How do I get around Chicago?

Chicago's L is the default. The elevated and subway rail network has been running since 1892 and currently moves about 1.6 million riders on weekdays across 8 lines. For a first visit, you need three of them. The Brown Line loops through the Loop (yes, that is where the name comes from) and runs north through Lincoln Park and Lakeview. The Red Line is the long north-south spine, connecting Wrigleyville to Chinatown with 24-hour service. The Blue Line also runs around the clock and connects O'Hare airport to the Loop in about 45 minutes for $5. A Ventra card costs $5 at any station kiosk, and single rides are $2.50 per tap. If you are staying 3 days or more, the $15 unlimited 3-day pass pays for itself by trip six. The platforms are outdoors and elevated through most of the city, so in winter you will feel the wind cut through you while you wait. In June, the steel rails throw off heat and the platforms smell like warm metal and grease.

Uber and Lyft both operate across the city, and a typical downtown-to-neighborhood ride of 3-4 miles tends to run $12-18. Surge pricing hits on Friday and Saturday nights near Wicker Park and River North, sometimes doubling the fare after midnight. That said, ridehail is the right call for anything south of 35th Street after dark, where L stations thin out and bus frequency drops to every 20-30 minutes. CTA buses fill the east-west gaps the L does not cover. The #151 Sheridan and #146 Inner Drive Express run along the lakefront and are probably the most useful routes for visitors. They connect Lincoln Park to the Museum Campus, where the Field Museum of Natural History has stood since 1893. Bus fare is $2.25 with Ventra, and a transfer within 2 hours costs $0.25. Taxis still cruise Michigan Avenue and you will hear their horns in the Loop traffic, but there is rarely a reason to hail one. The Chicago taxi flagfall is $3.25 with $2.25 per mile, which consistently runs more expensive than the app equivalent.

Downtown Chicago is flat and gridded, which makes walking straightforward if you can handle the distances. The Loop to Millennium Park is a 10-minute walk. Millennium Park to the Art Institute of Chicago, founded in 1879, is about 5 minutes across Monroe Street. But the Museum of Science and Industry in Hyde Park sits 7 miles south, and walking there is not realistic. Divvy bike-share stations appear every few blocks in the central neighborhoods, and a single classic-bike ride runs $1 to unlock plus $0.20 per minute. The Lakefront Trail stretches 18 miles along Lake Michigan, and on a June morning with humidity near 80% you will feel the lake breeze pushing damp air off the water. It smells faintly of algae and wet concrete. Worth noting, Chicago Water Taxi runs a Riverwalk route between Michigan Avenue and Chinatown for $6 per ride. The 30-minute trip gives you a view of the architecture from the river that the walking tours charge $40-50 to narrate.

The biggest first-timer mistake is buying a CTA day pass when you only need 3-4 rides. The $5 one-day unlimited pass breaks even at the third train ride, so it is worth it on a full sightseeing day but not for a lazy morning-and-evening pattern. The second mistake is underestimating distances on the north side. Wrigley Field in Lakeview sits about 5 miles north of the Loop, and the Red Line takes 20 minutes to get there. Walking it sounds reasonable on a map but takes over an hour. Mind you, the walk itself passes through good neighborhoods. Lincoln Park smells like cut grass and charcoal in summer, and you will hear the rumble of the L overhead every few minutes. If you are arriving at O'Hare, do not take a taxi downtown. The flat rate runs $40-50, and the Blue Line covers the same ground in 45 minutes for $5. Midway is similar. The Orange Line reaches the Loop in 25 minutes for $2.50.