Summer Festival Frolics | PenCities Chicago

Summer Festival Frolics


You’ve aced Lollapalooza with our guide on where to shop, eat and play during Chicago’s biggest and best music shindig, but the festival fun doesn’t stop there… In a city that’s all about making hay while the sun shines, you can barely move for alfresco events in August. Here’s the lowdown on what not to miss.

For Families

Broadway in Chicago (14 Aug). In town with the smalls? This symphonic music, dance, opera, and Broadway-hit extravaganza will take over the striking stage of the Jay Pritzker Pavilion in Millennium Park for one night only. Your aspiring musical stars will adore the top cast lineup and classic show tunes taken from musicals including Aladdin, Les Misérables, School of Rock, Wicked, and Carole King’s Beautiful. Foot-stomping fun for all the fam!

For Culture Buffs

Tuesdays on the Terrace (until 27 Sep). Hands-down one of our favourite cultural institutions in the US, the Museum of Contemporary Art (MCA) hosts a free jam session on its garden terrace every Tuesday – the perfect way to wind down after a day of browsing artworks, chilled rosé in hand, of course. The weekly lineup spotlights legends of the world-class Chicago jazz scene, from Mike Reed (23 Aug) and Corey Wilkes (9 Aug & 6 Sep) to Joshua Abrams (27 Sep). Pack a blanket and go hungry as there’s a decent fill-yer-boots buffet, or à la carte options from the smokin’-hot grill. If it's raining, fret not, the event simply moves inside to the MCA Café.

For Party People

Northalsted Market Days (12-13 Aug). A colourful, rowdy riot of street eats, flamboyant fashion and live music, the region’s largest street party struts into Chicago's Boystown this year. Highlights include a drag race, a men’s chorus, and a performance by 80s popstrel Tiffany (of  "I Think We're Alone Now" fame). The overall flavour of the event is LGBT but all are welcome; it often attracts revellers in the hundreds of thousands.

For Food Fanatics

Hot Dog Fest (11-13 Aug). So important is the wiener in this city of fast-foodies, that Chicago has coined its very own rendition – the ‘Chicago Dog’, a beef frankfurter stuffed in a poppy seed bun and laden with mustard, onions, sweet pickles, tomatoes and relish. A wildly popular weekend-long celebration of this signature snack will take place in Chicago History Museum's delightful grounds, with a variety of pro sausage-slingers manning the grills. But be warned, some purist vendors consider any adulteration of their toppings to be sacrilegious, so ask for ketchup at your own peril.

Broadway in Chicago / 14 Aug / Jay Pritzker Pavilion / Millennium Park / 205 E Randolph St /

Tuesdays on the Terrace / until 26 Sep / Anne & John Kern Terrace Garden / Museum of Contemporary Art / 220 E Chicago Ave / 5.30-8pm Tue /

Northalsted Market Days / 12-13 Aug / Halsted & Roscoe Sts / 11am-10pm /

Chicago Hot Dog Fest / 11-13 Aug / Chicago History Museum / 1601 N Clark St / 9.30am-4.30pm Fri-Sat, noon-5pm Sun / get 20% off food and drink by buying Dog Dollars in advance /