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This is the go-to spot for all your stepper-related inquiries about planning a trip to go to Chicago! Do you have stepper questions? Whether you’re a stepper planning a trip to Chicago or simply need guidance, use the form below to submit your question. For general inquiries, our team may add your question to our FAQs to assist other steppers with similar needs. We’re here to make your trip planning seamless and provide you with the right information, right when you need it!

Find out more about the city of Chicago on the City of Chicago website.

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.