Chicago’s lakefront is iconic. Conjure any image of the city, and it’ll likely include views of densely packed skyscrapers along Lake Michigan. Twenty miles long, Chicago’s Lake Shore Drive (LSD) is not only gorgeously scenic, but it also offers innumerable activities and places to explore, making it perfect for a micro-road trip.
During the six years I lived in the city, I chose neighborhoods along the lake, first in Hyde Park on the South Side and then Uptown on the North Side. As a runner, biker, and lake-loving Chicagoan, I spent a great deal of time on the lake, so I’m excited to share a few itineraries that’ll take you on curated adventures from north to south.
For the northern portion of each itinerary, I chose activities in the Montrose Beach area. The downtown activities are at Navy Pier or Museum Campus. And the southern portion is mostly within Jackson Park, except for Steelworkers Park. So if you’d like to mix and match itineraries, you should be able to leave the car at each stop and explore further. Also, hang around until the end for some need-to-know parking tips.
Otherwise, pack a lunch along with plenty of snacks, and tell the kiddos to keep their eyes on that blue gem as you drive from activity to activity — preferably cranking Lake Shore Drive with windows down to enjoy the breeze off the lake.
Writer Chelsey Stone on the Centennial Wheel
Itinerary #1: For the Adventure-Seekers
This itinerary will have you by the lake all day but spending more time in the air than in the water.
North
Want to learn the flying trapeze? Take a class with Chicago’s only flying trapeze rig at Get a Trapeze. These arial art classes will have you flying through the air (with a net below to catch you just in case), as you enjoy views of Lake Michigan.
Express Flying Trapeze classes are 90 to 120 minutes for $70 to 75. You can also take advantage of the 60-minute trampoline and aerial straps classes at $35 each. Ages 6 and up are welcome.
Downtown
Did you know the Ferris Wheel was invented in Chicago for the 1893 World’s Fair? Lead architect Daniel Burnham — whose 1909 Plan of Chicago is the very reason Chicago’s lakefront is the public park it is today — put out a call for an iconic structure that would rival Paris’ Eiffel Tower (created four years earlier for their own World’s Fair). George Washington Gale Ferris Jr. answered that call with the “Chicago Wheel,” an enormous structure that rotated 36 gondolas around a center axle, each one carrying 60 people. The attraction was a massive hit.
Fast-forward to today’s Centennial Wheel at Navy Pier, a celebration of that very first “Chicago Wheel,” and you’ll be able to soar nearly 200 feet in spacious climate-controlled gondolas with incredible views of downtown.
Tickets are $20 for adults and $18 for children ages 3 to 11.
South
Hog Butcher for the World,
Tool Maker, Stacker of Wheat,
Player with Railroads and the Nation’s Freight Handler;
These are the opening lines to Carl Sandburg’s poem, “Chicago.” When he wrote it in 1914, Chicago was already cemented as an industrial powerhouse from the decades that came before. Much of that legacy still lingers today, but it’s steadily adapting to offer more open spaces and public parks — like Steelworkers Park.
Originally part of the U.S. Steel Complex known as South Works, you can now walk on paths along Lake Michigan and among looming artifacts on the grass, like massive six-ton blast furnace bells. But the most adventurous part of this park is the climbing wall: Historic 30-foot ore walls have been converted into a climbing and bouldering wall.
If you don’t happen to have your own climbing equipment, spot your kiddos as they scale a few feet or time your visit to one of the Chicago Park District’s free or moderately priced ($10 to 20) community climbs and other events. The Kids Learn to Climb programs are reserved for those ages 11 to 15.
The climbing wall in Steelworkers Park
Itinerary #2: For the Nature Lovers
Speaking of the shift from industry to nature, this next itinerary includes some of the loveliest natural areas along the lake acting as sanctuaries — to wildlife and urbanite alike.
North
If flying like a bird isn’t your thing, you can watch natural aviators at Montrose Point Bird Sanctuary or, as locals refer to it, Magic Hedge. Bring your binoculars and help the kiddos spot any of the 300 bird species recorded here. Each year this natural area attracts tens of thousands of migratory birds seeking rest, food, and shelter. As you wander the outer paths, look south through the tall grasses and you’ll spot Chicago’s skyline in the distance.
In the summer, you may get to see the piping plover pair who come to the nearby beach to nest. Chicagoans love these birds; locals have fiercely protected them since their arrival June 2019 and named the parents, as well as their chicks each year. I’m also aware of at least one person who now has a piping plover tattoo.
Downtown
Millions of visitors to Chicago’s Museum Campus each year seldom realize that a large nature area sits just south of the Adler Planetarium. Northerly Island (which is now a peninsula) was first conceived of in Daniel Burnham’s 1909 Plan — yes, the same architect of Chicago’s World’s Fair and the same plan that gave Chicago it’s lakefront. It eventually became a downtown airport, which opened in 1948.
Now comes the juicy, only-in-Chicago part: For years after its lease was up, the use as an airport was renewed with the Park District, but then-Mayor Richard M. Daley had wanted to turn it into a park. He had once padlocked the gates in 1996, which led to a feud with the governor over the airport. Then one night, in 2003, Mayor Daley ordered the runway be destroyed by bulldozers that carved a giant X in the pavement, rendering it unusable as an airport and finally getting his way.
