— By Chelsey Stone —
Chicago’s lakefront is iconic. Conjure any picture of the town, and it’ll seemingly embody views of densely packed skyscrapers alongside Lake Michigan. Twenty miles lengthy, Chicago’s Lake Shore Drive (LSD) shouldn’t be solely gorgeously scenic, however it additionally provides innumerable actions and locations to discover, making it good for a micro-road journey.
Throughout the six years I lived within the metropolis, I selected neighborhoods alongside the lake, first in Hyde Park on the South Facet after which Uptown on the North Facet. As a runner, biker, and lake-loving Chicagoan, I spent an excessive amount of time on the lake, so I’m excited to share a number of itineraries that’ll take you on curated adventures from north to south.
For the northern portion of every itinerary, I selected actions within the Montrose Seashore space. The downtown actions are at Navy Pier or Museum Campus. And the southern portion is generally inside Jackson Park, apart from Steelworkers Park. So for those who’d like to combine and match itineraries, it is best to be capable of go away the automotive at every cease and discover additional. Additionally, hold round till the top for some need-to-know parking suggestions.
In any other case, pack a lunch together with loads of snacks, and inform the kiddos to maintain their eyes on that blue gem as you drive from exercise to exercise — ideally cranking Lake Shore Drive with home windows right down to benefit from the breeze off the lake.
Itinerary #1: For the Journey-Seekers
This itinerary can have you by the lake all day however spending extra time within the air than within the water.
North
Need to study the flying trapeze? Take a category with Chicago’s solely flying trapeze rig at Get a Trapeze. These arial artwork courses can have you flying via the air (with a web under to catch you simply in case), as you get pleasure from views of Lake Michigan.
Categorical Flying Trapeze courses are 90 to 120 minutes for $70 to 75. You may as well benefit from the 60-minute trampoline and aerial straps courses at $35 every. Ages 6 and up are welcome.
Downtown
Do you know the Ferris Wheel was invented in Chicago for the 1893 World’s Truthful? Lead architect Daniel Burnham — whose 1909 Plan of Chicago is the very motive Chicago’s lakefront is the general public park it’s at the moment — put out a name for an iconic construction that may rival Paris’ Eiffel Tower (created 4 years earlier for their very own World’s Truthful). George Washington Gale Ferris Jr. answered that decision with the “Chicago Wheel,” an infinite construction that rotated 36 gondolas round a middle axle, each carrying 60 folks. The attraction was an enormous hit.
Quick-forward to at the moment’s Centennial Wheel at Navy Pier, a celebration of that very first “Chicago Wheel,” and also you’ll be capable of soar practically 200 toes in spacious climate-controlled gondolas with unbelievable views of downtown.
Tickets are $20 for adults and $18 for kids ages 3 to 11.
South
Hog Butcher for the World,
Instrument Maker, Stacker of Wheat,
Participant with Railroads and the Nation’s Freight Handler;
These are the opening strains to Carl Sandburg’s poem, “Chicago.” When he wrote it in 1914, Chicago was already cemented as an industrial powerhouse from the many years that got here earlier than. A lot of that legacy nonetheless lingers at the moment, however it’s steadily adapting to supply extra open areas and public parks — like Steelworkers Park.
Initially a part of the U.S. Metal Advanced often called South Works, now you can stroll on paths alongside Lake Michigan and amongst looming artifacts on the grass, like huge six-ton blast furnace bells. However probably the most adventurous a part of this park is the climbing wall: Historic 30-foot ore partitions have been transformed right into a climbing and bouldering wall.
Should you don’t occur to have your individual climbing gear, spot your kiddos as they scale a number of toes or time your go to to one of many Chicago Park District’s free or reasonably priced ($10 to twenty) neighborhood climbs and different occasions. The Youngsters Be taught to Climb applications are reserved for these ages 11 to fifteen.
The climbing wall in Steelworkers Park
Itinerary #2: For the Nature Lovers
Talking of the shift from business to nature, this subsequent itinerary consists of a number of the loveliest pure areas alongside the lake appearing as sanctuaries — to wildlife and urbanite alike.
North
If flying like a hen isn’t your factor, you may watch pure aviators at Montrose Level Fowl Sanctuary or, as locals discuss with it, Magic Hedge. Convey your binoculars and assist the kiddos spot any of the 300 hen species recorded right here. Annually this pure space attracts tens of 1000’s of migratory birds looking for relaxation, meals, and shelter. As you wander the outer paths, look south via the tall grasses and also you’ll spot Chicago’s skyline within the distance.
In the summertime, it’s possible you’ll get to see the piping plover pair who come to the close by seaside to nest. Chicagoans love these birds; locals have fiercely protected them since their arrival June 2019 and named the dad and mom, in addition to their chicks every year. I’m additionally conscious of at the least one one that now has a piping plover tattoo.
Downtown
Thousands and thousands of holiday makers to Chicago’s Museum Campus every year seldom understand that a big nature space sits simply south of the Adler Planetarium. Northerly Island (which is now a peninsula) was first conceived of in Daniel Burnham’s 1909 Plan — sure, the identical architect of Chicago’s World’s Truthful and the identical plan that gave Chicago it’s lakefront. It will definitely turned a downtown airport, which opened in 1948.
