Chicago Outdoor Activities

Owner Valerie Beck and her team of chocophile tour guides lead guests on walking tours of Chicago’s historical bakeries and chocolatiers, narrating the history of beloved sweets while walking an easy route through vistas of Chicago’s stunning architectural heritage. While snacking on samples of sweets, guests learn about chocolate’s storied history, the cupcake’s rise to prominence, and how to guess the flavor of filling inside Oompa Loompas by sight. Tours convene throughout Chicago’s many neighborhoods, giving guests a sneak peek into Chicago's signature confections, boutique shops, and mobile sweet-vending trucks. The chocolate or cupcake jaunts provide the perfect setting for a girls’ day out or bachelorette party, showing tour-goers the sweeter side of the city without getting caught in construction sites of shoddily built gingerbread houses.

Chicago Electric Boat Company's canopied, comfortable vessels navigate the scenic waters of the Chicago River, stirring up the reflected lights of the Loop's skyline in their wake. Groups lounge in plush seating as their elected driver easily steers the boat, bobbing along at cruising speeds of 4–5 miles per hour. Integrated sound systems pump out sailing music from iPods and other devices, and onboard accommodations create ample space for staging drinks, light refreshments, and Battleship tournaments. The company keeps a roster of certified captains and tour guides on hand and offers catering services from six local eateries, including Pizzeria Uno and Bar Louie.

Led by a team of knowledge-packed guides, Joyce Walks Chicago introduces out-of-towners and natives alike to the Second City's historic hoods during a full schedule of weekly walking tours. Each unique jaunt showcases a variety of hidden gems and well-known attractions, such as the Lincoln Park and Old Town tour, which weaves along the lakefront, or the Loop Art & Architecture tour, which lets participants examine The Picasso and solicit autographs from famous skyscrapers. The company's well-researched repertoire also includes seasonal treks that unveil some of the city's most decorated dwellings, affording tour takers the chance to absorb winter's twinkling lights and summer's stickball games between neighborhood pigeons.

Students are in good hands with Chicago Yacht Share's Captain Norm Zable, who brings 45 years of sailing experience to his classes. Through CYS's progressive program, students can be out on the water this summer by earning their American Sailing Association credentials. They then move on to bareboat chartering opportunities aboard the performance cruiser named It's Your Time. This vessel is a 2012 Jeanneau 379, which was named "Boat of the Year" by Cruising World in 2012 due to its combination of speed and luxury. Bareboat charters allow sailors to enjoy a multitude of perks, such as never having to worry about upkeep, storage, or inconvenient mutinies. If students aren't quite ready to skipper, captained charters are also available.

The bronze likeness of Michael Jordan—the Bulls' #23 and basketball's undisputed king—leaps into the air in front of the United Center, ascending into the annals of sports history. Across town, the sound of Babe Ruth's most famous homer rebounds off of the iconic walls of Wrigley Field. The Roman-meets-modern architecture of Soldier Field—where Walter Payton, Mike Ditka, and "The Fridge" grew to larger-than-life—straddles Chicago's lakefront. The resounding Black Sox scandal clashes with the victorious 2005 World Series Champs banners at U.S. Cellular Field, where the White Sox's famous exploding scoreboard towers above the Bridgeport neighborhood.

During an air-conditioned bus ride, local comedians wax historic as tourists are brought within earshot and camera-shot of Chicago's proudest pro-sports franchises. The Chicago Sports Tour parades from the North to the South side, brushing shoulders with famous ballparks and weaving through more than a century of athletic anecdotes and civic pride. Augmented by laughs and entertainment, it reveals more than the brick-and-mortar façades of the famous stadiums. The guides bring each building to life with fascinating anecdotes, and rides from one stadium to the next cover neighborhoods such as Wrigleyville, Bridgeport, and Little Italy—where fans and players alike eat, drink, and argue about their favorite peanut vendors.:m]]

The Urban Assault Ride challenges cyclists to speed from obstacle course to obstacle course across their city during eco-friendly scavenger hunts that benefit local charities. Teams draft a road map to try to thwart the competition and be the first to complete the race, pausing at a series of checkpoints, where they must surmount such active roadblocks as slip 'n' slides, bike jousting, and reciting the Iliad in Pig Latin. The first team to conquer each challenge and cross the finish line is declared the victor, but all participants celebrate their efforts at a lively after-party stocked with snacks, beer, nonalcoholic drinks, and prizes.