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The 5 Biggest Mistakes Tourists Make When Visiting Chicago (and What to Do Instead)

Chicago Insider Guides
by Christine Pundavela May 16, 2018

So you’re on your way to Chicago and you have a kick-ass itinerary filled with deep dish pizza, the Willis Tower, and lots of Bean selfies — what an original Instagram feed you’ll have! Ok, yes these things are iconic to Chicago and you shouldn’t miss them, but don’t make the same sins tourists always commit and only experience these overdone (albeit enjoyable) clichés. Take it from a local and you avoid these five common tourists missteps, so you actually have an awesome, jealousy-inducing Chicago trip.

Mistake #1: Eating at fast food chain restaurants because you say you’re on a budget

Forget Arby’s. WE HAVE THE MEATS. As in, the juicy Maxwell Street Polish sausage and giant pork chop sandwich, snappy Vienna Beef hot dogs, award-winning burgers, towering corned beef sandwiches, and the dripping goodness known as the Italian beef. Not to mention the Cuban sandwich, Mexican torta, Puerto Rican jibarito, Greek gyro, Vietnamese banh mi… we have every ethnic meat-and-bread combo you could want and mom-and-pop spots that have been serving them for years. If you’re going the frugal sandwich takeout route, pass on the chains. These local haunts will certainly leave you more satisfied.

Mistake #2: Assuming that last call at midnight means last call for the night

When the clock strikes twelve and you’re out having a good time, don’t make like Cinderella and rush out to call your ride home. Last call at one bar is by no means the signal to call it quits. In Chicago there’s no shortage of 4 AM bars — with some even closing at 5 AM on weekends. Knowing this, plan ahead to extend your itinerary each night. Some ideas:

  • Fill up on sun, sand and waves at North Avenue Beach and after you close down Castaways, kick it with college co-eds, blues fans, and other tourists at Kingston Mines. This beloved late-night blues bar (open to 4 AM daily and until 5 AM Saturday) has bargain drinks, cheap covers, and a come-as-you-are philosophy.
  • Streeterville Social has strong rooftop game but after the 12 AM closing time, make your way to Celeste, another swanky downtown spot where it’s cocktail o’clock until 4 AM (5 AM on Saturdays).
  • In the thick of Logan Square’s nightlife scene, take this triangular bar hopping route for a spin. Craft distillery tour at Chicago Distilling Company, thirst quenchers on the patio at Spilt Milk, a round of retro drinks and duckpin bowling at The Pink Squirrel, and dancing after dark at East Room (open until 5 AM Saturdays and 4 AM every other night).

Mistake #3: Taking cabs anywhere and everywhere

Chicago is a great city for walking, but it also has a top-notch public transit system. By bus or train, you can get anywhere. And cheaply. So skip on the cab, or Uber/Lyft, when you can because:

  • Some routes have Instagram ready views, e.g. on the CTA Brown Line ‘L’ train around the Loop. You’re turning corners around skyscrapers, snooping into office building windows, and rumbling right over the Chicago River.
  • You’re saving time and money, e.g. traveling between the airport. Depending on the hour, traffic can really up the cost and time of that taxi ride from O’Hare or Midway, but by ‘L’ train (CTA Blue Line or Orange Line) those factors are set.

Mistake #4: Only trying deep dish pizza

Yes, Chicago will swear by its famed deep dish pizza and that zealous loyalty is deserved. Loads of cheese, chunks of meat and that golden crust — delicious. But those dense layers will have you slumped over in a casserole-induced stupor in your hotel room posthaste. So while Lou Malnati’s is fantastic, it’s also the definition of food coma. Instead, sample our city’s proud tavern-style pizza, made with a thin crust and square cut. Or have it all… exemplary examples of Neapolitan-, Sicilian-, Detroit- or New York-style can be had all around the city.

I could offer a very, very long list of recommendations but let me do one better. Take a Pizza City USA bus tour and let a local pro expertly guide you through four pizzerias in 3.5 blissful hours.

Mistake #5: Only doing architecture tours (and not packing your swimsuit)

The nickname Windy City doesn’t conjure up images or beaches, which is why most people just stick to run-of-the-mill architecture tours and don’t even pack a swimsuit. But in Chicago, you can actually have a beach getaway, even if it’s a nontraditional one. For trips between Memorial Day and Labor Day weekend, a swimsuit is essential for summer fun. Don’t be fooled by all the steel and concrete of downtown. You can shop The Magnificent Mile then dip your toes at Oak Street Beach, nestled between the skyscrapers, all in one swoop. With its bright blue waters and seemingly endless horizon, Lake Michigan from this vantage point will change the way you think about lakes. Be sure to also try kayaking down the Chicago River for an alternative view of those skyscrapers.

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