Chicago is a city of diverse neighborhoods, and there’s no better way to get to know them than by going to local festivals and events. The bulk of Chicago’s events take place in the summertime, but there are also exciting annual indoor activities going on during the cold and snowy months to keep locals and visitors entertained. Whether you’re looking for live performances, arts and cultural experiences, or spectacles to amaze the senses, here are some of the best events in Chicago to check out.


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Chicago Blues Festival Chicago Blues Festival
Chicago Blues Festival

Chicago Blues Festival (Nearby Hotels)

The heart and soul of Chicago can be heard in Blues music, and there’s a Blues music festival that takes place here each year in June. This is the largest free Blues festival in the world and takes place on four stages over three days. The impressive list of performers here includes the late Ray Charles, the late B.B. King, the late Bo Diddley, and Buddy Guy. This music event takes place at Millennium Park and is fun to stop by even just to hear a few songs while you’re walking through the city and doing some sightseeing.

St. Patrick’s Day Parade Flag Bearers Marching in Chicago Saint Patrick's Day Parade
Flag Bearers Marching in Chicago Saint Patrick's Day Parade

St. Patrick’s Day Parade (Nearby Hotels)

With a large Irish population and lots of local history, Chicago is an amazing place to spend St. Patrick’s Day. The parade is one of the top parades in the nation, and the city even dyes the river green to get in the Irish spirit. The parade steps off at noon on Columbus Drive and runs from Balbo Street to Monroe Street. There are so many Irish pubs throughout the city, especially on the Southside, that this is the perfect place to do a St. Paddy’s Day pub crawl in your most festive attire. It’s also fun to stop by the Irish American Heritage Center to attend the St. Patrick’s Day festival going on here.

Taste of Chicago Taste of Chicago, Chicago, Illinois
Taste of Chicago, Chicago, Illinois

Taste of Chicago (Nearby Hotels)

Chicago is definitely a city for foodies, and you can sample the best of the best at Taste of Chicago. This event typically draws in over 1.5 million people each year and is truly a celebration of Chicago’s foodie culture. You can find everything from fast food favorites to gourmet chef creations here, as well as well as live music and culinary demonstrations. This annual July event is free to attend, so you’ll only pay for the food and drinks you purchase. The festival is outdoors at Grant Park and has lots of activities for the whole family.

Lollapalooza Performer at  Lollapalooza
Performer at Lollapalooza

Lollapalooza (Nearby Hotels)

There are lots of music festivals that take place during the summer in Chicago, but one of the biggest and most popular ones is Lollapalooza. Here you’ll find over 100 bands on lots of different stages playing a wide range of rock, hip hop, indie, and dance hits. This music festival typically takes place in Early August in Grant Park. The festivities run for four days, and tickets sell out fast. Check the band lineup for the upcoming show on the Lollapalooza website.

Chicago Auto Show Jaguar at the Chicago Auto Show
Jaguar at the Chicago Auto Show

Chicago Auto Show (Nearby Hotels)

If you happen to be in Chicago in February, make a point to check out the Chicago Auto Show, which has been happening since 1901 and is the largest of its kind in all of North America. There are over a million square feet of exhibit space at this auto show that takes place at McCormick Place on the city’s Near-Southside area. The admission price for adults to attend is $13, and children ages six and younger are admitted for free. Come here to see vehicles made by dozens of manufacturers from all over the world, including convertibles, crossovers, pickups, luxury cars, hybrids, and electric cars. There are also interactive displays here, including indoor test tracks and a virtual reality dynamics lab.

Chicago International Film Festival Opening night at Chicago International Film Festival
Opening night at Chicago International Film Festival

Chicago International Film Festival (Nearby Hotels)

Chicago definitely has an artsy side and lots of local filmmakers and film fans living here. Each fall around mid-October, the city hosts the Chicago International Film Festival, which features documentaries, feature films and shorts made by filmmakers all around the world. Featured events include tributes, industry days, and filmmaker sessions. There are special events that take place at venues around the city during festival time, but all of the films and panels take place at the AMC River East 21 on East Illinois Street.

Chicago Air and Water Show U.S. Army Parachute Team Golden Knights landing at North Avenue Beach during the Chicago Air and Water Show
U.S. Army Parachute Team Golden Knights landing at North Avenue Beach during the Chicago Air and Water Show

Chicago Air and Water Show (Nearby Hotels)

As far as outdoor spectator events go, the Chicago Air and Water Show is one of the best in the nation. This show highlights high-speed jets, military aircraft, and other airborne vehicles, and it’s free to attend. This event takes place in mid-August and runs from 10am to 3pm each of two days. Come by part of the fun by heading to the lakefront between Fullerton and Oak streets. North Avenue Beach is always a big focal point for the event and a very popular place to be during the summer afternoons during the festival.

Christkindlmarket People pass through the Christkindlmarket in Chicago
People pass through the Christkindlmarket in Chicago

Christkindlmarket (Nearby Hotels)

You don’t have to travel all the way to Europe to experience an old-world Christmas festival with all of the crafts, decorations, and delicious mulled wine you could hope for. Chicago has an excellent Christkindlmarket event that takes place each year at Daley Plaza. This has been a local holiday tradition since 1996, and it has more recently expanded to additional locations in Naperville and Milwaukee. It is free to come to Christkindlmarket, and the event typically runs from mid-November through Christmas Eve. It’s an open-air market that’s festive, family-friendly, and the perfect place to shop for holiday gifts. The market is open daily during the season on Sundays through Thursdays from 11am to 8pm and until 9pm on Fridays and Saturdays.

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