How to Safely Explore 3 of Chicago’s Best Neighborhoods by Bicycle

With nearly 300 miles of bike lanes, Chicago is a lot more bike friendly than it looks from the outside. If the heavy traffic and car-congested streets have scared you off thus far, we don’t blame you—it can be intimidating! But we are here to show you three safe bike routes that will allow you to explore some of the city’s best neighborhoods by bike in comfort and ease.

When biking in big cities, whether as a visitor or as a resident, it is important to approach your ride as safely as possible. Many cities around the US are taking action to make their communities safer for bike riders, and Chicago is one of the major US cities leading the way.

The bike infrastructure in this Midwestern hub has been steadily improving in recent years. From an increased investment in protected bike lanes to the roll-out of the city wide bike sharing program with Divvy, Chicago is welcoming the popularity of the bike movement with open arms.

Tips for Safe Bike Riding in Chicago
Keep Your Eyes on the Road

Chicago’s roads take a beating each year with heavy traffic and harsh winters, which means road conditions can be challenging at times. Potholes are a regular issue as well as road debris, so make sure you keep your eyes on the road as you ride to avoid any unexpected flat tires or damage to your bike. If you’re a regular Chicago rider, you probably already know which routes and sections of road have the best conditions, but if you are less familiar, stick to the main streets and bike paths.

Google Map is Your Friend

When selecting your mode of transportation on Google Maps, there is a bike option in Chicago which is surprisingly well integrated with the local bike conditions. Google Maps has a good handle on the various bike lines, which streets offer protected lanes and the safest routes for bikers in the city. Before taking off on a ride to a new destination, always check the suggested route that Google Maps provides as it's likely to give you the easiest and safest route. We've even created a custom Google Map dedicated to this guide to help map out your neighborhood ride!

Look for the Bike Path Signs

Throughout the city, you’ll start to notice small green signs that tell you how far from the nearest bike-friendly street or lane is. Keep your eyes out for these! You’ll typically find them clustered near major bike lanes, like the 606 Bloomingdale Trail or the Lakefront Trail, but they can also point you to bike boulevards (dedicated bike streets where bikes have the right of way) or good thoroughfares for bikes.

Now, onto the three bike routes through three excellent Chicago neighborhoods!

Wicker Park Neighborhood

Located on the northwest side of the city, Wicker Park is a well-developed neighborhood that offers a diverse array of things to explore. This is the kind of area to spend an afternoon wandering around and discovering hole-in-the-wall spots.

The so-called “heart” of Wicker Park is probably six corners, an intersection of 3 streets right near the CTA Blue Line Station at Damen Street, but one of the best perks of Wicker Park is that it runs along a good portion of the 606 Bloomingdale Trail, a newly constructed elevated bike and leisure path. This is Chicago’s version of the High Line! The 606 path is about 2.7 miles long and offers mini parks, street art viewing and beautiful views.

Wicker Park has a little something for everyone from affordable and high-end shopping to quirky gift shops and beautiful street art murals! Less of a touristic area and more of an area for locals to hang out, Wicker Park gives you a taste of how neighborhood residents like to spend their time.  


Points of Interest in this Chicago Neighborhood:

Chicago Downtown & Lakefront

Perhaps the most famous of all the bike routes in Chicago is the 18.5 mile long lakefront trail that runs almost the entire distance of the city. It starts in Rogers Park at the north end of Chicago and runs all the way along Lake Michigan down to Hyde Park on the South Side. It is a dedicated bike trail so you won’t experience any car traffic on your ride. This stunning trail can’t be beat—you get lake views on one side and skyline views on the other!

The 4 mile section of the Lakefront trail from Oak Street Beach to Roosevelt Road covers the main stretch of Chicago’s downtown area, which is what we will primarily focus on for this neighborhood. Although car traffic isn’t a concern with the lakefront trail, pedestrian traffic is a reality and you need to lower your speeds on this route to accommodate people walking their dogs, playing with their kids and going on a run. This is a popular route for runners and commuters so we recommend avoiding it at peak commute hours (7:30-9:30 am and 4-6pm) if possible.

Points of Interest in this Chicago Neighborhood:

West Loop Neighborhood

Located to the west of downtown Chicago, West Loop is a trendy and foodie neighborhood that is incredibly popular for dates, drinks and nightlife. It is home to some of Chicago’s best restaurants and famed chefs, so this is definitely the area to come for eating! Due to its popularity and status, it is a good idea to make reservations ahead of time.

The United Center is also located in West Loop, which is where the Chicago Bulls (NBA) and Chicago Blackhawks (NHL) play during the sports season. In the off-season, the United Center will also host music concerts, performing arts shows, and other big name events.

West Loop can easily be explored by bike, but it is also quite pedestrian friendly. You might find yourself hopping on and off your bike as you wander your way through this neighborhood because there is so much to enjoy! On the weekends, this neighborhood also offers streets festivals like the monthly Randolph Street Market, Greek Food Fest in the late summer or Taste of Randolph Street Food Festival in the early summer.

Points of Interest in this Neighborhood:

Regardless of which of these Chicago neighborhoods you decide to explore, there will be lots of unique experiences to enjoy. From delicious food to beautiful lakefront scenery to adorable boutiques, there is a little something for everyone to discover in Chicago and there is no better way to explore this city than two wheels! Biking around Chicago can be intimidating at first, but with this helpful guide and custom Google Map, you can feel confident and safe taking on the city streets.

(Check out the full route for this ride here)

Megan Arzbaecher

I am a travel and food obsessed Midwesterner living in Chicago and dreaming of the world. At only 29 years old, I am lucky to have traveled quite a bit — 6 continents, 46 countries and countless cities. Since I was young, I’ve had a sense of adventure and desire to explore the world. And now as an adult, I am a full-fledged travel junkie!

Launched in 2015 as a resource for millennials looking to maximize their limited time off, Traverse Blog empowers young travelers to experience food & travel adventures at home and abroad through thorough and thoughtful planning.

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