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The Ultimate Guide to Summer Fun in Chicago 2019 Edition

Published on Jun 17, 2019 at 3:32 pm in Fun Stuff.

Excitement is in the air as temperatures rise and kids get out of school. No matter how long you’ve lived in the Chicago area, there’s always something new to checkout during summer.  That’s why we’ve compiled the ultimate guide to summer fun in the city. Whether you’ve looking to check out a festival, dine on a rooftop, learn something new on walking tour, or want to hang out on Chicago’s Riverwalk, you can use this guide to make plans with friends and family.

Summer Festivals in Chicago

Summertime in Chicago is festival season.  It seems that every weekend from June through August there’s something to do. While music festivals are the most common, many others are themed around food, beverages, and culture. Some of the most popular festivals are listed below.

  • World’s Largest Block Party. Old St. Pat’s Church will host the 35th annual World’s Largest Block Party on June 22. Thousands of people will attend for music, food, and fun, Ticket proceeds go to the social justice initiatives, outreach programs, and strengthening of the church.
  • Chicago Pride Fest. Pride Fest 2019 takes place from June 22-23. The 19th annual street festival expects up to 100,000 attendees, to celebrate LGBTQ+ life, culture, and community.
  • Frontier Days Festival. This year’s Frontier Days Festival takes place from July 3-7 at Recreation Park in Arlington Heights. There are a number of performers, events, and a Fourth of July parade.
  • Chicago Botanic Garden Art Festival. Only July 6 and 7, you can stop by the Chicago Botanic Garden for their Art Festival. You can peruse 90 juried artists. Paintings, ceramics, metal, fiber, wood, jewelry, and other pieces will be available for purchase and admiration.
  • Railroad Days Festival. The Railroad Days Festival takes place in Pioneer Park from July 11-14. During the four days, you can see great band and fireworks, check out the carnival, or participate in a 5K run/walk.
  • Pitchfork Music Festival. You can check out the Pitchfork Music Festival in Union Park from July 19-21. Celebrating its 14th year, this internationally recognized festival presents over 40 acts over the three-day span. They highlight the best new and emerging musicians. You can also check out the local craft vendors and food stands.
  • Fiesta del Sol. Fiesta del Sol is a four-day event that draws over one million visitors each year. You can experience live entertainment, local art and food, carnival rides, educational resources, and more on July 25-28.
  • Lollapalooza. From August 1-4, you can experience Lollapalooza in Grant Park. This festival started in 1991, and has continued every year. There are 8 entertainment stages, Chicago’s best eats, and a number of interactive areas to explore.
  • Chicago Southside Maker Faire. The Chicago Southside Maker Faire is an event for all. From engineers and scientists to artists and crafters, this family-friendly showcase of invention, creativity, and resourcefulness takes place on August 3.
  • Bud Billiken Parade. Since 1929, the Bud Billiken Parade has marched down King Drive. This parade unites African Americans throughout the city with music, dance, and food. This year’s parade takes place on August 10.
  • Edison Park Fest. Edison Park Fest takes place from August 16-18. What began as a sidewalk sale in 1972 has turned into one of the most popular street festivals in Chicago. Attendees can enjoy food, listen to live music, and participate in family-friendly activities.
  • DeKalb Corn Fest. DeKalb Corn Fest is one of the last free music festivals in Illinois. From August 23-25, all ages can enjoy live music, tournaments, contests, and plenty of corn.

Chicago’s Best Rooftop Bars and Restaurants

Chicago is a popular spot for rooftop bars and restaurants. The altitude provides a breeze that makes the heat a little more bearable and diners are treated to gorgeous views of the city. Whether you’re looking for a quick bite to eat for lunch or want to spend the night out on the town, these rooftop bars and restaurants are some of the city’s go-to spots.

  • Boleo. This beautiful rooftop bar at the Kimpton Gray Hotel features South American flavors in their drinks. Their fan-favorite empanadas pair well with their drinks. Diners can also enjoy their nightly specials and happy hour at Boleo.
  • Z Bar. Sip cocktails on this stunning rooftop lounge at the Peninsula. Z Bar also offers plenty of tasty snacks to go with their refreshing drinks.
  • Waydown. Waydown sits above the Ace Hotel. Their outdoor deck has ample seating, and live music and entertainment happens regularly.
  • Devereaux. This rooftop bar features a pool. Diners at Devereaux can enjoy their beverages with their toes in the water while waiting for appetizers like garlic fries with truffle aioli.
  • VU Rooftop Bar. This 13,000-square-foot rooftop bar in the South Loop features an extensive cocktail menu, broken down by spirit. Visitors at VU Rooftop Bar can enjoy this bar all-year-round.
  • Homestead on the Roof. This farm-to-table restaurant has a patio that seats 80. Homestead on the Roof’s menu draws ingredients from their organic rooftop garden.
  • Little Goat. This second floor space is complete with a glowing goat, so you won’t miss it if you’re looking for it. Little Goat features burgers, snacks, and cocktails.
  • Celeste. This romantic rooftop garden is filled with Victorian-style furniture and greenery. While at Celeste guests can enjoy small bites or go all in with a full entrée.
  • Taxim. Taxim features an 80-seat rooftop patio. You can enjoy a number of Greek eats, like seafood soup, grape-lead wrapped shrimp, and duck gyro. They also have an extensive wine list.
  • The Chop Shop. Located near one of Chicago’s busiest intersections, the Chop Shop is a great place to grab a bite to eat before visiting Wicker Park.

