10 Best Things to do in Chicago in the Summer

Flying into Chicago, we hovered over Lake Michigan and suddenly made a sharp U-turn to land at the Midway Airport. I stepped outside to the sticky heat and, within a few minutes, was walking into a Giordano’s restaurant for my first deep-dish pizza. It’s a classic start to a trip to Chicago in the summer.

Summer is, without a doubt, the best time to visit Chicago. After months of cold and snow, Chicago comes alive in the summer and attracts travelers from all over the world for good reason. Home to one of the seven Great Lakes, the all-American hotdog, and some of the country’s finest architecture, enjoying all the best of Chicago is just better in the summertime. 

I was lucky to have a local friend guide me through Chicago when I visited in July. My suggestions below highlight some of my favorite things that we saw and experienced that I highly recommend for your summer trip.

1. Visit Chicago landmarks on foot

Chicago is home to one of the most recognizable landmarks in the United States – the Bean! It sits in Millennium Park, near a digital display tower and modern splash pad that is great for people watching.

From Millennium Park, you’re about a 10-minute walk from several other Chicago landmarks. Some of the highlights nearby are: 

  • Buckingham Fountain – Buckingham Fountain is in Grant Park. The fountain resembles a three-tiered wedding cake and is one of the 10 tallest in the world. If you’re there at dusk or later, you can catch the fountain’s water and light show. 
  • Chicago Theater – The Chicago Theater dates back to 1921. Its iconic red Chicago light-up marquee gets your attention while you’re walking down the street. The theater is nostalgic to see from the outside, and if you plan to see a show, the interior will take you back to another century with its red-velvet chairs and dangling chandeliers.
  • The Picasso Statue – Spanish painter Pablo Picasso gifted a 160-ton steel statue to the city of Chicago. It sits in the Daley Plaza, and the untitled artwork is a little mysterious – it’s known simply as “the Picasso” without any explanation of what it is. Everyone that sees it makes their own interpretation. 
View of the Bean and tourists in Chicago, Illinois

2. Go to a local event or festival

Each week of summer, different parts of the city host events from food festivals to cultural events and weekly concert series at the park. It’s one of the best ways to blend in like a local, and you have plenty of options to choose from that fit your interests. You can check the full list of summer events by clicking here.

Some of Chicago’s summer events include:

  • Food festivals
  • Concerts like the Millennium Park Music Series and the mega festival Lollapalooza 
  • Art fairs and street food markets
  • Greek fest and Puerto Rican festival
  • Neighborhood festivals 
  • Summer film series

3. Watch a Cubs game at Wrigley Field

Wrigley Field was built in 1914 and is one of the oldest stadiums in the United States. Chicago has two Major League Baseball teams, the Cubs and the White Sox, but the Cubs are the only team that plays at Wrigley Field. It’s a great place to get a souvenir for your trip and hang out on a nice afternoon when the stadium roof is open, and you don’t need to be a huge baseball fan to enjoy it. 

4. Bike the Lakefront Trail 

The 18-mile trail runs along Lake Michigan and Lake Shore Drive. You can rent a bike at Bobby’s Bike Hikes and head north along the Lakefront Trail, stopping at city beaches and parks along the way. If you bike the trail all the way north, you can stop at The Waterfront Cafe with outdoor seating looking out toward the lake.

5. Explore trendy Wicker Park

The hip Wicker Park neighborhood is distinct for its well-maintained historic buildings dating back to the mid-1800s and its impressive Flatiron Arts Building. Vintage enthusiasts will love the second-hand book shops, vinyl records stores, and vintage apparel shops sprinkled throughout Wicker Park. And when you need an energy boost after walking through the area, you’ll find everything from plant-based restaurants to cozy coffee houses. 

6. Have a cocktail on the Robey rooftop

While you’re in the Wicker Park neighborhood, head to the old-timey elevator at the Robey Hotel and take it to the 13th-floor rooftop bar, the Up Room. On the outdoor rooftop, you’ll have one of the best panoramic views of the Chicago skyline and the above-ground railroad tracks crisscrossed throughout the city. Seating fills up fast here, so try to get there right when it opens at 5 pm. 

Panoramic view of Chicago skyline from the Robey Hotel rooftop

7. Watch fireworks at the Navy Pier

The Navy Pier hosts firework shows on Wednesdays and Saturdays from Memorial Day through Labor Day. Although it can get crowded, the pier is one of Chicago’s most well-known landmarks, and seeing the fireworks from the pier observation deck is worth it. For a unique view, you can try to get on the Ferris wheel as the firework show starts.

8. Brunch on the Riverwalk

Having brunch next to the Chicago River is a great way to start your morning exploring this part of town. River Roast is a popular brunch spot with live music and an outdoor patio hovering over the river, and you have a beautiful view. After brunch, you can stroll around the Riverwalk and cross the historic bridges linking both sides. Standing on the bridges, you have more amazing views of the river leading your eye to the skyscrapers and boat cruises ahead. 

View of the Chicago River from a Riverwalk bridge

9. Rooftop dining at Time Out Market

Time Out Magazine founded these markets, and they only have seven locations in the world. I’ve been a fan of Time Out Magazine for a while, so this was a fun novelty, and I was impressed with the food and atmosphere. It’s a modern take on a market food hall with cocktail bars and more than a dozen international food vendors inside. There’s casual, communal seating downstairs, but if you head to the top floor you can enjoy dinner on their rooftop patio at sunset. 

10. Indulge in Chicago’s favorite foods

Whether you’re re-visiting Chicago or a first-timer, you’ll want to have Chicago’s specialties – deep dish pizza, a Chicago dog, and popcorn. All of these essentials are easy to find as you’re walking through the city. Below are some of the best places to try each one:

  • Pizza at Lou Malnati’s or Giordano’s: Two staple deep dish pizza places that locals recommend are Giordano’s and Lou Malnati. I loved Giardano’s, and I’m told the difference between the two is that Lou Malnati’s uses less sauce than Giordano’s.  
  • Portillo’s Hot Dogs: Get Portillo’s traditional dog as is. It comes with a pickle spear, onions, and poppy seed bun. Don’t forget to add cheese fries on the side! 
  • Garrett’s Popcorn: Cheese and caramel popcorn at Garrett’s is something I didn’t know was a Chicago staple before I visited. The salty and sweet combination is addicting.
Buckingham Fountain in Chicago in the summer

What to pack for Chicago in the summer

The key to Chicago packing is comfortable street style during the day and simple yet classy at night. Keep in mind that it’s usually warm but cools off anywhere from 5 to 15 degrees at night, so you’ll need a few light layers. 

Below is a list of apparel and accessories I recommend packing for a trip to Chicago in the summer. I’ve added links to products I can personally recommend and a few that I haven’t bought, but want. Note: I don’t get compensated for providing links to any of these products. 

Women’s summer packing list for Chicago: 

Add your toiletries to the items above and you’ve got the perfect packing list for Chicago in the summer. I’m an over-packer but this list could last you for a three to five-day trip.

Crown Fountain display and splash pad in Chicago, Illinois

If you’re from Chicago, leave a comment on what you’d recommend for the best local things a visitor can do in Chicago in the summer. And if you bought anything from my packing list links, let me know how you like them! 

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