Everything You Need To Know About Biking In Chicago

Biking In Chicago 

Whether seeing a city for the first time or the hundredth time, cycling can offer a fresh perspective that leaves the rider with a unique view of their city. Chicago has an abundance of ways to move about the city, but none match the perfect blend of convenience, fun, and efficiency that cycling can offer. Chicago enjoys a reputation as one of the best cities for cycling in the country, which is a combination of environment, culture, and investment in infrastructure. 

Chicago Biking History

Chicago has a long history of bicycle culture, dating back as far as the invention of the bicycle in the 1860’s. While first models of bikes were heavy and expensive, improvements in design, manufacture, and affordability led to an explosion in popularity by the end of the 19th century. By 1900, Chicago boasted more than 50 cycling clubs, totaling more than 10,000 active cycling enthusiasts. At the time, Chicago was also a major manufacturer of bicycles, with approximately ⅔ of all bikes in the country manufactured within 150 miles of the city.

Bikes were so popular at the time that an early mayoral candidate, Carter H. Harrison II led a successful campaign with the slogan “Not the Champion Cyclist, but the Cyclist’s Champion.” That same attitude was furthered by Mayor Richard J. Daley, who oversaw the building of what would become a network of bike paths all over the city by the 1970’s, which proved to be an asset for Chicago as the gas crisis of the 1970’s encouraged more travel by bike. In the 1990’s, Mayor Richard M. Daley continued his father’s legacy of cycling advocacy and worked to expand that network further, which at present day stands at over three hundred miles of bike lanes and paths all over Chicago.

Bike Tours 

Even with a full network of bike lanes zigzagging all across Chicago it can be hard to know where to start. You might expect to think “where do I even start?“ This is the perfect reason to look up a bike tour with Bobby’s Bike Hike. We’ve already done the hard work of figuring out where to go and what to do when you get there, so all you have to figure out is what kind of ride you’d like to have!

Chicago City Biking

If it’s your first time in the city, or would just like to learn more about the great city of Chicago, check out our Ultimate City Bike Tour, which showcases some of Chicago’s must-see attractions, parks, and museums. Here you’ll learn all about some of Chicago’s most famous landmarks, including some of the best views of the skyline from the Museum Campus.If you prefer a more intimate view of the city, the Chicago Lakefront Neighborhoods Tour takes a path less traveled by visitors and gives a peek into some of the places that Chicagoans call home. This tour also showcases Chicago’s famous Lakefront Trail, which consists of 18 miles of car-free paths along Lake Michigan, which makes this another popular pick for first-timers.

Bike to Chicago’s Famous Foods

Chicago isn’t just famous for its sights, but also for the tastes and smells of Chicago-Style food! Biking in Chicago is even sweeter when you’re making stops along the way to sample our famous foods like deep dish pizza, Chicago hot dogs, brownies, and local craft beers, which makes our Bikes, Bites, and Brews Tour a perfect pick for anyone that wants to find out what makes this city famous. Our Westside Foodie Bike Ride takes another spin off the beaten path by featuring a tour of Chicago’s bustling western neighborhoods and the histories of the immigrant communities that are woven into the fabric of Chicago, along with tastes of pierogi, tacos, burgers, and more.

Family-Friendly Biking

Chicago is an excellent city for biking with kids. Families touring the city should be sure to book a trip on our Chicago Family Food and Bike Tour, which hits all the most popular sights while filling up on more of those famous Chicago foods. This tour is a perfect fit for riders of all ages and is sure to leave you with cherished memories of the city.

Chicago Biking for Every Level

With the help of our expert guides, everyone should expect to feel safe and comfortable on their tour, no matter their level of experience. Because Chicago is largely very flat and has excellent cycling infrastructure, even cyclists that have never ridden in the city will find that they can relax and enjoy their tour with ease. Chicago can be known for occasionally turbulent weather but our tours run rain-or-shine, so there’s never a worry about needing a last-minute change in plans. No matter if you’re looking for an outing for the whole family or something more grown-up, everyone will find the perfect tour at Bobby’s Bike Hike.

