Cycling in Chicago, a bike trip to enjoy this Windy City

Chicago’s biking infrastructure makes exploring this American city for cyclists, a pleasure, Cycling Country's Maggi Jones finds

Cycling Worldwide Bike Tours

Sustainability & Local Tour Operators

Day trip by Bicycle in American CitiesGoing green whilst on holiday for many means having fallen foul of Montezuma’s revenge on a choppy cruise ship. However, with our sky rocketing gas bills and polluted environment there is no better time than now to look towards sustainable holiday options. The City Bike Day Trip with a local operator is a perfect option and you can do it almost anywhere in the world these days. Thus, it was with relish that on a recent visit to Chicago, I found myself clambering, not on and off the expected rumbling diesel guzzling tour bus, but a powder blue retro circa 1950’s bike with wide white walled rubber tires and best of all, a jingley-jangley bell.  Taking an easy bike trek on your visit through one of the Great Lakes’ premier metropolitan centres is one of the best ways to get your bearings and explore this vast place of parks, museums, galleries and countless historical avenues.

Cycle Tour in Chicago
“Now I know some of you were nervous when you showed up and saw only one bike!” says Chad of Bobby’s Bike Hike pointing to the solitary bike parked beside him, as the group of us arrived this bright morning at the meeting point of Chicago’s Water Tower. It is an easily recognizable meeting place at the end of the Magnificent Mile, Chicago’s prestigious shopping district. The stone tower itself looking more Scottish castle than Chicago Victorian, was one of the few buildings to survive the devastating fire of 1871. “But fortunately, we have one for everyone,” he continues, part of a witty repertoire that lasts the whole three hours of the tour and introduces us to all the sights that make this city one of the finest in the U.S. for both sightseeing and cycling, as advocated by several bike enthusiast magazines.

An American City for Cyclists

Chicago City Bike Tour
Chicago’s motto “city in a garden” is certainly no misnomer. The town has several large green spots including Millennium, Grant and Lincoln Parks for residents to relax in after a week of making money. The driven work ethic arising from its 19th century pioneering spirit of the European immigrants that flowed here still exists and this morning several briefcase clad brokers have already rushed past by the time Chad has finished his talk on safety and basic road rules.

Cycling and Eating, go Hand in Hand

The city, which saw its population explode from 30 thousand to 300 thousand in a few short decades in the late 1800s, is home to a multicultural electoral constituency with sizeable Korean and East Indian communities, and the largest population of Polish residents after Warsaw. 
Try all the restaurants in Chicago on your cycling trip there
For the visitor this only leads to one thought, “What shall we try for dinner?” as the supply of options is endless as we glide past sushi, Italian pizza, breakfast cafes, Jewish cuisine and New Orleans’ spicy Cajon restaurants that saturate the River North district.

Stopping for a coffee in an American Diner

Cycling Chicago’s Varied Landscape

Biking around ChicagoCycling the leafy suburbs that extend north of the main centre gives you an idea of how varied the landscape is and we go from colossal skyscrapers to colourful clapboard cottages in a few short kilometres. This is truly a showplace of architecture as every city corner on a sunny day features more than one interesting shadow thrown down due to such luminaries having an influence on the city’s blueprint designs. From Frank Lloyd Wright to Frank Gehry, Chicago’s skyline is a virtual encyclopaedia of great architectural precedents and modern designs like the Sears Tower, a glass Goliath at 110 stories.

The Fiery History of Chicago

Cycling in Chicago
Chicago, originally a frontier town, situated on Lake Michigan of the Great Lakes (a body of water so big you could confuse it with an ocean) was named after the indigenous native word of Chicagal, a label for the local wild onion. It soon grew into an industrial town serving the expanding transportation and produce needs of the growing west in the burgeoning United States of the 1800s. However, the chance meeting of Mrs. O’Leary’s cow and a lantern in the shed, as the popular tune goes, certainly led to a “hot time in the old town” that night, and with the parched landscape and wooden buildings of a dry October 1871, Chicago became an inferno. Fortunately, Chicago’s residents didn’t let a little thing like complete devastation leaving 90,000 homeless get in their way, and the town rose again to be one of the most important trade centres in the entire country. You only have to stroll past the busy lobby of the art deco inspired Chicago Board of Trade (CBOT) building which still hosts one of the few trading pits where the stock exchange brokers in their multicoloured jackets exchange billions of dollars of futures every year.

