Flight
Have you ever heard of O'hare airport? It's really big and was often delayed until an 8.5 billion dollar runway redesign that took 15 years and finished in 2019. Now it's better, but expect to taxi for 20 minutes after landing. It was previously named Orchard airport (that's why the airport code is ORD), but was renamed in 1949 after Edward "Butch" O'Hare, a WWII naval flying ace. It opened to commercial traffic in 1955 and was the busiest airport in the world until 1998. Currently, it lists in the top 4. Terminal 1 is designed by Helmut Jahn and is beautiful. Terminal 2 is not beautiful and is getting demolished and redesigned by Jeanne Gang, finishing in 2028. O'hare is on the far northwest side of the city and closer to the weekend's activities, so favor this airport over Midway for your flight.
Train
The L is a fabulous and cheap option to get from O'hare directly to Logan Square, Bucktown, and Wicker Park. You'll often run into some interesting characters. Most of the country doesn't have public transit, so experience the joy we feel riding the rails.
Flight
Midway Airport is in the Southwest side of the city and farther than O'hare Airport to Logan/Bucktown/Lincoln park, but is where most Southwest flights go. The Orange line goes directly downtown where you can transfer to the blue, red, or brown lines to get to various places on the north side.