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Chicago’s lakefront is iconic. Conjure any picture of the town, and it’ll probably embrace views of densely packed skyscrapers alongside Lake Michigan. Twenty miles lengthy, Chicago’s Lake Shore Drive (LSD) shouldn’t be solely gorgeously scenic, nevertheless it additionally provides innumerable actions and locations to discover, making it excellent for a micro-road journey.
In the course of 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 Seaside space. The downtown actions are at Navy Pier or Museum Campus. And the southern portion is usually inside Jackson Park, apart from Steelworkers Park. So should you’d like to combine and match itineraries, it’s best to be capable to go away the automotive at every cease and discover additional. Additionally, hold round till the tip for some need-to-know parking ideas.
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 all the way down to benefit from the breeze off the lake.
Author Chelsey Stone on the Centennial Wheel
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
Wish 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 by the air (with a internet under to catch you simply in case), as you take pleasure in views of Lake Michigan.
Categorical Flying Trapeze courses are 90 to 120 minutes for $70 to 75. It’s also possible to make the most of 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 cause Chicago’s lakefront is the general public park it’s at present — 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 unlimited construction that rotated 36 gondolas round a middle axle, every one carrying 60 folks. The attraction was a large hit.
Quick-forward to at present’s Centennial Wheel at Navy Pier, a celebration of that very first “Chicago Wheel,” and also you’ll be capable to 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,
Software Maker, Stacker of Wheat,
Participant with Railroads and the Nation’s Freight Handler;
These are the opening traces to Carl Sandburg’s poem, “Chicago.” When he wrote it in 1914, Chicago was already cemented as an industrial powerhouse from the a long time that got here earlier than. A lot of that legacy nonetheless lingers at present, nevertheless it’s steadily adapting to supply extra open areas and public parks — like Steelworkers Park.
Initially a part of the U.S. Metal Advanced referred to as 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 essentially 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.
For those who don’t occur to have your personal climbing tools, 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 trade to nature, this subsequent itinerary consists of a few of the loveliest pure areas alongside the lake performing as sanctuaries — to wildlife and urbanite alike.
North
If flying like a fowl isn’t your factor, you’ll be able to watch pure aviators at Montrose Level Chicken Sanctuary or, as locals consult with it, Magic Hedge. Deliver your binoculars and assist the kiddos spot any of the 300 fowl species recorded right here. Annually this pure space attracts tens of 1000’s of migratory birds searching for relaxation, meals, and shelter. As you wander the outer paths, look south by the tall grasses and also you’ll spot Chicago’s skyline within the distance.
In the summertime, chances are 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 mother and father, in addition to their chicks annually. I’m additionally conscious of at the least one one that now has a piping plover tattoo.
Downtown
Tens of millions of holiday makers to Chicago’s Museum Campus annually 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.
Right now, 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 choose up in earnest till 1890, when Chicago was chosen to host the 1893 World’s Truthful. Jackson Park was designed by Frank Legislation 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 sequence of basins and lagoons.
Between the west and east lagoons lies the Backyard of the Phoenix. In the course of the World’s Truthful, the Japanese Authorities constructed the Ho-o-den, or Phoenix Temple, which remained as a present to Chicago on the truthful’s finish. Restored and revitalized many instances since then, you’ll be able to enter the Shinto gate to see the pavilion and cross the moon bridge. Make sure you come again within the spring for the six to 10 days when the cherry blossom timber are in peak bloom.
The emotions peace and calm listed below are excellent 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 Trip
If these pet canine eyes are breaking your coronary heart as you pack up the children and automotive to your LSD highway journey, concern not! I even have an itinerary fitted to the furriest member of the household (and everybody else, after all). As a frequent canine sitter to many a Chicagoan pal’s canine, I can let you know Chicago is a superb metropolis for canine.
North
Montrose Canine Seaside was Chicago’s first authorized off-leash canine seaside, providing a spot for canine to play and swim. Simply needless to say all canine — even guests — will need to have a Canine Pleasant Space tag to make use of the seaside, so make sure to plan forward. However the effort is properly price it as you watch your canine splash in regards to the water, swim out to gather their ball, and make new buddies.
And don’t fear, there’s a self-service dog-washing station, so you’ll be able to clear up earlier than bringing your furry pal again within the automotive for the subsequent cease.
Downtown
Architectural cruises are common 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 supplies 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. Canines should stay on their leash.
South
Jackson Bark in Jackson Park (get it?) is for the adventurous canine — the one who loves leaping by tires, climbing V-shaped planks, and wiggling by tubes. Varied highway indicators, development tools, and even police warning indicators have been repurposed to your canine’s delight. This canine park was featured in USA Right now’s 10 Finest in 2025 (runner up) and 2024 (#5).
With this ultimate alternative to get out any vitality they’ve left (and the way a lot might that actually be at this level?), you’ll have one very drained however happy pup on the automotive journey house — grateful for the prospect to spend the complete day with their household.
Lakefront Path close to Navy Pier
Parking Recommendation
Bear in mind as I supply parking recommendation that I don’t personal a automotive and traveled Chicago by bus, practice, bike, and foot. Nonetheless, I’ve some ideas based mostly on the inevitable ridesharing, driving with buddies, or simply expertise in these neighborhoods.
Montrose Seaside is a well-liked weekend vacation spot however will get quieter within the fall. There are loads of parking spots however most (if not all) at the moment are metered. You’ll be able to attempt your luck within the neighborhoods west of LSD. I lived close to W. Castlewood Terrace, which is a historic neighborhood of single-family houses with huge driveways and garages. Due to this fact, you’ll be able to normally discover parking right here, particularly farther down the road (not a by avenue). Simply keep in mind it’s a little bit of stroll (nevertheless it’s a beautiful one as you make your manner by Lincoln Park).
The downtown actions are, properly, 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’ll 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 providers stated it is a flat fee for the day at these garages. Bear in mind, this selection requires validation from the Navy Pier Visitor Providers Desk.
Northerly Island additionally has a small metered car parking zone.
To the south, Jackson Park just like Montrose Seaside provides neighborhood avenue parking and metered tons. However I all the time discovered Jackson Park to be comparatively quieter and don’t anticipate any challenge discovering parking, as long as it’s not a vacation weekend.
Embrace Chicago’s Lakefront Adventures
I hope you’re impressed to make the most of the unbelievable lakefront that Chicago’s visionary leaders left us. It might not be an epic highway journey by way of distance, however it’ll actually be an epic highway journey by way of recollections made.
Images by Chelsey Stone
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You will discover her at chelseygrassfield.com or on Instagram @chelseygrassfield.
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