The Food: Chicago’s Chinatown, just south of The Loop, is a truly glorious place. And grabbing dim sum is an exercise in delicious instant gratification. My favorite place to eat is The Phoenix, where servers briskly wheel giant carts piled high with incredibly delicious things you may not recognize. (There’s no shame in pointing and asking.)
Downtown and feeling snacky? Walk up to the window of The Doughnut Vault- with their insanely tasty daily specials (Coconut old fashioned? Cookies n’ cream?) and then be happy for the rest of the day. It’s just that simple.
And when you really want to indulge, you can’t miss the famed Margie’s Candies (patronized by politicians and British Invasion rockers alike). They have two locations, but the one on Western is like visiting a time capsule. A delicious time capsule with a gravy boat of homemade hot fudge.
The Sights: Sure, you’ve seen the lake and the boats. But how about at night? (And lit up like the 4th of July?) The 54th annual Venetian Night, one of Chicago’s coolest (and brightest) traditions, will light up the harbor with decorated boats and live music on Saturday, July 27th. (Gondolier shirt totally optional.)
What, you’re going to be in the Midwest and not go to a farmer’s market? The best of the best is the Green City Market, with chef’s demonstrations, musical performances, and more artisanal cheese than you can shake an organic cucumber at.
And if it’s not your first time seeing the skyline of Chicago, you probably have little need for the skyscraper views of the town. But how about…from the beach? Chicago boasts some downright fabulous beaches, with miles of sand, restaurants, sports and playgrounds. Some favorite spots are the 31st Street Beach (full of painted trees and a quieter atmosphere), Oak Street Beach (if you want to pretend you’re in Cali with a gazillion of your closest and most beautiful friends) and Foster Avenue Beach (super family friendly, clean, and close by to a dog park). And there’s nothing like seeing that skyline while seated in those gentle waves.
The Stuff: One of the prettiest bars- with the prettiest drinks- is The Violet Hour on the near northside, a modern take on a speakeasy which features couture cocktails and a lounge that will make everyone feel like a celeb. (Especially after your second Dame’s Delight.)
Chicagoans have access to some of the best theatre and comedy in the world. Check out a smaller show at IO (formerly ImprovOlympic); their Improvised Shakespeare Co. performances are pretty much guaranteed to make you wet yourself.
Or if you’re feeling something more chill, head up to the Old Town School of Folk Music and take in one of the best places to hear (or learn!) diverse and global music.
Whatever you choose, have a great visit. As you’ve probably realized by now, you really can’t go wrong in Chicago.