What should I avoid in Chicago?

Skip Navy Pier. It sits at the east end of Grand Avenue, about a 25-minute walk from the Loop, and the payoff tends to be fryer oil on the breeze, chain restaurants, and a Centennial Wheel ride that runs roughly $20 for 13 minutes. Willis Tower dates to 1971, and the Skydeck on its 103rd floor can mean a 60 to 90 minute wait on a July afternoon for about 90 seconds on a glass ledge. The better view is from the water: a 90-minute architecture cruise from the Chicago Riverwalk costs around $55, and the guide names every building while the diesel engine hums under your feet. The Magnificent Mile is 13 blocks of North Michigan Avenue lined with chains you likely have at home, so shop Armitage Avenue in Lincoln Park or Clark Street in Andersonville instead. Cloud Gate has stood in Millennium Park since 2004, and by noon you are photographing 200 strangers in its reflection. Go before 8am, when the steel is still cold to the touch.

The first mistake most visitors make happens at O'Hare. A taxi to the Loop currently runs $45 to $60 and can sit for 75 minutes on the Kennedy Expressway at 5pm, while the CTA Blue Line leaves from under Terminal 2, costs $5 from the airport, runs 24 hours, and reaches Clark/Lake in about 45 minutes. From Midway, the Orange Line takes roughly 25 minutes, though it stops running for a few hours after 1am. Ignore anyone in the O'Hare baggage hall who offers you a ride: licensed cabs wait only at the marked stands outside each terminal, and rideshares pick up on the upper level of Terminal 2. A rental car is the other thing to skip, since Loop hotels tend to charge $60 to $80 a night for valet parking, and the screech of the L over Wabash Avenue will remind you the train was faster.

Deep dish is the menu item that trips up first-timers in Chicago: it takes about 45 minutes to bake, one slice weighs close to half a pound, and a large for two at Giordano's is how a jet-lagged first night ends at 8pm. Order one small pie, and make it Pequod's on Clybourn Avenue, where the cheese burns into a black, crunchy rim against the pan. Most Chicagoans eat tavern-style instead, a cracker-thin crust cut into squares, and Vito & Nick's has baked it at 84th and Pulaski since 1965. At Al's #1 Italian Beef on Taylor Street, the counter will ask 'dipped?' and 'hot or sweet?' Dipped means the whole roll is dunked in beef gravy, and hot means giardiniera, a vinegary pickled-pepper relish that stings the lips. The ketchup-on-a-hot-dog rule at Portillo's is a joke locals enjoy more than they enforce. Jeppson's Malört, the wormwood liqueur bartenders in Wicker Park push on visitors, tastes like grapefruit peel and gasoline.

Chicago scores 5.8/10 for solo-traveler safety (see the TTDI Solo-Safety Index), and the number reflects a city where risk is very uneven by block: serious violence is concentrated in parts of the West and South Sides that sit miles from River North and the lakefront hotels. Avoid the CTA trains after midnight, when cars empty out, and pay the $15 to $25 for a rideshare. Keep your phone away from the train doors at stops like Jackson and Roosevelt, where snatch thefts tend to happen as the doors close. On Michigan Avenue, decline the men with clipboards who collect for a youth basketball team that may not exist, and the robed 'monks' who slip a bracelet on your wrist and then ask for $20. Don't stack the Field Museum, founded in 1893, and the Art Institute of Chicago, founded in 1879, into one day. It was 18.5°C and clear on the evening of October 11, 2026, but the wind off Lake Michigan can make the Museum Campus feel 5 degrees colder by November.