Whether you are a Chicago first-timer or a long-timer, the Chicago Lakefront Trail is an integral part of the Chicago experience and one of the reasons this city is regarded as a world-class place to ride a bike. The path itself is little more than a wide concrete slab that traces a route following Lake Michigan, but what it does for the city’s cyclists and how it came to be is an important step in understanding how vital the Lakefront Trail can be.

Guide to Biking The Chicago Lakefront Trail:

  • History of Chicago’s Lakefront Trail
  • Biking the Lakefront Trail
  • Bike Rentals to Bike the Trail
  • Safety Tips for Biking Chicago’s Lakefront Trail
  • Attractions Along Chicago’s Lakefront Trail Worth Stopping For
  • Events Along the Lakefront Trail
  • Beaches Connected to Chicago’s Lakefront Trail
  • Parks Connected to Chicago’s Lakefront Trail
  • Dining Along Chicago’s Lakefront Trail
  • Trails Nearby Chicago’s Lakefront Trail

History of Chicago’s Lakefront Trail

The official designation of the Lakefront Trail as Chicago’s first official bike path goes back to 1963 and Mayor Richard J. Daley, however the real history starts much earlier. If you’ve read Erik Larson’s Devil in the White CIty, a fantastic book surrounding Chicago’s Columbian Exposition of 1893, you might recognize the name Daniel Burnham. If you don’t recognize the name, you definitely recognize what he’s done for Chicago. His masterminding of what was at the time a world-renowned event led to the creation of several buildings surviving to this day, namely the buildings which are now more familiar as the Field Museum of Natural History, the Art Institute of Chicago, and the Museum of Science and Industry. Just over a dozen years after the fair closed, Daniel Burnham published The Plan of Chicago, which was one of the most ambitious proposals for city planning at the time. In it, Burham wrote that Chicago’s lakefront is “public ground” and must “remain forever open, clear and free of any building or other obstruction.” Thanks to the wild success of the Columbian Exposition, Burnham had the influence (and financial backing) to make sure that the area we now call the Lakefront Trail survived all attempts at construction or land development to the present day.

Chicago in the winter

Though the trail has been kept free from development that would keep the lakefront area from being anything but public-use land, it has been updated, upgraded, and changed a number of times in its decades of use. Some of the most notable changes in the last 15 years include the Navy Pier flyover, a bridge that bypasses Navy Pier to allow safer and a more uninterrupted ride for trail users. Some sections of the trail have also undergone the proposed transformation that would separate cyclists and pedestrians, which can be seen over a number of miles north of North Avenue Beach. Additionally, there have been many improvements to the trail as a result of nearby facelifts of Millennium Park or Lincoln Park, making it easier to visit each of these sights.

Today, the trail and its surrounding parks see as many as 70,000 visitors on a nice summer day, encompassing all sorts of activities from cycling, walking, running, rollerblading, dog walking, and more. Though the typical busy times of year for the trail span from Memorial Day to Labor Day, it sees regular use year-round by locals as well as some more intrepid visitors.

Biking Chicago’s Lakefront Trail

Riding your bike on the Lakefront Trail really can be as simple as getting there and going for a ride. Chicago’s investment in the infrastructure of the path means that everybody has a safe and fun place to ride without needing to take the same kind of precautions they might if they were riding in traffic. Although there are some important safety guidelines to keep in mind, the most likely questions you may need to answer are “How do I get there?” and “Where should I ride?”

Chicago’s Lakefront Trail runs for 18.5 uninterrupted miles of paved paths between the 5800 block of N Sheridan Road to 7100 S South Shore Dr. All along its length you will see several parks, beaches, and points of interest that might range from a quick snapshot of the skyline to an all-day tour of several museums, zoos, or parks. There are several restaurants, seasonal snack shacks, water fountains, and public amenities along the way, so no matter what you need, if it’s not on the path itself, it is probably accessible in one of the 13 neighborhoods the path runs along. While the parks it runs through usually have posted hours until 11 pm, the trail itself is accessible all around the clock.

Lakefront Trail in Chicago South Shore Drive Starting Point

Thanks to Chicago’s grid of perpendicular streets, there are several regularly-spaced access points all along its length. In fact, the biggest obstacle to getting to the Lakefront Path is simply Lake Shore Drive itself, which is a multi-lane highway running parallel to Lake Michigan. If you approach the Lakefront Trail on foot or bike there are many underpasses that cross Lake Shore Drive. If you arrive by car, there are a variety of places to park in the area of the many beaches and parks regularly scattered along the trail. Even if arriving by public transit, there are dozens and dozens of nearby bus stops and most of the trail is no more than seven or eight blocks from a Red Line or Green Line stop.

