16 things to know before traveling to Chicago

Chicago is an incredible place to visit – the architectural landmarks and historic sites alone could fill up your itinerary – and tourists rightfully flock here every year. I’ve lived in the city for more than 30 years, and I gathered the top insider tips to ensure a smooth visit to the Windy City.

The first recommendations I make to all of my visitors are to take public transportation, hit the neighborhoods and drink Malört (a liquor famous for tasting awful) at your peril. Then you need to know about local sports culture, the ridiculous taxes and the ketchup rule – and that’s just for starters.

Here's all my advice on everything you need to know to prepare for your trip to Chicago.

People stand in front of a large mirrored sculpture; buildings and the people are reflected on its surface. — "Cloud Gate" in Millennium Park. Loren Toney for Lonely Planet

1. Plan on staying 3 to 5 days

It’ll take you 2 or 3 days to see the top sights in Chicago, like the Art Institute, Wrigley Field, Millennium Park and Willis Tower. Adding a couple more days to your visit allows you to move out of the center and into the neighborhoods, where Chicago’s true heart beats, and maybe get in a day trip.

Pilsen and Logan Squares welcome you with great eats and vibrant street art. Bronzeville has galleries and soul food restaurants, and Andersonville is a jazzy, cafe-laden LGBTQ+ hub. Hyde Park, Wicker Park and Humboldt Park are other troves of great restaurants and attractions.

2. Pack a warm coat or maybe a swimsuit

Chicago sits on the shore of vast Lake Michigan, which has a wild effect on the weather. It whips up heavy snow in winter and windy conditions year-round; pack a warm coat, a hat and sturdy shoes when visiting November through March. Even in the summer months of June through August, the temperature can drop fast, so bring a sweater when you head out for the day.

That’s not to say you shouldn’t also bring your bathing suit in the summer, which is the best time to visit city beaches that beckon with sand and surf.

A glass-paneled dome in a rotunda, with a stained glass design at the apex; an elaborately detailed archway is in the foreground, framing the dome. — Chicago Cultural Center. Loren Toney for Lonely Planet

3. Buy museum and theater tickets in advance

Many museums, including the Art Institute, encourage visitors to purchase tickets online in advance. A day or so prior should do it, unless there’s a blockbuster exhibit going on.

It’s also wise to book the hottest theater tickets beforehand, whether it’s for a world-class opera or booze-addled Shakespearean improv. A week ahead is usually plenty of time. Browse Hot Tix for same-week drama, comedy and performing arts tickets for half price – a gift if you're visiting Chicago on a budget.

Also check schedules for free events at the Chicago Cultural Center and Millennium Park.

4. Make restaurant reservations

Prepare to fork into platefuls of Michelin-starred comfort food and eat like royalty. Reservations are key, though, especially for weekend dining. Book through Tock, OpenTable or Resy. A week or two in advance will work for most places, though dining hot spots such as Alinea and Girl & the Goat need to be reserved a couple of months out. Prime dining times are between 6pm and 8pm.

Two people walk by a stone railing; a city street runs below them, and a train station crosses over it. — South Loop. Loren Toney for Lonely Planet

5. Where you stay depends on what you want to do

Downtown has loads of cool architectural hotels near the sights, but limited eating and drinking options after dark – not ideal if you're looking to party but good if you're traveling to Chicago with kids.

Next door the Near North has hotels and evening action, but it’s pricey and a bit cookie-cutter. The West Loop, Lincoln Park, Lake View and Wicker Park all have abundant nightlife to keep you entertained. They’re not close to the main sights but are easy enough to access via public transportation. Book accommodations a month or two in advance if possible.

6. Prepare for hefty taxes

A tax is levied on most goods and services in Chicago. It’s 17.4% for lodgings, 10.75–11.75% in restaurants and bars (it's higher the closer you are to downtown), and 10.25% for other items. The tax is typically not included in the price but added to the bill when you pay.

7. Don’t drive, especially downtown

Driving in Chicago is no fun. Traffic snarls not only at rush hours but also most times in between. Road construction on the major highways further adds to the nightmare. What’s more, parking is hard to find and costs a fortune, particularly downtown near the sights – garages routinely charge around 45 US dollars (US$) per day.

Spare yourself the annoyance: ditch the car and use public transportation instead. It’s easy-peasy to get around Chicago on public transit, mainly by train, called the L (for "elevated"), which runs on both aboveground and subway tracks. The L will get you to most sights and neighborhoods into the wee hours. Buses pick up the slack in areas that the L misses.

