College guidebooks may insist that romance at Northwestern is dead, but maybe we’re not trying hard enough. It takes more effort than drinks at the Keg followed by a swoon-worthy 3:30 a.m. dinner at BK to win hearts. If your excuse for having Joy Yee’s for the eighth date in a row is that you’re worried there’s nothing that suits you in Chicago, stop fretting. With this list, you can appease even the most finicky of dates. Be warned: you may have to actually talk on the El.
If the sun never set on your British empire
Take heart colonialists, there is even something for you. Suggested accessories: top hat and monocle.
Get in touch with your inner Brit with high tea at the Drake Hotel. Enjoy live harp music while sipping your tea and discussing how uncivilized everyone else is. Reservations are recommended; the teeming masses can be so inconvenient. Red Line to Chicago
If you’re up for a journey, marvel at the wonders of the modern age at the Museum of Science and Industry (originally the Palace of Fine Arts during the World’s Columbian Exposition in 1893). #10 bus South
If going south of the Loop is too much for your delicate constitution, ride the Ferris Wheel at Navy Pier to celebrate the Exposition’s debut of the original. Red Line to Grand
Come dinnertime, how better to indulge your imperialist tendencies than enjoying a Shanghai Sling while white-coated waitstaff bring you pho at Le Colonial for French Vietnamese cuisine? Red Line to Chicago
If your only excuse is you’re broke
Penniless students can have fun too. Suggested start: your very own kitchen. Make a picnic dinner and head to the gloriously free Lincoln Park Zoo. If polar bears and baby monkeys can’t make your date happy, you probably can’t either. Picnic on the lawn outside. Red Line to Fullerton
If you want to splurge, see the Neo-Futurists’ Too Much Light Makes the Baby Go Blind for $9 plus a roll of the die ($10-$15 total) – not bad for 30 plays in 60 minutes. Red Line to Berwyn
If you’re pining for study abroad
Visions of exotic locales may dance behind your lids every time you close your eyes, but how do you get to those far-off shores without selling a kidney for a plane ticket? Try and take the edge off with some of Chicago’s cultural neighborhoods.
If you’re yearning for a different kind of Greek life head to Greektown on the West Side. Stores and restaurants named after practically every island or god in the pantheon should soothe your inner Classicist. If you’re just in it for the food, try the Taste of Greece festival at the end of August. Blue Line to UIC/Halsted
If your tastes lie farther East, Chinatown Square features the standard food and shopping, as well as the Pan Asian Cultural Center and Ping Tom Memorial Park on the river. Check the Chicago Chinatown Web site for festival days like the Autumn Moon Festival. Red Line to Cermak/Chinatown
If Chicago is your kind of town
Despite what those East Coast kids mutter about “flyover country,” there’s plenty that’s worthwhile in the Windy City besides Barack Obama. This one’s for you, classic Chicago fans.
If you want to go a little more upscale for dinner, pick one of Chicago’s many steakhouses – head toward the river if you really want to impress. Try Fulton’s on the River if you can afford the view. Red Line to Grand
For something lighter (at least on your wallet), go for the deep-dish pizza. Its origins remain shrouded in mystery, but Pizzeria Uno stakes a decent claim on creatorship. Red Line to Grand
Venture to the Green Mill, a historic jazz club and cocktail lounge. If the jazz itself isn’t Chicago enough for you, the Mill has a long and nefarious history of involvement with Al Capone and his associates. So raise your glass and tip your fedora, but please keep the machine gun under the table. Red Line to Lawrence