One of my favorite things about living in Chicago is that every summer the city completely comes alive. After months of cold weather, everyone heads outside to enjoy festivals, patios, concerts, and everything that makes Chicago one of the best summer cities in the world.
As someone who loves to travel, I also love playing tourist in my own city. Whether I’m introducing out-of-town visitors to Chicago or simply looking for a fun weekend without getting on a plane, these are the places and experiences I find myself coming back to year after year.
If you’re planning a trip to Chicago—or you’re a local looking for some summer inspiration—here are my favorite things to do and places to eat during my favorite season of the year.
Top Things to Do in Chicago During the Summer
Taste of Chicago
If there’s one Chicago festival I never get tired of, it’s Taste of Chicago.
Growing up, this was one of those summer traditions my family looked forward to every year. We would spend the entire day walking from booth to booth, trying different foods, listening to music, and simply enjoying being outside together. Some of my favorite childhood memories include sharing a giant plate of fresh fried potato chips from Harry Caray’s and cooling off with one of the huge watermelon slices from Dominick’s. Yes, I’m definitely dating myself because neither of those vendors are there anymore, but those memories are such a big part of what made me fall in love with Chicago summers.
What I love most about Taste of Chicago is that restaurants from all over the city come together to proudly represent Chicago’s incredible food scene. The “Taste” portions are one of the best parts of the festival because you can sample dishes from several restaurants instead of committing to one full meal. Every year I discover something new while still making room for some of my favorites.
Some of the most memorable bites I’ve had over the years include the legendary Cursebreaker Burger from Billy Goat Tavern, delicious quesabirria tacos, and countless other local specialties. Even though the restaurants change from year to year, I still get that same feeling I had as a kid—walking around one of the best food cities in the world, soaking up the summer sunshine, and making new memories centered around great food.
Visit Chicago’s Zoos
One of my favorite ways to spend a beautiful summer afternoon is visiting one of Chicago’s incredible zoos.
Since I live just a few minutes from Lincoln Park Zoo, I find myself stopping by often. One of my favorite things about the zoo is that it’s free, so you don’t have to dedicate an entire day to enjoy it. Sometimes I’ll simply walk through for an hour before heading over to the lakefront or grabbing dinner nearby. I also love making the trip out to Brookfield Zoo whenever I’m looking for a bigger adventure.
Every visit feels a little different depending on which animals are active, but I always make a point to visit the lions, gorillas, giraffes, and penguins. Recently, the alpacas at Lincoln Park Zoo have quickly become one of my favorite additions—they’re always fun to watch.
After spending so much of the winter indoors, there’s something refreshing about seeing both the animals and the city come alive again during the warmer months. It’s a great excuse to get outside, enjoy the fresh air, and get plenty of steps in while exploring.
Attend a Concert or Movie in the Park
One thing Chicago does incredibly well is free outdoor entertainment.
Every summer I try to attend at least a few concerts at Millennium Park or catch one of the Movies in the Parks held throughout the city. There’s just something magical about bringing a blanket, grabbing dinner beforehand, and spending the evening outside with the Chicago skyline as your backdrop.
One event I never miss is the Broadway in Chicago Summer Concert every August. I’ve been attending it for years, and it’s been amazing to watch how much it’s grown. I remember when the concert was part of Taste of Chicago, and while it was always popular, it wasn’t nearly as crowded as it is today. Now, if you want a good seat, you need to arrive early because Millennium Park reaches capacity well before the performances begin.
The concert gives you a preview of many of the Broadway shows coming to Chicago over the next season, making it a perfect event for both longtime theater fans and anyone looking to discover their next favorite show.
Windy City Smokeout
I’m honestly not a huge music festival person, but Windy City Smokeout is one festival I happily return to year after year.
Of course, the country music lineup is always fantastic. Over the years I’ve seen Carrie Underwood, Kane Brown, and Blake Shelton perform, and every year the lineup seems to get better.
But if I’m being honest, the barbecue is the real reason I keep coming back.
One of my favorite parts of the festival is trying barbecue from restaurants that I normally wouldn’t have access to without traveling. I’ve had incredible smoked brisket from Panther City BBQ in Fort Worth and Terry Black’s BBQ from Austin, and both were absolutely worth the wait. It’s like taking a barbecue road trip without ever leaving Chicago.