Though there are many places to access the trail, a few places are always popular choices. The underpass at east Ohio St. will leave you near Bobby’s Bike Hike, where you can rent a bike or book a Chicago tour that will teach you even more about the Lakefront Trail and surrounding areas. This access point puts you near Navy Pier, and Ohio Street Beach, both must-see attractions. Monroe Street is also a great choice, which puts you in between Millennium Park and Buckingham Fountain. Slightly further south is the Museum Campus, which will take you near the Shedd Aquarium, Adler Planetarium, the Field Museum of Natural History, and Soldier Field. Just because this area is packed with sights, don’t overlook the nearby Grant Park and Northerly Island Park for some of the crucial green space that highlights the Lakefront Trail. In addition to the always popular Burnham Park, Lincoln Park, and Montrose Beach, there are several more access points, so determining where to start a bike ride on the trail may be answered simply by what you would like to see or what is most convenient. No matter which way you choose, you won’t have to go out of your way to get on the trail.

Looking for a Bike to Cruise Chicago’s Lakefront Trail?

Choosing a bike for the trail shouldn’t be stressful. The experts at Bobby’s Bike Hike can help you figure out what kind of bike makes the most sense for your ride. Bobby’s variety of rental bikes means there is something for everyone’s taste and skill level, and we can guide you through the process.

Biking with a Hybrid Bike

The Lakefront Trail is entirely paved and almost entirely flat, so your choice of bike may be mostly influenced by your goals or destinations, because there will be very few kinds of bikes that will be incompatible with the Lakefront Trail. The most popular pick is always a comfort hybrid bike. They feature a more upright and relaxed stance for the rider that makes longer tours more comfortable. They also have tires with a light tread pattern that make for less resistance while riding, which results in less fatigue over a longer distance. Our comfort hybrids also include 7 speeds, which will make light work of Chicago’s few hills and inclines. Bobby’s fleet of comfort hybrids also come equipped with a rear rack, fenders, and a handlebar bag, so your ride can be as convenient and comfortable as possible.

Biking with a Road Bike

If you would instead prefer to have a faster, more strenuous ride, Bobby’s also has several choices in performance road bikes. These feature a sportier, more aerodynamic riding position that makes long distance rides at a higher speed much easier. Traditionally, road bikes have a larger diameter, smoother, and narrower tire that means you won’t be losing all your effort to friction with the road. They are most often equipped with an 18 or 22 speed drivetrain to maximize the speed and distance on your ride. These types of bikes rarely have room for a lock, so if you plan to take a break along your ride, expect to bring a backpack for any extra equipment.

Biking with a Tandem Bike

If you are doing your tour of the Lakefront Trail as a pair, a tandem bike can be a fun and memorable experience. Tandems are most similar to hybrids as they are more upright and comfortable than other sportier styles of bikes. Everything the above paragraph says about comfort hybrids is also true about tandems, but with the extra feature of having a co-captain on your trip! It is usually a good idea to start out slow and feel out for how the tandem might be a different kind of bike than you are used to, but most first-time riders are surprised by how quickly they adapt. Our tandems also feature a 7 speed drivetrain, as well as upgraded brakes to better handle the additional rider weight. When on the Lakefront Trail, make sure to allow some extra stopping distance and don’t expect the same handling you are used to in smaller, sportier bikes. The longer frame translates to a wider turn, so make sure you signal your turns and take them as gently as you feel is safe.

Biking the Chicago Lakefront Trail with Children

For those with kids in tow, Bobby’s also stocks a large amount of children’s bikes and equipment so nobody will be left behind. For kids that are already comfortable, experienced riders we offer a selection of 20” to 24” bikes that are usually the best pick for children between the ages of 5 to 11. Ultimately, the right size is based on height and experience, so no worries about getting the wrong size because we can fit everyone with the best bike for their needs. For children that are not quite ready to ride on their own, we also have equipment from child seats, trailers, and tagalongs that make sure the whole family can ride together.

In addition to finding the right bike, we will also find you the right equipment and accessories for your ride. All rentals include a helmet, lock, and flat repair kit, so any rental will have you fully equipped for your ride.

In addition to rentals that will let you roam freely, Bobby’s also runs several bike tours that take full advantage of the Lakefront Trail. For adults that want a sampling of the foods and beers that make Chicago famous, our Bikes, Bites, and Brews tour offers a day and evening route that will fill you up with deep dish pizza, Chicago style hot dogs, Italian beef, and more, while exploring the city on bike. The Family Food and Bike Tour offers a similar sampling sans beer (though a VIP upgrade beer package is available) that also takes advantage of the same stunning views that the Lakefront Trail can offer. If you’d rather forego the food for a tour around the city, check out the Lakefront Neighborhoods Tour or Chicago’s Ultimate tour.

