Explore Chicago's neighborhoods with these top tours
With 77 community areas, Chicago is—without question—a city of neighborhoods. And while an urban existence makes it easy for you to never leave the boundaries of the 'hood in which you live, it would be a shame to miss out on the cultural diversity thriving outside your comfort zone. I often love to just hop on the L, get off at a random stop and start wandering, but if you’re the kind of person who requires a bit more direction, check out these organized tours that highlight Chicago’s finest nooks.
Get fit while exploring
The Chicago Cycling Club
Arguably the best way to see the city is by bike, but it can be intimidating to hit the pavement on your 10-speed solo. The Chicago Cycling Club (CCC) offers rides every Saturday and Sunday from April through October, as well as a handful of mid-week evening rides. Friendly and informative CCC members, who are familiar with the rules of the road, lead the group rides, which can range from having just a few people to a whole gaggle of cyclists. The distance and speed varies, depending on whether the ride is mainly for social or training purposes, but the trips almost always involve tours of Chicago neighborhoods and often the chance to score some tasty eats. The first excursion I ever took with the club, the Superdawg Ride to Chicago’s legendary hot dog-slinging drive-in, takes place June 29 and will wind its way through Albany Park, Jefferson Park, Norwood Park and Edison Park. For a complete schedule of rides, click here. Most rides are free, but why not support the cause and become a member by forking over the $20 annual fee.
Fleet Feet’s Historic Runs
I’m not a big fan of jogging with a group, as it usually means gasping for air while trying to hold a conversation with a complete stranger. But, when someone else is doing the talking and I get a history lesson to boot, I’m a happy camper—er—runner. Fleet Feet, a store for all things running-related, hosts a handful of four- to six-mile organized runs that tell the history of a neighborhood. Most of the tours leave from the store's Lincoln Square location and cost $5. The next tour, slated for September, involves a trolley ride to Jackson Park on the South Side, where the runners will explore the scene of the World's Columbian Exposition of 1893. For the entire schedule, check out Fleet Feet's website.
Fun for foodies
Rebecca Wheeler’s Ethnic Market Tours
If you’re the kind of person who’d rather talk about the construction of pastry than a historical building, you may want to skip the traditional tours and go straight for one that focuses on grub. Longtime chef, cooking instructor and culinary traveler Rebecca Wheeler hosts foodie-focused tours of some of Chicago’s great chow ‘hoods, including the Devon Avenue strip flanked by Indian restaurants and Argyle Street’s Vietnamese treasures. Though the three- to four-hour tours ring it at a relatively pricey $100 per person (minimum of four people required), the fee includes a light lunch and snacks, and you’re bound to walk away with recipes, history lessons and the skills to navigate any ethnic market in the city. For a first-person account of the tour of Argyle Street, check out this story here. To schedule a tour, call or email Rebecca at (773) 368-1336 or beccawheeler@comcast.net.
Best bet for visitors
Chicago Neighborhood Tours
The Chicago Office of Tourism offers a bevy of affordable tours ($20-$50) of the city’s great neighborhoods year-round. From Wicker Park and Bucktown to Pullman and Bronzeville, the tours cover historic ‘hoods on the North and South Sides and run about three hours long. The office also offers “Summertime Samplers,” where you can knock out three neighborhoods in one afternoon, like a trifecta tour of Chinatown, Greektown and Little Italy that’s available every weekend summer-long. A smattering of special interests tours, covering topics like the Great Chicago Fire, churches and the city’s Irish history, will make any out-of-towner swoon, though the tours are enlightening enough to not bore locals. Tours depart from the Chicago Cultural Center, usually at 10 a.m. For more information or reservations call (312) 742-1190 or visit the official website.
Other fun-filled tours of Chicago 'hoods:
- Bobby's Bike Hike offers a Lakefront Neighborhoods Tour that winds through popular attractions like Lincoln Park, North Avenue Beach and the Gold Coast. You can't miss the bikers: The group of mostly tourists climbs on bright blue cruisers and always seems to be having a blast.
- The Chicago History Museum has walking, boat and bus tours, but why not take a page out of my book and sign up for an L Tour? Guests hop on a certain train line and exit at a few strategic stops leading to the best sights the neighborhoods have to offer. Of course, you can expect plenty of historical trivia along the way.
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Explore Chicago's neighborhoods with these top tours
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