Now comes the juicy, only-in-Chicago half: For years after its lease was up, the use as an airport was renewed with the Park District, however then-Mayor Richard M. Daley had wished to show it right into a park. He had as soon as padlocked the gates in 1996, which led to a feud with the governor over the airport. Then one evening, in 2003, Mayor Daley ordered the runway be destroyed by bulldozers that carved an enormous X within the pavement, rendering it unusable as an airport and at last getting his manner.
As we speak, the island is a quiet city oasis. The park options prairie and savanna landscapes; a five-acre pond; and paths for admiring the wildlife, lake, and a singular view of Chicago’s skyline.
South
Plans for Jackson Park started within the 1860s however wouldn’t decide up in earnest till 1890, when Chicago was chosen to host the 1893 World’s Truthful. Jackson Park was designed by Frank Regulation Olmsted, the primary to make use of “panorama structure” to explain his work and the designer of New York Metropolis’s Central Park. His theme was water, tying in Lake Michigan’s proximity to a collection of basins and lagoons.
Between the west and east lagoons lies the Backyard of the Phoenix. Throughout the World’s Truthful, the Japanese Authorities constructed the Ho-o-den, or Phoenix Temple, which remained as a present to Chicago on the honest’s finish. Restored and revitalized many occasions since then, you may enter the Shinto gate to see the pavilion and cross the moon bridge. Make sure to come again within the spring for the six to 10 days when the cherry blossom bushes are in peak bloom.
The emotions peace and calm listed below are good to finish your day after exploring a few of Chicago’s greatest pure areas on Lake Shore Drive.
Northerly Island
Itinerary #3: When Your Pup is Alongside for the Experience
If these pet canine eyes are breaking your coronary heart as you pack up the youngsters and automotive to your LSD highway journey, worry not! I even have an itinerary fitted to the furriest member of the household (and everybody else, in fact). As a frequent canine sitter to many a Chicagoan good friend’s canine, I can let you know Chicago is a superb metropolis for canine.
North
Montrose Canine Seashore was Chicago’s first authorized off-leash canine seaside, providing a spot for canine to play and swim. Simply remember that all canine — even guests — should have a Canine Pleasant Space tag to make use of the seaside, so remember to plan forward. However the effort is nicely value it as you watch your canine splash in regards to the water, swim out to gather their ball, and make new associates.
And don’t fear, there’s a self-service dog-washing station, so you may clear up earlier than bringing your furry good friend again within the automotive for the following cease.
Downtown
Architectural cruises are well-liked in Chicago, however do you know there’s a cruise that welcomes canine too?
Get out on the waters of Lake Michigan and the Chicago River and benefit from the 90-minute, pet pleasant Canine Cruise. The tour features a narration of Chicago historical past, full with dog-friendly highlights. The cruise offers water bowls for thirsty pups and a full-service bar for thirsty people.
Tickets are $45 for adults and $20 for kids ages 4 to 12. Canine should stay on their leash.
South
Jackson Bark in Jackson Park (get it?) is for the adventurous canine — the one who loves leaping via tires, climbing V-shaped planks, and wiggling via tubes. Numerous highway indicators, building gear, and even police warning indicators have been repurposed to your canine’s delight. This canine park was featured in USA As we speak’s 10 Greatest in 2025 (runner up) and 2024 (#5).
With this remaining alternative to get out any power they’ve left (and the way a lot may that basically be at this level?), you’ll have one very drained however happy pup on the automotive trip house — grateful for the prospect to spend your entire day with their household.
Lakefront Path close to Navy Pier
Parking Recommendation
Take note as I supply parking recommendation that I don’t personal a automotive and traveled Chicago by bus, prepare, bike, and foot. Nonetheless, I’ve some suggestions based mostly on the inevitable ridesharing, driving with associates, or simply expertise in these neighborhoods.
Montrose Seashore is a well-liked weekend vacation spot however will get quieter within the fall. There are a variety of parking spots however most (if not all) are actually metered. You may strive your luck within the neighborhoods west of LSD. I lived close to W. Castlewood Terrace, which is a historic neighborhood of single-family properties with huge driveways and garages. Due to this fact, you may often discover parking right here, particularly farther down the road (not a via avenue). Simply keep in mind it’s a little bit of stroll (however it’s a stunning one as you make your manner via Lincoln Park).
The downtown actions are, nicely, downtown, which is chaotic and costly in any main metropolis. Navy Pier has two garages with 1,500 spots, so that you shouldn’t have a problem securing one, however it’s going to value $35 for as much as two hours alone. There are discounted “distant alternate parking garages” at Grand Plaza Park and elsewhere for $15. Navy Pier visitor companies stated this can be a flat charge for the day at these garages. Take note, this feature requires validation from the Navy Pier Visitor Companies Desk.
Northerly Island additionally has a small metered car parking zone.
To the south, Jackson Park just like Montrose Seashore provides neighborhood avenue parking and metered tons. However I all the time discovered Jackson Park to be comparatively quieter and don’t anticipate any difficulty discovering parking, as long as it’s not a vacation weekend.
Embrace Chicago’s Lakefront Adventures
I hope you’re impressed to benefit from the unbelievable lakefront that Chicago’s visionary leaders left us. It might not be an epic highway journey by way of distance, however it’s going to actually be an epic highway journey by way of recollections made.
Photographs by Chelsey Stone
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You’ll find her at chelseygrassfield.com or on Instagram @chelseygrassfield.
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