The Most Bike-Friendly Neighborhoods in Chicago

When it comes to city living, Chicago knows how to roll. With miles of protected bike lanes, scenic lakefront paths, and a growing network of bike-friendly infrastructure, biking the city is the ultimate traffic hack. Ready to ride? Go ahead and skip the gridlock, cruise past the gas pumps, and give a wink to planet earth as you reduce your carbon footprint.

But where should you live if you want to make the most of Chicago’s bike culture? That’s where we come in. We surveyed our own team of Chicago’s best leasing agents, as well as building managers at the city’s best apartments, to get the inside scoop on the most bike-friendly neighborhoods and best bike-friendly apartments.

So, strap on your helmet and let’s take a ride through bike-friendly Chicago’s best ‘hoods.

Pedal Power: Chicago’s Cycling Craze

Biking in Chicago isn’t just a weekend hobby; it’s a full-blown movement, with a whopping 119% growth between from 2019 to 2023. With each passing year, more Chicagoans are trading four wheels for two, and the city’s commitment to expanding its bike-friendly infrastructure is paying off. 

Chicago’s casual bikers and hardcore cyclists alike enjoy: 

• Over 400 miles of designated bike lanes, including protected lanes.
• The Lakefront Trail, a cyclist’s paradise stretching 18 miles along Lake Michigan. 
• Bike-sharing program Divvy, with thousands of bright blue bikes docked through the city.

But wait, there’s more! Enter the Chicago Bike Plan, a roadmap to a more bikeable city. This ambitious plan aims to add even more miles of bike lanes, neighborhood greenways, and bike-friendly intersections. And let’s not forget Vision Zero, the city’s initiative to eliminate traffic fatalities and serious injury from traffic crashes.

So is Chicago bike friendly? The answer is a resounding YES!

Where to Live in Chicago for the Best Biking Experience

Not all Chicago neighborhoods are created equal—at least when it comes to life on two wheels.

What Makes a Neighborhood Bike-Friendly?

• Plenty of Lanes: Bonus points for protected lanes!
• Trail Connections: Easy access to gems like the Lakefront or 606.
• Favorable Streets: Less traffic, more bike signals.
• Bike Shops Galore: Fix it fast, ride on.
• Scenic Vibes: Parks and pretty routes for the win.

Lucky for you, we’ve tapped into our own team of 40 Chicago locals (seriously, we dare you to challenge their city knowledge) to round up the best neighborhoods for cyclists. Whether you’re a daily commuter, a weekend trail cruiser, or someone who just likes to pretend they’re training for the Tour de France, this is where you want to be!

Top Neighborhoods for Cyclists in Chicago

Wicker Park: The Best Bike-Friendly Neighborhood in Chicago

Living in Wicker Park means embracing the hustle and flow of one of Chicago’s most vibrant neighborhoods. From quirky coffee shops and vintage boutiques to buzzing bars and locally-loved taco joints, this area’s got it all. And the best part? You can explore it all on two wheels. Here, the bike-friendly vibe isn’t just a perk; it’s a way of life.

Our team didn’t have to think twice about this one; Wicker Park pedaled straight to the top! Here’s why we crowned it Chicago’s best bike-friendly neighborhood:

Bikes > Cars

In Wicker Park, cars often play second fiddle to bikes. With dedicated lanes zig-zagging through the neighborhood and traffic signals that prioritize cyclists, it’s clear that two wheels rule the road. Some days, it feels like the bikes outnumber the cars—and honestly, they probably do!

Bike Culture Galore

Cyclists are practically part of the scenery here. It’s not uncommon to see friends pedaling side by side, decked out in stylish gear, or a group of bikers parked outside a café, sipping lattes and swapping tire tales.

The Hipster Highway

Milwaukee Avenue, affectionately nicknamed the “Hipster Highway,” is Chicago’s most famous bike corridor, and Wicker Park is right in the middle of it. The steady stream of cyclists cruising down this bustling stretch is a testament to just how bike-friendly the neighborhood is.

Repair and Ride

Got a flat? Need a quick tune-up? No problem. Wicker Park is home to neighborhood bike shops like Stellar Cycleworks, where mechanics greet you like an old friend and get your ride back on the road in no time. Whether it’s a quick adjustment or a major fix, help is always just around the corner.

