A Guide to Summer in Chicago

chicago summer activity guide

Summer in the city: there’s nothing quite like it. Chicagoans live for these summer months, so we tend to make the most of it! I’m often asked for local recommendations, so I created a guide of ‘must do’ activities and favorite spots to enjoy during summer…


Visit a farmers market

One of the first signs of summer are the various farmers markets that pop up over the city. Each neighborhood seems to have their own, but look out for my personal favorite: Green City Market in Lincoln Park (every Wednesday and Saturday).

Hit the lakeshore

What makes Chicago stand out from other major cities, in my opinion, is it’s incredible lakeshore. Skyscrapers are set against the backdrop of Lake Michigan, which appears as an aqua blue in color in the summer months. The lakefront path spans 18 miles, allowing for running, biking, walking, beach volleyball and more.

Catch a baseball game

Chicago is home to two major league teams, the Cubs (on the north side) and the White Sox (on the south side). Whether you’re loyal to one side or the other, both teams provide great experiences for a sports outing in the city.

Dine al fresco

Chicago’s food scene is vibrant — and it heats up during the summer months. Warmer weather encourages restaurants to open outdoor dining spaces all over the city. Some of the best places to dine al fresco are: Le Colonial, Blue Door Kitchen, Parson’s, Piccolo Sogno, The Allis, Ace HotelTied House, Somerset, and much much more.

Enjoy patio or rooftop cocktails

Just like outdoor dining, summer presents lots of options to enjoy drinks and such outdoors. A few of my personal favorites? RM Champagne, Celeste, Devereaux, Drumbar, Cold StorageLondon House, Cindy’s, Barcocina, Sheffield’s, City Winery on the Riverwalk, and the little outdoor garden atop Restoration Hardware.

Go out on the water

In addition to Lake Michigan, the Chicago River offers opportunity to get out on the water. Take an architectural tour by boat, rent kayaks, take the water taxi, or simply stroll along the riverwalk. On the lake, you can charter a sail, rent a boat, hop aboard an entertainment cruise, or enjoy a public beach (try Oak Street).

Attend a festival or concert

Chicago has so many festivals and concerts during the summer season. Some of my favorites include: Wells Street Art Fest in Old Town, Windy City Smokeout, Do Division, and Chicago Air & Water Show. You’ll notice smaller street fests, too, happening all over neighborhoods in the city. Any excuse for a fest: Chicago will find it! The city also hosts free concerts in major parks and fun movie screenings.

Visit a museum

Any season is a good season to visit one of Chicago’s museums, but summer presents a few special experiences. Attend Jazzin’ at the Shedd, Tuesdays on the Terrace at the Museum of Contemporary Art, dine outside at The Art Institute and stay for Thursday night music.

Linger for brunch

Chicago takes its brunch scene seriously, especially in summer. For great brunch spots in Chicago, try: Blue Door Kitchen, The Allis, Nellcote, Maple & Ash, Summer House Santa Monica, Bernie’s, Margeaux Brasserie, Left Coast and Beatrix.




Leave a Comment


  1. Sydney wrote:

    Baseball games are my favorite!! Love this list Laura!
    xo, Sydney

    Posted 6.4.18 Reply
  2. Marina wrote:

    Great list of things to do as the weather warms up! I love both Northerly Island and Ravinia for outdoor concerts in Chicago. Both settings are so beautiful and add to the entire experience!

    Posted 6.4.18 Reply
  3. joe wrote:

    Best Chicago guide travelling during summer times loved the way you described Thank you so much 🙂

    Posted 10.30.19 Reply

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