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Best Things to Do in Chicago in June 2021

Searching for what to do in Chicago this June? Here are the best things to do in Chicago in June 2021 (from a local).

June is a popular month to visit Chicago especially this year now that most attractions are opening up, events and festivals are being allowed and restrictions are being relaxed.

For out of town visitors, please note that the weather in Chicago in June is usually warm but the weather can be unpredictable and temperatures can vary greatly from day to day or even hour to hour. Be prepared for both summer and spring temperatures as well as rain. Make sure to pack a travel umbrella, layers and check the weather right before your visit to know what to expect.

Things to Do in Chicago in June 2021


Disclosure: This article contains affiliate links. I may make a small commission if you make a booking using my links at no extra cost to you. As an Amazon Associate I earn from qualifying purchases.

Below are the best things to do in Chicago in June 2021. I suggest bookmarking this blog post as I plan to update it regularly with any new events and information.

Take an architecture river cruise

river cruise is one of the best things to do in June

Chicago has amazing architecture and the best way enjoy it is joining an architecture river cruise.

Hang Out on the Riverwalk

hicago riverwalk travel blog

The Chicago Riverwalk is one of the best spots in Chicago for boat and people watching. There are also restaurants, bars, shops and spots to sit and relax along the way. You can also hop on a water taxi here.

June is one of the best times of the year to visit Chicago

Where: Along the south bank of the Chicago River in downtown Chicago from Lake Michigan to west of Franklin Street. You can see a map of attractions on the Riverwalk here.

Hours: Open daily from 6 a.m. to 11 p.m.

Go Kayaking in the River

A fun way to explore the city is to go kayaking in the Chicago River. There are several companies that offer kayaking tours in Chicago including Urban Kayaks, Kayak Chicago and Wateriders.

Please note that you will get a little wet so bring a waterproof case for your phone and water-resistant or quick-drying clothing.

See the Bean at Millennium Park

The Bean at Millenium Park

If you have seen photos of Chicago on social media, chances are you have seen photos of Cloud Gate (also called The Bean), the famous mirrored sculpture in Millennium Park. Millennium Park is a free attraction and is a portion of the Grant Park. In addition to Cloud Gate, Millennium Park also includes the Jay Pritzker Pavilion, the Crown Fountain sculpture (more below) and Lurie Garden.

Although the Bean is very very touristy, don’t skip it. It is one of the most instagrammable places in Chicago and it is a great photo spot.

Hang out at Navy Pier

Navy Pier can be somewhat of a tourist trap but it is a must do if you are visiting Chicago with toddlers or kids. There are fun attractions at Navy Pier including a Ferris wheel, restaurants, shops, the Chicago Children’s Museum, and the Chicago Shakespeare Theater. Navy Pier is also the starting point for various sightseeing tours and cruises.

See Buckingham Fountain

Buckingham Fountain, a well known Chicago Landmark in the center of Grant Park, is one of the largest fountains in the world. The water will be turned on sometime before Memorial Day.

When the water is turned on, it produces a major water display for 20 minutes every hour with a center jet shoots water to a height of 150 feet into the air. Beginning at dusk, a spectacular light and music display accompanies the major water display. Major displays begin daily at 9:00 a.m. and continue thereafter, every hour on the hour, except for the final major display in the evening whch begins at 10:35 p.m.

Old Town Art Fair

The Old Town Art Fair in the heart of the charming Old Town Triangle Historic District is one of the best art festivals in the USA. There will be 200+ nationally acclaimed artists, an estimated 10,000 art lovers, a Garden Walk, Live Music, Food Court and Children’s Corner.

When: Saturday, June 12, 2021 from 10:00 am to 7:00 pm & Sunday, June 13, 2021 from 10:00 am to 6:00 pm. Tickets will be sold in advance and entry to the Fair will be timed for entry by hour.

Where: Old Town Triangle Historic District, 1763 N. North Park Ave, Chicago, IL 60614

Cost: Suggested Donation is $12. Click here to pre-register in advance.

Listen to Live Jazz Music at the Museum of Contemporary Art Tuesdays on the Terrace

The Museum of Contemporary Art will host Tuesdays on the Terrace this summer starting on June 1. Enjoy free music highlighting artists from Chicago’s internationally renowned jazz community at at MCA’s Anne and John Kern Terrace Garden. There are two sets of live music beginning at 5:30pm hosted by Al Carter-Bey, WDCB 90.9 FM and Richton Guy Thomas, WHPK 88.5 FM, in a safe, socially distant outdoor environment. Light refreshments and a full bar with cold beverages, wine, and cocktails are available for purchase on the upper terrace.

When: Every Tuesday, from June 1 to August 31 at 5:30 pm (in case of inclement weather the event will be canceled by 2pm). Tickets may be reserved May 14 at noon CT for MCA Members, and May 19 at noon CT for everyone else.

Where: Museum of Contemporary Art, 220 E Chicago Ave, Chicago, IL 60611

Cost: Free tickets must be reserved in advance.

Shop (or Window Shop) on the Magnificent Mile

Join the throngs of visitors and locals shopping (or window shopping) on The Magnificent Mile. The Magnificent Mile (or The Mag Mile), is an upscale section of Michigan Avenue, running from Oak Street to the Chicago River. Although some of the stores on Michigan Avenue are pricey, it is totally free to window shop. Landmarks on the Mag Mile include the 360 Observation Deck, the historic Chicago Water Tower and the Tribune Tower.

