10 Mistakes Tourists Make While Visiting Chicago (According To Locals)

Visiting Chicago soon?

Just like any tourist destination, Chicago has its own set of unwritten rules that leave locals rolling their eyes if you break them.

Don’t worry, we’ve got your back.

We sifted through hundreds of comments from real Chicagoans on Reddit to get the scoop on the little things that drive them crazy.

This is your ultimate insider’s guide to the 10 biggest rookie mistakes tourists make…and, more importantly, the local-approved fixes that will save you a whole lot of side-eye.

Read on to experience Chicago like a pro.

Mistake #1: The Sidewalk Swarm

The Mistake: Walking three, four, or even five people abreast, taking up the entire sidewalk. This is, without a doubt, the #1 pet peeve for locals. As one person put it, “It’s a side-WALK, not a side-WAIT.”

The Local Fix: The golden rule is to walk no more than two-wide. If the sidewalk is crowded or someone is trying to pass, be mindful and switch to single file. And please, if you need to stop to check your phone or take a photo, step to the side. Don’t just freeze in the middle of pedestrian traffic.

Mistake #2: L Train Fumbles

The Mistake: Standing directly in front of the train doors as they open, trying to board before anyone can get off. Or, standing on the left side of the escalator.

The Local Fix: Stand to the sides of the doors and let people exit the train before you try to enter. As one local bluntly put it, “If you don’t let people off before you enter… you deserve to be shoulder checked (and probably will be).” For escalators, the rule is simple and sacred: Stand on the right, walk on the left.

Mistake #3: Calling It “Chi-Town”

The Mistake: Using nicknames that make locals cringe. The top offenders are “Chi-Town” and “The Windy City.” While not technically wrong, they are almost exclusively used by tourists and marketing campaigns from the 80s.

The Local Fix: Just call it Chicago! It’s a great name. If you want to sound like a real insider, refer to the downtown business district as “The Loop.”

Mistake #4: Only Seeing “Downtown”

The Mistake: Thinking that Chicago is just the Loop, River North, and the Magnificent Mile. One local shared their biggest pet peeve: “My friend from Wisconsin once asked me how far we were from the city when we were eating in Logan Square.”

The Local Fix: The real soul of Chicago lives in its 77 unique neighborhoods! Dedicate at least half a day to exploring one. Hop on the L train and visit the vintage shops of Wicker Park, the historic homes of Lincoln Park, the incredible Mexican food in Pilsen, or the lively streets of Andersonville.

Mistake #5: Going to the Wrong Tourist Traps]

The Mistake: Spending hours and a small fortune at Navy Pier.

The Local Fix: If you want amazing skyline views, walk along the lake or Chicago Riverwalk (both free)

Mistake #6: Putting Ketchup on a Hot Dog

The Mistake: It’s the most famous rule in Chicago for a reason. Ordering a Chicago-style hot dog and asking for ketchup.

The Local Fix: A true Chicago dog comes with yellow mustard, chopped white onions, bright green sweet pickle relish, a dill pickle spear, tomato slices or wedges, pickled sport peppers, and a dash of celery salt. Trust the process! The tomatoes provide all the sweetness and acidity you need. If you absolutely must have ketchup, just order a plain hot dog.

Mistake #7: The Empty Train Car Gamble

The Mistake: Seeing a crowded train pull up with one mysteriously empty car and thinking, “Jackpot!”

The Local Fix: Avoid that car at all costs. As one local wisely warned, “If you see a train is full except for one car, avoid going into that car. There’s a reason it’s empty.” It’s usually due to a biohazard of some kind (a terrible smell, a mess, or a disruptive person). Squeeze into the crowded car and thank us later.

Mistake #8: Calling It “Chiraq”

The Mistake: Using the derogatory and outdated term “Chiraq” or coming to the city to “tour” dangerous neighborhoods like “O Block.”

The Local Fix: Don’t. It’s deeply offensive to residents and trivializes real-world problems. Chicago is a vibrant, beautiful, and overwhelmingly safe city for visitors who use common sense.

Mistake #9: Underestimating the Weather

The Mistake: Visiting in April without a proper coat, or in October without layers. Chicago weather is notoriously fickle.

The Local Fix: Check the forecast, then pack for a 15-degree drop in temperature just in case. The wind off the lake is no joke. Layers are your best friend, no matter the season.

Mistake #10: The Malort “Dare”

The Mistake: Letting a local “friend” trick you into taking a shot of Malort without knowing what it is.

The Local Fix: Actually, you should probably do this one! Jeppson’s Malort is a legendary Chicago liqueur known for its… unique… taste (think grapefruit-meets-gasoline). Taking a “Malort face” picture is a hilarious rite of passage for visitors. Just be prepared, and have a beer ready to chase it with. It’s a mistake you’ll be glad you made.

Mistake #11: The Divvy Bike Sidewalk Cruise

The Mistake: Renting a Divvy bike or an e-scooter and riding it on the sidewalk, ringing the bell at every pedestrian in your path.

The Local Fix: Sidewalks are for walking. Period. Chicago has an extensive network of bike lanes for a reason. Riding a bike on a busy downtown sidewalk is not only against the rules and dangerous, but it’s also one of the fastest ways to get on a local’s bad side. Use the bike lanes—that’s what they’re there for.

Mistake #12: Engaging with the “Street Team”

The Mistake: Stopping to talk to the “monks” offering bracelets, the overly-positive people with clipboards, or the person trying to sell you candy from a gym bag on the train.

The Local Fix: This is a classic big-city survival skill. The consensus from locals is clear: a polite but firm “no thanks” while continuing to walk is the only response needed. Don’t stop, don’t engage in a conversation, and definitely don’t take the “free” bracelet (it’s not free). As one local put it, “Sometimes if you talk to them they take it as an invitation to keep the convo going.” Keep your head up, be aware of your surroundings, and just keep moving.

Mistake #13: Getting Lost on Lower Wacker Drive

The Mistake: Seeing Lower Wacker on your GPS and thinking you’ve discovered a brilliant shortcut to beat downtown traffic.

The Local Fix: Don’t do it. Just… don’t. Lower Wacker is a multi-level, subterranean labyrinth where GPS signals go to die, street signs are cryptic suggestions at best, and every turn looks identical. Even seasoned locals avoid it unless absolutely necessary. As one person hilariously noted, “I love how GPS will happily take you there and then stop working, because it’s underground.” Stick to the upper streets; the traffic you can see is better than the maze you can’t.

Mistake #14: Giving Your Luggage Its Own Seat

The Mistake: Getting on a crowded L train from the airport (especially the Blue Line) and putting your suitcase or backpack on the empty seat next to you.

The Local Fix: Your bag does not need its own seat. During rush hour, the train is packed with commuters who need that spot. The proper local etiquette is to place your luggage on your lap or on the floor between your feet. It’s a small act of courtesy that shows you understand you’re sharing a space with people trying to get to and from work.

Mistake #15: Mistaking Directness for Rudeness

The Mistake: Getting offended when a Chicagoan gives you a very straightforward answer, seems a bit cold, or even pokes fun at you.

The Local Fix: Understand the local culture. As one Reddit user perfectly explained, many Chicagoans are “friendly on the surface but very direct underneath.” It’s not meant to be rude; it’s about being efficient. If someone gives you a blunt answer, they’re likely just trying to be helpful without the fluff. And if they poke fun at you (especially about being a tourist), it’s often a sign of affection, not aggression. Don’t take it personally—it’s just part of the city’s no-nonsense charm.