Things to Do in Blue Island

Creativity, collaboration, and carbs. The owners of Bespoke Cuisine advocate all three. According to their company manifesto, they also believe “eating well is a life skill,” “a little fat never hurt anyone,” and “anyone can cook delicious food.” The staff expounds on these and other company principles at public and private cooking parties, which give visitors a glimpse inside Bespoke’s commercial kitchen on Randolph Street's Restaurant Row without stowing away in a gravy vat. During these BYOB events, chefs help guests construct their own meals and teach basic cooking skills before the group retires to the dining room to eat the fruits of their labor. For those who prefer a hands-off experience, Bespoke also caters events or hosts them in a chic private-event space.

The massive schooner gently bobs in the Lake Michigan waters as the Chicago skyline towers on the shore. Onboard, hardy sailors relate tales of piracy and the rumrunners who filled the city's speakeasies as they train their passengers to tie knots and unfurl sails. Period lessons abound onboard the Windy, one of Tall Ship Adventures’ three ships helmed by U.S. Coast Guard-certified captains and crews. These nostalgic vessels are used to educate visitors on the lake's maritime traditions and explore coastal waters. Though the Windy plays host to themed adventures that include fireworks shows, pirates explaining city architecture, and pirates complaining about the popularity of pool noodles, captains also conduct day, evening, and night sails aboard the Red Witch, a wooden tall ship, and the Pianissimo. Crews strive to make each tour unique, with sailors who expound on their skills as well as performers and educators versed in history, maritime lore, art, and theater.

The Chicago branch of Gray Line's global sightseeing operation organizes a wide variety of tours and excursions throughout the Windy City, from architectural tours that send passengers coasting on the river and lake for sun-drenched educational cruises to shopping odysseys at Chicago Premium Outlets, where travelers can zip through more than 100 stores and restaurants after being shuttled to the retail utopia. Blues outings treat music lovers to raw licks, soul food, and real tears at celebrated concert venues such as Buddy Guy's Legends and Rosa's Lounge.

Gray Line's cherry-red trolleys transport visitors and residents alike to famous Chicago sites. Just north of the river, the vehicles idle before the Wrigley Building's sparkling white terra cotta façade, which in the 1920s stood as the first major skyscraper outside of The Loop. From there, the trolley may motor north to the John Hancock Center, where elevators to its observatory sweep guests 96 floors in 39 seconds. The trolley could also steer south to the Willis Tower, which lost its maiden name of Sears after being charmed by a passing cumulus cloud.

Slice of Chicago Pizza Tours takes a novel approach to acquainting visitors and locals alike with the region’s famous cuisine. Over the course of two hours, the team escorts pizza lovers throughout River North in search of delectable, cheesy morsels on a history-filled tour of three of the city’s most iconic pizzerias. The tour, which caters to all ages, leaves guests sated but not stuffed as they sample the various crusts, sauces, and toppings that formulate Chicago’s most famous food and second most popular raffle prize.

Proclaiming itself Chicago's only licensed jet-ski rental company, the outdoor enthusiasts at Windy City Watersports let visitors ride off into Lake Michigan from the tip of Montrose Beach. Every rental—which may be secured online or by flashing the lights atop the tallest nearby building in Morse code—includes life jackets, fuel, and storage for riders' possession.

Founder Amanda Scotese, an avid traveler and freelance writer for Rick Steves's renowned travel guides, delegates sure-footed guides to lead sightseers to iconic landmarks and down the back alleys and lesser-known nooks of the Windy City. Tours probe the ins and outs of the Chicago's neighborhoods, such as the Loop, where they fill eyes with the sights of world-renowned architecture and minds with the secrets of the Pedway, an underground walkway that connects buildings throughout the business district with the Ninja Turtles' lair. Blues tours explore historic neighborhoods on the North and South sides, and include diversions such as harmonica lessons from a bona fide blues blower.