Bike Rentals 

Best Bikes for Biking Chicago

Since Chicago has done the work of providing plenty of places to ride a bike, all you have to do is find a bike so you can start riding. If you’re coming to Chicago for the first time and plan to bring your own, you should know that most styles of bikes are going to work well enough, from road to mountain and everything in between. However, since Chicago is a very flat city and almost all our paths are paved, road bikes and hybrids tend to be some of the best picks for a comfortable ride anywhere you go.

Chicago Bike Rental Options

If you need to find a bike while you’re here, there are two popular rental options; Divvy and Bobby’s Bike Hike. Divvy is a popular bike share program that offers utility-style bikes that can be rented for short rides around the city. Divvy has had a partnership with Chicago since 2013 and has added numerous docking stations at many points throughout the city. This can be a popular option for locals looking for a simple commuter bike without the costs of bike ownership.

Bike Rentals for Every Age through Bobby’s Bike Hike

In addition to offering tours of Chicago, Bobby’s Bike Hike has a fleet of bike rentals in assorted styles and sizes to fit any would-be rider. Similar to Divvy’s utility bike, Bobby’s most popular pick is a comfort hybrid bike, featuring seven speeds, cargo rack and fenders, and a relaxed, upright style of riding that makes even long distance rides a breeze. For the ultimate in comfort and ease ask about e-bike rental options, which offer dozens of miles of assistance with the same comfortable fit as our most popular bikes. If going fast is more your speed, we also carry a large number of road bikes, both standard and carbon fiber options, which can be the perfect choice for rides that may take you to the city limits and beyond.

For duos looking for a perfect touring vehicle, our tandem bikes are a great pick, and while Chicago may not have mountains, Bobby’s also carries mountain bikes for those that may want to get out of town for some muddy fun. Rounding out our roster of bikes is a large assortment of children’s bikes and equipment so between child seats, trailers, and kid-friendly sizes of bicycles we have everyone covered.

Included in each rental with Bobby’s Bike Hike is all the equipment you could possibly need, including a flat tire repair kit, helmet, and map of Chicago’s most popular attractions. No matter your level of skill, our expert shop staff will help you find the right kind of bike and fit you with the proper size to make sure your ride is as comfortable as possible, plus offer you some tips on your ride so you can experience the city just like a local!

Bike Rental Locations

Rentals are subject to availability, so make sure to book in advance if you can. Since Divvy bikes aren’t localized, you may have to plan ahead if your nearest station doesn’t have any bikes available, which can happen at peak times. Bobby’s is situated in the heart of downtown Chicago near Navy Pier, Millennium Park, and the Lakefront Trail, and even during the busiest months of bike-riding season you’ll never have to hunt for an available rental.

Bike Trails in Chicago 

Biking in Chicago doesn’t just mean the network of hundreds of miles of city bike lanes. Chicago has a number of established bike trails that are completely separated from traffic so you can comfortably ride at your own pace without worries. 

The Lakefront Trail

Chicago’s best-known trail is nearly 20 miles of uninterrupted paths for cycling, walking, jogging, roller blading and more. Stretching from Hollywood ave on the north end to Calumet Beach on the south end, the Lakefront Trail runs adjacent several beaches and parks, but also has some of the best views of the skyline. Since this is the city’s most popular beach you can expect it to be open year-round, and although the parks and beaches do have posted closing times, the path itself remains accessible all day. Each of the beaches and parks the Lakefront Trail passes through feature different amenities, including many beachside restaurants and refreshment stands.

If you are driving into the city with your bike, the Lakefront Trail is the best of Chicago’s trails to ride due to the ample amount of parking at any of the multiple parking lots all along the path. Bobby’s Bike Hike is centrally located just across from the Lakefront Trail, so anything you might need from renting a bike to getting yours fixed, we’ve got you covered.

