Chicago is an incredible with lots to offer and visitors rightfully flock here every year. But with so many great options comes the dilemma – where to even start?
I’ve lived here for more than 30 years and this is what I tell all of my visitors: take public transport, hit the neighborhoods and drink Malört 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. I’ve gathered together all the top insider tips you need to ensure a smooth visit to the Windy City.
1. Plan on 3 to 5 days to visit
It’ll take you two to three days to see the highlights, like the Art Institute, Wrigley Field, Millennium Park and Willis Tower. Adding an extra couple of days to your visit allows you to move out of the center and into the neighborhoods, where Chicago’s true heart beats.
Pilsen and Logan Square welcome you with chowhound eats and vibrant street art. Bronzeville has galleries and soul food restaurants and Andersonville is a jazzy, cafe-laden LGBTIQ+ hub. Hyde Park, Wicker Park and Humboldt Park are other troves of great restaurants and attractions.
2. 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 main highway through town has only added 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 per day. Ditch the car and use public transportation to spare yourself the annoyance.
3. Buy a Ventra Card for public transportation
It’s easy-peasy to make your way around Chicago on public transport – mainly the L trains, which run on both elevated and subway tracks. They’ll get you to most sights and neighborhoods into the wee hours. Buses pick up the slack in areas that the L misses.
To save time and money, buy a rechargeable Ventra Card to use on transit and add value as needed. Cards are available at any L station (including at the airports) and save around $0.75 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, too.
Whether using a plastic or digital card, simply tap it at the turnstile as you enter the L station or at the farebox as you get on the bus. If you’ll be riding three or more times per day, consider buying an unlimited ride day pass for additional savings.
4. Use the L to get to and from the airports
The aforementioned traffic is no joke. Taxis and ride-shares 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 to 40 minutes and cost $2.50 to $5. Not only are travel times often quicker on the L, but it’s about 10 times cheaper than a cab.
5. Book museum and theater tickets in advance
Many museums, including the Art Institute, encourage tickets to be purchased online in advance from the museum’s website. A day or so prior should do it, unless there’s a blockbuster exhibit going on.
It’s also wise to book 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 traveling on a budget.
6. 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, Open Table or Resy. A week or two in advance will work for most places, though 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.
7. Pack a warm coat, but also a bathing suit
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, hat and sturdy shoes when visiting November through March. Even in summer, 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 from June through August. The city has several beaches that beckon with sand and surf.
8. 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 a good option if you’re traveling with young 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 into the wee hours. They’re not close to the main sights but are easy enough to access via the L. Book accommodations a month or two in advance, if possible.
9. 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.
10. 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 a diehard rivalry: the Cubs are the more moneyed North Side squad, while the White Sox are the blue-collar, 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, but they’re typically not very good. They’re followed by basketball’s underachieving Bulls, hockey’s try-hard Blackhawks, and soccer’s middling Fire.
11. Dress casual
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!
12. 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.
13. 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. Blame it on summer, when sunny days make beer gardens and sidewalk patios so splendid.
Beer is the drink of choice. No surprise given Chicago is home to more breweries than any other US city. 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. It’s a local liquor famous for tasting awful. Downing one is a Chicago rite of passage.
14. 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.
15. Be courteous on the L
Let passengers get off the train before getting on yourself – wait beside 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.
16. 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.
17. Don’t let the headlines scare you away
Chicago has the unfortunate reputation of being the USA’s murder capital. While it’s true the city has the largest total number of homicides of any American municipality, it ranks much lower on the list when considered on a per capita basis.
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.
Overall, serious crime in Chicago has been dropping in recent years, according to city statistics. Still, 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.
This article was first published Sep 16, 2021 and updated Aug 10, 2024.