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Start planning your trip to Chicago for a stepping experience in The Mecca of Stepping. An online place for resources and information to help you understand what it takes to make it to The Mecca. Learn about Chicago’s year-round weather surprises and the best time to enjoy the city and what you like to do. Be one step ahead on getting around the city and knowing the neighborhoods around you. With Chicago’s seasonal weather, know what to wear and watch the fashion ideas in the Chicago Stepping community. If you do not know where to start to find accommodations or a hotel haven to rest during your stepping adventures, StepintheChi can help guide you. StepintheChi is here to help every stepper make a trip to Chicago one they want to repeat.

When to Go to Chicago

The best time to enjoy Chicago is all up to you. Chicago offers a season for everything that can appeal to a stepper’s delight, no matter what you love or want to experience in the city on and off the dance floor. For many steppers, deciding when to visit Chicago can depend on different factors. Chicago’s seasonal weather, activities during certain times of the year, and personal budget are some of the basics that influence steppers’ travel plans.

WHAT IS THE WEATHER LIKE TODAY IN CHICAGO? MAYBE THE TIME TO GO IS NOW.

CHICAGO WEATHER

In Chicago, the winters are very cold and the summers can be very hot and humid. The best time for the average visitor to enjoy Chicago is May to September. Find out more about the average temperatures, snow, and other weather factors year round at Weather Spark. Although it isn’t really the windiest city, Chicago is called the Windy City. Check out some fun facts about Why Chicago is called the Windy City. Chicago is enjoyable any season of the year. Once you’re dressed properly for the season nothing will stop your fun. There is always something to do for steppers year-round whether you want to stay on the dance floor, enjoy the outdoors, go skating, or attend the many cookouts and picnics. Find your time of year and find your fun.

Planning for Chicago’s Most Popular Steppers Weekends

The major events that attract steppers from across the nation to Chicago just to dance are on major event weekends primarily hosted by the Majestic Gents. There are primarily four major steppers weekends in Chicago driven by events.

Worlds Largest Steppers Contest in the Fall

First, the most popular weekend is the World’s Largest Steppers Contest Weekend in September. Usually, the contest is held on the last weekend of the summer. Thousands of steppers from cities everywhere go to Chicago to compete for cash prizes and bragging rights. The contest is always on a Saturday but there is a cluster of events around that Saturday by other promoters and hosts that make it a grand weekend spanning from a kick-off set on Wednesday and ending with a close-out set usually at Hero’s Sports Bar and Grill on Sunday.

March

Secondly, Pete Frazier’s birthday party in March. Pete Frazier is the CEO of the Majestic Gents and tons of steppers show up to celebrate him on his birthday weekend. Despite this being one of the coldest and snowiest winter months in Chicago the turnout is great and the weekend is one to remember.

Summer

The third is the White Party Weekend which is hosted in July. This is one of the most crowded weekends because there are other major summer events attracting both steppers and non-steppers to Chicago at the same time. Be ready to wear white all weekend and dance until you drop.

Christmas and New Year’s Eve

Last, but not least, are the end of year holidays. The Majestic Gents’ New Year’s Eve Celebration is one of the best parties to end the year and the Majestic Gents know how to put on a great party. Andre Blackwell and Rose Wellington have birthdays in December during the Holiday Season and Rose Wellington’s party in December is a great way to welcome and celebrate the holidays with many other steppers.

To be certain, steppers can party every day and night in Chicago of any week but the time to connect with steppers from everywhere visiting Chicago is for one or all of these four events. If these are the types of stepper weekends you want to experience on your trip to the Mecca think about planning your trip for December, March, July, or September. To be certain, if you are traveling solo, from my experience there are some weekends that may be a challenge to get a dance because these are times when couples are out. New Year’s Eve, Mother’s Day weekend, and Valentine’s Day are times that couples are out for some QT and may not readily dance with other partners besides their significant others on the stepper set. Just something to consider in your planning and choices.

Traveling on a Budget to Chicago

Sometimes how much you can spend to travel is the most important factor in any trip plan. Traveling to Chicago and spending time in the city can be expensive but with planning and knowing what resources are available, you can make it affordable and fit your travel plans into a reasonable budget. Chicago summers are a “thing” and appeal to many tourists and steppers. In my experience, the summer is the most expensive time to travel to Chicago. Airfare, accommodations, and car rentals tend to be more pricey during the summertime.

Planning a road trip with friends, booking Airbnbs instead of hotels, and looking at other transportation options can help to cut down on expenses in the summer. The cheapest times to fly to Chicago are in the late fall and winter months. Airfare and transportation are lower in cost. You can save a lot of money traveling in the dead of winter. Ain’t nothing wrong with a little snow and cold.

PLANNING A TRIP TO CHICAGO

LOTS OF STEPPERS ON THE WAY TO CHICAGO HAVE LOTS OF QUESTIONS. ASK AND GET READY TO GO!

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

Chicago Midway (MDW) airport is located on the Southside of Chicago and closest to places like the Fifty Yard Line and other stepping venues. Using the Fifty as a landmark, O’Hare is further north and 22 miles from the iconic steppers sports bar while Midway is only 9 miles away. Midway serves mainly domestic flight routes and is less busy than O’Hare airport which caters to many more passengers for both domestic and international flights. Midway is also a sub for Southwest Airlines and many of the flights out of Chicago are direct. The nearest airport to Tinley Park is Chicago Midway (MDW). 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, be ready to go from set to set in a single night. Sometimes set hopping means traveling from the Southside of Chicago to the Westside. It can become expensive if you opt for Uber or Lyft.

Do you recommend Uber/Lyft in Chicago?

When traveling in any city, practice safety and be vigilant of your surroundings. Be careful, stay aware of your surroundings, and exercise care on all rideshare options. If you choose to rideshare please read and 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 will prove to be convenient.

What should I pack to wear for my trip?

Chicago weather can change quickly. Plan for it with clothing you can layer 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.

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Plan A Fun Stepping Time in Chicago

WHERE DO YOU WANT TO START? I FEEL A TRIP COMING ON.