The 606

The 606 Tail is a new addition to Chicago’s network of trails, and it shows. Developed over the last decade but opened to the public in the last couple of years, The 606 Trail had a previous life as the Bloomingdale elevated rail line, running from Ridgeway ave to the Kennedy expressway on the east, just north of the Humboldt Park neighborhood on Chicago’s near west side. As the Bloomingdale rail became disused, the 606 Trail was built to reclaim some green space for public use. It now runs for nearly three miles through several neighborhoods with access points about every quarter mile.

The bike path is open from 6 AM to 11 PM, though hours can change from season to season, and though it is very well-groomed, it can be slow to see snow removal in the winter. Since the trail cuts across and adjacent to many shopping districts, there is plenty of access to several bike shops, boutiques and stores, and bars and restaurants. There is no dedicated parking for The 606, but you can expect metered street parking all around the route, or just take the Blue Line to Western Ave or Logan Square.

North Branch Trail

First-time visitors to Chicago are often surprised by how much dedicated green space can be found in the city of Chicago. The lake and nearby parks are a popular place to spend an afternoon, but to “get away from it all” without needing to get away from it all, you need look no farther than the north branch of the Chicago River.

Running for nearly 20 miles, the North Branch Trail connects Foster Avenue all the way to the Chicago Botanic Gardens in Glencoe. Just like The 606, there are access points at regular intervals, though there is a limited amount of parking available at some of the parks along the trail. Although this trail does wind through several neighborhoods, it follows the river and is surrounded by forest preserves for much of its length, so prepare some snacks or plan a picnic because it can occasionally feel as though you’ve left the city entirely. This path also stays open from sunrise to sunset, so plan an early start and take a tour of the Botanic Gardens before turning around and heading back to Chicago.

Rules of the Road for Bikes in Chicago 

Just like any other city, common sense rules the road. If it doesn’t feel safe to do then you always have the option to dismount and walk to safety. Fortunately, Chicago has a generally pretty great reputation as a safe city for cycling, so safety should not be much of a concern.

  • On the trails, exercise good etiquette by letting a slower moving person in front of you know you are approaching. If you have a device such as a bell this can be helpful, but it is always appropriate to call out to whomever you may be about to pass that you are coming up on their left. It is just as important to do this while riding on the road for the benefit of other cyclists as well as pedestrians.
  • It is also a good idea to wear hi-viz gear, or at least clothing that is light in color and ideally reflective.
  • Helmets, while not required by law for adults, are always a smart idea, which is why Bobby’s Bike Hike includes one with every bike tour or rental.
  • Since most places in Chicago are fairly well lit, you won’t need a headlight or tail light that are too powerful, just something that increases your visibility at a distance. 

When riding around cars, it is important above all to ride predictably with the flow of traffic. If a motorists doesn’t have to guess where you might ride then there is less of a chance of any accidents occurring. This also means to signal your turns when you can, which used to mean a series of specific hand signals, but it is commonly accepted to simply fully extend your arm and point in the direction you intend to go.

Remember that when you are riding, if a bike lane has been established on the road you are riding, you are obligated to use it rather than the same lane as traffic, provided it is safe to ride. When it is not safe to ride, you may use the lane, but it is usually a smarter idea to dismount and use the sidewalk, but remember – there is no riding allowed on sidewalks, though you may walk your bike.

Riders are also required to maintain a single file line when on the road, with the exception of dedicated bike lanes. Otherwise, riders are expected to obey the same rules of the road as other motorists, including signs, traffic signals, and speed limits.

When you lock up your bike it is only legal to use an approved bike rack. The city of Chicago has installed more than 10,000 of the approved racks so there should be little reason to lock your bike to something inappropriate.

