The Chicago Guide: 10 Things to Do This Summer


Hey ya’ll! It’s been a bit since I’ve done a post on this not so little place I call home and wanted to showcase some of Kollin and I’s favorite summertime activities in the city. Chicago truly comes alive in the Summer and reminds everyone who lives here why they just stuck out 9 months of winter! Now on our 4th summer in the city, we’ve come to really love certain annual events and activities. I’ve rounded up 10 fun things to do in Chicago in the summertime below with a little bit on why we love them!

Millennium Park Summer Film Series

Tuesdays at 6:30PM June - August | Free Admission

Every summer, Millennium Park hosts a film series and releases the schedule in June of what movies will be shown each Tuesday at 6:30PM. While the timing of this is not ideal for tourists, it’s a really fun and unique experience if you’re able to make one! Kollin and I usually go right from work and bring a little picnic to snack on while we’re watching. Hosted in the Pritzker Pavillion that features a huge lawn, big screen and amazing sound system, people bring blankets, chairs and all the food and wine. Movies range from comedies, classics, fan-favorite cult movies and even some horror films. So grab a blanket, some vino and snacks and enjoy! You can view the movie schedule here.


August 1 -4 | Grant Park | $$-$$$

Opinions on this event vary as the age of attendees seems to be dropping every year and the lineups have been hit or miss the last couple years. While Kollin and I have never been, people flock to the city for this huge music festival that seems to draw some big names in the industry. You can buy tickets for one day of the four day festival or buy packages for all four. See the lineup and tickets here.

Chicago Air & Water Show

August 18-19 | Free Admission

This weekend brings in one of the most crowded times in Chicago summertime. Millions (yes, literally) of people flood to North Avenue Beach and the lake front to watch the air show of fighter jets, planes, and the Blue Angels fly over the city. My best tip for this weekend? If you have friends in the city with a rooftop or your hotel has one, hang out there rather than the beaches. Some of the best views are from several stories up! If you do head to the beach be sure to get there early to get a spot. See more about the show here.

Spend a Day at the Beach

Beaches in Chicago | Free Admission

Offering 26 miles of shoreline, one of the most unique parts of Chicago is how close the beaches are to the city. Whether you’re looking for more of a party vibe on North Avenue Beach at Castaways Bar and Grill or wanting to take your dog to Montrose Beach, there are many to choose from. We love packing a bag and drinks and heading to one of the beaches for the day. While it definitely gets hot here and you’ll want to take a dip in the lake, be sure to check the temperatures as Lake Michigan takes a while to heat up. It’s the middle of July as I’m writing this and the water is still only about 57 degrees so swim if you’re brave!

We love the beaches that are further north so we can escape the large crowds. Foster Avenue Beach and even some beaches up into Evanston are quieter and to be totally honest, a lot cleaner.

Neighborhood Festivals

Various Locations | Free Admission - $$

Sometimes deciding how to spend your time in the city can be hard. There are so many options to choose from every single weekend here. One of the best parts about Chicago is the many different neighborhoods that make up the city. Each neighborhood has it's own vibe, culture and food scene. To celebrate this there are usually anywhere from 3-15 festivals happening a weekend, if not more. Ranging from Taco & Tequila in Lincoln Park to Roscoe Village Burger Fest, there is something for everyone. The majority are food and drink focused, but also include art festivals, culture festivals and block parties. Find the best festival for you here.

Our Favorites:

  • Gold Coast Art Fair (June)

  • Clark After Dark (August)

  • Taste of Randolph (June)

  • Taste of Chicago (July)

  • Windy City Smokeout (July)

Head to a Museum

Various Locations | Free Admission - $ - $$

Chicago is full of some of the most amazing museums in the world. From world-renowned art at The Art Institute of Chicago, to getting lost in the huge Field Museum of Natural History, you could spend your entire trip in these buildings. While the city does offer a “City Pass” where you can spend $100 and get access to some great tourist options for the entire weekend, we suggest breaking them up unless you want sore feet and exhaustion to hit pretty quickly. A museum can be a great way to escape the heat and if you’re here on some weekends there could be events at them as well.

