We asked a number of them to weigh in with their recommendations on how to relax, recreate, make art and generally optimize the beautiful Great Lake at our doorstep. Here’s what they recommend.

Start the day with a dip. 

Dan O’Conor has been jumping off the Montrose Ledge almost daily since June 2020, first as a way to beat the pandemic blues and later, when people started asking how they could support his practice, as a way to highlight Chicago’s independent music venues that were shuttered by inviting musicians to play as he did his signature front flip into the lake.

It cured his depression. And now after six years he still jumps daily, largely from the Montrose Ledge south of Montrose Harbor. Folks who want to jump with him find him on social media or show up, usually around 7 a.m., for the plunge.

He’s still unsure about the benefits of cold water plunging that has become so trendy in wellness circles. “For me it’s more of a mental cleansing, to start the day fresh,” he says.

Though he has been known to jump from the Chess Pavilion between North Avenue and Oak Street beaches as well as in front the Adler Planetarium, the Ledge is still his favorite.

“It has an amazing view of the city,” says O’Conor. “You’re jumping into the skyline.”

Leave screens behind. 

As the director of programming for the Printers Row Lit Fest, Amy Danzer reads a lot and flips through, she estimates, at least a hundred books a year. Sometimes that happens on the lakefront — her favorite places to read along Lake Michigan include the Northwestern University campus in Evanston, Montrose Beach and the tucked-away Leone Beach Park where Touhy Avenue meets the lake.

“It’s a different lakefront from different parts of the city,” says Danzer.

But for her reading by the lake isn’t just about escaping into a story. It’s about being in real life. Which means pausing to listen to the water and other people’s conversations,  to people watch and “to get a respite from all the screens and phones and laptops,” she says. “It’s so important to be out in the world and to connect with nature.”

Play with friends on the sand. 

The lakefront is a recreational magnet from wall climbing at Steelworkers Park to open-water swimming at Promontory Point, fishing at Northerly Island and kicking a soccer ball around the Foster Turf Fields.

Chicago Sport & Social organizes leagues around 15 sports, many on the lakefront including its most popular program: beach volleyball.

Most kids learn in childhood that an essential part of play is making friends, and that’s a key selling point for Chicago Sport & Social. Teams of two, four and six flood the sand courts at North Avenue Beach, though the public can also rent the courts outside of the league schedule. Teams of two demand greater skills to cover the court than larger teams. For the bigger groups, competition is a way to get together and get more people involved. 

“At events, they get together with friends and coworkers and meet new people,” says Chris Hastings, the president of Chicago Sport & Social. “About 95 percent are co-ed so that creates a very social environment.”

Share the path. 

The Chicago Area Runners Association typically has over 20,000 registrations a year at its races and events. And groups of runners within the group formally train 47 of 48 weeks a year, typically taking a break after the Chicago Marathon. On Saturdays, groups set out from five locations on the lake from Hyde Park to Montrose, broken down by pace.

Tim Bradley, executive director of the Chicago Area Runners Association, knows every bottleneck on the 18-mile lakefront path and warns people away from the Chess Pavilion near Oak Street Beach and the tennis courts at Waveland.

“We spend a lot of time on path etiquette,” says Bradley, noting that group training leaders school runners not to run more than two abreast, to get off the path before stopping for water, to always pass on the left and let someone know they’re coming — as in “Passing on the left!” — and never to “swarm” a walker or slow runner by passing on both sides. 

“The section between Fullerton to Wilson is my go-to,” says Bradley. “If you’re looking for a quieter section, I would start at Montrose or Wilson and go south then back north.”

Finish with sprints up Cricket Hill for the novelty of elevation along the lake.

See the lake like an artist. 

Nature photographer and Chicago native Lincoln Schatz has been photographing Lake Michigan since September 2015. What started as a 20-day experiment to see what he could capture that didn’t feel nostalgic or overdone turned into a practice as fall weather worsened. 

“As the winds got fierce, I found myself increasingly drawn to it,” says Schatz. “I think I was drawn to this feeling of being alive.”

Working with a medium format camera, he splits the frame, giving equal attention to sky and lake.

For folks who want to gain a similar perspective, Schatz recommends places without a break wall that provides a wide perspective. His favorites are the “scorpion tail” shaped jetties at Montrose or North Avenue Beach.

The lakefront, he says, is a “wall between the city and the wilderness. There’s not that many places you can move fluidly between the two.”

Turn your commute into the best part of your day. 

You might have to dodge traffic to get there, but once you hit the 18-mile recreational path that follows Lake Michigan, it’s a scenic, car-free shot to downtown used by bike commuters north and south. 

“I use the lakefront as a means of transportation,” said Brian Gladstein, the executive director of Friends of the Parks, a nonprofit advocate for green spaces in Chicago, who bikes 11 miles along the lakefront several times a week to reach downtown. 

“We see the interest,” added, pointing to the popularity of Bike the Drive, the annual event each September that closes DuSable Lakeshore Drive to cars. “It gets people thinking about alternative transportation.” 

Make sunrise (or sunset) a daily ritual. 

Hyde Park resident Mike Rouse, a board member with SitStayRead, a nonprofit that uses reading assistance dogs to encourage literacy skills in Chicago children, likes to walk his Jack Russell Terrier-beagle mix Pumpkin on the lakefront around 41st Street. 

“We do the concrete part of the lakefront because Pumpkin can be snooty and doesn’t like the sand so much,” says Rouse. 

What both enjoy there is the daybreak panorama.

“One of my favorite things is to get out in the morning and watching the sunrise,” says Rouse. “There’s a great view of the city and the sun coming over the lake. It’s top tier.”