Finally, the best way to ride safely is to plan your route in advance. While the city is generally safe for cyclists, there are some streets that may be too narrow or have too high a speed limit for every rider to feel comfortable. Google maps has an excellent bike lane feature that will show the best places to ride that won’t have you fighting traffic. The city of Chicago also publishes a handy map of the network of paths and roads with bike lanes that will keep you on the right track.

Cycling Events in Chicago 

In addition to all the casual cycling you may do day-to-day, Chicago also features many cycling events that draw thousands of people from across the country.

Need a Bike Rental for the Chicago Triathlon?

The Chicago Triathlon is one of the biggest events of the year, and for nearly four decades has been drawing tens of thousands of triathletes and their fans and families from all over the world. This race is offered in a number of different lengths, as well as kids-only events. Because of Chicago’s location on Lake Michigan, favorable August weather, and flat terrain, the Chicago Triathlon is many athletes’ first event. If you’ve been thinking of moving up from 5k or 10k races to a larger event, the Triathlon may be just what you’re looking for. This event typically sells out months in advance, so make sure to book early when you can.

A lot of first-timers rent an appropriate road bike for their first Chicago triathlon, just to make sure they have the perfect bike for the event without needing to commit to the full cost of buying themselves a new bike or bringing one with them. Since this event pulls competitors from around the world, there are many that don’t want to travel with their personal bike and for them, a premium road bike rental from Bobby’s is a great solution. The more experienced triathlete should expect to have more demanding needs and a carbon fiber bike with higher end components are the must-have gear for a next-level athlete. No matter your level of skill or enthusiasm, Bobby’s has multi-day rental packages available for this event.

Chicago’s Popular Bike the Drive Event

Each year on Memorial Day weekend, Chicago closes off a 15 mile section of Lake Shore Drive for several hours to allow thousands of cyclists to ride their bikes as a benefit for the Active Transportation Alliance, a nonprofit that works to make Chicago a safer and more fun city for cyclists, walkers, and riders of public transit.

This event is a ride, not a race, so you can ride at any pace you like for the duration of the event. There are also staged areas for concessions on both ends of the course where riders can grab refreshments, and when you’ve had your fill you can go back to the starting area for live music, more food, and a number of vendors. While this event is very popular, it allows for far more participants than most Chicago events, you can usually get early bird pricing when registrations are first announced.

Bobby’s also offers rental packages for this event, and no matter what kind of bike you would prefer, we have all kinds. Since this is typically a casual event that is always popular with families, the most rented bike is a comfort hybrid bike. With a large padded saddle and more upright posture, this is an excellent pick for someone looking to take a long tour without the normal stress you might expect from a lengthy bike ride.

Critical Mass

Many of the amenities that Chicago cyclists currently enjoy are largely thanks to the efforts of rides such as Critical Mass. Dating back to October of 1997, thousands of Chicago’s cyclists have gathered at 6pm on the last Friday of every month (yes, even the winter months) under the Picasso statue at Daley Plaza (50 W Washington) for a lengthy ride through Chicago’s streets. This ride aims to increase the visibility of cyclists and advocate for safe and effective places to ride. This event is free and inclusive, so there is a place for everyone to ride for a good cause. With favorable weather, Critical Mass crowds can reach into the hundreds and sometimes thousands, and can be a great way to meet fellow cyclists in Chicago. There are also Critical Mass rides in cities around the country, but if you come to Chicago from a place that could benefit from this kind of advocacy, then this is a great activity to bring home with you.

Just like Bike the Drive, Critical Mass doesn’t require any specific kind of bike, so ride to your comfort level and length. Since the route and length of the event aren’t set in stone, you can decide how much or how little you would like to ride. This is an evening ride, so be prepared with the right clothes and of course all the lighting and safety accessories you think appropriate.

Over the last several decades, Chicago has worked tirelessly to help show that biking in the city doesn’t have to be scary. First time urban riders often find that seeing the city by bike lends a new perspective that they can’t get any other way. Better yet, it’s easy, fun, and good exercise!