the City at the Adler Planetarium


9. Stargaze in the City at the Adler Planetarium

Chicago’s Adler Planetarium is an often-overlooked treasure for stargazers. In addition to its impressive collection of antique instruments for celestial observation, the planetarium’s telescope offers breath-taking views of the night sky and special programs that bring the cosmos closer to the public. Best time to visit: for the least light pollution, go on a clear weeknight.



 Slide Down the Sculptural Slides at Maggie Daley Park


10. Slide Down the Sculptural Slides at Maggie Daley Park

Maggie Daley Park’s sculptural slides are not just for kids; they’re an architectural feature that merges art and play. The 40-foot towers feed into a curving, twisting slide which plunges down to the base, offering a fun and thrilling way to survey the Chicago skyline. It’s a delightful twist on the traditional park experience. Best time to visit: afternoon to burn off lunchtime energy.



Making the Most of Public Transportation in Chicago


Practical Tips for Exploring the Kitschy Side of Chicago


Making the Most of Public Transportation

The Chicago Transit Authority (CTA) is the lifeline of the city’s public transportation system. Venturing out via the 'L' train or bus routes can not only save you money but also ease the burden of parking in a city notorious for traffic. Plus, it's a great way to see more of the city's neighborhoods.


Family-Friendly Options

For those traveling with kids, consider the Chicago Children’s Museum at Navy Pier, the Lincoln Park Zoo for a fun day out, or a scenic boat tour along the Chicago River. These family-friendly destinations are low-stress and high-reward.


The Art of Safety in a Big City

Chicago is generally safe for tourists, but it's always smart to practice common sense. Stick to well-lit, populated areas, be mindful of your belongings, and consider using digital wallets or travel insurance for added peace of mind.



10 Kitschy Things to Do in Chicago this Summer


Local Insights on Chicago’s Kitschy Allure

Local Chicagoans appreciate the city’s kitschy side as a part of its character. They recommend exploring neighborhoods like Pilsen, Wicker Park, or Andersonville to see grassroots culture at its most colorful. And don't forget to try the local food – from a Chicago-style hot dog to a deep-dish pizza.


OVERVIEW

Chicago’s summer scene is a mosaic of kitschy activities that promise more than mere entertainment. They offer an immersion into the city's rich history, innovative culture, and eclectic charm. This list is just the starting point; Chicago has countless other surprises tucked away in its vibrant neighborhoods.


Whether you’re drawn to the relics of the past, the artsy present, or the breathtaking skyline, Chicago’s kitschy experiences will enrich your stay and leave you with a new appreciation for the city. Remember, the true magic of travel lies in the stories you bring back with you, and in Chicago, there’s no shortage of stories waiting to be lived.

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