Everything you need to know before visiting Chicago

15.08.2023 - 22:25 / lonelyplanet.com / Willis Tower

I’ve lived in Chicago for more than 30 years, and these are the top tips 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.

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 LGBTQI+ hub. Hyde Park, Wicker Park and Humboldt Park are other troves of great restaurants and attractions.

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.

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.

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 $3 to $5. Not only are travel times often quicker on the L, but it’s about 10 times cheaper than a cab.

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.

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