Chicago's Midway International Airport Is Changing How People See Airports With A Unique Family Night

Flying with children can be a challenge, and being around other people flying with kids can also be annoying. Although there are plenty of tips and tricks for how to make traveling with kids a less stressful experience, sometimes the most difficult part for first-time fliers — kids and parents — is not knowing what to expect. That's why in September of 2025, Chicago's Department of Aviation (CDA) is hosting two free family nights at Midway International Airport called Midway Family Night: Flying with Kids 101, giving parents or guardians and children a chance to explore the airport and get comfortable with travel procedures before the real deal. The first event took place on September 13, and an upcoming family night with two sessions, one from 4 p.m. until 6:30 p.m. and another from 5 p.m. until 7:30 p.m. on Tuesday, September 30, is already sold out (as of this writing).

Midway International Airport is one of America's most convenient airports, but it's also known as one of the worst due to its limited space, outdated facilities, and rampant delays. Family Night aims to help Midway redeem itself and make things just a little smoother by helping kids and parents prepare for travel. "Few experiences are as magical for a child as their first flight — and much of that wonder begins before the plane ever leaves the ground," CDA Commissioner Michael McMurray said in a City of Chicago press release. "At Midway Airport Family Night, we want young travelers and their families to feel that same sense of excitement and confidence as they move through the airport. This event is a chance to explore the journey together — from check-in to boarding — and to show kids that flying isn't just about the destination, it's about the adventure of the whole trip."

During the Family Night event at Midway International Airport, families will first check in at the counter of the regular Departures floor as if for a standard flight. They can bring luggage as if it's a real trip, and even get boarding passes from Frontier Airlines (the September 13 Midway event partnered with Southwest Airlines). Then, families will head to security, where Transportation Security Administration (TSA) agents will greet them and guide them through the security screening processes. Once everyone's through security, airport personnel will hold a Q&A session with families and a small tour, helping everyone get oriented with the airport's layout as they walk to their gate. After that, families will have a chance to board a parked, non-moving plane and practice getting into their seats, buckling up, and getting familiar with the airplane cabin, all in a calm, low-stakes setting.

Additional practical tips for surviving the airport with kids that parents and guardians will learn from airport staff, airline staff, and TSA agents include: Checking baby gear, gate-checking strollers, how to go through security with milk, juice, medications, car seats, and large baby gear such as strollers. Hands-on activities for kids will feature giveaways, stickers, snacks, coloring books, and more.

As with real travel, participants will go through legitimate TSA security screenings. Adults over the age of 18 are required to have a REAL ID-compliant driver's license or a passport to check in, and all security screening laws apply — no sharp objects, large liquids, etc. will be allowed, even though participants will not be taking off from the airport. Since registration is already closed, if you're interested in getting on the waiting list or hearing about future Midway events, check the official FlyChicago.com website for updates about future events.