Hang out at the Beach

Most people don’t think of Chicago as a beach destination but Chicago has many beaches on Lake Michigan. The most popular beaches are located downtown (Oak Street and North Avenue) but they are also the busiest. Two of the best beaches for more of a local feel include Kathy Osterman Beach and Foster Avenue Beach which are both located north of downtown.

Explore the Lakefront

Chicago lakefront
Chicago’s Lakefront Trail is a paved path on a 18-mile-long stretch along Lake Michigan. In the summer and especially on weekends, the lakefront is packed with locals and visitors walking, running and riding bikes. Walking or biking all or part of the trail is a great way to enjoy the Chicago skyline, people watch and get some exercise. Here is a map of the trail as well as its access points.

Look for Street Art

Moose Bubblegum Bubble by Jacob Watts

Chicago is full of street art and there are always new murals popping up. One of the most famous Chicago murals is “Moose Bubblegum Bubble” (pictured above) by Jacob Watts located at 33 E. Ida B. Wells Drive. It is part of the Wabash Arts Corridor which is walking distance to Millennium Park, The Art Institute of Chicago and other tourist attractions.

Another famous mural is the Greetings From Chicago Mural at 2226 N Milwaukee Ave, in Chicago’s Logan Square neighborhood. Pilsen is another neighborhood where you can find tons of street art (and great Mexican food).

Watch a Baseball Game

wrigley field Chicago

Chicago is known for their love of their sports teams, so if you are visiting in June you might want to attend a baseball game. To those unfamiliar, historic Wrigley Field is home to one of the city’s baseball teams – the Cubs. Whether a fan of the Cubs, baseball in general or just a fun atmosphere, a day at the 100 year old ballpark is a must for locals and tourists alike. You don’t need to enjoy baseball to enjoy a Cubs game – it is fun to just soak in the atmosphere. You can find their schedule here.

Visit Local Farmers Markets in Chicago

You can find many farmers markets around Chicago in June. These markets are a great place to buy healthy, local, farm-fresh foods. Two of the best farmers markets in Chicago include the Green City Market in Lincoln Park and the Logan Square Farmers Market. You can see the list and schedule of all Chicago farmers markets here.

Lincoln Park

Lincoln Park, a large park along the lakefront, is a must see summer attraction.

Lincoln Park has a few great instagram spots including the bridge over the South Pond which has a great Chicago skyline view. Another nearby photo spot is the Peoples Gas Education Pavilion (aka the Honeycomb) in the Nature Boardwalk.

The park is home to Lincoln Park Zoo (which offers free admission), the Alfred Caldwell Lily Pool, the North Pond Nature Sanctuary, the Lincoln Park Conservatory, the Chicago History Museum and the Peggy Notebaert Nature Museum.

Walk The 606

The 606 is Chicago’s version of The Highline in NYC, an elevated trail goes through 2.7 miles of the city’s northwest side neighborhoods: Wicker Park, Bucktown, Humboldt Park, and Logan Square. It is a bit off the beaten tourist path but it great place to walk, run or bike. There are several access points so you can get off the trail to explore the various neighborhoods.

Pride in the Park

Pride in the Park is a two-day Pride and music festival celebrating Chicago Pride, hosted in historic Grant Park. Pride in the Park will expand in 2021 to two days and will include Pride Stage; the new CircuitMom Dance Floor featuring top international and local musical talents; performers and activist speakers; and a wide variety of food, drinks, merchandise vendors, and sponsor activations. Proof of vaccination or a negative COVID-19 PCR test is required.

When: Sat, Jun 26, 2021 – Sun, Jun 27, 2021

Where: Butler Field – Grant Park

Cost: Tickets start at $75.00 plus fees for general admission. See prideintheparkchicago.com/tickets/ for full prices and to purchase tickets in advance.

Eat or Drink on a Rooftop

Chicago has several rooftop bars and restaurants with amazing views of Chicago. Here are some of the best rooftops in Chicago:

Cindy’s (12 S Michigan Ave) – Restaurant and bar on the rooftop of the Chicago Athletic Association Hotel located across Millennium Park which offers panoramic instagram worthy views of Millennium Park and Lake Michigan. This is a popular spot and the wait for the elevator can be long but if you visit around the time it opens you can enjoy the great views without the crowds.

LH ON 22 (85 East Wacker Drive) – Enjoy classic cocktails and small bites from the outdoor LH terrace of LondonHouse Chicago which offers great views of the Chicago River, Lake Michigan and the Magnificent Mile.

The J. Parker (1816 N Clark St) on the rooftop of the Hotel Lincoln with great views of Lincoln Park.

Kennedy Rooftop (1551 W North Ave) on top of the Hyatt Place Wicker Park, has amazing skyline views.

As you can see there are many things to do in Chicago this June. If you are looking for more things to do in Chicago in June or the rest of the summer, see my list of the Best Things to do in Chicago in the Summer.


Planning a trip to Chicago? Check out my Chicago guides and itineraries:

savvyglobetrotter

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