The Intern’s Guide to Chicago
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Welcome to Chicago! Summer in this city is quite possibly the most wonderful thing in the world (not like I’m biased…). I’m here to help you navigate Frank Sinatra’s kind of town like a pro and not a tourist. Because while going to look down from the top of the Sears Tower (don’t even think about calling it the Willis Tower) Sky Deck is a touristy essential, Chicago has so much more than just Michigan Ave and Navy Pier to explore.
And a lot of it is very tasty food. Nom nom nom.
Best Cupcakes: Molly’s Cupcakes has hands down the best cupcakes in the city. Right between the Fullerton and Belmont Red line stops, Molly’s can be a bit of a walk but is SO worth it. Everything there is delicious, but their Cookie Monster cupcake is my personal favorite. It is a cupcake FILLED with cookie dough! Plus, Molly’s also has the cutest decor with swings as seats, board games to play, and is open until midnight on the weekends.
Best Chicago Style Pizza: Although this is a very controversial topic, Giordano’s is my personal favorite. And if you go to a location that isn’t in the heart of downtown, you’ll avoid the crazy crowds and long waits.
Best place for a drink Cesar’s Mexican Restaurant is known for their killer margaritas (which, I might add, were named that for a reason). One mega margarita is enough to get me drunk, but for non lightweights, you can upgrade to a jumbo for only $1 more. And the Mexican food isn’t bad either, though everything tastes better after a jumbo mango marg.
Best bar hopping neighborhood: Wrigleyville is hands down the place to go. There are so many bars that if one is dead (or maybe questions your ID), you can just head to the one next door. Bars around both the DePaul and Loyola areas are pretty lax on IDs as well…. not that I’m condoning that!
Best Late Night Food: Wiener’s Circle in Lincoln Park. You can get Chicago hot dogs, burgers, fries and more, all served up with a side of major sass from the infamous employees. Just don’t ask for a chocolate milkshake… it is NOT what you think it is.
If you’re not near this Chicago institution, try Ian’s Pizza in Wrigleyville (a University of Wisconsin favorite that boasts Mac & Cheese pizza, S’more pizza and more!).
Hit the Beach: Most people don’t know it, but Chicago is a major beach town in the summer. If you’ve got a need for some sun and sand, head to North Ave. Beach. The crowds can be a little overwhelming, but the people watching, view of the Chicago skyline, and hundreds of open volleyball courts are worth the fight for towel space. Plus, Castaways, an awesome restaurant/bar that looks like a giant ship, is only steps away from the water.
Chicago Freebies: One of the biggest reasons to love Chicago is the variety of totally free, totally awesome activities that are always going on. Did you know the Lincoln Park Zoo is 100% free? Just walk right in and enjoy the cuteness. For those of you looking to stay in shape this summer (not me), Millennium Park offers free workouts every Saturday, including everything from cardio to, my personal favorite, Pilates.
If you want to get some culture, head back to Millennium Park for their free concerts on Monday and Wednesday nights. You can even bring food and wine to make it a truly classy event. Thursday nights at the Chicago Art Institute and Tuesday nights at the Museum of Contemporary Art are also free. And both the Shedd Aquarium and the Field Museum have free days during the summer as well! And if you want a fun weeknight activity that is quintissentially Chicago, check out the Navy Pier fireworks every Wednesday and Saturday night at 10 pm.
Looking for some new threads? You could head down to the Magnificent Mile for your fill of your everyday stores, but if you want something a little different (and a lot less touristy), try the adorable and affordable boutiques lining Belmont and Clark, or haul your ass over to Wicker Park to peruse their more upscale shops. Just remember, the sales tax here is right around 10%, so be prepared for the inflated prices!
Cubs game, duh. Wrigley Field is one of the only original baseball fields left in the country and even if you don’t like baseball, spending a day in the sun sipping beers and eating hot dogs is totally worth the cost of a bleacher seat.
Chicago takes its architecture pretty seriously and they should – there’s a lot of beauty in this town. Check it all out on the Architecture Boat Tour. It’s only $22 and gives you a chance to cruise the Chicago River while learning all about the city’s exciting history. OK, so it doesn’t sound that interesting, but I promise you it is awesome.
And don’t forget to make some time for a Second City comedy show. Some of comedy’s biggest stars got their start on that very stage and after a long day of interning, you’ll appreciate a night of laughing until you pee.
Everyone has different highlights on their personal tour of Chicago, so these are just a few of mine. Take the time to explore the different neighborhoods yourself and comment with other places that I’ve missed!