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An itinerary for the perfect summer week in Chicago

A quintessential summer week in Chicago means farmers' markets, beaches, street festivals, music and more

Photograph: Grace Allen

Summer in Chicago can be overwhelming. Whether you’re a tourist or have lived near the city your entire life, you’re still faced with a multitude of options each day. Which of the 25 best attractions will you see? And with only so many days in the week, what rooftop bars will you laze on or what brewery tours will you take? Here, let us help you. When you’ve only got a week to do it all, we’ve got the itinerary for a perfect seven days of summer in Chicago.  

RECOMMENDED: Find more of the best things to do in the summer in Chicago

 

The perfect summer week in Chicago

Saturday

Saturday

Start your weekend off right by visiting one of the city's many summer street festivals—it's also a great way to explore a new neighborhood. During the summer, you're bound to find competing street fests each weekend, but we suggest the funky bike- and beer-friendly Tour de Fat on July 9 in Logan Square, Wicker Park Fest on July 23 and 24, and Northalsted Market Days on August 13 and 14, for starters.  

 

Sunday

Sunday

While you can find a farmers' market in Chicago any day of the week, Sunday farmers' markets offer plenty of time to peruse the produce. Check out the ones in Pilsen, Logan Square or Portage Park, among others.

Monday

Monday

You’re still here? Good. Take the opportunity to go to one of Chicago's best beaches while the rest of the city heads into work (suckers!). North Avenue and Oak Street beaches offer knockout views of the skyline, while Montrose Beach, a little farther north, allows dogs and is a bit more family-friendly.

Wind down in the evening with a
free concert in Millennium Park. If you can't make it on Monday, you can also check the schedule of free Thursday shows. Jose Gonzalez comes to the park on August 1 and Tortoise closes out the season on August 25.

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Tuesday

Tuesday

Spend a (free) day touring the Museum of Contemporary Art with an Illinois ID. Then kick-start a relaxing evening with a jazz performance as part of Tuesdays on the Terrace at 5:30pm at the museum.  

Thursday

Thursday

The city also hosts a bevy of free museum days for anyone holding onto their wallet a little tighter. On Thursdays from 5–8pm, Illinois residents get into the Art Institute of Chicago for free.  

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Friday

Friday

What a week! Whether you live here full-time or are just visiting, a summer Friday in the city is magical, from Cubs and Sox games to a night at any one of the Chicago’s best music venues. If you've got the evening free, check out the Hoyle Brothers for a free set of honky tonk music at 5:30pm each Friday at the Empty Bottle. 

 

Comments

1 comments
Jim N

Summer's here!