7 Quintessential Summer Experiences in Chicago

Written By Alla Levin
March 04, 2021

7 Quintessential Experiences: Summer in Chicago

Chicago is the third-largest city in the United States, and it’s the most centrally located. It’s so easy to travel to and offers everything you could hope for from a big city. When it comes to summer destinations, Chicago is the perfect place to spend a long weekend.

If you’re planning a summer trip to Chicago but you aren’t sure what to do, look no further. In this article, we’ll cover seven classic Chicago activities that you absolutely need to include on your trip this summer. These experiences include the absolute best that Chicago has to offer when it comes to making the most of warm summer days.

Sit in the Bleachers at Wrigley Field

You haven’t truly enjoyed summer in Chicago until you’ve attended a Cubs game at Wrigley Field. The Cubbies are one of the most beloved teams in all of major league baseball, with loyal fans who backed the team through a 108-year drought before taking the 2016 World Series.

With such a loyal fanbase, Wrigley Field tickets sell fast, and they can be a bit pricey. If you’re willing to sit with the salt-of-the-earth Chicagoans, the bleacher seats are (in my opinion) the best way to experience a Cubs game. This area is more affordable and there’s a special camaraderie among the bleacher folk. You might even catch a home run ball.

Wrigley Field became a National Historic Landmark just last year. You really can’t take a trip to Chicago in the summer without seeing a game.

Summer in Chicago: Get Dinner at an Outdoor RestaurantSummer in Chicago

Chicago is home to some of the best restaurants in the nation, maybe even the world! If you’re planning a summer visit to Chicago, you better not be found eating at a chain restaurant. The city is awash in hole-in-the-wall restaurants, first-of-their-kind restaurants, experimental and unique places.

To make the most of the warm summer weather, find somewhere that you can eat outside. Many places take advantage of lake views or the city skyline, so keep an eye out for patios, rooftop restaurants, or seating that’s just off the sidewalk. It’s the perfect way to kick up your feet, get re-energized, and hit the city for more summer fun.

Watch an Outdoor Movie

Every summer, Millennium Park holds a Summer Film Series. This past summer, the series was canceled due to COVID-19, but it’s sure to come back when things open back up.

In recent years, this film series has included movies from just about every genre a viewer could want. You can catch a recent hit like Black Panther or an old favorite like The Muppet Movie. Occasionally, viewers can vote on which movie should be shown.

On a warm summer night, pull up a lawn chair or picnic blanket and enjoy a movie with family and friends. Admission is free and the movies usually start at 6:30 pm. The park gets pretty packed, so be sure to show up early and stake out your spot!

Spend the Day at Navy PierSpend the Day at Navy Pier

Navy Pier is one of the hottest tourist spots in Chicago. It hosts hundreds of free public events every year, dining options are plentiful, as are shopping and entertainment choices. You could easily spend the entire day there and not run out of things to do.

Don’t pack up and leave just because the sun has set. Every Wednesday and Saturday during the summer, you can watch the fireworks show over the water. Stick around and catch the show, then ride the Ferris wheel one last time for an unforgettable view of the sparkling city.

Party on a Chicago Rooftop

When you’re partying in the city, there’s no better way to take in the beauty of your surroundings than with a rooftop party. With the warm summer nights, you can stay out well into the early hours of the morning. This Party Slate list of Chicago’s best rooftops has some excellent options.

According to Party Slate, the best choice in the city is Joe’s on Weed St. This industrial, warehouse-style restaurant is incredibly spacious, accommodating up to 120 guests. It’s perfect for engagement parties, retirement parties, or small wedding receptions. With a beautiful location, great food, and bar service, it will certainly be a night to remember.

Go to a FestivalDuring the summer months

During the summer months, Chicago hosts some of the most popular festivals in the U.S. If it’s delicious food you crave, you have to visit during the Taste of Chicago. It’s a multi-day festival where vendors from all of the most beloved Chicago-based restaurants, food trucks, and pop-up spots show off their skills.

For those who love the music festival scene, Lollapalooza pulls huge names like Ariana Grande, Donald Glover, Twenty One Pilots, and The Strokes (and that was just in 2019). The festival is held in Grant Park and runs for four days. With multiple stages running at once, it’s a non-stop concert that you will never forget.

Enjoy the Water

One of the best things about Chicago is the combination of city life and natural outdoor beauty. You can spend the day on the beach or on a boat, and then spend the evening in the city going to clubs and eating great food.

In the summer, there are plenty of ways to enjoy the water in Chicago. You can rent a boat and go out on the lake and fish in one of the many approved fishing areas.  You might prefer to try out a paddleboard or kayak, or to go on a boat tour… there’s something for everyone.

On those hot summer days, there’s nothing better than cooling off in the water. Between the Chicago River and Lake Michigan, you can plan an entire day besides, on, or in the water. So the next time you visit, be sure to bring your swimsuit!

Chicago has much to offer when it comes to summer activities. From spending the day on the water to enjoying the beautiful view from a rooftop bar, you can easily fill your trip with unforgettable moments. The next time you plan for a summer destination vacation, remember Chicago.

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