Safety Tips for Biking Chicago’s Lakefront Trail

One of the best features of the Lakefront Trail is its seclusion from traffic, making it one of the safest places in the city to ride a bike. There are still a few things to keep in mind that will help ensure that riders arrive at their destination happy, healthy, and safe.

First, make sure your bike and all associated equipment are in good working order. If you are renting a bike from Bobby’s, you can be assured we’ve already done all this for you, but for your own bike make sure your brakes and gears are functioning correctly and your tires are pumped up to the pressure range printed on the sidewall of your tires. If you think your bike may need a little attention before the summer, call us up and we can tell you more about the maintenance we offer at Bobby’s Bike Hike.

Next, the other main safety considerations on the trail are being aware of your environment and how to share space on the trail. The trail is open 24 hours a day, 365 days a year so there will be days when the weather will be less than ideal. For the most part, this won’t have to keep you from riding, but when there are high water levels or a very strong wind, you may want to avoid some sections of the trail that are immediately on the water as there is a chance of flooding or of waves cresting onto the path itself. Fortunately, this should never catch you by surprise as this usually only happens in very severe weather and in some cases the trail may be temporarily closed in those sections.

The rest of the guidelines to keep safe on the Lakefront Trail will probably feel like common sense, but it is important to note that because many sections are mixed-use, there is a good chance you may be contending with slower riders, walkers, joggers, dog walkers, children, and more. The most important thing is to be aware of your surroundings and watch for possible obstacles as they become apparent. This may mean slowing down in some sections, dismounting as directed when passing through some underpasses, and obeying traffic signs and signals in the few occasions you have to cross traffic at the entrance of some of the parks. As you approach others from behind, it is considered appropriate to call ahead to let them know you are passing them, which should always take place on the rider’s left-hand side. The same alert can be performed with a horn or bell if your bike is equipped. Above all, you should let the amount of traffic on the path dictate what pace is safe to ride and to always ride in a predictable manner around others on the path.

Map of the Chicago Lakefront Trail

Attractions Along Chicago’s Lakefront Trail Worth Stopping For

The Lakefront is far from just a place to stretch your legs for an afternoon. In addition to a great workout and a way to see the city, the trail is in close proximity to several attractions that will make your visit memorable.

The Museum Campus has three of Chicago’s most well-known museums within a short distance: the Field Museum, Adler Planetarium, and the Shedd Aquarium. Each of these museums are renowned in their respective fields and no trip to Chicago would be complete without at least stopping by to admire the stunning architecture that makes them perfect backdrops to a panorama of the city skyline. Each museum typically has a touring exhibit so consult their website for all the information about what to see and hours of availability before your trip. Immediately across from the Field Museum is also Soldier Field, home of the Chicago Bears and occasional stadium-level musical acts. Drop by in the right season and expect to see a large field of blue and orange tailgating most Sunday’s.

Further south, you can find the Museum of Science and Industry set into scenic Jackson Park. The Chicago MSI is one of the largest science museums in the world and has exhibits featuring a real-life tornado indoors, a walk through a World War II submarine, a tour through the streets of yesterday and much, much more. When visiting the Museum of Science and Industry it is simply impossible to avoid feeling childlike wonder, no matter your age!

Nearer the halfway point of the Lakefront Trail is Navy Pier, Chicago’s second most visited attraction. Originally built in 1916 and based on the Daniel Burnham’s 1909 Chicago Plan, it has gone through several uses, including a naval training center, a dock for transport ships, and college campus. Since 1995 it has been an attraction open to the public where one can take a boat tour on Lake Michigan, see a play at the Chicago Shakespeare Theater Company, or ride the giant Ferris wheel. If you ride by on the Lakefront Trail in the summer, make sure you check out the fireworks display happening at a couple times of each week.

Events Along the Lakefront Trail

As should be expected for any city with millions of residents, there is always something of interest going on and while that changes somewhat from season to season, the Lakefront hosts many events every year.

From Lollapalooza in Grant Park to Blues Fest in Millennium Park, Chicago is host to large-scale musical events all year-round so make sure to follow your favorite musicians to see when they’re coming through town. The city hosts many concerts throughout the year, so there’s always an opportunity to find a new favorite artist.

