What should I avoid in Chicago?

Navy Pier pulls about 9 million visitors a year, and most of them seem confused about what they came for. The Centennial Wheel runs $18 per ride for 15 minutes at 196 feet, and the view is worse than what you get standing free at the Lakefront Trail near North Avenue Beach. The food court sells $12 hot dogs. The souvenir shops sell "Chicago" hoodies for $45. To be fair, the Chicago Shakespeare Theater at the pier's east end is worth a visit if you've got tickets, and the free fireworks on Wednesday and Saturday nights in summer still pull locals from the Gold Coast. But the chain restaurants and gift shops feel like a suburban mall that happens to sit on Lake Michigan. Walk to the end, look back at the skyline for 5 minutes, and leave.

The biggest money mistake first-timers make at O'Hare is grabbing a taxi. A cab runs $40-50 before tip, and Uber or Lyft hits $55-70 during peak arrivals. The CTA Blue Line departs from inside Terminal 2, rumbles through the northwest suburbs, and drops you at Jackson in the Loop in about 45 minutes for $5. You'll smell the hot brakes at each underground stop and hear the doors chime in that flat CTA monotone. It's not glamorous. But it puts you 2 blocks from most downtown hotels. If you're heading to Lincoln Park or Lakeview on the North Side, a rideshare saves you a transfer and likely costs $25-30 off-peak. From Midway, the Orange Line does the same trip for the same $5, reaching the Loop in 30 minutes.

Don't eat deep-dish at the downtown Giordano's on Rush Street or the Magnificent Mile Lou Malnati's on a Friday night. The wait hits 60-90 minutes, and the pizza tastes identical to what you'd get at the Lincoln Park Lou Malnati's on Clybourn Avenue with a 10-minute wait. Mind you, most Chicagoans eat tavern-style thin-crust pizza, not deep-dish. Pat's Pizza on Lincoln Avenue or Vito & Nick's on Pulaski Road in the Ashburn neighborhood serve the square-cut, cracker-thin pies that locals actually order on a Tuesday night. The Garrett Popcorn line on Michigan Avenue can stretch 30-40 minutes. The same CaramelCrisp is sold at the Garrett in O'Hare Terminal 3 with no line. Skip any steakhouse in the Loop with a promoter outside waving discount cards at you.

Chicago's weather shifts fast. A June afternoon at 25°C can drop 10 degrees by 6pm when the lake breeze rolls in, and that cold, damp wind off Lake Michigan cuts right through a cotton t-shirt. Pack a light jacket even in July. January and February are brutal, with wind chills reaching -20°C along the lakefront. Locals call the lake wind "the Hawk." It will numb your face in 5 minutes walking north across the Michigan Avenue bridge. For safety, the neighborhoods in the headlines, Englewood, Austin, West Garfield Park, are residential areas far south and west of anything a tourist would visit. The Loop, River North, Lincoln Park, Wicker Park, and Hyde Park near the University of Chicago campus are all walkable and fine. That said, the CTA Red Line gets quiet south of 35th-Bronzeville-IIT after dark. Stay aware on late-night trains.

The Willis Tower Skydeck (the tower opened in 1971, still called Sears by half the city) charges $28-41 depending on the package, and the line to stand on the glass Ledge boxes at the 103rd floor can take 90 minutes on a summer Saturday. 360 Chicago at the top of 875 North Michigan Avenue costs $30 and rarely has more than a 20-minute wait. The north-facing view from 360 is better. You see the full lakefront curve past Montrose Harbor, the Lincoln Park Zoo canopy, and the Gold Coast rooftops. Willis Tower faces south toward Chinatown and Pilsen, which is interesting but lacks the same pull. If you want the skyline without paying anything, walk the Lakefront Trail from the Shedd Aquarium past Monroe Harbor. On a clear evening the light catches the glass towers around 7pm, warm and copper-toned, and it's the kind of view no observation deck can match.