Are you as excited as we are about all that's happening in Chicago this weekend? Sure, there's a lot of must-see attractions that you can't miss but there are also a ton of festivals, parties and fairs you're sure to enjoy. Whether you're looking to enjoy a weekend full of German music and cuisine, a huge party along The 606 trail, craft beer or gospel music in Millennium Park, Chicago is the place to be. If that's not enough, check out this list of trips ideas and Chicago travel itineraries for all the classic Chicago activities. It's time to make weekend plans — check out the top 8 picks below.


June 1-4


Enjoy a lively weekend full of German bands, dancers, and authentic German cuisine. Guests can enjoy traditional polkas, crowd-pleasing sing-a-longs, and classic hits as well as a maypole dance and other traditional German presentations. The 18th annual festival takes place in the heart of Chicago's German community: Lincoln Square. Entrance to Maifest is free and the street is full of neighbors and new friends enjoying the start of Chicago's summer festival season.


Chicago Friday Night Flights
June 2

Chicago Friday Night Flights

Chicago Friday Night Flights kicks-off the season on this weekend in the Bridgeport neighborhood and will feature the breweries from the Bridgeport, Pilsen and Pullman neighborhoods. All three neighborhoods have seen a resurgence in recent years and the beer being produced in these neighborhoods should be on everyone’s radar. Food for purchase from the acclaimed The Duck Inn and local entertainment will round out your experience of these neighborhoods. Participating breweries include: Mad Mouse Brewing, Lagunitas Brewing Company, Marz Community Brewing Company, Argus Brewing, Whiner Beer Company, Lo Rez Brewing, Alulu Brewpub.


Chicago Gospel Music Festival
June 2-3 // FREE

Chicago Gospel Music Festival

Celebrating the genre's deep Chicago roots with traditional choirs and contemporary urban gospel music in the city where the genre was born, the 32nd Chicago Gospel Music Festival features local and national artists on June 2 and 3 at the Chicago Cultural Center and Millennium Park.


The Artwork of Matt Hirschfeld: Chicago
June 2-3 // FREE

The Artwork of Matt Hirschfeld

Entertainment illustrator Matt Hirschfeld will be coming to the Elephant Room Gallery for a first time exhibit in the windy city. Hirschfeld, who has appeared in such publications as Variety and the New York Times, is known for his celebrity caricatures of modern stars from film, television, sports and politics. On display will be many of the artist’s works including the casts of Saturday Night Live and Star Trek. Entrance is free to the public and there will be a special limited giveaway print to those in attendance.


Do Division Street Festival
June 2-4 // $5


Chicago’s quintessential summer street festival is also one of the first of the season. Now in its 11th year, Do Division Street Fest & Sidewalk Sale 2017 kicks off June 2 – 4, promising the return of over 10 blocks of local food, shopping, art and live tunes. This year’s blacktop bash includes two fests-within-a-fest; Family Fun Fest and Do Fashion Fest, in addition to a multi-block sidewalk sale, crafts, artisans and plenty of ice cold beer. The highlight of the three-day mêlée is the live music programmed by iconic Chicago venues, Subterranean and Empty Bottle Presents. Music critics and fans alike usually rate the lineup among the best of fest season – and at only $5 it’s one of the least expensive too. Do Division Street Fest gives attendees each year a taste of what makes West Division Street one of the coolest destination corridors in the city!


Lincoln Park Greek Festival
June 2-4 // FREE

Lincoln Park Greek Fest

Authentic Greek cuisines, music, dance performances, kids' activities and, of course, Hellenic culture and pride are celebrated at this festive 40th annual happening on Sheffield Avenue. The festival will include fun games for the children to enjoy while parents enjoy the music and food.


The 606 Block Party
June 3 // FREE

The 606 Block Party

It's the perfect weekend to check out The 606. Check out the third annual 606 Block Party: A Walk with Neighbors — a day-long celebration of the community spirit of The 606. Take part in A Walk with Neighbors, listen to live music at two stages, and celebrate the start of summer with a community-centered street festival on Humboldt Boulevard featuring hands-on fun for all ages. Activities kick off at 10 a.m. and include music performances by Jonathan Langford and the Four Lost Souls, Cumbanchero: A Tribute to Rafael Hernandez, ¡ ESSO! Afrojam Funkbeat and others; beer from Revolution Brewing, a bicycle rodeo, poetry, crafts, and more.


57th Street Fair
June 3-4 // FREE

57th Street Art Fair

The momentous 70th annual event will be held in Chicago’s Hyde Park neighborhood. The fair features a range of categories including glass, jewelry, leather, photography, printmaking, painting, sculpture, wood, ceramics and fiber art so there is something for almost everyone!


Get summer ready with our Ultimate Guide to Chicago Festivals, which breaks down the biggest events of 2017 by month, or snag the NEW Chicago Official Visitors Guide packed with itineraries and planning tips.