The Worst Mistakes First-Time Visitors Make in Chicago: 16 Things to Avoid
First time in Chicago? The city’s skyline, food, and rich culture are easy to be dazzled by. However, even the most well-meaning traveler can trip into common pitfalls that ruin the experience. Chicago is a city that punishes those who don’t plan wisely or stay a step ahead of rookie mistakes — from braving the wrong weather to misjudging distances.
This guide is your map to avoiding the typical missteps that so many first-timers make. Whether you’re interested in a weekend getaway or a week-long stay, these tips will save you time, money, and frustration to ensure you embrace everything the Windy City has to offer.
Skip the Public Transit System
Chicago’s CTA (Chicago Transit Authority) trains and buses are surprisingly easy to navigate, efficient, and affordable — many newcomers rely solely on taxis and rideshares, but it’s not necessary. The “L” trains (so-called because their tracks are elevated) tie in key neighborhoods and attractions. It’s a budget-friendly way to explore as a single ride will cost you only a couple of dollars. Plus, dodging traffic on the train? Priceless.
Misjudging the Distance to Other Cities
A quick side trip to Milwaukee or even Detroit might be doable but Chicago’s size and traffic could make it difficult or impossible. Unless you’re in town for a stretch, stick to close suburbs or nearby attractions like Evanston or Oak Park instead of wasting hours in transit.
Failing to Budget for the Sales Tax
At 10.25%, Chicago’s sales tax is one of the highest in the U.S. Many visitors forget to include this in their budget, and are in for a shock at the register. Factor sales tax into your plan, and put a tad bit extra for emergencies.
Skipping the Willis Tower for “Cooler” Views
Yes, the Willis Tower Skydeck is touristy, but there’s a reason it’s so popular—it’s got great views. It’s usually an easy pass for first-time visitors who assume the views aren’t much different and it’s a bit less crowded somewhere else. Of course, options such as the 360 CHICAGO Observation Deck at the John Hancock Center are good, but the Skydeck’s Ledge (a glass box jutting out from the building) is a bucket-list experience. Avoid long lines by just booking tickets in advance.
Underestimating the Wind and Weather
Chicago’s nickname, the “Windy City,” refers to the wind — and for good reason: The weather here can be vicious. In the winter, first-time visitors tend to show up underdressed, and in the summer without sunscreen. Always check the forecast before heading out, and layers are your best friend.
Only Eating Deep-Dish Pizza
It’s true that Chicago is known for its deep-dish pizza, but sticking to this tourist staple will keep you from discovering some of the city’s other incredible local fare. Whether it’s jibaritos, Chicago-style hot dogs, or Italian beef sandwiches, the city is a culinary playground. Deep-dish is great, but don’t let it steal the spotlight.
Overbooking Attractions
There’s so much to see in Chicago, but it can be overwhelming to pack in more than can fit into one day. Zipping between attractions can be a logistical nightmare because of the city’s size and traffic. Instead, dedicate your time to one or two areas per day (like the Museum Campus or River North) and take it all in, stress-free.
Ignoring the Neighborhoods
For first-timers, the Magnificent Mile or Millennium Park are the go-to downtown hotspots, but Chicago’s magic lies in its neighborhoods. Visit Pilsen’s murals, Wicker Park’s vintage shops, and Chinatown’s restaurants. Each area has its own vibe and treasures waiting to be discovered.
Visiting Navy Pier Expecting Local Culture
Navy Pier is a tourist magnet and while the views are lovely, it’s far from authentic Chicago. Locals hardly ever go there unless they’re catching a play at the Chicago Shakespeare Theater. If you want a bit more authentic outing, take a stroll on the Riverwalk or through a nearby park.
Mispronouncing Local Names
Knowing it’s “Chi-CAW-go” and not “Chi-CAH-go” — as it is pronounced — can help you save a little bit of side-eye from locals. Street names like Paulina (Paw-LINE-ah) and Goethe (GER-tuh) are the same. A little effort goes a long way toward blending in.
Driving Everywhere
Chicago is not the place for the faint of heart when it comes to driving around. The parking is expensive, the traffic is unrelenting, and remembering which streets are one-way can be a headache. If you absolutely have to drive, try downloading a parking app (like SpotHero) to locate cheaper spots. Otherwise, get around using public transit, walking, or biking.
Skipping Free Attractions
Many first-timers spend a fortune on big-ticket attractions and forget about Chicago’s amazing and free options. Many free things are worth the visit: Lincoln Park Zoo, Garfield Park Conservatory, and Grant Park’s Buckingham Fountain. Pro tip: Many museums have free days for Illinois residents, but check their schedules before you go.
Assuming All the Beaches Are the Same
Chicago’s beaches aren’t all the same. North Avenue Beach is bustling and very popular for people-watching; Montrose is dog-friendly and much more laid-back. Stunning skyline views are featured from Oak Street Beach. Do the homework and choose the one that resonates with your vibe.
Eating Pizza at the Wrong Places
Deep-dish pizza is not created equal. For many tourists, the mistake is making for subpar spots that don’t live up to the hype. The real deal is Lou Malnati’s, Pequod’s, and Giordano’s. Don’t order deep-dish from some random chain, it’s like getting sushi from a gas station.
Overlooking the Chicago River Architecture Tour
Missing an architecture tour is like going to Paris and missing the Eiffel Tower. Some of the most iconic buildings in the world are located along the Chicago River, and it’s fun to learn about the architectural history of the city. Plus, the views from the water are quite unbeatable.
Underestimating the Lake
First-time visitors are often shocked by how vast Lake Michigan is, it often feels like an ocean. Don’t miss out, enjoy it! Rent a kayak, cycle down the Lakefront Trail, or simply admire from the shore. Little wonder it’s one of the city’s most striking natural features.
Disclaimer: This list is solely the author’s opinion based on research and publicly available information.
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