Chicago: know before you go

Chicago has two airports, and both connect to downtown by train. O'Hare is the big international hub, and the Blue Line runs from its lower level into the Loop in 40 to 45 minutes, all day and all night. Midway is smaller and closer, with the Orange Line making the run to the Loop in 20 to 25 minutes. A taxi from O'Hare costs about $40, and a rideshare runs about $35 to $50 before surges. From Midway, a taxi is about $25.

Everything local runs on Ventra, and you do not need to buy a card in advance. Tap a contactless credit or debit card, or a phone in Apple Wallet or Google Wallet, at any L turnstile and the standard fare is deducted. Buses cost $2.25 and trains $2.50, and transfers are free for up to two additional rides within two hours. If you plan to move around a lot, the $5 one-day pass pays for itself after three rides, and the seven-day pass is $20. The L is not a tourist ride; it is the fastest way across a city where neighborhoods sit miles apart.

Chicago's main levy on visitors is the 4.5% hotel accommodations tax on the gross room charge. Vacation rentals and shared housing add a 6% surcharge, so a short-term rental carries a 10.5% city tax before state and county taxes appear on the bill. Large downtown hotels also began carrying a 1.5% Tourism Improvement District charge in 2026. Sales tax and tipping follow the national patterns in the United States country guide, so there is no separate Chicago rate to memorize.

Chicago is a city of neighborhoods, and the parts you are most likely to walk, the Loop, River North, the Gold Coast, and the lakefront, are busy, well lit, and patrolled. Keep the same habits you would use in any large city: hold your phone firmly on crowded trains, and do not drift alone into unfamiliar blocks late at night. Call 911 for emergencies, and use 311 for non-emergency city services like noise, graffiti, or a blocked sidewalk. The lakefront is safe by day, but the winter wind off Lake Michigan drops the real-feel temperature fast, so a short walk can turn cold quicker than the air temperature suggests.

Chicago tap water comes from Lake Michigan and is safe to drink straight from the faucet. A refillable bottle is the right call, since parks and museums have fountains and bottle-fill stations. Summers run humid, so wear sunscreen even when the lake breeze feels cool. The real hazard is winter: wind chill off the lake can make a 32°F day feel like the teens, so pack a coat, hat, and gloves that can handle a walk across the Loop.

Cellular service is strong across the city, including in the Loop's subway tunnels, and every major carrier holds up fine. The one app worth downloading before you land is Ventra, which stores transit passes, checks balances, and can buy Metra tickets if you ride out to Hyde Park or the suburbs. Museums, libraries, and most coffee shops run free Wi-Fi, so a heavy data plan is a convenience rather than a requirement.

Chicagoans walk fast, especially downtown at rush hour. Stay to the right on stairs and escalators, step out of the flow before you check your phone, and do not stop at the top of an escalator. Doors close quickly on the L, so do not hold them for a friend unless the train is empty. Tipping works exactly like the rest of the country, and the country guide covers it. Locals call the trains the L, pronounced ell, and nobody expects you to say the El, though they will understand.

English is the working language everywhere you will need it. Spanish is widely spoken on the South and West Sides, above all in Pilsen and Little Village, where many signs and menus are bilingual. A few local terms help: the L is the train system, the lakefront means the parks and paths along Lake Michigan, and the Loop is both the downtown core and the elevated train circuit around it. Streets run on a grid that starts at State and Madison, so an address like 800 North sits eight blocks north of the center.

The Loop, the lakefront, and the museum campuses are flat and mostly curb-cut, which makes getting around by wheelchair easier than in older, hillier cities. CTA buses all kneel and carry ramps, so the bus is the most predictable accessible option. Many L stations have elevators, but not every older station does, so check elevator status on the CTA site or in the app before you rely on a specific stop. Ride-hail and taxi fleets include wheelchair-accessible vehicles, but book them ahead rather than flagging one down.

Chicago's own event calendar moves crowds and closes streets more than the national holidays do. St. Patrick's Day turns the Chicago River green and packs downtown around the Saturday parade in March. Lollapalooza takes over Grant Park for a long weekend in early August, closing parts of the lakefront and pushing hotel prices up for blocks around. The Chicago Marathon shuts down streets through much of the city on a Sunday in October, so do not plan a car or taxi itinerary that morning. Check the city event calendar for your dates and book hotels around the big weekends.

You do not need a reservation for most of Chicago, but a few things genuinely sell out. The architecture river cruise run by the Chicago Architecture Center is the city's single most popular tour, and summer departures often fill days ahead, so book it before you fly. Timed entry at the Art Institute and the Museum of Science and Industry is worth reserving on busy weekends. Deep-dish restaurants run long dinner waits, but most seat walk-ins early; only a small number of the fancier rooms require a booking weeks out.