Top Ten Things to Do in Chicago This Summer

With Memorial Day 2016 upon us, it’s finally summer time in Chicago! The city explodes with activities once the mercury gets above 60, so here’s a list of the top ten things to do in Chicago this summer.

top things to do in Chicago this summer millennium park concert
Taking in a free concert in Millennium Park is one of the top things to do in Chicago this summer. (Photo Credit: TonyTheTiger – Wikipedia))

1. Millennium Park Concerts

From May until September, Millennium Park’s Pritzker Pavilion hums with the sound of musicians from around the globe. Not only are all of the concerts free, but Pritzker Pavilion and its Great Lawn are one of the few park spaces that allow alcohol consumption. So check the schedule, grab a cooler, and head on down to enjoy the music with your fellow Chicagoans.

2. Street Festivals

Every summer weekend offers a variety of street festivals from the cultural to the culinary. Some festivals are like a huge party, such as the Puerto Rican Festival in Humboldt Park, one of the largest Latino heritage festivals in the country. Alternately, head to an event like the 57th Street Art Fair and browse the fine arts in the great outdoors.

3. Head to the Beach

Jus because it’s a no-brainer, doesn’t mean it’s not one of the top things to do in Chicago this summer. The magnificent Lake Michigan beaches are some of the city’s most popular spots in the summer. The Oak Street Beach is perpetually the most popular, but smaller spots like Lane Beach Park provide the same relief from summer’s heat. You can read our Chicago Detours “Chicago Beach History” blog post if you’re curious.

things to do in Chicago this summer kayak Chicago River Urban Kayak
Chicago Detours Executive Director, Amanda, and Tour Coordinator, Pawel, kayak down the Chicago River. Photo Credit: Elizabeth Tieri

4. Myriad Boat Tours

You’ve been on a boat tour, I’ve been on a boat tour, and all of our aunts have been on a architectural boat tour. Try something else! A kayaking tour on the Chicago River can get you real close to the water. The entire Chicago Detours team went on a sunset kayaking adventure with Urban Kayaks and had a blast. Or get your friends together to charter a yacht with Anita Dee Yacht Charters, where Amanda recently gave architectural talks for executives from TransCanada.

Or have you ever gone sailing on Lake Michigan? If not, an evening cruise from companies like Chicago Sailboat Charters are one of the great things to do in Chicago this summer. Be sure to bring a camera!

5. Wrigley Field Tour

Summer means baseball season, with the joys of Chicago hot dogs and beers. Everyone will try to catch a game while the Cubs are one of the best teams in baseball and work towards ending the Curse of the Billy Goat this fall. The real treat for baseball fanatics may be taking a non-game day tour of the Friendly Confines. Tour guests get to see normally off-limits spots like the press box and the Cubs’ dugout.

6. Rooftop Bars

Bars and skyscrapers are both iconic parts of Chicago’s landscape. It only makes sense that combining them would be one of the best things to do in Chicago this summer, especially around sunset. Downtown spots like Roof and Vertigo Sky Lounge are always popular, but don’t forget the lower-key charms of Fountainhead out in Ravenswood. Here is TimeOut Chicago’s recent list of Best Rooftop Bars and both a rooftop bar list and a list of 8 great rooftop hotels from The Rooftop Guide.

7. Maggie Daley Park

We wrote about this fun new addition to downtown a few months ago. What was true in the spring is true now – Maggie Daley Park is one of the best places for Chicago’s kids to have fun. Grownups can have their own fun on the rock climbing walls, though certification is required.

top things to do in Chicago this summer bike
Biking the lakefront path is always a treat. (Photo Credit: Tony Bailey – flickr)

8. Biking the lakefront or 606

Chicago has a growing reputation as a very bike-friendly big city. If you haven’t experienced that for yourself, then test out these beautiful park paths. Both the new 606 trail, which runs along the former Bloomingdale rail line through Logan Square, and the 18.5-mile lakefront trail are safe, green, and eminently enjoyable.

9. Chicago Walking Tours

Of course, you can always have some summer fun by joining one of our many public walking tours with Chicago Detours. The Best Architecture Tour Since Sliced Bread explores the intersection of architecture and pop culture in a quick 90-minute- chronology of Chicago history. Or our new Old Polonia and Wicker Park Walking Tour with Food launches June 14th and includes corn smut quesadillas, Polish perogies, and gourmet donuts among stories of immigration, gentrification, and hipster neo-bohemia.

