Chicago, IL Motorcycle Rental

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Chicago, IL Motorcycle Rental

Largest Selection of Motorcycle Rentals in Chicago, Illinois

Chicago is one of those few American cities that truly is a cultural capital of international repute. Although you wouldn’t be able to tell just from looking at the concrete skyscrapers of Chicago, the “Prairie State” of Illinois offers anyone on the back of a motorcycle rental midwestern stretches of scenery. 

Ranging from quaint farmland to cool waterside haunts, the Summer On The Rivers motorcycle route will take you on a 180-mile loop through the most midwestern parts of Illinois and neighboring Wisconsin. If iconic routes are more your fancy, Historic Route 66 is an essential ride for any serious motorcycle enthusiast. Once you rent a motorcycle, you don’t have to worry about anything except seeing some beautiful fields and a whole lot more in the Prairie State!

Riders Share is the new way to rent Chicago motorcycles. Rent online in minutes instead of waiting hours at the rental counter. We offer lower-priced motorcycle rentals belonging to real riders like you. We are a peer-to-peer motorcycle marketplace with a huge selection of motorcycles to choose from in Chicago.

Best Motorcycle Rides in Chicago

Don't be intimidated by the hustle and bustle of Chicago's urban core. There are plenty of scenic routes that motorcycle riders can take in and around the city, such as Lakefront Trail, Route 66, Sheridan Road, and Starved Rock State Park.

Lakefront Trail

Arguably the most popular motorcycle route in Chicago, Lakefront Trail offers an 18-mile stretch along Lake Michigan. Chart your path by starting at the north side of Ardmore Avenue and catching some of the city's top landmarks, like the Navy Pier and Grant Park, before working your way down to the south side.

Route 66

This iconic road slices through America's Heartland. This 2,400-mile route starts in downtown Chicago and ends in Santa Monica, California, offering the quintessential American road trip. Popular stops include Chicago's western suburbs, the Illinois countryside, and the Dixie Truckers Home in McLean, a historic truck stop and restaurant serving road trippers for nearly 100 years. If you're a trucking enthusiast, Dixie Truckers Home is the mecca.

Starved Rock State Park

Although a bit further away (100 miles southwest of Chicago), Starved Rock State Park is a rider's favorite. It boasts 13 miles of hiking trails, winding roads, waterfalls, and jaw-dropping rock formations as far as the eye can see. So for a break, hit up the Starved Rock Lodge and grab a piece of Route 66 memorabilia, check up on your motorcycle gear, or replenish with food or drink.

Sheridan Road

Cutting through Lake Michigan's North Shore, Sheridan Road offers a 30-mile stretch that runs through some of Chicago's most popular suburbs, including Evanston and Highland Park. We love it for its diverse topography, equal parts lake, and light forest. Be prepared to practice your cornering ability with its maze of winding roads.

For a complete list of day trips in and around Chicago, check out the Best Motorcycle Routes Near Chicago. And for longer trips on Route 66, we got you covered. 

Best Places to Visit in Chicago

Chicago is one of the more dynamic cities in the country, offering the best urban and scenic routes. Visitors and residents can enjoy top spots like Lincoln Park, the industrial-heavy West Loop, hipster Wicker Park/Bucktown, luxurious Streeterville, and historic Hyde Park with its quaint tree-lined streets.

Be sure to ride your bike to a Chicago sporting event, comedy shop, or just to eat one of their famous hot dogs or pizzas. 

Best Motorcycle Hangouts in Chicago

The city of Chicago is full of historical and contemporary motorcycle hangouts attracting riders of all skill levels. Here are some of our favorite ones:

  • Jimmy Mack Bar
    Affectionately known as "Bo's Jimmy Mack Bar," strategically located near Lakeshore Drive, this bar offers a laid-back atmosphere and an outdoor patio space with enough room for your motorcycle. Kudos for their signature Jimmy Mack Burger and endless beer specials.
  • Twisted Spoke
    The Twisted Spoke is one of Chicago's most popular neighborhood biker bars. Located in the city's West Town neighborhood, it is well known for its massive whiskey collection with over 500 different kinds, along with 50+ beers on tap. Plus, there's plenty of motorcycle memorabilia, including vintage motorcycles and an entire wall lined with license plates. Of course, no visit to Chicago or the surrounding areas is complete without enjoying a beer or burger at Twisted Spoke.
  • Delilah's Chicago
    Located in Chicago's eclectic Lincoln Park neighborhood, Delilah Chicago offers a punk band-style atmosphere attracting riders from all across the county. It may even have a more impressive collection of whiskeys than Twisted Spoke, with 800 varieties and counting. Not to mention 300-plus types of craft beers. You can't get any better than Delilah's Chicago for the ultimate resting spot.

Best Times of Year to Rent a Motorcycle in Chicago

With Chicago's blistering cold winter temperatures, we highly recommend renting and riding from June to August, where temperatures average in the mid to high 70s °F. Spring is okay, albeit more unpredictable, with occasional cold fronts and rainy showers.

Tips for Renting a Motorcycle in Chicago

One of our best tips for renting a motorcycle in Chicago is to be aware of its unpredictable weather. Riding during the winter requires a well-insulated jacket (think synthetic or down) with water-resistant materials (e.g., Gore-Tex). Plus, you'll be battling large wind bursts, so we highly recommend CE-rated shoulder/elbow/back armor and adjustable cuffs and collars to deflect wind better.

Earn Money from Your Chicago Motorcycle

Riders Share allows motorcycle owners and riders to monetize their motorcycles or book their next ride with a user-friendly platform.

With renters earning an average of $150 per booking, earning thousands of dollars a month by renting out your motorcycle is not out of the question.

Take advantage of Riders Share's large community of like-minded motorcycle enthusiasts, list your bike for rental, get vetted/approved within hours, and start earning money today!