Tour of duty
No matter what relative is coming to town, you can wow 'em with one of these tours.
Granny’s a little freaked out you’re living alone in such a dirty, crime-ridden metropolis. Show her that even Chicago is home to a few good God-fearing folks on Chicago Neighborhood Tours’ Chicago’s Magnificent Churches. The tour covers the Prairie Avenue Historic District’s Howard van Doren Shaw–designed Second Presbyterian Church, a treasure trove of awesome Louis Comfort Tiffany windows and Arts & Crafts design. Reservations are required. Meet at the Chicago Cultural Center, 77 E Randolph St (312-742-1190, chicagoneighborhoodtours.com). Nov 7 at 10am. $50; seniors, youth ages 8–18 $45.
Recovering frat-boy brother
Most of the city’s art and culture would be lost on your doofus bro, but mention the Bears, and he’s suddenly spouting off stats and plays with the eloquence and enthusiasm of a poetry-slam finalist. Treat him to an inside look at historic Soldier Field—and the shiny flying saucer that apparently landed on top of it. Sights include the Doughboy statue, United Club and colonnades, Sky Suites, visitor’s locker room, West Den and more. Soldier Field, 425 E McFetridge Dr (312-235-7244, soldierfield.net). Available select dates Mon–Fri by appointment; $15, students $10, seniors $7, kids ages 4–10 $4, kids 3 and under free.
A.D.D.-suffering nieces and nephews
Great. Your brother dumped his brood of wild-child curtain climbers on your doorstep so he and his wife could indulge in a three-hour dinner at Moto. Rather than wreak revenge for not inviting you, show the tykes how much more awesome you are than their parents by taking them on one of O’Leary’s Chicago Fire Truck Tours. Led by retired Chicago fire captain George Rabiela, the excursions load kids onto real retired fire trucks for kid-friendly, open-air, informational tours of the Loop, weather permitting. Meet at 505 N Michigan Ave (312-287-6565, olearysfiretours.com). By appointment; $20, kids $10.
You might be embarrassed to take her UGG-wearing ass out with you to your local hip-as-hell coffeehouse/study hovel, but when it comes to shopping, she’s the one who knows what’s what. Impress her by showing off some of the city’s best homegrown fashions on one of Chicago ShopWalk’s Made in Chicago Designer Tours. Danielle Lutz, your fashionista guide, will take you to private studios where you’ll meet some of the designers, plus you’ll check out boutiques, sample sales even receive great discounts at local boutiques. Location varies (773-255-7866, comchicagoshopwalk.com). By appointment, $70.
Hacky Sacking high-school bud
His shirt reads “UW Bong Team” and he’s always hungry. This guy’s either got a tapeworm or he’s been out to lunch with Mary Jane again. Either way, take him on one of Chicago Food Planet’s Bucktown/Wicker Park Culinary Tours. You’ll be treated to tidbits about local history and architecture and, of course, make half a dozen pit stops to sample cuisine from local eateries. Bonus: With stops for dogs at George’s Hot Dogs, dessert at HotChocolate, pizza at Piece and more, none of the tastings should be too exotic for his picky suburban palate. Meeting location will be provided with required reservations (773-425-2727, tickets 212-209-3370, chicagofoodplanet.com). Wed–Sat, Apr–Nov; $42.
Your smart, successful sis is hard to impress; she did just get back from a pretty amazing internship with a senator on the Hill, after all. Dazzle her by going just a little closer to her all-time hero on Bobby’s Bike Hike’s Obama Bike Tour. It says it’s the only company granted permission to ride past the President’s home. Also, check out the University of Chicago campus, the Museum of Science and Industry, Obama’s barbershop and the Jackson Park basketball court where he would shoot hoops. Meet at Hyde Park Art Center, 5020 S Cornell Ave (312-915-0995, bobbysbikehike.com). Most days: difficult ride 9am, leisure ride 10am; $32, students and military $23, kids under 12 $18.