Chicago Trip Planning for Steppers

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CHICAGO WEATHER TODAY. MAYBE THE TIME TO GO IS NOW.

“Planning a trip to Chicago to step in the Mecca of Chicago Stepping but unsure where to start? StepintheChi is your go-to guide for tackling key trip-planning challenges like weather, events, and budget. From seasonal tips and fashion advice to finding the best accommodations and exploring vibrant neighborhoods, we provide everything you need to make your Chicago experience unforgettable—and worth repeating.”

Chicago Weather

Chicago is a year-round destination for steppers drawing people across the nation to weekend events – no matter the weather. Discover why it’s called the Windy City, and find the perfect time to go!

While May to September is ideal for most visitors due to warm weather
Seasonal activities include skating, cookouts, and picnics
Proper preparation ensures nothing stops your fun.

Budgeting for a Trip to Chicago

While visiting Chicago can be expensive, careful, smart planning can make the trip affordable. Summers are popular but are also the priciest time to visit, with higher costs for airfare, accommodations, and car rentals. To save, consider road trips with friends, booking Airbnbs instead of hotels, or exploring alternative transportation options. For the best deals, travel during the late fall or winter months when airfare and other expenses are significantly lower. A little snow and cold shouldn’t stop you from enjoying all the city has to offer!

Stepping Events in Chicago in Every Season

Enjoy dancing, competing, and socializing on the Chicago Stepping scene to connect and enjoy the community all year long.
Get ready for an exciting lineup of stepper events throughout the year! Check out Cynthia Bean’s Weekly newsletter to keep up with everything happening in Chicago.

Spring

March – Pete Frazier’s Birthday Party hosted by Majestic Gents

Summer

June – July – Prelims for World’s Largest Steppers Competition
July – All White Weekend Extravaganza hosted by the Majestic Gents
August – Taste of Bellwood hosted by Ken Bedford

Fall

September – World’s Largest Steppers Competition – WLSC – hosted by Majestic Gents
November – Black Friday Thanksgiving Weekend Party hosted by Majestic Gents

Winter

December – Rose Wellington’s Birthday Party, Christmas Eve Ball hosted by Majestic Gents, New Year’s Eve Extravaganza hosted by Majestic Gents
January – DJ Sam Chatman’s Capricorn Party and Birthday Celebration hosted by DJ Sam Chatman

Plan a fun Stepping time for your Chicago trip

Ready to get to Chicago. See popular FAQs from steppers. Plan how to get there, how to get around the city, and places you can find a comfortable place to sleep and enjoy the night.

No matter where you’re coming from, there are many ways to get to Chicago. Whether you prefer to travel by plane, train, or automobile, explore your options and find the best way to start your journey to the heart of stepping culture!

Getting there

You can move around the city in different ways. The Chicago Transit Association (CTA) provides public transportation, rental vehicles, and other transport making it convenient to find options to make your way to and from the set.

Get around the city

Find the affordable options. Whether you’re planning a weekend getaway or a longer stay, there are plenty of budget-friendly options to help you enjoy the city without breaking the bank.

Where to stay

Learn from the questions and experiences from other steppers.

Which airport should I fly into – Midway (MDW) or O’Hare (ORD)?

Chicago Midway (MDW) airport is on the Southside. MDW is 9 miles from the Fifty Yard Line while the O’Hare airport is 22 miles away. MDW is the airport closest to Tinley Park. This airport serves mainly domestic flight routes and is not as busy as O’Hare which caters to more passengers for domestic and international flights. MDW is a hub for Southwest Airlines. MDW serves many direct domestic flight routes. We recommend Midway!

Do I need a rental car for my trip?

We recommend that you arrange to have personal transportation to get around. If you are in Chicago to step and plan to set hop daily you could be traveling from the Southside of Chicago to the Westside. It can become expensive if you opt for Uber or Lyft.

Should I use Uber/Lyft in Chicago?

When traveling in any city, practice safety and be vigilant of your surroundings. Be careful and aware of your surroundings. Exercise care on all rideshare options. Follow Uber Safety Tips and Lyft Safety for Riders. Beyond safety considerations, Uber and Lyft can become a pricey option eventually, especially if in Chicago for more than a single day. Having personal transportation to hop from set to set in a single night can be less expensive.

What should I pack to wear for my trip?

Chicago weather can change quickly. Watch the weather, plan your wardrobe. Bring layers and always have a coat. Chicago is known as The Windy City so be sure to have your windbreaker ready. On the stepping circuit, you may see themed parties calling for specific colors or styles. Plan ahead by reading Cynthia Bean’s weekly newsletter to know which parties to plan for on your trip. Know that Chicago is a great place to find unique styles and fashion at the malls, high-end stores or small clothing boutiques, and other retail clothing stores. Find tips on dressing for themed stepper parties and with pizazz for Chicago’s ostentatious fashion in Essentials and Fashions for Steppers.