The Frisky Guidebook: The Windy City

The best Chicago date ever might have been the one in Ferris Bueller’s Day Off. Really, how can you beat a Ferrari, a Cubs baseball game, a fancy meal, and “Twist and Shout”? But for the kind of fun even Cameron would enjoy (well, if he had a girlfriend), try these Chicago spots, and do your best to avoid the Magnificent Mile, unless you like friendly tourists.


iO Theater
3541 N. Clark St.

There are plenty of high-production shows in Chicago, but the city is known for its improvisation theater. Head to the iO Theater for a taste of legendary long-form improv (alums include Tina Fey, Amy Poehler, and The Upright Citizens Brigade). Our sexy pick? Children of a Lesser God, where four retired cage dancers explore their rich past.

Hot Doug’s
3324 N. California Ave.
(773) 279-9550,

Hot dog lovers unite! The best dog in town can be found at Hot Doug’s, where there’s always a new menu of sausages, including such greats as the gyros sausage with spicy raita and olive tapenade, and the beef landjaeger with bacon-garlic mayonnaise, Leyden cheese and crispy fried onions. Don’t forget an order of their specialty, duck-fat French fries — sounds gross, tastes delish!

The Museum of Holography
1134 W. Washington Blvd.
(312) 226-1007,

If you can’t be cheesy with a date, what’s the point? The Museum of Holography exudes sweet irony. Check out the hologram of Chicago native Michael Jordan, then take home a Beethoven hologram as a souvenir of the date.


Hotel Allegro
171 W. Randolph St.
(312) 236-0123,

This recently renovated hotel is in the heart of the city, and its modern style screams “sexy.” Create an “In The Mood” playlist on your iPod, because each room has a bedside docking station, not to mention a Jacuzzi spa tub featuring Mr. Bubble bubble bath.

The Peninsula
108 East Superior St.
(312) 337-2888,

Got some extra cash and really want to treat yourself? Spend a night in Swanksville. The lobby alone has 20-foot-high gilded ceilings and floor-to-ceiling windows facing Michigan Avenue, a shopper’s paradise. The pool has been voted the best in the city. One tip: Try not to spend your entire weekend in the bathroom, where you can soak in the deep tub while you watch your steam-free television or chat on the hands-free phone.

Windy City Urban Inn
607 W. Deming Pl.
(773) 248-7091,

If you’re looking to head out of the downtown Loop, go to Lincoln Park, one of the city’s hippest neighborhoods. After a night on the town, it’ll be nice to get a good night’s sleep at this urban B&B, where rooms have fireplaces and eclectic furniture. Plus, the breakfast buffet is delicious.


The Violet Hour
1520 N. Damen Ave.
(773) 252-1500,

Speakeasies have a certain forbidden mystique about them — and that’s exactly what you’ll find at The Violet Hour. This wood-paneled bar is a little tricky to spot since there isn’t a sign, but it’s worth the hunt — the cocktails are made to perfection, using homemade bitters, simple syrups, and twice-filtered ice cubes.

Empire Liquors
1566 N. Milwaukee Ave.
(773) 278-1600,

Somehow, this Wicker Park bar makes the dank-warehouse look feel inviting. They serve everything from beer and champagne to create-your-own spiked Italian sodas, and the energy picks up when the DJs hit the booth. We love Dance Party Magic night.

Guthrie’s Tavern
1300 W. Addison St.
(773) 477-2900

This low-key neighborhood bar comes equipped with a nautical feel and dim lighting, and the latter is a must if you plan on making out. Grab a drink from the bar’s extensive beer list, then snag one of the bars’ well-known selection of board games. Twister anyone?

The Green Mill
4802 N. Broadway St.
(773) 878-5552,

The Mill is believed to be the oldest continuously run jazz club in the United States. Luckily, you don’t have to be a jazz aficionado to hit up this scene. Check out the upcoming shows, from cool jazz to big band, and enjoy the moody, old-timey atmosphere.


619 W. Randolph St.
(312) 715-0708,

In my opinion, one of the best dates is when you both experience something unlike anything you’ve had before. With Blackbird’s ever changing menu, you’re sure to accomplish this. The flavor combinations awaken your sleeping senses. (Try the breakfast-for-dinner dessert option, which hazelnut ice cream goes between two Belgium waffles, and it all gets topped with meringue and a piece of crispy bacon—mmm!).

1466 N. Ashland Ave.
(773) 252-1466,

For a more intimate experience, visit this cozy restaurant, where food is art. The multi-course tasting menus start at $55 per person, and the chefs — who are constantly trying out avant garde culinary techniques — are your waiters. It’s BYOB to boot!

2039 W. North Ave.
(773) 395-7100,

Located in a former bathhouse, the dining room is located in a sunken area where the pools used to be. The food — New American (whatever that means) with a strong Asian influence — and atmosphere will engage all five of your senses. Well, maybe touch will be put to use later on in the night.


Isabella Fine Lingerie
840 W. Armitage Ave.
(773) 281-2352,

One woman’s addiction to fine European lingerie led her to open her very own Midwest lingerie boutique. While you’re at the store checking out bras, underwear, and blindfolds, have the Boobologist fit you. It’s never too late to discover your true bra size.

Vosges Chocolate
951 W. Armitage Ave.
(773) 296-9866,

The only thing better than chocolate is chocolate swallowed down with a swig of wine. Stop by the Vosges Chocolate Boutique for a box filled with your choice of red, white, or bubbly, nine truffles, and tasting notes. Two aphrodisiacs plus a wine lesson in one!

G Boutique
2131 N. Damen Ave.
(773) 235-1234,

When two women got sick of trudging around town and visiting multiple stores getting supplies for a romantic (or kinky) evening, they founded G Boutique. Finally, a place where you can feel comfortable shopping for fabulous lingerie, sex toys, videos, whips, cuffs, and lubes, all screened for female clientele.