Every August, the Chicago Air and Water show gathers thousands along the waterfront to see aircraft and water vessels, both modern and historical. The event is centered at North Avenue Beach and draws as many as a million visitors each day. Annual highlights include a flashy flight demonstration from the famous Blue Angels Flyers. Around the same time is Chicago Comic and Entertainment Expo, better known as C2E2, held at McCormick Place just south of Soldier Field, it is one of the largest events of its kind and held at the largest convention center in all of North America.

If you find yourself with a free evening in Chicago and want to take advantage of some of the events and entertainment along the Lakeshore or one of the city’s many parks, look for an updated list of events on the Chicago Park District’s website for all the details.

Beaches Connected to Chicago’s Lakefront Trail

Since the beginning of the 20th century, Chicago residents have been avid beachgoers. In fact, even before the Army Corps of Engineers reversed the flow of the Chicago River to avoid polluting Lake Michigan, the demand was so great that the city created acres of additional beaches for public use. Now, there are dozens of beaches along the Lakefront Trail that are perfect places to soak up some sun, play volleyball, go for a swim, and more. Most of the beaches are open year-round from sunrise to sunset, though occasional beach closures due to inclement weather mean it is always smart to check for updates on the Chicago Park District’s website before planning your trip. Fortunately, the Lakefront Trail that connects them is always open, so even if you can’t go for a quick swim you can always visit.

Near the north end of the Lakefront Trail, Montrose Beach is Chicago’s largest, and among its most active beaches. It is one of Chicago’s only beaches that functions as a small watercraft launch, making it a popular pick for kayaks and canoes. It is also one of only two dog beaches in the city, including a fenced area for off-leash play. In addition to hosting dozens of events on summer weekends, Montrose is also host to Chicago’s north-side July 4th fireworks display. Montrose Beach also has the most parking of any Lakefront Beach, so getting there is very easy, but if you prefer a little quieter experience you may expect this beach to be quite busy on a nice day.

Hollywood Beach (also known as Osterman Beach) is a popular, though less-trafficked beach on the north side. As it features no on-site parking, it can be a good alternative to some of the busier beaches to the south. The north half of Hollywood Beach also features a long stretch of shallow water that makes this one of the best picks for families with younger children. As this is one of the northernmost beaches accessible by the Lakefront Trail, it is always a popular pick for families to get a full day rental of bikes and children’s equipment from Bobby’s and spend the day riding to Hollywood Beach for a fun day of sun and sand.

Because Chicago’s beaches can vary quite a bit, there are a lot of activities that you might expect to see at certain beaches that happen nowhere else in the city. North Avenue Beach is a hotspot for beach volleyball leagues, as well as a host of professional teams competing annually. Ohio Street Beach, which unusually faces north, is a popular spot for open water swimming, which along with 12th Street Beach, makes it an ideal spot for athletes training for the annual Chicago Triathlon at the end of each summer. Further south, 63rd Street Beach has Chicago’s oldest and one of its largest beach pavilions, making it a popular spot for families and picnickers. At the south end of the Lakefront trail near Jackson Park is South Shore Beach and the South Shore Cultural Center, notable to fans of Chicago cinema as the filming location of the fictitious “Palace Hotel Ballroom” in The Blues Brothers (1980).

North Avenue Beach on the Lakefront Trail

Oak Street Beach features Chicago’s only chess pavilion as well as a site for deep water diving that draws SCUBA enthusiasts. Oak Street Beach owes some of that popularity to its unique topography, which originally began in the mid 1800’s as a place that silt from the Chicago River settled due to a nearby shipping pier. By the end of the century, a colorful character by the name of George Streeter, a land speculator, former circus owner, and all-around scoundrel, had run his steamship into a silt bar until it was no longer able to move. According to local legend, he then encouraged the dumping of refuse and rubble around his boat until it resembled an island, which later grew enough to connect to the mainland. This led to land disputes with city officials which occasionally resulted in skirmishes and outright gunfights until George Streeter was officially ousted from the area. Later land development followed the Burnham plan of 1909 and shaped this area into a public land for all to enjoy. Although George Streeter never fully reaped the rewards of his schemes, his legacy lives on in the name of Streeterville, the Chicago neighborhood where you can now find the headquarters of Bobby’s Bike Hike!

Parks Connected to Chicago’s Lakefront Trail

Just as the Lakefront Trail connects multiple Chicago beaches, it does the same for some of the city’s most well-known parks. While the sheer amount of greenery one might see from an aerial view might suggest that the lakefront was one long park, there are actually four main parks: Lincoln Park, Grant Park, Burnham Park, and Jackson Park.