Our favorite museums:

  • The Art Institute of Chicago: the largest and oldest art museum in the United States houses amazing works by Monet, Pollock, Van Gogh, Manet, Georgia O’Keefe, Grant Wood, Pablo Picasso, Salvador Dali and more.

  • The Field Museum: Chicago’s museum of natural history is a big one.I personally wouldn’t recommend trying to see the whole thing in one day unless you’ve got some serious time on your hands. But there are some pretty amazing exhibits there including the largest dinosaur ever found, Ancient Egypt, and a hall of gems.

  • The Shedd Aquarium: boasting one of the largest tanks in the US, the aquarium is a really fun spot. With tons of wildlife, a range of shows and animal encounters, this is a great way to spend some time especially with kids. If you happen to be here during the week on a Wednesday, check out Jazzin at The Shedd.

  • Museum of Science and Industry: I’ve personally never been here, but Kollin and his brother have visited and loved it! Ranging from engineering, physics, manufacturing and space, this museum dives deeper into the space of innovation and invention. Truly one of the most unique museums, you’ll learn a lot here in an interactive space.

See Hamilton

We were a little late to this train, but if you haven’t already, seeing Hamilton in Chicago is a fun experience. Back in the early 20th century, going to the theater was quite the event and it feels like that in the city too. Hosted in the CIBC Theater downtown, the production is magical, funny, sometimes sad and overall fun. Kollin and I saw it back in May and loved it. We saw a matinee show which was not only cheaper, but let out at the perfect time to grab dinner! Find more and tickets here.

See a Cubs Game at Wrigley Field

Wrigleyville | $-$$$

One of the most Chicago things I’ve experienced (and loved) was eating a Chicago dog in Wrigley Field watching the Cubs play. My family has been Cubs fans since I was little so to see the iconic stadium (the second oldest in the US behind Fenway Park) was really cool. It still features its original structure and architecture that brings some real charm to the stadium. Even if you aren’t a baseball fan, visiting the stadium and surrounding neighborhood of Wrigleyville is great. There are fun bars, restaurants, and a definite party scene at night. Since the Cubs won the World Series, ticket prices have gone way up and go quickly for big games so be sure to try and find tickets well in advance.

Have a rooftop drink(s)

One of my favorite things that Chicago offers is the option to drink beverages several stories up. There are so many rooftop bars, cocktail rooms, eateries and even clubs on rooftops. If you haven’t experienced a Chicago rooftop, to drink or not drink, I highly suggest doing so! Some of the best views I’ve seen are from rooftops and it’s not like any other regular bar on ground level. With a variety of options and several neighborhoods to choose from, you’ll be sure to find something! I’ve rounded up some of our favorites:

  • Cindy’s

  • LH Rooftop in the LondonHouse Hotel

  • Cabra

  • The J.. Parker at The Lincoln Hotel

  • Apogee

  • The Signature Room in the John Hancock Building (96 floors up, FYI)

  • Upstairs at The Gwen Hotel

  • Z Bar at the Peninsula Hotel

  • Streeterville Social in the Loews Hotel

Chicago Architecture Tour

Kollin and I did this the first summer we moved here and loved it. We’ve been on one since and it varied slightly so each tour company is going to be different on what they offer and cover. Our first trip we booked through the Chicago Architecture Association and it focused much more on the history and features of the buildings (which we nerded out on and really enjoyed). The second tour we took a few weeks ago was more pop-culture and random facts related than the true Chicago history, but still really enjoyable! In both cases we saw amazing views, great weather and had a memorable time. I think this also definitely depends on your tour guide and their approach to the tour. Either way, we highly recommend as it’s only 1.5 hours and there are several departure times!

Summertime Chi is the best time to visit this bustling city. The temperature is finally above freezing (lol), there are endless events happening, and the city comes alive with energy. I hope this post was helpful, but as always if you are planning a trip to Chicago and want some more details or ideas I’d love to hear from you! Check out my first Chicago Edit: Part One here for some of our favorite restaurants and activities from 2017 (still great options!).

Have a great week everyone and thank you so much for reading!

Amanda Sign Off.png