Explore the best cycling and bike touring routes in Raleigh, from scenic greenways to wooded trails and smooth city rides—perfect for a vacation on two wheels.
BEST CYCLING AND BIKE TOURING ROUTES IN CHICAGO
Thinking about bringing your bike on your next trip to Chicago? Good call. The Windy City is a hidden gem for cyclists—flat terrain, scenic lakefront, historic neighborhoods, and miles of protected bike lanes. Whether you're into casual rides or multi-day bike touring, there’s a route here with your name on it. This guide will show you the best bike paths, loops, and urban trails to explore Chicago like a local—on two wheels.
Lakefront Trail highlights
The Lakefront Trail is the crown jewel of Chicago's cycling scene. Stretching 18 miles from Ardmore Avenue in the north to 71st Street in the south, this path runs right along Lake Michigan, offering postcard views of the skyline, beaches, parks, and marinas.
What makes it special?
Besides being incredibly scenic, it’s car-free and well-maintained, making it perfect for riders of all levels. You can pedal past Navy Pier, Grant Park, Museum Campus, and South Shore Cultural Center—all without leaving the trail. Plus, there are plenty of bike-friendly cafés and rental shops along the way, so you’re never far from a snack or a tune-up.
Best segments to ride
North Avenue to Museum Campus – City skyline meets green space. Ideal for photos and quick sightseeing stops.
Montrose Beach to Navy Pier – Wide paths, fewer crowds, and beachy vibes.
31st Street Beach to 63rd Street – Less touristy, with more local flavor and relaxing park views.
Just remember, weekends get packed. If you're riding for peace and pace, hit the trail early on weekdays or before 10 AM on Saturdays. And always stay right unless passing—Chicago cyclists are fast and proud of it.
Neighborhood tours by bike
Want to really get to know Chicago? Ditch the tourist buses and cruise through its neighborhoods. Each area has a unique vibe, and the city’s grid layout makes navigation easy—even without GPS.
Top neighborhoods to ride through
Lincoln Park – Start at the conservatory and zoo, then weave through quiet streets lined with historic homes.
Wicker Park and Bucktown – Artsy, hip, and packed with murals and coffee shops. Great for stopping and snapping pics.
Pilsen – Mexican culture, street art, and serious taco game. Roll slow and take it all in.
Hyde Park – Home to the University of Chicago and the Museum of Science and Industry, with leafy streets and lakeside access.
Logan Square – Chill neighborhood vibe with boulevards, vintage shops, and dive bars. Perfect for late afternoon rides.
Tips for riding neighborhoods
Stick to bike boulevards and use Chicago’s bike map to plan routes with protected lanes. Always lock your bike—even if you’re just grabbing a coffee. And if you're up for it, try a self-guided mural or architecture ride with stops mapped out ahead of time. Apps like Ride with GPS or Komoot have solid pre-made tours for tourists.
Multi-day rides and touring
If you're the kind of traveler who packs panniers and dreams of long rides with epic views, Chicago has some killer touring options that start right from the city. With flat terrain and tons of trails that link to state routes, you can easily ride out for a few days and explore beyond the city limits.
Best touring routes from Chicago
North Branch Trail + Green Bay Trail – Ride from Chicago to the Chicago Botanic Garden, then continue up to Highland Park or even into Wisconsin. Total distance: ~40–70 miles depending on how far you go.
Illinois Prairie Path – A rails-to-trails classic. Head west to Wheaton, Aurora, or Elgin. Multiple branches and well-marked paths make it a great beginner tour.
Fox River Trail – Connect via the Prairie Path or Metra train. Winds through forest preserves and riverside towns like Geneva and St. Charles. Scenic and packed with spots to rest and eat.
Lakefront to Indiana Dunes – Want a real challenge? Ride the entire Lakefront Trail, then connect to trails that lead into Indiana. Camp or Airbnb near the Dunes and soak up lake views.
Touring tips and logistics
Always check the weather—wind off the lake can turn an easy ride into a grind. Pack extra tubes and layers, and take advantage of Metra’s bike-friendly trains if you want to skip the return ride. Chicago also has solid bike shops for last-minute gear: check out places like The Recyclery or Comrade Cycles for community vibes and quality repairs. And if you’re flying in, Midway and O’Hare both allow bikes as checked baggage—just pack smart and call ahead.
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