Woohoo Ring that Bike Bell!  

Alex Calder Sculpture, "Flamingo"
However it wasn’t all work and we glide past Hugh Hefner’s place, the creator of one of the most popular “girlie magazines” in America. The original Playboy Mansion is an innocuous brick building, looking respectable in this tree lined exclusive residential area. Home to the free love 1960’s microcosm of sexual excesses and bohemian lifestyle alongside the cold war intrigue era, stories of trysts in the James Bond secret compartments, leopard print sofas and a front doorbell that read “if you don’t swing, don’t ring,” abound. Hefner sold it to Chicago’s Art Institute for one dollar in order to go to California in 1978. “After all Hef is a silk pyjama kind of guy and Chicago is definitely a flannel set place,” Chad jokes as we move past the rich-set walking their afghan hounds and chatting on mobile phones.


Easy Cycle Tour in a Big American City

Exploring Chicago on Bike past older neighbourhoods
Heading out of the River North borough, we roll easily. It is a comfortable, flat ride (the generously wide cushy saddle is a bonus) and you don’t even have to break into a sweat. This is advantageous as this lakesides weather can be unpredictable with scorching summer days and winter days where the thermometer plunges as if doing an impressive leap off a high diving board. Interestingly, the windy city moniker that most people associate it with doesn’t come from any particular climatic pattern, having more to do with Chicago’s showcasing of the World Columbian Exhibition of 1893 and the boastful hot air her politicians spouted in order to lobby for it. However, it was this Fair that added to the skyline a rounder shape than its squared granite skyscrapers. Down at Navy Pier, a little jutted out piece of amusement park, where you get both Royal Shakespearian entertainment and “Bubba Shrimp” meals, her elegant Ferris wheel turns. Today’s wheel is only a half replica of the original design built by Mr. Ferris himself for the world’s fair.

Recorded as being 250 feet in diameter with railway-sized cars it would have been a sight, leaving the visitors agape at its immensity. A stance they would have been used to in Chicago no doubt by the end of their visit as the city became home of the first 19th century skyscrapers. In a country where a couple of floors produced sighs of wonderment, one can only guess at what was said at the 16th or 18th floor creations of this town during this time.

Today’s scaled down wheel still is attractive, especially so in the setting sun that illuminates its profile and coats everything in its east-west axis with molten gold.  As this wealthy town moves from being paved in bullion to a platinum vibrancy of bustling nightlife and glowing street lamps, the best vantage point is essential and one of the finest is the Hancock Observatory’s 96th floor Signature Lounge. Here for a price of a few drinks, you can relax and take in the alchemist Mother Nature truly is.

Cyclists come in all Shapes and Sizes

Bike Tour down Chicago's Lakeshore
For the picture snapper, Chicago’s skyline is awesome and luckily there are several panoramas to view (some actually not up in the clouds thankfully for vertigo sufferers). We follow each other in a rolling line of 1950’s powder blue and cream fendered bikes out to a sandy spit on North Avenue Beach that everyone scrambles to get their camera out for and fit the rising forest of high-rises into their viewfinders. The groups of us out on this day ride are pretty varied ranging from a couple just finishing their triathlon training to another who hadn’t ridden bikes since 1970’s banana seats were vogue, but we cheerfully follow each other in an easy pace affording a great chance to peer around at the scenery lazily moving by. 

Ride on Bike to Chicago's beaches

Chicago a City for Cyclists, Trying to go Green!