Live the Bike Life

Forget the hassle of parking. In Wicker Park, everything you need is a pedal away. Groceries? Check. Coffee? Absolutely. Your go-to dive bar for a post-ride pint? You bet. Living here means your errands turn into joyrides. And you can extend those joyrides seamlessly by hopping onto the Bloomingdale Trail—better known as The 606—which stretches along the neighborhood’s entire northern edge.

Lakefront in a Snap

When the call of the lake becomes irresistible, Wicker Park’s location makes it easy. A breezy ride east leads you straight to the Lakefront Trail, where you can soak in skyline views, feel the breeze, and maybe even dip your toes in the water. It’s the ultimate reward for a ride well done.

River North: The Best Neighborhood For Bike-Commuters

Choose to live in River North and you get the best of both worlds: a neighborhood with world-class dining, buzzing nightlife, and sleek high-rises, all within pedaling distance of downtown’s business district. Whether you’re commuting to the Loop for work or cruising to a nearby neighborhood for brunch, River North makes biking a breeze.

For those who commute by bike, River North was our clear winner for a few reasons: 

Easy Downtown Commutes

Say goodbye to the stress of gridlock. In River North, a quick bike ride gets you to the Loop in no time. With dedicated bike lanes and plenty of low-traffic routes, you’ll be zipping to the office faster than most cars can crawl. Plus, no parking fees!

Smoother, More Protected Rides

The bike routes from River North to the Loop cater to riders. Well-maintained bike lanes, many with protective barriers, line the streets, making it easy to navigate without battling bumper-to-bumper traffic. 

Neighborhood Connections

Need to swing by West Loop for happy hour or head to Old Town for a Sunday market stroll? River North’s central location means you’re just a quick ride away from some of Chicago’s most beloved ‘hoods. 

Weekend Lakefront Vibes

Commuting during the week is great, but weekends are when River North’s bike perks really shine. A scenic ride along Lake Michigan is practically a city ritual. Soak in the skyline views, cruise by Navy Pier, or find a sunny patch of grass for a lakeside picnic.

Lincoln Park: The Best for Recreational Biking 

Living in Lincoln Park is like having the ultimate backyard playground. With tree-lined streets, charming brownstones, and a buzzing neighborhood vibe, it’s a slice of classic Chicago. But for biking enthusiasts? It’s paradise. Whether you’re cruising to the lake, exploring the park, or pedaling to your next brunch spot, Lincoln Park offers endless ways to ride for fun.

Chicago’s lakeshore is peppered with incredible neighborhoods, but only one could hold the top spot for recreational biking. Here’s why we can’t get enough of this northside gem:

Lakefront and Beach Access

Why drive when you can bike straight to the shore? Lincoln Park’s proximity to the lake means the beach is always within reach. Pack a picnic, dip your toes in Lake Michigan, or simply soak in the skyline view all without worrying about parking.

Long-Distance Biking Bliss

For cyclists craving a longer ride, the Lakefront Trail is a dream come true. With dedicated bike lanes that stretch for miles, you can cruise all the way from downtown to the northern suburbs or down to South Shore without a single car in sight. It’s pure, uninterrupted riding joy. Pro tip: Snag an apartment on the neighborhood’s east side for quick access. 

Explore Lincoln Park (The Park!)

Yes, Lincoln Park is a neighborhood, but it’s also home to the Lincoln Park—a massive green space packed with bike-friendly trails. Coast past the zoo (free admission, by the way), circle the tranquil North Pond, or pedal through the beautiful gardens. Every ride feels like a mini adventure.

Neighborhood Adventures

When it’s time to trade your helmet for a cocktail glass, Lincoln Park delivers. Bike to happy hour at a rooftop bar, cruise to your favorite coffee shop, or pedal to local boutiques for a little retail therapy. With so many spots just a short ride away, every day’s a “bike and see where it takes you” kind of day.

Additional Insights from our Agents and Buildings

We didn’t stop with our agents—we also surveyed over 250 of our building partners to find out what makes their communities bike-friendly. We’re happy to report that 65 of them responded with some great insights!

