Old Town in Chicago, IL, is home to a variety of special events and annual festivals. Being home to the Second City comedy troupe and many historical Victorian-era buildings, there is not only an abundance but also a variety in family friendly activities that can entertain even the most traveled visitors.

Wells Street Art Festival
This annual summer festival features hundreds of local Windy City artists with a variety of styles and mediums. Sculpture, paintings, performance art, and other mediums of expression are celebrated. The festival draws art fans from across the city and generally features a silent auction and live music. Vendors also provide the best food the area has to offer. There is a great mix of activity for children, parents, and grandparents.

Chicago Air & Water Show
This late summer classic can be seen in full from Old Town. The city encourages viewers to bring their own blankets, snacks, and umbrellas. The best part is that the show is free to watch! This three day event shows skilled stunt pilots fly in formations and perform aerobatic tricks, as well as boat motorists riding the waves of Lake Michigan. This celebration of aviation is not to be missed!

The Chicago Marathon
The Chicago Marathon runs right through Old Town, and along with is comes all the buzz, activities, and specials as Chicagoans cheer on some of the most impressive and athletic residents of the city. The marathon even offers real-time text message tracking for specific runners. Many of the pubs and restaurants open early and run great deals for runners and spectators alike!

Living Old Town: Celebrate Old Town
There’s nothing like a Chicago winter, and every November at Burton Place Park, the gorgeous Old Town tree is lit. Community members and visitors enjoy the sense of community, and dozens of the shopping centers and stores run special one-night discounts. It’s a great way for families to see Old Town during the holiday season while still getting shopping done in advance.

Crush in Old Town
This end-of-summer music festival is a great way to welcome the fall weather. More intimate and affordable than Grant Park’s Lollapalooza, Crush features two stages and a children’s area. There are food vendors, interest booths, and art sales. Not to mention, all the proceeds go to the development and revitalization of the neighborhood.