Late Summer Fun In Chicago

Say it isn’t so. Summer is coming to an end. While Labor Day typically signals the beginning of fall, we actually have a few more weeks to enjoy summer temps and maybe a few sultry evenings. Fall doesn’t officially begin till Sept. 23. So look away when you see the Halloween and Christmas decorations going on display! There are still plenty of things to do in Chicago before the end of Summer,  including activities to savor in the South Loop!  Embrace the last few weeks of the season, as well as the upcoming crisp, clean days of fall with this list of things to do!

1. Get Outside and Enjoy the Beautiful Summer Weather.

Take a walk or bike ride along the lakefront. Plan a picnic and spread your blanket on a quiet spot on Museum Campus, your local park or 18th Street beach!


2. Dine Al Fresco in the South Loop

 From Sofi Restaurant on S. Dearborn and the Chicago Firehouse on S. Michigan, to The Spoke and Bird on 18th, Flo & Santos on S. Wabash, and Cafe Bionda on S. State, this neighborhood has an incredible array of great outdoor dining options.


3. Enjoy a Drink with a View

Sip a cocktail at one of the city’s amazing roof top bars or enjoy people watching at an outdoor beer garden or patio. The South Loop offers a number of options including: Reggies’ Trainwreck Rooftop Deck Bar (2109 S. State St.), VU Rooftop Bar (133 E Cermak Rd, 22nd Floor of Hilton Garden Inn Chicago McCormick Place), SX Sky Bar (Essex on the Park, 808 S. Michigan Ave.), and Cindy’s (12 S. Michigan).  Just a short walk from the South Loop check out LH Rooftop (85 E Wacker Dr.) and Cerise (Virgin Hotel 203 N. Wabash). If you prefer to be on the ground level, grab an outdoor table at the Bulldog Ale House (901 S. State St.), Kasey’s Tavern(701 S. Dearborn St.), or any of the easy going establishments in and around Printer’s Row – Flaco’s Tacos, Hax, Bar Louie, or Sociale (800 S. Clark St.).


4. Spend an Evening at your Local Park District.

Many still have free concerts, movies, etc. scheduled through September. Ping Tom Park is hosting a World Music Fest at the pagoda near 19th Place and the Chicago River on Friday, Sept. 20 from 6-8 p.m.


5. Visit a Farmer’s Market yet. 

Check out our Listing and Make the Most of it. Stock up on those amazing summer fruits and vegetables, and start thinking about the wonderful recipes for delicious autumn produce.


6. More Fun Things to Do in Chicago – Cheer on Your Favorite Professional, College, or High School Team.

Catch some rays while you watch the Cubs or the Sox. Get to a Bears game before the temperatures drop. Reminisce about the good old days when you catch a high school or college football game.

Celebrate the Chicago Bears’ 100th season! On Sept. 5, check out the NFL’s Kickoff Experience in Grant Park. This free festival includes football activities and a live concert featuring Meek Mill, Meghan Trainor, and Rapsody. Plus, former Bears players will sign autographs, Chicago restaurants will be on hand to tailgate, and an NFL Museum will have all 53 Super Bowl rings on display. Festivities will start at noon and continue up through 7 p.m.

7. Attend an Outdoor Festival in the South Loop or Near South Neighborhoods.

They’re not over yet! ThePrairie District Neighborhood Alliance will host its 13th annual family friendly Festival on Prairie Avenue on Sat., Sept. 7, from noon to 6 p.m. at 1800 S. Prairie.

Check out the Printer’s Row Art Fest on Sat., Sept. 14 – 15. Held on Dearborn Street from Polk to Harrison, the Printer’s Row Art Fest will be a buying opportunity for art lovers of all ages


8. Explore the Chicago River.

Whether you stroll along the Riverwalk, watch the boats go by as you take advantage of one of the many dining and drinking establishments, or actually get in the river and go kayaking, now’s the time to get out and enjoy these unique things to do in Chicago!  Check out their calendar of events for some great ways to celebrate summer and the beginning of fall, including Art on the MART. Their fall launch will take place on Saturday, September 21, unveiling new works by artists Charles Atlas and Petra Cortright.


9. Why Let the Tourists Have All the Fun?

 Explore things to do in Chicago at one the most beautiful times of the year. Whether it’s a walking or boating architecture tour, a double decker bus tour, or a CTA ride to a different neighborhood, discover something new about our amazing city! Take advantage of free days for Illinois residents at the Shedd Aquarium (Sept. 3, 4, 9-11, 16-18, 23-25, 30), Adler Planetarium (Sept. 5-6, 12-13, 19-20, 26-27),

Museum of Contemporary Art (every Tuesday, year round), and the Art Institute of Chicago (Illinois residents every Thursday, 5:00–8:00).


10. Check Out an Open House in the South Loop and Other Neighborhoods!

In late summer, the weather is perfect to walk around neighborhoods and see what’s available. Whether it’s a single family home, luxury townhome, or highrise condo, September is the perfect opportunity to see what’s out there. You can use my Property Search tool to explore Chicago real estate by zip code, neighborhood, specific address or building address, or available school district! And, always look for my signature OPEN HOUSE BALOON signs and common in.


Take Advantage of Things to Do in Chicago before the End of Summer – Enjoy the late Summer fun!

So, don’t let another summer day go by without taking advantage of what Chicago and the South Loop have to offer. What are your favorite things to do to celebrate the end of summer and the beginning of fall? Share your ideas with us. We’d love to hear from you.

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