People exit a silvery train; tall towers are in the background. — An L station in Wicker Park. Loren Toney for Lonely Planet

8. Take the L to the airports – and be courteous

Taxis and rideshares can take forever to get between the city and airports. Instead, use the L train. The Blue Line from O’Hare and Orange Line from Midway take 30–40 minutes and cost US$2.50–5. Not only are travel times often quicker on the L but it’s about 10 times cheaper than a cab.

However, be conscious of your luggage and don't block other passengers' pathway through the cars or to the doors. When you are boarding, let people get off the train before getting on yourself – wait to the side of the open door until everyone has departed. When you take the escalator in the stations, stand on the right side and walk on the left side.

9. Get a Ventra Card for public transportation

To save time and money, buy a rechargeable Ventra Card to use on public transit and add value as needed. Cards are available at any L station (including at the airports) and save around a US$1 per ride over disposable fare tickets. You can also download the Ventra app and buy a digital Ventra Card. The app has the bonus of providing L and bus times.

Whether using a plastic or digital card, simply tap it at the turnstile as you enter an L station or at the fare box as you get on the bus. If you’ll be riding three or more times per day, consider buying a day pass with unlimited rides for additional savings.

Two people sit at the end of a long wooden bar across from a bartender. There are round stools with black seats, and wooden booths against the wall. — Big Star in Wicker Park. Loren Toney for Lonely Planet

10. Grab a seat at the bar

Locals love to hang out in drinking establishments. Blame it on the long winter, when folks need to huddle together somewhere warm. Or blame it on summer, when sunny days make beer gardens and sidewalk patios so splendid.

Beer is the drink of choice. Grab a seat in a neighborhood taproom and you’ll be conversing about the Bears or the mayor in no time. You might even get offered a shot of Malört – downing one is a Chicago rite of passage.

11. Cheer on the sports teams

Chicagoans are rabid sports fans – get to know the city's teams and you’ll make friends wherever you go in town.

Chicago’s two baseball teams inspire die-hard devotion: the Cubs are the more moneyed North Side squad, while the White Sox are the working-class team on the South Side. Both have had great success in recent years. Then again, both have had their bad times in recent years too! Usually, one team is up when the other is down.

The football-playing Bears ignite lots of fervor. They're followed by basketball's underachieving Bulls, hockey's try-hard Blackhawks and soccer’s lately improving Fire.

Racks of clothing in a store with wood floors and lots of natural daylight. — Round Two in Wicker Park. Loren Toney for Lonely Planet

12. Dress casually

Chicagoans dress informally. The apex of fashion for most men is a pair of khakis and a button-down shirt. Women's style is similarly low-key, valuing comfort over high fashion. And don't worry about getting your best on for the evening. It's perfectly fine to wear jeans and casual clothes to dinner or the theater at night. No judgment here!

13. Never put ketchup on a hot dog

Weird but true: the red condiment does not go on local wieners. No one really knows why. One theory is that the famed Chicago-style hot dog – which is topped with mustard, sweet pickle relish, chopped onions, tomato slices, a dill pickle spear, sport peppers and celery salt – already has a perfect flavor balance. Adding ketchup is redundant and ruins the meaty harmony.

People walk by a river; there is a yellow ferry in the water and a bridge behind them with a sign that reads "Wabash Avenue." — Riverwalk. Loren Toney for Lonely Planet

14. Don’t smoke pot in public

Even though it’s legal to buy recreational marijuana throughout the city – at licensed dispensaries, cash only – you can only toke on private property. A backyard or balcony is fine; a car or cafe is not. Always check with the property owner to make sure they allow it.

As for cigarettes, you can’t smoke inside bars, restaurants and other public places, or within 15ft of the entrance.

15. Use the Pedway

Come wintertime, when the going gets tough and icy sleet freezes your face, head down to the Pedway. Chicago has a 40-block labyrinth of underground walkways, built in conjunction with the subway trains. The system isn’t entirely connected, and it’s confusing to figure out directions, but it’s also a dandy way to escape the elements. Look for "Pedway" signs above ground at points of entry.

People walk across a crosswalk in the direction of a tall white skyscraper. — The Tribune Tower. Loren Toney for Lonely Planet

16. Don’t let the headlines scare you away

Chicago has the unfortunate distinction of being the USA’s murder capital. Most of the violence is concentrated on the West and South Sides, where a handful of neighborhoods account for more than half of all shootings. These are communities where segregation and isolation have intensified inequality, and local gangs account for much of the bloodshed.

While violent crime rates in Chicago have been dropping in recent years, it’s wise to take normal, big-city precautions, especially if solo at night. Many crimes involve cell phone theft, so be subtle when using yours. If driving, stay aware of your surroundings.