A How-To Guide to Being A Chicago Tourist

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You’ve done it. Made the flight reservation, booked the hotel, even sent the kids to Grandma’s house a week early. You’re ready for your trip to the big city… or are you? Millions of people journey to Chicago every year, but many have not done the proper leg work necessary to ensure a pleasant trip. Before they know it they’re stuck wondering where the next bus to the Museum of Science and Industry is as they search endlessly through their fanny pack for their misplaced sunglasses and take pictures next to every tall building in hopes that one of them is the Willis Tower. Here are a couple of pointers to make sure you don’t end up like so many Windy City wanderers before you.

Tip #1: Bring a Map and, what the heck, use it!

The cool thing about maps is that they tell you where you are. Sure, you can ask a passerby on the street, but they may not give you the most detailed advice you need. Plus you can’t bribe him or her to stay by your side to guide you all day long, no matter how many sticks of gum you have. Another helpful hint is to learn about our public transportation or at least grab a map of the CTA system. The Chicago Transit Authority (CTA) is the second largest transit system in the country with 8 train and 140 bus routes, making it even easier to understand and travel around town. If you’ve got a smart phone, you can even track the next approaching vehicle just by going to the CTA website. You’ll save a ton of money on cab fare and might even trick some people into thinking you’re a local.

Tip #2: Plan Ahead

Be sure to get as many details nailed down about your trip as possible before you leave the comforts of your own home. Check the weather, duration of tours, start times for plays or concerts and estimated travel time between attractions. The more you know going into your trip, the more relaxing it will be. You’ll have a more prepared and realistic view about what you can accomplish. Discuss with those you are traveling with as well so that everyone is on the same page about how your days will be spent. Need a little help? Visit our Plan Your Trip article or request a Custom Itinerary (we’ll do the planning for you!).

Tip# 3: Be Financially Savvy.

Chicago can be a bit of pricey town, but there are lots of ways to cut your costs. Aside from utilizing public transportation and keeping your eyes peeled for discount coupons and sale signs, another great trick is to mix and match expensive outings with cheap ones. If you’ve got your heart set on eating at Gibson’s for dinner in hopes of rubbing elbows with a celebrity, follow it with a free walk in the Lincoln Park Zoo. If you really have to have those custom pictures of you and your family next to the Ferris wheel at Navy Pier, stick around afterwards to watch the free fireworks display. This way you won’t feel like you’re missing out on the real Chicago experience without breaking the bank in the process.

Tip #4: Don’t Forget the Three Essentials: Walking Shoes, Sunscreen and Bottled Water

When you’re trekking mile after magnificent mile, it’s important to have comfortable and supportive shoes. And if you’re already carrying around a backpack for a camera and snacks, why not throw in a bottle of Coppertone and some water? The last souvenirs you want to be taking home with you are blistered ankles, a sunburned face or, worse yet, a bill for a hospital trip for dehydration.

Tip #5: Get an Early Start

Waking up with the sun might seem like the last thing you’d want to consider doing on a vacation, but it can really make or break a day of sightseeing. You’ll avoid the heat and big crowds in the summer by seeing some attractions early. Plus, you’ll pack more into your day. It will also make you less rushed throughout your stay, so you’ll feel more relaxed than if you stayed in bed staring at ugly hotel artwork until two in the afternoon.

Tip #6: Watch Where You’re Going

This may sound simple and maybe even a little condescending, but you’d be surprised as to how many people — tourist or not — pay no attention to where they’re walking. Checking a cell phone, reading a map or discretely picking a wedgie are all distractions from the task of putting one foot in front of the other. With so much going on downtown, this mistake could cause you major pain. Not only do you run the risk of running into others, but you could walk into an intersection too early, not see sidewalk construction (and trust us, there’s plenty of it), or encounter an endless number of other unexpected obstacles. At the very least, you’ll save yourself a stubbed toe, a lost wallet and maybe even a few blocks walking in the wrong direction just by keeping your eyes up and on the cement path in front of you. An added bonus: you actually get to see and enjoy the city you’ve come to visit.

Tip #7: Pace Yourself

Big cities like ours can be a tad overwhelming. With so much to see and do, it’s a wonder where to begin. Take a moment. Breathe. The first thing to accept is that you can’t do it all in one trip. Pick the things you think are most important for you to experience. If you get to the other stuff, bonus.

Tip #8: Budget Money for Unexpected Costs

Cab rides after a long day of texting everyone back home how much fun you’re having come up from time to time. So does the occasional snack when the wait time at Giordano’s is two hours, or the quick trip to the Walgreen’s to buy a disposable camera because little Billy thought playing with yours in Lake Michigan was a good idea. Make sure you have a little extra cash for unplanned events that inevitably arise. Also, don’t forget we have one of the highest sales tax in the country!

Tip #9: Venture Out of Downtown

If your trip allots for it, exploring other areas of the city is a must. Chicago has over 200 neighborhoods, each with a different personality and feel. Not only are there all kinds of street fests, restaurants and shops to discover, but they also give you a peek into how Chicagoans live and play. Research neighborhoods to find one you might like to visit and how to get there via train or bus.

Tip #10: Stay Informed

Knowledge about the place you are visiting will only increase your enjoyment of it. For instance, running into Rahm Emmanuel at Portillo’s Hot Dogs probably wouldn’t be quite as exciting if you didn’t know he just became our city’s mayor, or that Portillo’s has one of the best Chicago dogs in the city. The Windy City is great for activities, but it will be even better if you know a little about who we are and what we are up to.

That said, spend some time exploring UPchicago, then get out there and actually DO IT. We guarantee you’ll have a blast.

Jessie Stegner

About Jessie Stegner

Jessie has been living in Chicago since 2007 and loved every minute of it. Her only setback is, due to growing up in Sierra Madre, California, she can't feel her toes between the months of November and June. With a degree in Theatre from the University of Colorado at Boulder and training from Second City and Improv Olympic, Stegner can usually be found on a stage somewhere trying to make people laugh. She enjoys falling asleep to the sound of the El train, drinking Blue Moon, jogging on the lovely streets of Ravenswood, eating Thai food and watching White Sox baseball.

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