6 Chicagoland Neighborhoods for Cycling Lovers

Cycling is rabidly popular in Chicago, as it’s fabulous exercise, good for the environment, and helps you beat the ever-present traffic congestion.

We’re also lucky enough to have Divvy, the most extensive bike-sharing program in the US, which also includes e-bikes and electric scooters for when you want to switch up your two-wheel motion. 

If you’re looking to move to an area that’s more conducive to riding your bike to all of your favorite places, we’ve got you covered with this comprehensive list of the best Chicagoland neighborhoods with plenty of parks, trails, cycling shops, restaurants, and that certain ineffable something you’ll love. 

Lincoln Park

This world-renowned destination has it all — stunning lakefront views, miles of trails, a zoo, shopping, a huge park, botanical gardens, top-notch dining destinations, and so much more. 

What makes it truly unique is the abundance of green space and the charming mix of modern construction and historic homes. Once the northernmost outpost of the city, it’s now one of the most popular and affluent neighborhoods in the entire country

You can bike up to Insta-famous North Avenue Beach, cruise around the Alfred Caldwell Lily Pool, or reward yourself after a hard ride with the city’s best haute cuisine at Alinea, the only restaurant in town that boasts 3 Michelin stars.

Logan Square

Head northwest to this vibrant community and check out the many hip boutiques, retail bike and repair shops, eclectic housing, and artsy enclaves. 

Originally settled in the 1830s by farmer Martin Kimbell (the namesake of famously misspelled Kimball Avenue), it was annexed into the city proper in 1889 and renamed for a local military hero and politician, General John A. Logan.

Known for its wide boulevards and park-like atmosphere, Logan Square is rich with eateries, cool places to hang out, and three of the city’s most opulent churches in the “Polish Cathedral Style” — St. Hedwig’s, the former Cathedral of All Saints (now Covenant Presbyterian), and St. Mary of the Angels.

Hyde Park

Enjoy some amazing rides through one of our most picturesque community areas. Hyde Park offers gorgeous views, lakeside parks, and urban beauty, and it’s also where former President Barack Obama spent 12 years as a professor at the University of Chicago Law School.

If the weather is cooperating, be sure to roll by the Museum of Science and Industry, check out the cherry blossoms in Jackson Park, or get some fresh air and some drinks with friends at Castaways Beach. 

Plot a trip from Wooded Island, down the scenic Midway Plaisance to Payne Drive, and stop for a break at the Fountain of Time. Head over to the Washington Park Natural Area and Bynum Island to cycle some outstanding nature trails. 


Now a haven for foodies, Irish, German, Czech, and Polish families settled in this area in the 1850s and built a plethora of magnificent churches. An energetic and family-friendly neighborhood, it offers an unbelievably diverse array of dining selections, a mix of modern and historic housing, and a surprisingly affordable cost of living.

A quick ride from the iconic Monastery of the Holy Cross, you’ll find some of Chicago’s most tempting eating establishments where you can get anything from authentic Mexican to gargantuan gyros, traditional Italian fare, and Korean-Polish street food. 

Local hipsters love the Marz Community Brewing Company, a gathering spot that’s perfect for eating pizza, drinking craft beer, and an entertaining evening with friends. 


A bit more suburban, this North Shore community may be preferable for those who are looking for an area that’s got something of a college-town vibe. 

Only 12 miles from downtown proper, Evanston is home to Northwestern University and was a dry (no alcohol) community until 1972. These days, there are loads of places to wet your whistle, like quirky gastropub Peckish Pig. Sip a Randy Shandy and nibble on some whipped goat cheese and honeycomb on toast points before a leisurely afternoon adventure.

Bike west until you reach the water at beloved Juneway Beach, then ride north along the lake and check out South Boulevard Beach, Garden Park, Clark Square, and Burnham Shores Park. Stop to catch your breath at the lovely and secluded Evanston Beach between Dempster and Greenwood Streets.

Wicker Park

This charming and relatively small neighborhood is one of Chicago’s favorite gems. It’s a cyclist’s dream, with everything you need within a short ride. The area is rife with cafes, trendy shops, record stores, art galleries, and more. 

The 606 is a former railway track that’s been transformed into an almost 3-mile-long living work of art. Various installations and murals await the curious, along with specially-planted flowering trees and shrubbery. Pedal from Walsh Park, past Damen Arts Plaza, through Humbolt Park, and all the way to the Exelon Observatory. 

Lots of regulars ride to the famous Emporium Arcade Bar on Milwaukee Avenue for old-school video games, pinball, air hockey, foosball, and an impressive selection of craft beers and cider. 

Explore Your Home

Chicagoland residents love to ride, and despite the harsh winter weather, we’re one of the country’s most bike-friendly cities, with over 200 miles of lanes, the 18.5-mile Lakefront Trail, over 13,000 public bicycle racks, and hundreds of Divvy bike-share stations. 

Finding the right neighborhood to call your own can be challenging. You want somewhere that’s safe to bike or walk around but that’s also affordable, and offers all the amenities you want and need. 
That’s why you should partner with the local experts at Baird and Warner. We live and work in these areas and our agents can help you navigate Chicago’s many unique communities and discover the perfect one for your household. Give us a call today!

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