Chicago

The currency is the US dollar, and cards are accepted almost everywhere, including buses and taxis. A few old-school hot dog stands and several longtime Pilsen taquerias still take cash only. Price ranges in 2026: coffee $4–6; hot dog $5–8; Italian beef $10–15; simple lunch $15–25; sit-down dinner $40–75 per person without drinks; draft beer $7–11; cocktail $15–19; museum admission $25–40; mid-range hotel $180–330 a night in high season and about half that from January to March. Two taxes change the math. Sales tax rose to 10.5% in August 2026 and never shows up on the price tag. Lodging adds about 17.5% in city and state taxes to the nightly rate, and since May 2026 hotels with a hundred rooms or more in and around downtown charge another 1.5%, close to 19% in total. Tipping is part of the price and isn't optional: 18 to 22% at restaurants with table service, $1 to 2 per drink at the bar, 15 to 20% for taxis, $2 to 5 a day for housekeeping. Check the bottom of the bill before you add it up: since the pandemic, many restaurants tack on a 3 to 5% service charge that doesn't replace the tip, and the city has only banned charging it without notice, not the charge itself.

The Blue Line runs 24 hours to the Loop

O'Hare airport (ORD) is 27 km northwest of downtown and is served 24 hours a day by the CTA Blue Line, which takes about 45 minutes to the Loop. Leaving the airport carries a special $5 fare when you pay with a single-ride card or stored value (2026), but if you go through the turnstile with a day pass you don't pay that surcharge. A taxi or rideshare costs $45 to $75 and takes 40 to 75 minutes, depending on traffic on the Kennedy Expressway. Midway (MDW), 16 km southwest, is served by the Orange Line, about 25 minutes to the Loop at the regular fare, and a taxi runs $35–50. Both airports have shared vans at an in-between price, slower because of the stops.

Subway: eight color-coded lines, with the “L” elevated above the city

Within the city, the CTA runs eight color-coded train lines (the “L,” for elevated) and more than 120 bus routes, with the Loop's ring of tracks at the center. The fare is $2.25 on the bus and $2.50 on the train, and up to two transfers within two hours are free. The CTA canceled the 25-cent increase that was to take effect in February 2026. A one-day pass costs $5, a three-day pass $15, a seven-day pass $20 and a thirty-day pass $75. Pay with a Ventra card, sold at stations and drugstores, or tap a credit card or phone on the reader. For the suburbs, Metra trains leave from four downtown stations with their own tickets, and the South Shore Line runs to Indiana. The Divvy bike-share network has about a thousand stations, with protected bike lanes on Milwaukee, on Dearborn and on the Lakefront Trail, 29 km along the lake. Walking is easy in the Loop and the North Side neighborhoods, thanks to the numbered grid. Renting a car only makes sense for day trips.

Chicago's reputation is bigger than the risk a visitor faces. Lethal violence is concentrated in a few West and South Side neighborhoods, such as Austin, Englewood and West Garfield Park, far from the areas where tourists stay and get around. The Loop, Near North, Lincoln Park, Wicker Park, Hyde Park and Pilsen have rates comparable to other big American cities. The practical risks are different: phone snatching at the train door just as it closes, bike theft, break-ins to cars and occasional muggings at empty stations late at night. Put your phone in your pocket before the doors open, as locals do. After midnight, avoid deserted platforms, especially on the Blue Line and at the ends of the lines, and take a rideshare instead. On summer nights, crowds on Michigan Avenue and at the beaches sometimes end with police closing off the block. If the crowd changes direction, leave with it, without rushing. The emergency number is 911, and for lost items and city complaints the number is 311.

Ketchup on the hot dog

Asking for ketchup on a hot dog isn't forbidden, but most stands don't even keep the bottle on the counter, and someone will say something. The local standard is mustard, relish, onion, tomato, pickle, sport peppers and celery salt, and ketchup on fries is fine.

Stand right on the escalator

At L stations and airports, the left side is reserved for people walking up. Standing side by side blocks the way and earns a polite elbow.

Respect “dibs” in winter

After a snowstorm, whoever digs out the street spot marks it with a chair, cone, or bucket. It isn't law and the city removes the objects, but taking a marked spot is the fastest way to start a fight on the block.

Pick a team and don't mix them

“Cubs or Sox?” is an introductory question, and answering “both” sounds like not answering. Picking a side in jest is perfectly fine; wearing both jerseys isn't.

Tipping in the US: part of the server's wage

The 18 to 22% at a restaurant is part of the server's wage, unrelated to exceptional performance. Leaving 10% is read as an explicit complaint.

On the bus and the train, let people off first

The L's doors are narrow and the platform is short at several stations. Wait beside the door, give up the front seats without being asked, and take your backpack off your back during busy hours.

Deep-dish as an everyday pizza

Assuming deep-dish is everyday pizza. It's as heavy as a whole meal, it's mostly visitor food and it spends 30 to 45 minutes in the oven, so if you order it, do so as soon as you sit down. To eat like locals, go for tavern-style, thin and cut into squares.

Michigan Avenue is colder than your neighborhood

Underestimating the wind off Lake Michigan. In winter, with average highs of 0 to 3 °C and lows that drop past −10 °C, it pushes the wind chill well below what the thermometer says, and it blows hardest on Michigan Avenue and the river bridges. Pack a hat and gloves from November to March, even when the forecast looks mild.

The food is 20 or 30 minutes away by train

Sticking to the Loop and Michigan Avenue. Downtown empties out at night, and the food is in the neighborhoods: Pilsen, Logan Square, Chinatown, Argyle Street, Devon Avenue and Bridgeport are 20 or 30 minutes away by train, and that's where people eat dinner.