Chicago is A City full of Gardens to Cycle
Biking offers one of a myriad of alternatives to seeing this multi faced city as well as making us all feel a little bit more healthier doing it. Though upon saying that the toned bronzed bodies soaking up the late summer sun on the Lincoln Park beach show these city dwellers are already in full support of outdoor living. The beach stretches for miles, bordered by the greenery of Lincoln Park and Lake Michigan lying beguilingly, a flat calm in which the buildings are mirrored. Lincoln Park renamed after Abraham Lincoln’s assassination is a joyous green in the summer alive with roller blades (Chicago is the birthplace of this sport) and the happy shouts from baseball playing families (home to 2 national league teams, including the former 2005 World series champions, the White Sox). Here the large bronze statue of the noble president is supposed to be one of the most lifelike (his 6 foot 4 inch frame looking relaxed in a backdrop of trees). The park also holds the world’s biggest free zoo, but we have no time for this as we pedal by the gaggling geese on the lawn.

Building Cycling infrastructure in North American Cities

Cyclists in Chicago use a Bike Centre
Fortunately, America’s streets are wide and afford a comfort level for city cycling that claustrophobic cobbled streets of Europe don’t and we gaze around feeling non threatened by the big American motor vehicles that move past. The city started to increase its cycling profile in part thanks to former Mayor Richard M. Daley, a cyclist himself who vowed to make Chicago, “the most bicycle-friendly city in the country.“ Working to create a strong infrastructure for 2 wheel trippers and commuters, the mayor’s advisory council worked closely with citizen’s groups, cycling associations (they also tried to win the 2016 Olympics) and the board of transportation to create an integrated system that benefits cyclists. Chicago currently has more than 200 miles of on-street protected or shared bike lanes, off street trails (including the 30km Lakefront Trail), more than 13,000 bike racks, and sheltered, high-capacity, bike parking areas at many CTA rail stations., a cycling ambassador program and summer Bike festivals, Critical Mass demonstrations, bicycle themed cafes and Millennium Park’s $3.1+ US million “Bike station” (with showers, mechanics and parking for 300) are part of the landscape. Plans for 2020 is impressive with The Chicago Streets for Cycling Plan calling for a 645-mile network of biking facilities to be in place by 2020 to provide a bicycle accommodation within half-mile of every Chicagoan.

Only visiting Chicago, No problem, get on that Bike

For local and international 2 wheel trippers it is perfect for those wanting something different in their holiday visit. “Cycling is a perfect way to see the country and become friends with interesting people. It’s healthy and it does nothing but good,” says Jeremy Lewno, the founder of Bobby’s Bike Hike. From joining a bike tour whilst in Germany, to buying a bike and making it his sole form of transportation, Jeremy believes that it’s important for the company to be an ambassador of such a sustainable tour option. “Our guides are great people, but more than that, they are all involved in cycling on both a personal level as well as in business.” He certainly has picked the right city to start such a venture, for luckily Chicago is at the forefront of seeing cycling as a viable city transportation form and recreation for tourists. The trails that wind around Chicago will take your entire vacation to explore.
Go out and enjoy and be converted to the holistic cycling experience and plan for that Cycling Utopia!

Travel Tips for the Cyclist in Chicago

Chicago City Bike Trip There are several ways to explore the city by bike. Bobby’s Bike Hike meets daily and offers both day and evening tours in the summer, spring and autumn months.

Millennium Park’s north east corner has cycle facilities at McDonald's Cycle Center which also provides bike hire, lockers, etc. 

If you bring your own, buses are equipped to carry bikes and there are several options to get into and around the city centre. Maps are available at tourist offices and the city’s official tourist website is helpful regarding information on upcoming events.

When to Go: Chicago is a year round destination with cultural events, festivals and attractions throughout the calendar, including the Jazz festival in September and the Magnificent Mile winter lights festival through November. Temperatures throughout the year are ever changing so come prepared for the season. Generally cycling tours and rentals slow down during the snowy winter months!


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