After reviewing all of the responses, we put these fun facts together.

Chicago’s Best Apartments for Bike-Lovers

When it comes to finding a place to live in Chicago, our agents know the ins and outs of every neighborhood—and all the best apartments to rent if you love to bike. After years of helping apartment hunters find their perfect spot, we’ve pedaled our way to these top picks for bike-friendly living.

Free Bike Rentals for Residents

• Solverre in Uptown
  Why own when you can borrow? Solverre makes it easy to ride Lakefront Trail with complimentary bike rentals for residents. Just five minutes from Montrose Beach, you may become a bicycling beach bum! 
• The Residences at Addison and Clark in Lakeview
  Need a bike for a quick ride to brunch on Southport Avenue or a lakeside picnic? Residents here also enjoy free bike rentals, perfect for spur-of-the-moment city explorations.

Closest to Bike Trails

• MiCA in Logan Square
  Nestled at the intersection of Milwaukee Avenue’s iconic “Hipster Highway” and the 606 Trail, MiCA is a cyclist’s dream. Whether commuting or joyriding, you’ve got miles of bike lanes and trails at your doorstep.

Most Well-Connected to the City

• West77 in River North
  City cyclists, rejoice! West77’s prime location means easy access to bike-specific traffic signals and dedicated lanes that guide you through downtown. Plus, the building has its own bike maintenance and repair station, making it easy to keep your ride in top shape.

Easy In and Out

• 3450 North Lake Shore Drive in Lakeview
  Want to hit the Lakefront Trail? This building is all about convenience with a dedicated bike entrance and exit, direct access to the trail, and free, secure bicycle storage. And with an active community of fellow cyclists, you’ll always have a riding buddy nearby.

The Best Paths, Routes and Biking Trails in Chicago

When it comes to trails and bike paths, Chicago offers everything from postcard-worthy lake views to lanes that keep you protected from those crazy city drivers. Here’s where to bike in Chicago:

Lakefront Trail

Stretching 18 miles along the Lake Michigan shoreline, the Lakefront Trail is Chicago’s crown jewel of cycling. From Edgewater to South Shore, you’ll breeze past sandy beaches, parks, and iconic skyline views. Morning rides come with unbeatable sunrise views, while an afternoon pedal is perfect for people-watching.

The 606 Trail

This 2.7-mile elevated greenway was once an old railway line, but now it’s one of the most Insta-worthy biking spots in town. Winding through Wicker Park, Bucktown, Logan Square, and Humboldt Park, The 606 is the ultimate urban bike trail. Cyclists love the art installations, gardens, and glimpses of the city’s unique architecture along the way.

North Branch Trail

Looking to trade city sounds for bird songs? The North Branch Trail has you covered. This peaceful, tree-lined bike path runs for 20 miles, connecting Chicago to the northern suburbs of Glenview, Morton Grove, Niles, Northbrook, Northfield, Skokie and Winnetka. It’s the perfect trail for those who crave a little wilderness without straying too far from the city.

Boulevard System

For a ride with a side of history, check out Chicago’s Boulevard System. Originally designed to connect the city’s parks, this network of wide, tree-lined streets now offers a scenic route through neighborhoods like Logan Square and Humboldt Park. Cyclists love the wide lanes, green medians, and historic architecture along the way. Plus, the city’s Boulevard Enhancement Program has been working to make these routes even more bike-friendly with better signage, improved paths, and added greenery.

Major Protected Bike Lanes

If you’re more of a commuter or urban adventurer, Chicago’s growing network of protected bike lanes has your back. Popular routes like Dearborn Street and Milwaukee Avenue offer cyclists a smooth ride through the heart of downtown and the city’s vibrant neighborhoods. Bonus: No dodging double-parked delivery trucks!

