Summer may be winding down, but August and September are packed with plenty of special events and fun activities in Chicago and Milwaukee. The DMG team and our Chicago/ Milwaukee apartment residents love the summer season. The DMG team is sharing a list of some of our favorite things to do in August and September. Whether you’re looking for big festivals or family attractions, arts and culture, sports or live music, you have choices galore to fill your calendar.
Check out Chicago’s late summer events – from the field to the air
Northalsted Market Days – August 6-7
The 40th edition of this summer favorite event will feature five stages of live music, arts vendors, food and drinks on a half-mile through the landmark Northalsted neighborhood.
Retro on Roscoe – August 12-14
The 25th annual event in Roscoe Village features live music and vendors as well as a family area with inflatables, face painting, balloon artists, and rides.
Chicago Bears Preseason Opener – August 13
The Bears open the preseason at Soldier Field against the Kansas City Chiefs.
Evanston Art & Big Fork Festival – Aug. 19-21
This annual event in downtown Evanston presents high-end work from over 130 juried artists from around the country.
Chicago Air and Water Show – Aug. 20-21
Chicago’s signature summer event features jaw-dropping aerial displays on the lakefront.
The Second City’s Major League Soccer team takes on NYC’s squad at Soldier Field.
Chicago Jazz Festival – Sept. 1-4
The Labor Day weekend tradition returns to Millennium Park.
The Notebook: A New Musical – Sept. 6 – Oct. 16
See the world premiere musical at The Yard at Chicago Shakespeare.
Ravenswood Art Walk – Sept. 10-11
Enjoy the outdoor artist alley featuring local creators, beer garden, live music and food trucks.
Movie Fest at Lincoln Park Zoo presented by Alamo Drafthouse – September 16
See the Lion King with your family along with the zoo’s own lion pride – including new cub Pilipili.
Milwaukee has music and more to wrap up summer
Wisconsin State Fair – Aug. 4 – 14
For more than 170 years, attending the Wisconsin State Fair has been a tradition for Wisconsin families. Take in music and entertainment on 30 free stages, try food specialties from around the state, and check out the agricultural exhibits (racing pigs, anyone?).
Firefly Art Fair – Aug. 6-7
Hosted on the grounds of the historic Victorian Kneeland-Walker house, the Firefly Art Fair is an outdoor celebration of art including paintings, photography, ceramic, glass, acrylic, jewelry, sculpture, fiber, and more.
Center Street Daze – August 13
Classic cars, a cart race, carnival games, live music, and great food from local restaurants make the Center Street Daze in the Riverwest neighborhood a perennial favorite for everyone.
Milwaukee Brewers vs. LA Dodgers – Aug. 14-17
A night at the ballpark is always fun, especially when the Central division-leading Brewers host the best of the West for a four-game series in August.
Milwaukee Night Market – August 17 and September 21
Eat, drink, shop and explore downtown Milwaukee after dark. The Milwaukee Night Market was created as a free, vibrant, safe and interactive place in downtown for people to experience culture at night.
Zoo a la Carte – Aug. 18-21
Head to the Milwaukee County Zoo for four nights of live music, local food and special activities all among 2,000+ animals. Bella Cain, Spin Doctors, Plain White T’s and De La Buena headline each night.
Milwaukee Irish Fest – August 18-21
The world’s largest Irish music and culture festival is held in Milwaukee’s own Henry Maier Festival Park – Sláinte!
Milwaukee Oktoberfest – August 26-28
Enjoy authentic German food and beer and music and fun activities like stein hosting and the wiener dog pageant to wrap up summer and get in the mood for fall.