State and Madison is zero, 800 per mile

Ignoring how addresses work. All numbering starts at the corner of State and Madison, at 800 numbers per mile, so “2400 North” is three miles from zero. Reading the number before you head out tells you how far you'll walk and saves you an unnecessary taxi.

Renting a car to stay in the Loop

Renting a car to stay downtown. A Loop garage costs $35 to $60 a day, Lake Shore Drive jams up during both rush hours, and the L covers almost everything. Save the car for a day trip to Oak Park or the dunes. A single day of parking costs more than the $20 week pass.

The L

Chicago's urban train, short for “elevated.” Nobody calls it the subway, even on the underground stretches.

Pop

Soda. Asking for “soda” marks you as an outsider on the spot.

Dipped, hot

How you order italian beef: the whole roll dunked in the juice, with spicy giardiniera. There's also “wet” (just a little juice) and “sweet” (with sweet peppers).

Dibs

The informal claim on a parking spot you dug out of the snow, marked with a chair or cone. Holds from December to March, by consensus, not by law.

Cubs or Sox?

“Cubs or White Sox?”. A social identification question that places you on the north or south side of the city.

The lake is east

'The lake is east.' The orientation rule everyone uses, since Lake Michigan appears at the end of any street running eastward.

The plain, the lake, and the reversed river

Chicago sits on a nearly flat glacial plain about 180 m above sea level, at the southwest tip of Lake Michigan, and its highest natural point barely reaches 205 m. The lake defines everything: 48 km of shoreline within the city, almost entirely given over to parks and public beaches, a result of the principle of keeping the lakefront “forever open, clear and free” that dates to the 19th century and was cemented in Daniel Burnham's 1909 Plan of Chicago. The Chicago River enters downtown and splits into a Y (north branch, south branch, and main branch) and it's this Y that gives the North Side, South Side, and West Side their names; since 1900 it has flowed inland rather than into the lake.

The grid and the rectangle of the Loop

The street network is a near-perfect grid aligned with the compass points, with numbering starting at the intersection of State Street and Madison Street: 800 numbers per mile, eight blocks per mile, so that any address tells you the exact distance to downtown. The CTA's elevated lines form the rectangle of the Loop over Lake, Wabash, Van Buren, and Wells streets, and the business district grew within and around that ring.

The climate and the lake breeze

The climate is humid continental, with hot, humid summers, long cold winters, and a lake breeze that in summer keeps the shoreline several degrees cooler than the inland neighborhoods, and does the opposite in winter.

Great Migration electric blues and Chess

Chicago's musical legacy comes in two waves. The first is electric blues: musicians who came up from the Mississippi Delta during the Great Migration plugged in their guitars to be heard in noisy bars, and Chess Records, at 2120 South Michigan Avenue, recorded Muddy Waters, Howlin' Wolf, Willie Dixon and Chuck Berry between 1950 and 1967. That repertoire is what brought the Rolling Stones to record in the same room in 1964. The second is house music, born in the early 1980s at the Warehouse club, where Frankie Knuckles blended disco and soul records with drum machines; the city exported the genre to the whole world. Alongside all that are the Chicago Symphony Orchestra, the modern gospel Thomas A. Dorsey created in the 1930s, the avant-garde jazz of the AACM (1965) and a rap scene that runs from Common and Kanye West to the drill of the late 2000s and Chance the Rapper.

The Second City (1959) and Steppenwolf (1974)

Chicago is also a center of theater and literature. The Second City opened in 1959 and turned improv into a method for training comedians; Steppenwolf, founded in 1974 by a group that included John Malkovich and Gary Sinise, established the raw, physical acting style that defined American theater outside Broadway. In literature, Carl Sandburg dubbed the city “City of the Big Shoulders” in 1914; Richard Wright published “Native Son” in 1940; Gwendolyn Brooks, from Bronzeville, became in 1950 the first Black person to win a Pulitzer; Nelson Algren, Saul Bellow, and Studs Terkel wrote the city from the inside, and Mike Royko did the same in a daily newspaper column for thirty years.

Cubs to the north, White Sox south of Madison

Sports work as a geographic divide. The Cubs play at Wrigley Field on the North Side and the White Sox on the South Side, at 35th and Shields; the informal dividing line is Madison Street, and the question “Cubs or Sox?” is a test of where you're from. The Bears play football at Soldier Field (1924), on the lakefront, and the Bulls won six NBA titles between 1991 and 1998 with Michael Jordan, which is why the red number 23 jersey shows up on streets all over the planet. Beyond the stadiums, the city keeps a strong neighborhood life: more than 570 parks, farmers markets from May to October, public beaches with flags and lifeguards in summer, and a nearly weekly calendar of street festivals between June and September.

“The Devil in the White City,” Erik Larson (2003)

Recounts the building of the 1893 World's Columbian Exposition alongside the crimes of a serial killer. Explains the ambition, the rush, and the engineering that defined the city at the end of the 19th century.

“Native Son,” Richard Wright (1940)

A novel set on the South Side of the Great Migration, written by someone who came from Mississippi to Chicago at 19. The most direct read on the racial geography that still shapes the city's map.

“The Blues Brothers,” John Landis (1980)

Shot on real locations across the Daley Center, Maxwell Street, and the South Side, with Aretha Franklin, James Brown, Ray Charles, and John Lee Hooker on screen. Captures the city and its music shortly before downtown was rebuilt.