Popular Summer Walking Tours in Chicago

Locals and visitors alike will enjoy the numerous walking tours Chicago has to offer. The most popular revolve around the city’s unique and extensive architectural history. You can also learn about ghost lore or prohibition, or join a food walking tour to try the city’s most delectable bites.

  • Chicago Architecture Center’s Walking Tours. The Chicago Architecture Center offers a number of diverse walking tours. To learn about and examine the city’s skyscrapers and design, sign up for one of their tours.
  • Tastebud Tours. If you want to learn about the city’s history while trying a number of local foods, the Tastebud Tour is for you.
  • Bizarre Bucktown. The Bizarre Bucktown walking tour combines history and magic. You’ll learn about the history, mystery, and ghosts of Bucktown.
  • Chinatown Walking Tour. To learn about Chinatown and it’s history, take a walking tour with the Chicago Chinese Culture Institute.
  • Chicago Food Planet. This walking tour led by Chicago Food Planet is perfect if you want to try the city’s signature hot dogs, deep dish pizza, and other culinary delicacies.
  • Chicago Crime Tours. Chicago has a decorated past. This includes gangsters like Al Capone and speakeasies. If you want to learn about Chicago’s crime history, this tour is for you.
  • Underground Donut Tour. Take this tour to sample the Windy City’s tastiest donuts. You’ll visit different donut shops with your tour guide in the city’s Loop neighborhood.
  • Chicago Prohibition Tour of Historic Speakeasies. This walking tour visits four historic bars that have been in operation since Prohibition in Chicago. You’ll walk through the once-illicit establishments in Old Town, Wicker Park, and the Chicago Loop.
  • Discover Chicago’s Underground City. To experience a lesser-known side of Chicago, take the Underground City tour with Chicago Elevated. You’ll walk through heated passageways, tunnels, and corridors that link some of the city’s most iconic building.
  • Chicago Loop Walking Tour. This two-hour tour of the Loop with Wild Onion Walks takes you through the city’s downtown. You’ll learn about Chicago’s rich history and architecture, while figuring out your way around town.

Attractions and Events on Chicago’s River and Riverwalk 

Chicago’s Riverwalk is a 1.25-mile stretch along the Chicago River. It runs from Lake Shore Driver to Lake Street. Pedestrians can enjoy activities like kayaking, cruises, concerts, and more.

The Riverwalk is made up of six coves. Each has its own nickname, activities, and urban landscape. The Marina connects the Vietnam Veterans Memorial to the newer Riverwalk additions in the west. You can stop for a snack or rent a kayak at the Cove. If you’re looking for some shade, the River Theater is the place to be. If you want to have some fun in or near the water, you should check out the Water Plaza and the Riverbank. To learn more about river ecology, stop by the Jetty.

Some of the Riverwalk’s most popular activities and events include the following:

  • McCormick Bridgehouse & Chicago River Museum. The McCormick Bridgehouse & Chicago River Museum celebrates the Chicago River and its movable bridge. Visitors can explore the historic bridgehouse, view the massive gears, and learn about the river’s history.
  • Urban Kayaks. Urban Kayaks offer premier kayaking experiences on the Chicago River. Their trip options are based on skill level, so there’s something for everyone.
  • River Cruises. The Chicago Architecture Foundation Center offers a world-famous river cruise that both locals and tourists will enjoy. On the tour, you’ll learn about Chicago’s history and buildings. If you’re looking for a food-based river cruise, you can hop aboard a Wendella Sightseeing’s Beer & BBQ Cruise.
  • City Winery Chicago Riverwalk. City Winery on Chicago’s Riverwalk allows visitors to engage with the city in a unique way. Locally and sustainably-made products are available. In addition to wines, they have an extensive cocktail and spirits list.
  • Centennial Fountain. The Centennial Fountain creates an arc across the Chicago River for ten minutes on the hour with a 90-foot jet stream. Cool off in the fountain when it’s hot. It’s open every day May 1 – October 1, 10 am to midnight.
  • Live Music on the Riverwalk. Most days of the week there’s someone performing on the Riverwalk. Checkout the official schedule here.

Wishing You Summer Fun from Krzak Rundio Law Group

With all the activities and events happening this summer, there’s something for everyone. The personal injury lawyers at Krzak Rundio Law Group admire our city and strive to be active members in the community. Have a fantastic summer, Chicago.

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