The “Don’ts” of Chicago: Vacation Tips for First-Time Visitors
Greetings from Millennium Park in Chicago! Most travel blogs tell you what to do when you travel, but we like to tell you what not to do. With these Chicago travel tips, you will be better prepared for your visit. Whether you’re here for the great museums, awesome people or amazing food, keep these “don’ts” in mind when you visit Chicago.
Chicago Vacation Tip #1: Don’t Drive
Chicago traffic is horrible; year-round, every day, all day. Whether you are driving in from the airport, or driving in from elsewhere, driving in Chicago is not a pleasant experience. The drivers are pretty aggressive, so it can be stressful. Also, parking in Chicago is really expensive. We recommend using public transportation to get around. Both Chicago airports are served by the CTA system, so there’s no need to rent a car. If you are driving to Chicago, then just park at your hotel once and leave it the whole time you’re visiting. Use Uber, public transit or even the bike rental system to get around once you arrive in Chicago.
Chicago Vacation Tip #2: Don’t Skip Public Transportation
The CTA (Chicago Transit Authority) system is actually really tourist-friendly, so don’t worry about not driving while in Chicago. The El, or Elevated Train, will take you pretty much anywhere in the city. The bus system is also great, and easy to use. Pretty much any tourist attraction in Chicago is served by the CTA. It’s also really affordable to use public transportation in Chicago, so don’t miss out!
Chicago Vacation Tip #3: Don’t Worry About Being Bored
Chicago is chock-full of world-class museums, festivals, concerts and food! The Art Institute is one of the best art museums in the world. The Shedd Aquarium is one of the best aquariums in the world, and the Field Museum is one of the best natural history museums. For science, head to the Museum of Science & Industry. Not into museums? No problem! Check out Broadway classics for a fraction of the price you’d pay in New York. Chicago is great for families, too. There are amusement parks, zoos and playgrounds. In the summer, there are festivals nearly every week. Our favorite is the Taste of Chicago. Sports fans can choose from NFL, NBA and two MLB teams and soccer.
Chicago Vacation Tip #4: Don’t Just Stay in the Loop
Most visitors to Chicago stay in the Loop and River North areas, but there are so many cool neighborhoods and suburbs of Chicago to explore. Make sure to set aside time to check out areas like Evanston, Lincoln Park, Greektown and many others. Public transportation makes this easy. If you’re leaving the city, you’ll use the Metra train system.
Chicago Vacation Tip #5: Don’t Expect Evening Activity in the Loop
Chicago’s true downtown is really a business district, so after work hours, it gets pretty quiet in the Loop. If you’re staying downtown, this can be surprising, especially in such a big city. The shops will also close earlier as downtown workers make their way home after 6 or 7 pm.
Chicago Vacation Tip #6: Don’t Be Lackadaisical About Safety
Chicago has a very dangerous reputation, but probably one of the biggest dangers for a tourist is crossing the street. So, pay close attention when walking around, especially with traffic lights. If at any time you feel uncomfortable on the street, just pop into a store or restaurant and call a cab or an Uber. There are definitely areas of Chicago you want to avoid, but they aren’t areas you would accidentally end up in. It’s always a great idea to ask your hotel for advice and suggestions. Use your normal “travel sense” when going around Chicago, just as you would any other city in the world.
Read: 13 Most Common Methods for Pickpockets
Chicago Vacation Tip #7: Don’t Mess Around with Falling Snow or Falling Ice
If you visit Chicago in the winter, the snow and ice can be dangerous. An icicle falling from 30 stories up can be really dangerous, so when you see the warning signs, heed them, don’t stand around where there might be ice falling.
Chicago Vacation Tip #8: Don’t Skip Chicago in the Winter
Chicago in winter can be magical. Yes, it can be cold, windy and snowy, too. Many of Chicago’s best attractions are indoors, so you can visit those world-class museums with fewer crowds, and the weather won’t matter. Spring, summer or fall are all better times to visit Chicago, but don’t be afraid to come in the winter. From ice skating to Zoo Lights to the Christkindl Christmas market, there are lots of things to do in Chicago in winter.
Chicago Vacation Tip #9: Don’t Miss the Architecture Boat Tour
Chicago has a rich architectural history and is home of the skyscraper. Make sure you stretch your neck before your Chicago visit, because you’ll spend a lot of time craning your neck to take in all the amazing architecture. The architecture boat tour on the Chicago River is the best way to take in all of the cool buildings, and you’ll get the history behind the buildings as well.
Chicago Vacation Tip #10: Don’t Call it Willis Tower with Locals
The tallest building in the city is always going to be the Sears Tower for locals, even though the name changed to Willis Tower in 2009. Old habits die hard in Chicago, so calling it Willis Tower is a sure way to stand out as a visitor in Chicago. Whatever you call it, you can go up to the observation decks at the top for great views of the city, as well as the famous Skydeck observation boxes.
Chicago Vacation Tip #11: Don’t Think You Have to Pay for Great City Views
While you can pay to go to the top of the Sears Tower, or the Hancock building, there are other places to get great aerial views of the city. On the 96th floor of the Hancock building, you can visit the Signature Room bar for free. Spend your money on a drink at the bar rather than admission to the observation deck.