I also love that the festival highlights local favorites like Green Street Smoked Meats. Every time I grab something from their booth, it reminds me that I need to make another visit to the restaurant long after festival season is over.
It’s still hard to believe that the United Center parking lot transforms into one of the biggest food and music festivals in Chicago every summer.
Kayak the Chicago River
When most people visit Chicago, they book an architecture river cruise—and don’t get me wrong, I absolutely recommend doing one.
But if you really want to experience the Chicago River, I think kayaking is even better.
The first time I climbed into a kayak, I’ll admit I was a little nervous being surrounded by tour boats and city traffic. After the first few minutes, though, all of those nerves disappeared.
I’ve done an architecture kayak tour as well as a longer paddle all the way to Chinatown, and both experiences completely changed the way I see the city. Looking up at Chicago’s skyline from the water while you’re doing the paddling yourself makes you feel like you’re truly part of the city instead of simply observing it from a boat.
If you’re looking for a fun way to stay active while sightseeing, kayaking is one of my favorite recommendations. I’ve had wonderful experiences with Urban Kayaks and would absolutely recommend them to first-time paddlers.
My Favorite Summer Restaurants in Chicago
One thing you’ll quickly learn about me is that I plan many of my trips around food—and Chicago is no exception. Summer means patios, frozen treats, riverfront dining, and long evenings spent catching up with friends over great meals. These are the restaurants I find myself recommending again and again.
Michael’s Pizza
Michael’s Pizza has become one of my favorite summer traditions located in Uptown.
After our softball games, my team almost always heads there to celebrate a win—or laugh off a loss. Sitting outside on the patio with teammates has become one of those simple summer traditions I look forward to every season.
Michael’s is known for its incredibly thin-crust pizza that comes out piping hot with the perfect crispy bite. Pair a fresh pizza with an ice-cold beer after spending an evening outside, and you have one of my favorite ways to end a summer day.
Chicago Brewhouse
If you’re looking for one of the best patios on the Chicago Riverwalk, Chicago Brewhouse is always one of my top recommendations.
There’s nothing better than sitting outside, watching boats cruise along the river, and enjoying classic Chicago comfort food with a local craft beer.
I almost always order their footlong that’s split between a traditional Chicago-style hot dog and a Polish sausage. It’s such a fun way to enjoy two Chicago classics in one meal, and it pairs perfectly with one of the many beers on tap.
Chicago Cut Steakhouse
Chicago Cut has become one of my annual summer traditions.
At least once every summer, I make it a point to grab a table on the patio, order an incredible steak, and spend the evening enjoying one of the best riverfront views in the city.
It’s one of those iconic Chicago restaurants that continues to live up to its reputation. The steaks are phenomenal, the service is outstanding, and somehow I always find room for dessert because they’re every bit as memorable as the main course.
It’s definitely a splurge, but one that’s always worth it.
Brothers Frozen Custard
Anyone who knows me knows I have a weakness for frozen custard.
Brothers Frozen Custard in Lakeview East is my go-to dessert spot during the summer, and honestly, you’ll probably find me there at least once a week once the weather warms up.
Their concretes are incredible, but my absolute favorite is the seasonal Key Lime concrete. Every summer I count down until it’s back on the menu because it’s that good.
Living within walking distance of a frozen custard shop is definitely dangerous—but I wouldn’t have it any other way.
Hopleaf
Hopleaf has been one of my favorite Andersonville restaurants for years.
Their beautiful backyard beer garden is one of my favorite patios in the city and the perfect place to spend a warm summer evening with friends.
I almost always order the mussels and frites because they’re consistently one of my favorite meals in Chicago. Pair that with one of the many beers on their extensive menu, and you really can’t go wrong.
It’s one of those neighborhood restaurants I find myself recommending over and over again because every visit reminds me why I love it so much.
Final Thoughts
One of the biggest reasons I love Chicago is that you don’t have to travel far to feel like you’re on an adventure. Every summer brings new festivals, outdoor concerts, incredible restaurants, neighborhood patios, and endless opportunities to explore.
Whether you’re visiting Chicago for the first time or have lived here your entire life, I hope this list encourages you to experience the city the way I do—with an appetite for great food, a sense of adventure, and an appreciation for everything that makes summer here so special.
Some of my favorite travel memories have happened halfway around the world, but some have happened right here at home. Chicago continues to surprise me every summer, and I hope it does the same for you.
Journey on and happy travels!
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