[Skip to Content]

Must-do activities before summer ends


Posted  54 days ago  in  Trending, Things to Do

7 MIN READ – Summers are fleeting in Chicago, only to give way to our brutal winters, so get out and enjoy the weather while it lasts. Do everything on your summer bucket list, like having a picnic, going on a bike ride, swimming, hanging out on a boat, and visiting the Chicago Loop’s best attractions while it's still warm.


Come together for Sundays on State, a free interactive block party in the Chicago Loop. On select Sundays this summer, traffic will be closed from Lake to Madison to make way for a street festival like you’ve never seen before. Get involved in this immersive experience connecting people from every Chicago neighborhood. Experience art, culture, active recreation, shopping, food, drinks, and local attractions. Be a part of everyone’s neighborhood, the Chicago Loop! The event is free and open to the public, but those register to attend here are automatically entered to win a $1000 Loop staycation package. #SundaysOnState

Sundays on State credit Chicago Loop Alliance


Wander off the beaten path and through the Loop’s alleys on a self-guided tour of downtown’s street art. The Loop Mural Walk is a free experience available now through September 6. Featuring 21 murals by international household names as well as emerging artists, the Loop Mural Walk highlights a side of the Chicago Loop you have never seen before.  While a few of the featured murals are prominent pieces you may already know, many others are more obscure, often left behind after Chicago Loop Alliance’s popular ACTIVATE alley events. Share your adventure on social media using #LoopMuralWalk for a chance to win a $100 gift card to The Dearborn.

CLA LMW Website 1920x1080 TitleLogo


Festivals are back! Don’t miss the Chicago in Tune Festival this summer. This citywide festival is a tribute to Chicago’s diverse and illustrious music scene.  And you can also attend the Grant Park Music Festival, featuring free classical concerts at the Jay Pritzker Pavilion in Millennium Park.  If you’ve missed the sound of music reverberating off of downtown buildings as you sit on a blanket with a glass of wine, come out before summer ends.

Grant Park Music Festival v2


Skydeck Chicago is the perfect summer activity, as it provides a can’t miss, one-stop attraction to discover and see all that the city of Chicago offers from an incomparable vantage point. The recently renovated Skydeck encompasses the attraction’s lower level, delivering an interactive experience that celebrates the unique personality, history, neighborhoods and sites of Chicago. The lower-level museum is further complemented by a visit to the internationally recognized observation deck to take in the city from 103 floors up and step out on The Ledge; the four thrilling glass floor balconies extending from the Tower. There is no better view of the city than the view from The Ledge on a sunny summer’s day.

Skydeck Chicago


The Loop is home to some of the best museums in the country, as well as smaller, niche museums you’ll only find here. Go to the Museum of Illusions where you can truly experience the impossible. Illusions allow us to see things differently, and they expose a lot about how the brain interprets reality. Visit the Museum of Illusions Chicago where nothing is quite as it seems! Or wander through the Art Institute and see historical pieces as well as contemporary works in the modern wing.  Experience the power and elegance of the Obama portraits. Featuring a Kehinde Wiley painting of President Barack Obama and an Amy Sherald portrait of former First Lady Michelle Obama, this exhibit is not to be missed. Visit now through August 15. Find out about more Loop museums to check out here.

Obama portraits aic


While it's nice outside, walk throughout the Loop and shop. Explore State Street and beyond with plenty of great retail options. Go to Macy’s if you’re considering a new look or want to refresh. Macy’s personal stylists provide free consultations for all your style, beauty, and home selections both online or in-store. Book your free appointment today. And while you’re at Macy’s, be sure to stop by the Walnut Room. Enjoy brunch at the first restaurant opened in a department store. The space is exquisite with beautiful Circassian walnut paneling and Austrian crystal chandeliers. This elegant and comfortable dining experience offers delicious meals, cocktails, and a variety of wines. Definitely try Mrs. Hering’s chicken pot pie, which has been a favorite on the menu since the 1880s. Make reservations for the Walnut Room here.



Soak up the sun and appreciate outdoor patios and rooftops before the summer ends. Take your dining experience to a whole new level at one of the Chicago Loop’s finest rooftop bars, offering some of the best views in the city. Consider ROOF on theWit for a modern, Mediterranean ambience; Cindy’s for a stellar view of Millennium Park; LondonHouse Rooftop Lounge for the height of luxury; IO Godfrey Rooftop Lounge for hip, chic vibes; Raised for an incredible view of the Chicago River and skyline; or AIRE for cozy fire pits and 360-degree views.

Cindy's Rooftop

Or stay down-to-earth with sunny patios, like Beatnik on the River. This bohemian venue is an exotic escape with food from around the world and eccentric cocktails. The riverfront patio is decorated with Indonesian daybeds, Moroccan lanterns, and plush greenery. If you’d like to try another Riverwalk spot, check out City Winery for a classy outdoor patio experience just steps above the Chicago River. Feel as if you're floating when you dine on their exclusive patio. Or for views of “Chicago’s front yard,” try Grant Park Bistro, a contemporary American eatery with an exclusive view of Grant Park. Sip cocktails on the bistro’s large outdoor patio, located right off of Michigan Avenue. See what’s on the lunch menu here.

Beatnik On The River 2019 Francis Son Top Pics 05


Take a stroll or a bike ride (if it’s not too crowded!), read a book, or simple sit and enjoy the views along the Chicago Riverwalk. Feel as if you're floating as you take in the cityscape along the water. This pathway rests along the bank of the Chicago River for an exclusive view of the Loop’s world-class architecture, with a variety of restaurants, bars, and attractions along the way.

Chicago Riverwalk 2 v2


Add a Shoreline Sightseeing Architecture River Tour to your summer bucket list to experience Chicago’s famous landmarks along the beautiful Chicago River. Shoreline’s expert and entertaining guides highlight more than 40 of the city’s best-known buildings, both historical and 21st Century! Depart from Michigan Avenue Bridge or Navy Pier for your 75-minute tour. Don’t forget your camera to capture close-up views and great photo ops on your Shoreline Architecture Tour. Looking for a special evening activity? Check out Shoreline’s Fireworks Tours every Wednesday and Saturday through September 4. Visit here for tickets or call 312-222-9328.

boat tour

For a beachier vibe, rent a private boat for 6-36 people from Island Party Hut: Tiki Bar and Grill. Where you go is up to you—cruise the lakefront, party down the Chicago River, or anchor to slip down the waterslides and go swimming. Liven up your party with live music and games. They offer bocce ball, bag games, Jenga, and the Bimini Island Ring game. Enjoy tropical drinks at this tiki bar on the Riverwalk.  


Take advantage of the weather and spend some time at Maggie Daley Park. Keep yourself and the kids busy all day with activities like mini golf, wall climbing, and scooter and rollerblade rentals. Also treat yourself to hot dogs and ice cream for the ultimate day out.

Scooter Photo Courtesy of Maggie Daley Park


Cool off with a swim, play volleyball or frisbee, listen to music, have a barbeque with friends, or lay out in the sun and relax with your toes in the sand. Check out Ohio Street Beach just north of the Loop, or 12th Street Beach a little to the south. After some fun in the sun and sand, mosey along the Lakefront Trail to the Loop proper for some gorgeous views of the skyline and Millennium Park.


Enjoy the weather and get a workout while you’re at it. Enjoy the Loop’s protected bike lanes and the Lakefront Trail for a safe, easy breezy ride. If you don’t own a bike, rent a Divvy bike for easy access to the city. Find more tips for riding a bicycle in the city here.



Pack some food and refreshments to enjoy on the lake or Millennium Park. Bring some music and relax all day. Find a list of the best downtown picnic spots here.


There’s way too much to do and see in the Chicago Loop for just one day, so stay the weekend or plan a staycation at one of the Loop’s hotels. Find a room with exclusive access to Chicago culture, food, attractions, and shopping. Hotels offer a luxurious stay or an affordable one. A unique stay or a classic one. A lavish stay or a practical one. Choose the hotel that’s right for you. The Palmer House is one of Chicago's most luxurious and iconic hotels, featuring a new indoor pool. Book the Palmer House here. Hilton Chicago, a historic hotel, is the ideal stay for those looking for great lake and Grant Park views, conveniently situated on Michigan Avenue. Book the Hilton Chicago here. In the heart of Chicago’s theater, arts, and shopping district, theWit Hotel boldly stands as a tribute to creativity and expression with stunning views. A newly renovated rooftop bar, ROOF on theWit and ballroom event spaces serve to entertain you and host events. Book theWit here. Find more hotel options here.

Huber Presidential Suite Living Room view 2302