Today, the island is a quiet urban oasis. The park features prairie and savanna landscapes; a five-acre pond; and paths for admiring the wildlife, lake, and a unique view of Chicago’s skyline.
South
Plans for Jackson Park began in the 1860s but wouldn’t pick up in earnest until 1890, when Chicago was selected to host the 1893 World’s Fair. Jackson Park was designed by Frank Law Olmsted, the first to use “landscape architecture” to describe his work and the designer of New York City’s Central Park. His theme was water, tying in Lake Michigan’s proximity to a series of basins and lagoons.
Between the west and east lagoons lies the Garden of the Phoenix. During the World’s Fair, the Japanese Government built the Ho-o-den, or Phoenix Temple, which remained as a gift to Chicago at the fair’s end. Restored and revitalized many times since then, you can enter the Shinto gate to see the pavilion and cross the moon bridge. Be sure to come back in the spring for the six to 10 days when the cherry blossom trees are in peak bloom.
The feelings peace and calm here are perfect to end your day after exploring some of Chicago’s best natural areas on Lake Shore Drive.
Northerly Island
Itinerary #3: When Your Pup is Along for the Ride
If those puppy dog eyes are breaking your heart as you pack up the kids and car for your LSD road trip, fear not! I even have an itinerary suited for the furriest member of the family (and everyone else, of course). As a frequent dog sitter to many a Chicagoan friend’s dog, I can tell you Chicago is a great city for dogs.
North
Montrose Dog Beach was Chicago’s first legal off-leash dog beach, offering a place for dogs to play and swim. Just keep in mind that all dogs — even visitors — must have a Dog Friendly Area tag to use the beach, so be sure to plan ahead. But the effort is well worth it as you watch your dog splash about the water, swim out to collect their ball, and make new friends.
And don’t worry, there’s a self-service dog-washing station, so you can clean up before bringing your furry friend back in the car for the next stop.
Downtown
Architectural cruises are popular in Chicago, but did you know there’s a cruise that welcomes dogs too?
Get out on the waters of Lake Michigan and the Chicago River and enjoy the 90-minute, pet friendly Canine Cruise. The tour includes a narration of Chicago history, complete with dog-friendly highlights. The cruise provides water bowls for thirsty pups and a full-service bar for thirsty humans.
Tickets are $45 for adults and $20 for children ages 4 to 12. Dogs must remain on their leash.
South
Jackson Bark in Jackson Park (get it?) is for the adventurous dog — the one who loves leaping through tires, climbing V-shaped planks, and wiggling through tubes. Various road signs, construction equipment, and even police caution signs have been repurposed for your dog’s delight. This dog park was featured in USA Today’s 10 Best in 2025 (runner up) and 2024 (#5).
With this final opportunity to get out any energy they have left (and how much could that really be at this point?), you’ll have one very tired but satisfied pup on the car ride home — grateful for the chance to spend the entire day with their family.
Lakefront Path near Navy Pier
Parking Advice
Keep in mind as I offer parking advice that I don’t own a car and traveled Chicago by bus, train, bike, and foot. Still, I have some tips based on the inevitable ridesharing, driving with friends, or just experience in these neighborhoods.
Montrose Beach is a popular weekend destination but will get quieter in the fall. There are a lot of parking spots but most (if not all) are now metered. You can try your luck in the neighborhoods west of LSD. I lived near W. Castlewood Terrace, which is a historic neighborhood of single-family homes with massive driveways and garages. Therefore, you can usually find parking here, especially farther down the street (not a through street). Just bear in mind it’s a bit of walk (but it’s a lovely one as you make your way through Lincoln Park).
The downtown activities are, well, downtown, which is chaotic and expensive in any major city. Navy Pier has two garages with 1,500 spots, so you shouldn’t have an issue securing one, but it will cost $35 for up to two hours alone. There are discounted “remote alternate parking garages” at Grand Plaza Park and elsewhere for $15. Navy Pier guest services said this is a flat rate for the day at those garages. Keep in mind, this option requires validation from the Navy Pier Guest Services Desk.
Northerly Island also has a small metered parking lot.
To the south, Jackson Park similar to Montrose Beach offers neighborhood street parking and metered lots. But I always found Jackson Park to be relatively quieter and don’t anticipate any issue finding parking, so long as it’s not a holiday weekend.
Embrace Chicago’s Lakefront Adventures
I hope you’re inspired to take advantage of the incredible lakefront that Chicago’s visionary leaders left us. It may not be an epic road trip in terms of distance, but it will certainly be an epic road trip in terms of memories made.
Photos by Chelsey Stone
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About the Author: Chelsey Stone is a freelance travel and health & fitness writer who’s written for National Geographic, Runner’s World, and Bicycling. She lives in the D.C. area and loves to use books and running as a means to explore the city and anywhere she travels to.
You can find her at chelseygrassfield.com or on Instagram @chelseygrassfield.
