As August cruises toward an end, we’re taking advantage of some of the last summertime street festivals and outdoor events in Chicago. If you don’t catch us running around these events in Chicago this weekend, you might find us eating alfresco on one of these off-the-path patios or indulging in these desserts unique to the city. Header photo credit: 


Chicago Friday Night Flights
August 25 // $15 Pre-purchase pass *Note: now sold out

Begyle Beer, Friday Night Flights

Come on out for the final Chicago Friday Night Flights, a summer-long neighborhood craft beer series, in the Ravenswood Corridor. Eight craft breweries are joining us and the Illinois Craft Brewers Guild for the event, and one pass gets you ten samples. Joining for the final event:  Begyle Brewing Company, Half Acre Beer Company, Spiteful Brewing, Dovetail Brewing, Band of Bohemia, Old Irving Park Brewing, Maplewood Brewing and Alarmist Brewing.


Logan Square Food Truck Social
August 25-27 // $5 suggested donation

Love a good food truck? Find your new favorite during the Logan Square Food Truck Festival. More than 25 trucks will come through over the weekend to feed festival goers, and stick around for live music. If you know that you’re ready for a variety of tastes, we recommend purchasing the sampler pass for only $20.


Taste of Greektown
August 25-27 // Free admission

Taste of Greektown

Get your Mediterranean food fix on Halsted at a Taste of Greektown. For 28 years, this has been the top festival for anyone who loves a good gyro, baklava, souvlaki and spanakopita can find it here, and entertainment will bring the sounds of the Greece to you.


SummerDance Celebration at Millennium Park
August 26 // Free admission

Chicago SummerDanceThere's no excuse to sit indoors this Saturday when the SummerDance Celebration is happening in Millennium Park. Stop through for nonstop movement; from competitions to lessons and performances, there won't be a dull moment between noon and 9:30 p.m. 


Field Market Days at The Field Museum
August 26 // Free admission

Swing through Museum Campus this weekend to experience the Field Market Days, a farm-to-table market with entertainment, shopping and craft beers that are named after the famous T-rex fossils, SUE.

While you’re there, swing through The Field Museum. Not only is Jurassic World: The Exhibition ready to amaze you, but Tattoo is still running through Labor Day weekend. Celebrity tattoo artist Joel Molina will be inking guests throughout the weekend in the on-site tattoo shop.


TransAmerica Chicago Triathlon
August 26-27 // See site for details

Triathlon ChicagoEven if you aren’t ready to grab a bike, swim some laps and run a while, plenty of athletes are coming to Chicago this weekend to do it all. Now in its 35th year, this race will host 9,500 athletes from 44 states and 20 countries. Feel free to spectate from the sidelines or join in on ancillary events (such as the inaugural Gildan Underwear Run or the Expo).


Randolph Street Market Festival
August 26-27 // $8 and up

Randolph Street Market crowd

Go on the hunt for the home decor, custom art, vintage furniture or modern statement necklace at the Randolph Street Market Festival. More than 300 vendors will get together in the Fulton Market District to show off inventory, and you can learn more about what to expect here


Wicker Park Bucktown Rack and Roll Sidewalk Sale
August 26-27 // Free admission

Businesses along Damen, Division, North and Milwaukee are ready for the Rack and Roll Sidewalk Sale this weekend. Browse special promotions and jam to live music while you shop brands, boutiques and record stores, and stop by the runway during the Rock Fashion Show on Saturday afternoon.  


Still need a few ideas? Navy Pier hosts fireworks twice each week during the summer, but see a bonus Friday show in celebration of Leinenkugel’s 150th anniversary. Labor Day rounds out the summer season, so take advantage of the shorelines before the crowds come for the last hurrah. If art is up your alley, we're nearing the end of summer incredible summer shows, including Gauguin: Artist as Alchemist at the Art Institute of Chicago and Takashi Murakami's The Octopus Eats Its Own Leg at the Museum of Contemporary Art. No pressure to choose right away, though. Feel free to talk about it over brunch.