Chicago Vacation Tip #12: Don’t Expect to See Locals at Navy Pier
Navy Pier is a popular tourist destination in Chicago, and is great for visitors. However, it’s pretty rare to see locals at Navy Pier. It’s one place they really don’t hang out because Navy Pier is all about the tourists.
Chicago Vacation Tip #13: Don’t Expect to Hear the Chicago Accent
The Chicago accent is famous, thanks to SNL skits about Ditka and “Da Bears” but people don’t really talk like that in most areas of Chicago. Chicago is a city of transplants, so you’ll have to get into some real working class neighborhoods to hear that thick Chicago accent. (If you’re set on hearing it, head to a White Sox game!)
Chicago Vacation Tip #14: Don’t Believe Everyone is From Chicago
Most likely, when someone says they’re from Chicago, they’re actually from the suburbs. The city of Chicago is actually fairly small, so most of the population is located in the suburbs. People who were born and raised in Chicago will let you know the difference, and are quick to call out any “posers” who claim to be from Chicago when they actually grew up in Naperville.
Chicago Vacation Tip #15: Don’t Come to Chicago on a Diet
The food in Chicago is legendary; with huge portion sizes and lots of meat and grease, you will have a hard time sticking to a diet in Chicago. Chicago-style pizza is so thick you’ll struggle to eat more than one piece. Chicago has some really great restaurants; it’s not all just pizza and hot dogs. There are tons of ethnic neighborhoods with amazing cuisine, like Greektown and Little Italy. Chicago has great Mexican food, Polish food and German food, too.
Watch: Five Things to Eat in Chicago
Chicago Vacation Tip #16: Don’t Think You Can Finish a Deep Dish Pizza
You might think that you can finish of a deep dish pizza in Chicago, but it’s nothing like the deep dish you order from Pizza Hut back home. With all of the meat and cheese, Chicago deep dish is so filling, it’s hard to finish one or two pieces. If you’re traveling alone, go for the individual deep dish pizza; it will be more than enough! Don’t be surprised that it takes around 45 minutes to bake one of these pizzas, and don’t let them talk you into appetizers while you wait!
Chicago Vacation Tip #17: Don’t Put Ketchup on Your Hot Dog
If you get a Chicago hot dog, don’t put ketchup on it! Chicago dogs come with so many toppings, like pickles, onions, tomatoes, relish and mustard, that you really don’t need ketchup. Locals might even call you out for putting ketchup on your dog!
Chicago Vacation Tip #18: Don’t Forget to Bring the Whole Family
There is something for everyone in Chicago and the whole family will have a great time. Even some of the big museums, like the Museum of Science & Industry have exhibits that kids will love. We can spend an entire day there and not get bored. Don’t think Chicago is just for romantic weekends or adults-only getaways; it’s a lot of fun for the whole family.
Read: Best Family Travel Hacks
Chicago Vacation Tip #19: Don’t Miss a Baseball Game at Wrigley Field
Even if you’re not a big baseball fan, spending a day at Wrigley Field is a classic Chicago attraction. The whole area around the stadium, Wrigleyville, is an experience, too. There are tons of bars and restaurants, and the streets fill with baseball fans before and after the games. Most games are during the day, so you can sightsee in the morning, catch an afternoon game and still have a fun night out. If the Cubs aren’t playing during your visit, you can still go to the Wrigleyville bars to watch the away games on the big screen.
Chicago Vacation Tip #20: Don’t Underestimate O’Hare Airport
Chicago has two airports, with O’Hare being the larger one. It’s one of the busiest airports in the U.S. so don’t underestimate the time it can take to get through everything when you are arriving or departing. Give yourself plenty of time, and follow whatever guidelines the airline recommends, whether that’s two or three hours prior to your departure time. You’re likely to find long check-in lines, long security checkpoints, and big distances between gates and terminals. If you are arriving on an international flight and connecting to another flight, you’ll have to exit the international terminal, and go through security again at the domestic terminals, so leave plenty of time between flights.
Chicago Vacation Tip #21: Don’t Expect a Lot of Public Toilets
There aren’t many free toilets in Chicago, and you may not want to use the ones you do find. Your best bet will be to buy something in a shop or a restaurant so that you can use the bathroom inside.
Chicago Vacation Tip #22: Don’t Forget to Buy Metra Tickets Before You Board the Train
If you’re taking the Metra trains anywhere, make sure to buy your tickets inside the station before you get on the train. If you buy your ticket on the train, you will pay a surcharge for doing so, and you’ll have to pay cash.
Chicago Vacation Tip #23: Don’t Pass Up Chicago
Chicago should really be the first city you visit in the States. Because of the culture, the sports, festivals, food and awesome people make Chicago one of the best cities in the world.
Don’t let these “don’ts” scare you off. Chicago is an amazing city, with fantastic culture, friendly people, and amazing food. If you’ve been to Chicago, feel free to add more “don’ts” in the comments below! For more travel tips, check out these blog posts and videos: