Chicago Summer Bucketlist

August 2, 2021 | By Lauren Bozarth
Reading Time: 5 Minutes

There truly is nothing like a Chicago summer. From the exciting attractions to the fantastic outdoor space, you can always find something to do during this time of the year.

Whether you’re new to the Windy City or have lived here for a long time, here are some fun things to do during your Chicago summer.

Great Restaurants with Equally Great Outdoor Spaces

Spending a meal outside with friends and families is an everyday summertime activity. Chicago offers plenty of killer restaurants with fantastic outdoor dining options and breathtaking views.

Be sure to add these restaurants to your summer bucket list:

  • London House: London House is home to Chicago’s only 3-level rooftop venue. It has stunning views of the city with dining indoors and out. Level 22 features the outdoor terrace with views of The Chicago River, Magnificient Mile, and Lake Michigan. Enjoy small bites and great cocktails at this one-of-a-kind space. 
  • Raised: Located in the Renaissance Chicago Downtown Hotel, this garden lounge welcomes guests to enjoy the indoor/outdoor bar and open roof deck. It features private outdoor spaces that overlook Chicago’s River. They serve small plates, creative cocktails and have an extensive list of craft beer. 
  • Cindy’s: Known as the “jewel in the crown” of The Chicago Athletic Association Hotel, Cindy’s is an open-air terrace with 360-degree views of the city. Enjoy classic drinks and delicious food while taking in the views of the Art Institute, Lake Michigan, and Millennium Park. 
  • The Godfrey: On the fourth floor of The Godfrey, you will find an urban rooftop oasis. With uninterrupted views, a fire pit, gorgeous water elements, and a retractable roof, The Godfrey in River North has unique amenities unlike any other venue in the city.

After a meal in the city, consider finding a fun activity!

Free Summertime Activities

Lincoln Park Zoo

If you’re on a budget but don’t want that to keep you from your summer bucket list, take advantage of Chicago’s free activities.

  • Lincoln Park Zoo: If you’re a fan of wildlife, take a trip to this impressive zoo at no cost. Along with all your favorite animals, you can also admire the gorgeous Chicago skyline in the backdrop.
  • Chicago Lakefront Trail: Walk, run, bike or rollerblade this scenic 18-mile paved path that follows the Lake Michigan shoreline on the city’s eastern edge trail. It’s a great way to get your body moving and soak up the Chicago scenery while doing so.
  • The Beach: Visit one of the Chicago beaches located right along Lake Michigan. Spend the afternoon at Oak Street Beach if you’re looking for a beach near downtown, or take your pup to Montrose Beach for a  great pet-friendly option. Be sure to look into which beaches allow swimming if you feel like taking a dip.
  • Chicago Riverwalk: Stroll along the infamous Riverwalk for a great way to admire all of the beautiful Chicago architecture. Along the way, you’ll find plenty of dining and drinking options.
  • Milleneum Park: This popular spot is worth a visit if you haven’t yet been. Here you will find the “Bean,” one of Chicago’s most iconic public sculptures, along with plenty of other free activities and events. You can take a walk through Lurie Garden, rock climb at Maggie Daley Park, or enjoy a show at the Great Lawn.
  • Hyde Park Art Center: Stop by the oldest alternative exhibition space in Chicago at no cost. The art center is a hub for contemporary arts and features incredible artists and creative works.
  • Garfield Park Conservatory: Venture a few miles out of downtown Chicago to find one of the nation’s largest and most stunning botanical conservatories. This 184-acre park boasts a swimming pool, fishing lagoon, athletic fields, tennis courts and more.
  • Summer Fireworks: Every Wednesday and Saturday night from Memorial Day weekend through Labor Day weekend, Navy Pier hosts a dazzling free fireworks display. Sit along the beach or find a nearby rooftop to enjoy the show!

Summer Art Festivals

If you love music and art festivals, you’ll be glad to know Chicago hosts plenty during the summer. While some big events have passed this summer, you can always add these festivals to next summer’s bucket list.

Here are a few popular events worth considering:

  • Bucktown Arts Fest: Every year, the Bucktown neighborhood hosts its annual arts festival on August 24th and 25th across from Holstein Park. For over 30 years, this festival has showcased hundreds of artists who work in oil, watercolor, photography, textile, sculpture, jewelry, and more. 
  • Renegade Craft Fair:  On September 8th and 9th, Wicker Park will host Renegade Chicago’s largest event of the year right along Division Street. Here you can find over 400 artists and designers from throughout the country. The fair will also feature local DJs, workshops, art installations, food trucks, nonprofits, adult beverages, and more.
  • Wicker Park Fest: Over the summer, Wicker Park hosts its own annual fest for residents, neighbors, and visitors alike. The five-day festival occurs at the end of July and reflects the neighborhood’s rich musical heritage, vibrant nightlife, and acclaimed restaurants. Attendees can also find local artisans and arts and crafts. While this year’s fest may have passed, it’s not too early to start planning for next year.
  • Lollapalooza: Towards the end of July, Grant Parks hosts this iconic four-day event featuring some of the world’s best music artists. During the show, attendees can also enjoy some of the best views of the Chicago skyline and shores of Lake Michigan. Next year’s Lollapalooza takes place July 29th through August 1st.

Spend Time in Lincoln Park

North Pond Restaurant

As the second most visited public park in the entire United States and the largest park in Chicago, Lincoln Park is a hot spot in the summer.

During the sunny months, residents and guests alike take full advantage of this sprawling green space situated just north of the Loop right along Lake Michigan.

Boasting nearly 1,200 acres, this park offers plenty of activities. You can enjoy a scenic picnic or go for a bike ride along the trails. Or, if you’re looking for more of an activity, you can visit the zoo, conservatory, museum, driving range or catch a show at the Theatre on the Lake.

You can also find a couple of restaurants right in the park, including North Pond and Barcino’s Italian Grill.

Nearby the park in the Lincoln Park neighborhood, you can find a handful of great dining options and fun options. Those who enjoy shopping can also browse all of the eclectic boutiques throughout the area.

Make this Chicago summer your best one yet! Be sure to mark your calendar with your favorite events and activities.

Looking to make the move to Chicago? Get in touch with one of our experienced brokers today! We’d be happy to show you around the city.

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