Order a Chicago Handshake: Malort Shot With an Old StyleWalk into any old dive bar and order a shot of Jeppson's Malort with an Old Style beer back. Locals will applaud, then watch your face fold in half.Food & DrinkMedium30 min
Pay Respects to the Shit FountainStand before Jerzy Kenar's bronze poo fountain at 1001 N Wolcott Ave in Bucktown, an artist's eternal plea to neighbors to scoop after their dogs. Yes, it really dribbles water.WeirdEasy15 min
Worship 30,000 ButtonsPop into the free Busy Beaver Button Museum at 3407 W Armitage Ave in Logan Square, the world's only museum devoted to pinback buttons. Find the weirdest slogan and report back.CultureEasy40 min
Find the Stained-Glass Windows in the PedwayDescend into the Pedway and find the backlit Victorian stained-glass windows beneath Randolph Street between State and Wabash, near the Macy's entrance. Daylight is overrated.Hidden GemMedium45 min
Find the Tin Man in Lincoln ParkHunt down all four Wizard of Oz statues scattered around Oz Park at Webster and Burling, including a Tin Man welded from old car parts. Author L. Frank Baum was a local.Photo HuntEasy30 min
Browse Chicago's Weirdest BookstoreLose yourself in the zines, comics and ephemera at Quimby's, 1854 W North Ave in Wicker Park, where the buyer favors the unusual, the aberrant and the lowbrow. Buy something strange.Local DetailEasy30 min
Eat Smoked Fish in a Parked CarOrder smoked shrimp from the one-room shack at Calumet Fisheries, 3259 E 95th St, then eat it in your car beside the bridge the Blues Brothers jumped. No seats, James Beard award.Food & DrinkBold1 hr
Visit the Fern Room at Garfield Park ConservatoryDuck into the free Fern Room at Garfield Park Conservatory, where Jens Jensen recreated swampy ancient Chicago with a hidden lagoon. The best winter hideout in the city.Rainy DayEasy50 min
Order a Volcano at a 1964 Tiki BarMake the pilgrimage to Hala Kahiki at 2834 River Rd in River Grove, the Midwest's longest-running tiki lounge, and pick one of 100-plus tropical drinks under the bamboo. No, there's no beer on tap.SocialBold1 hr 15 min
Crane Your Neck at the Nine-Sided TempleTake the train north to the free Baha'i House of Worship at 100 Linden Ave in Wilmette, a lace-like white dome with nine sides and nine gardens, open to everyone. Sit in total silence inside.FamilyMedium1 hr
Run the Lakefront Trail before the bikes wake upLace up at the Montrose end of the 18-mile Lakefront Trail and run south along Lake Michigan while the skyline turns gold. Stick to the runner's side, beat the cyclist rush hour, and let the lake wind decide how far you go.ActiveMedium45 min
Jog the 606 Elevated TrailThe 606, aka the Bloomingdale Trail, is a 2.7-mile elevated park built on a retired freight line floating above the northwest side. Jog its rubberized path past murals and treetops, then drop into Logan Square feeling smug about your shortcut through the air.ActiveEasy40 min
Get spat on by a 50-foot faceAt Millennium Park's Crown Fountain, two glass towers project giant Chicagoans' faces that purse up and gush water from their mouths into a shallow splash pool. Wait for the spout, position the kids (or yourself) directly in the line of fire, and accept your soaking with dignity.FamilyEasy30 min
Conquer the Slide Crater play gardenMaggie Daley Park's free three-acre Play Garden hides an Enchanted Forest, a pirate ship, and a tower-and-slide zone called the Slide Crater. Turn the kids loose, climb the nets yourself when no one's watching, and try to leave before sunset.FamilyEasy1 hr
Pet a goat at the free zoo's barnyardLincoln Park Zoo is free every single day, and tucked across the South Pond is Farm-in-the-Zoo, a working barnyard where kids can greet goats, ponies, and cows in the middle of the city. Visit the Dairy Barn, then loop the rest of the zoo without paying a cent.FamilyEasy1 hr 15 min