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Celebrate In Chicago This Weekend!

Looking for things to do in Chicago before or after the Rock ‘n’ Roll Chicago Half Marathon? We have some suggestions.

Written by: John Mendelsohn

Chicago, that toddlin’ town, is the biggest city in the American Midwest, a longtime stronghold of the Democratic party, and home to the world’s surliest airport employees, namesake of a popular blues style, and a fun place to visit, except in months when it’s absolutely beastly, like July and August and January and February.


Make the best of it by touring the city on Segways, self-propelled personal transportation devices designed for use in pedestrian environments. City Segway Tours – Chicago uses the latest, self-balancing generation of Segway — the i2. Ask for Steve! Absolutely Chicago also offers Segway tours.

For those willing and able to expend a bit more energy, Bobby’s Bike Hike invites visitors to see the sights on well-maintained bikes, with a safety-minded tour guide who knows when to shut up. You’ll see not only all the usual suspects  —Millennium Park, Oak Street Beach, Buckingham Fountain and the Sears (Willis) Tower — but also Oprah’s home, Hugh Hefner’s (his friends call him Ner) first Playboy mansion and a place where Al Capone used to like to drink. Tell them you want Hank as your guide; they’ll know what you mean.

Carl Sandburg called Chicago The City of Big Shoulders, but nowadays it might just as accurately be called The City of Remarkable Views, none more remarkable than that from the Skydeck on the 103rd floor of the Willis/Sears Tower. On a clear day, you can see 40-50 miles, into Michigan, Indiana, and Wisconsin, not that there’s much beyond a lot of cheese to see in Wisconsin.

The 50-inch flat screen monitors in the elevators make you feel as though you’re being shot into space. Hi-tech, high-powered telescopes are available for a closer look at the city. Non-acrophobes will enjoy the new Sky Ledge, a glass box that enables you to look down at the ground, 1353 feet below, between your own feet.

Things you can’t see from the Skydeck are visible from the John Hancock Center / Observatory. If you’re one of those who believes that alcohol makes even the most spectacular view a little more pleasurable, skip the observatory in favor of the bar way down on the 95th floor. The view from the bar’s ladies’ room may be the best ladies’ room view in all the world, but of course gentlemen are not welcomed.

Other view savorers may skip both of the above in favor of Aeroballoon Chicago, which invites one to gape at the Chicago Skyline and Lake Michigan from an anchored, helium-filled, state of the art balloon 350 feet above Navy Pier. As many as 17 passengers at a time can enjoy breathtaking 360-degree panoramas of downtown Chicago and Lake Michigan.

The Art Institute of Chicago offers not only a wealth of sculpture and paintings, but also enough antique furniture to keep antique furniture enthusiasts oohing and aahing for hours. Generally a better bet than the Museum of Contemporary Art.

The Millennium Park, completed four years too late for the last millennium and 996 years too early for the next one, includes a large amphitheatre, shops, and dozens of interesting art pieces. The Crown Fountain area is popular with children, while “The Bean,” as Chicagoans call Cloud Gate, is a 110-ton elliptical sculpture forged of a seamless series of highly polished stainless steel plates that reflect the city’s famous skyline and the clouds above. A 12-foot-high arch constitutes a sort of “gate” to the concave chamber beneath the sculpture, in which a certain kind of visitor delights in seeing his image reflected distortedly.

Lincoln Park Zoo is an exemplary urban zoo, made even better in recent memory by the addition of the great ape house, with huge modern glass enclosures that allow you to get up close and personal with the animals, to their considerable dismay. The bird and reptile houses are also noteworthy. Be forewarned that the pigmy hippo, popular with the kiddies, is rather a showoff. There’s a good food court, and seagulls are unlikely to swoop down out of the sky to snatch your hot dog away, as they do at the San Francisco Zoo, for instance. Afterward, the botanically minded will want to sneak a peek at the indoor gardens and the orchidae room!

Wrigley Field, the second oldest major league ball park in the country, is conveniently located beside a CTA stop. Its amenities aren’t going to win any prizes — there are troughs in the men’s room, rather than personalized urinals — and the food selection isn’t sensational. The fans are appealingly boisterous, though, and Cubs manager Lou Piniella throws a wonderful tantrum.

Shoreline Sightseeing offers both a Lake Michigan tour at dusk and an architectural river tour during the day. On the former, you’ll enjoy views of the Chicago skyline that you may well be tempted to describe as awesome. There’s booze on board, and a band.  Be sure to wear sunscreen and/or bring a hat on the river cruise, as the boat may not offer any covers. Don’t worry about which side of the boat to sit on, as you return the way you came.

On the official Chicago Architecture Foundation River Cruise, aboard Chicago’s First Lady, CAF-certified volunteer docents tell you all about the most architecturally notable buildings on the river.  Don’t worry if you don’t know Mies van der Rohe from a hole in the ground; the docents are trained to make everything enjoyably comprehensible to all! If you’re waiting for the next tour and feeling peckish, grab a “Chee-buger” at the nearby historic Billy Goat Tavern. If it looks like rain, grab the seats at the rear of the top floor, by the stairs, so you can dash downstairs and get a seat inside at a moment’s notice.

Guests on the Progressive Dining Tour are chauffeured in a stylish coach bus to enjoy hors d’oeuvres at one restaurant, entrees at a second, and dessert at a third. At each, your table will be waiting eagerly for you!

Chicago Food Planet Food Tours’ Bucktown/Wicker Park tour fills you with scrumptious local delicacies while exposing you to much of cultural and architectural interest. Have a small breakfast to leave plenty of room for a whole Chicago hot dog, a 10-oz cup of a delicious iced chocolate drink with a homemade marshmallow, an antipasto pasta salad, a slice of New Haven-style pizza, a falafel on half of a large pita, and a small scoop of the best ice cream in the Midwest. The bad news is that you’ll wind up bloated about a mile and a half from where the tour began, and thus might become dizzy and disoriented trying to get back to where you once belonged.

Inevitably, given that Chicagoland has more hot dog restaurants than McDonald’s, Wendy’s, and Burger Kings combined, you’ll also get a hot dog on Tastebud Tours’ small guided personal walking explorations, during which you’ll learn, if that’s the right word, that the brownie was invented locally, and will visit appetizing restaurants and bars, and will browse at shops much beloved by local foodies. During your four-hour tour, you’ll get some deep dish pizza, gourmet cupcakes, and root beer to rival the ice cream on the Chicago Food Plant tour.

Supernatural Chicago isn’t a tour, but rather a one-man theater show featuring self-described necromancer Neil Tobin. Neil is likeable enough, but his show is actually more about sleight-of-hand tricks than about the stories of the paranormal they’re meant to enliven. Kids and even teenagers are likely to find the pacing a bit sluggish, and the nightclub in which it takes place will evict under-21s the minute the show is over, meaning that, like so much in life, it’s very much a use-‘em-or-lose-‘em proposition with your free drink tickets.


The multitalented John Mendelsohn is a writer, graphic artist, and singer/songwriter who lives near New York City. Check out his new song collection, Sorry We’re Open.