10. Chicago Swimming Pools

Fighting through the crowds at the lakefront sound like a hassle? Check out Chicagoist’s list of the ten best swimming pools in the city. Not all of them are open to the public, but that list should give you a leg up when it comes to belly-flopping off a diving board.

Now get out there and have some fun in the sun with all these things to do in Chicago in summer!

-Alex Bean, Office Manager and Tour Guide


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Private Tour Coordinator and Tour Guide

There is no shortage of things to discover in Chicago—I love being an urban explorer and uncovering its hidden places. I have an MA in Public History from Loyola University Chicago, and I have worked as a museum educator and kindergarten teacher. My desire to learn new things fuels my passion for educating others, which I get to experience every day as a Chicago tour guide. I live in the northern neighborhood of Rogers Park.

“Our guide Ellen was exceptional and gifted with a great personal touch.”


Tour Guide

Whether you are a first-time visitor or a lifelong resident, the vibrant history and modern majesty of Chicago never ceases to amaze. I’m a graduate of Columbia College with an M.A. in Interdisciplinary Art. I’ve worked for many years as an educator at City Colleges of Chicago. As tour guide at Chicago Detours, I integrate my enthusiasm for culture and architecture with my passion as an educator. West Town/Noble Square area is home for me.

“Jen was a perfect storyteller and kept us spellbound for hours.”


Tour Guide

With our Chicago neighborhoods, vibrant cultural institutions and nearly two centuries of larger-than-life stories, there’s never a dull moment here! I’m a fifth generation Chicagoan and a graduate of Washington University in St. Louis. In addition to guiding tours, I’m a creative writer and amateur genealogist. I also enjoy the city’s dynamic theater scene. You can also read overlooked stories from 19th-century newspapers on my “Second Glance History” blog. I live in River North.


Tour Guide

Chicago is unique as it always evolves into the future while holding on to the past. I’m fascinated by how people latch on to old architecture but happily pave over others. My background is in theater and performance and I’ve been a tour guide here for more than 10 years. Currently I’m finishing my Master’s in Public History at Loyola University because I love to teach the history of this scrappy city. I’m in the Edgewater neighborhood.


Operations Coordinator and Tour Guide

Chicago’s history is so fascinating, you could spend a lifetime uncovering its secrets…I’m willing to give it a try! I have an M.A. in US History from the University of Nevada-Las Vegas and then pursued doctoral studies in Urban History at the University of Illinois at Chicago. I love to learn new aspects of Chicago’s rich history and then share my knowledge as a tour guide with Chicago Detours. I live in Ravenswood.

“Marie was a bubbling fountain of information and contagious enthusiasm.”


Operations Coordinator and Tour Guide

As a fourth generation Chicagoan, I have been living and loving Chicago by bike, on foot, public transit or automobile. I am a graduate of UIC where through the College of Urban Planning and Public Affairs, began my eagerness to understand the nature, history and impacts of urban planning and development. It is incredibly rewarding to give back to this wonderful city by helping out in the office of Chicago Detours. I live in the incredibly diverse neighborhood of Albany Park.
“Sonny was extremely knowledgeable about all things Chi-town.”
Wade K


Content Manager and Tour Guide

Chicago has so many neighborhoods, buildings, and by-ways that it’s hard to go long without seeing something new, or something familiar from a new angle. I studied Cinema History for my M.A. from the University of Chicago. I’ve worked as a culture writer for various publications and as an educator of the humanities at the City Colleges of Chicago. I’m thrilled to share my love of this city’s busy past and unique architectural spaces with Chicago Detours. I live in the Chicago neighborhood of Lincoln Park.

“Alex was fascinating to listen to. He clearly knows his history and it shows.”
Katie K

Amanda Scotese

Executive Director and Tour Guide

I’m an interpreter of personal stories from the past and the city’s landscape. I love to imagine what originally happened inside old unmarked buildings, and what forces have shaped their design. I studied Chicago history, architectural history, and anything Chicago-related through my M.A. in the Humanities at the University of Chicago. My love for stories was enriched by my B.A. in Literature from the University of Michigan. I’ve written travel articles for publications like Rick Steves’ Italy best-selling travel guides, the San Francisco Bay Guardian, and The Chicago Food Encyclopedia. I live in the Chicago neighborhood of West Avondale.
“You can TELL Amanda is hyper-passionate about doing the research and getting the story that nobody’s heard before.”
Shelby F

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