Chicago’s Best Resources for Cyclists 

Whether you’re a seasoned cyclist or just getting started, Chicago offers plenty of resources to make your ride easier and safer. Here are a few worth checking out:

• Divvy Bikes: Chicago’s Divvy bike-share program with thousands of bikes and hundreds of stations across the city.
• Chicago Department of Transportation (CDOT): Chicago Complete Streets provides maps of bike lanes, safety tips, and updates on bike infrastructure projects. 
• Bike Chicago App: Real-time updates on bike-sharing availability and biking routes.
• Active Transportation Alliance: A nonprofit advocating for better walking, biking, and public transit in Chicagoland.
• Chicago Park District: Maps and details about biking trails through Chicago’s beautiful parks

Biking in Chicago FAQ

How bike-friendly is Chicago?

Oh, Chicago’s pretty darn bike-friendly—and it just keeps getting better! From dedicated bike lanes to the ever-expanding Divvy bike-share program, it’s a city that’s giving two-wheeled commuters a lot of love.

What are the best places to bike in Chicago?

You’ve got options, my friend! The Lakefront Trail is a classic, with lakeside views, iconic skyline backdrops, and plenty of people-watching. Then there’s the 606 Trail, an elevated urban path that zips through Wicker Park, Bucktown, and Logan Square.

If you’re in the mood for a nature escape, the North Branch Trail will take you straight to the Chicago Botanic Garden. And let’s not forget the city’s historic Boulevard System, a scenic network of wide, tree-lined streets that’ll make you feel like you’re part of a Ken Burns documentary.

What is the length of Chicago’s main bike path?

That’d be the Lakefront Trail, which clocks in at a breezy 18 miles. Stretching from Edgewater in the north all the way down to South Shore, it’s like the expressway for cyclists.

What does the Chicago Streets for Cycling Plan include?

Think of it as Chicago’s bike-centric glow-up. The Streets for Cycling Plan 2020 was all about making sure cyclists have a safer, smoother ride. We’re talking 645 miles of bikeways, neighborhood greenways, and bike boulevards that’ll make your commute feel like a joyride!

Are bicycles allowed on sidewalks in Chicago?

Not unless you’re under 12 years old—sorry, grown-ups! The sidewalk is strictly scooter and tricycle territory. But don’t worry, Chicago’s streets have plenty of bike lanes and paths to keep you cruising more safely.

Tips for Biking in Chicago

Thinking of joining the pedal-powered masses? Excellent choice. Whether you’re commuting, cruising, or just out to flex those quads, these tips will keep your ride stress-free.

Best Times of Year to Bike

Chicagoans are a hardy bunch, but let’s be real…winter in Chicago isn’t for the faint of heart. The best time to ride? Late spring through early fall. May through October offers prime biking weather, with warm temps, sunshine, and plenty of lake breezes to keep you cool. 

Safety Tips for City Biking

• Know your lanes: Chicago has protected bike lanes, painted lanes, and shared lanes. Get familiar with what’s available on your route.
  
• Stay visible: Bright clothing and lights are your BFFs, especially at dawn, dusk, or in cloudy weather.
  
• Watch for doors: “Dooring” (when someone swings open a car door without checking) is a rite of passage for city cyclists—but it doesn’t have to be. Ride cautiously near parked cars.
  
• Mind the intersections: Always assume that a driver might not see you. Eye contact is a great way to make sure they know you’re there.
  
• Follow the rules: Biking in Chicago means obeying traffic lights and signals. Think of yourself as a very eco-friendly car.

How to Use Divvy & Bike-Sharing Programs

No bike? No problem. Chicago’s Divvy bike-share program has you covered with thousands of bikes stationed all over the city. Here’s how to ride like a pro:

• Download the Divvy app: It’s your key to unlocking bikes and checking station availability.
  
• Choose your ride: Traditional blue bikes are perfect for a quick errand or joyride. Electric bikes (aka e-bikes) give you that extra boost—great for tackling headwinds on the Lakefront Trail.
  
• Park responsibly: Return your bike to any Divvy station or park an e-bike at a designated bike rack. Just don’t be that person who leaves one in the middle of the sidewalk. No one likes that person.

Pedal Into Your Perfect Apartment

There’s no doubt about it—Chicago is a dream city for urban cyclists. From breezy lakefront rides to scenic neighborhood trails, you’ll never run out of paths to explore. And when it comes to finding a bike-friendly apartment? That’s where we come in. Give us a shout and let us match you up with the perfect place for you and your two wheels.