Lincoln Park, one of Chicago’s most famed examples of its dedication to green spaces, is a seven mile long park that has been in continuous operation since 1860. It most notably is home to the Lincoln Park Zoo, the fourth largest zoo in North America and one of only a few that offers free admission. The park is also host to several museums, a conservatory, a large variety of fields for different sports, and several examples of statues and public art.

Closer to downtown, Grant Park is a hotspot for sightseers looking to see a lot in a very short trip. Originally opened in 1844 and renamed to honor Ulysses S. Grant in 1901, Grant Park is where to find some of Chicago’s most well-known sights, from Cloud Gate (a.k.a. The Bean) in Millennium Park, Buckingham Fountain, The Art Institute of Chicago, to the Museum Campus on the Lakefront itself. Grant Park also hosts some of the city’s largest summer festivals, including Blues Fest (June), The Taste of Chicago (July), and Lollapalooza (August).

Burnham Park, so-named for the above-mentioned Daniel Burnham was created in 1920 but has origins starting from the 1860’s, as many of the smaller parks on the lakefront gradually became annexed and interconnected to each other. At its northernmost point it meets the Museum Campus of Grant Park with Soldier Field, built in the 1920’s and named in honor of the soldiers of the first World War. While Lincoln and Grant Parks venture further inland, Burnham holds firmly to the shoreline and its immediate area.

The final of the major parks you should visit on the Chicago Lakefront Trail is Jackson Park on the near south side. Originally conceived in 1871 and developed over the next twenty years, Jackson Park was home to the 1893 World’s Columbian Exposition, remnants of which still survive to this day, including the Museum of Science and Industry and a Japanese strolling garden later renamed “Garden of the Phoenix”. At present, the park also features many athletic fields, a golf course, and 63rd Street Beach. Jackson Park is also a popular site for birdwatchers, due to the restoration of prairie in some areas as well as a large population of monk parakeets that live on the park grounds.

All of these parks are open year-round, from dawn to dusk. While some amenities offered are seasonal, the Lakefront Trail is open and accessible at all times of the day and times of the year, so a bike tour of these famous parks is always a great choice.

Dining Along Chicago’s Lakefront Trail

Chicago is a foodie town and the Lakefront Trail is no exception. In addition to the thousands of choices you can expect to find just slightly inland, the trail itself is home to several places to eat, from small cafes to upscale restaurants with a stunning view of the lake.

If you need a quick pick-me-up on your ride without stopping for long, there are a number of cafes running along the lake. The Clocktower Cafe just south of Montrose Beach or Juicy on the northeast corner of Grant Park near Monroe Street both offer quick bites that will give you fuel to keep riding after a short breather.

For heartier, but still down to earth eats that would be great picks for a lunch or dinner, 57th Street Grill at 57th Street Beach, Relish Chicago Hot Dogs in front of Navy Pier, or the shops in Navy Pier itself have simple American fare that can make for a great lunch in the middle of a long day of bike riding. If you prefer something more unique without spending too much money, Whispers on Oak Street Beach is a popular pick for relaxed, beachy eats.

Those looking for a more upscale experience can try North Pond or The Lakefront Restaurant, both in Lincoln Park. They both feature a higher end experience and you can choose from the view of Lake Michigan at The Lakefront or the quieter locale of North Pond across from Diversey Harbor at North Pond in Lincoln Park.

As always, hours and menus vary so check for the latest info before you go and you may want to plan a reservation for some of these picks.

Trails Nearby Chicago’s Lakefront Trail

The Lakefront trail represents just 18.5 of Chicago’s hundreds of miles of bike lanes and trails that cover the city. Since most of the east-west streets that would access the trail also have some kind of nearby cycling infrastructure, there is a seemingly never ending network of places to ride.

If you find yourself riding the lakefront and just can’t get enough, the Lakefront Trail ends where others begin. Riders on the north end of the trail can travel west a few blocks to Clark Street, which they can ride north to Evanston and the Green Bay bike trail, which goes as far north as Kenosha, Wisconsin. On the south end of the Lakefront Trail, cyclists can easily cross the state line and find the Erie Lackawanna Trail, which will take them as far southeast as Crown Point, Indiana.

There are also a number of trails in the surrounding suburbs that will allow access to a national network of bike trails, so where to ride might only be limited by how far you feel like riding. For a fuller view of the trails in Chicago and its nearby communities, be sure to check our blog post on Chicago Area Bike Trails for all the details.

One of the best things about cycling on the Chicago Lakefront Trail is the sheer amount of things to do, see, and experience. No matter if you are visiting the city or have never lived anywhere else, the stunning views, the seemingly endless amount of activities, and best of all – the bike riding will make you agree that the Lakefront Trail a necessary part of what Chicago such an incredible place to be.