Do not be deceived by the fact that I was born in Akron and lived my first years there. Chicago, the City of the Big Shoulders, is forever my place.
Getting around
Ventra covers CTA trains and buses, Pace, and Metra. For CTA and Pace, you can tap a Ventra card, the Ventra app, or just a contactless bank card or phone. Taps within two hours of the first tap are free. Metra tickets are sold on the app or at a station. Fares
The L: Red runs north–south straight through downtown; Blue runs from O'Hare through Logan Square, Wicker Park, the Loop, and UIC to Forest Park; Brown runs from Albany Park through Lincoln Square, Lakeview, and around the Loop; Green goes west through the West Loop to Oak Park and south toward Bronzeville and Woodlawn; Orange goes from the Loop to Midway; Pink from the Loop to Pilsen; Purple to Evanston; Yellow to Skokie. Red and Blue run all night, with reduced frequencies.
Google Maps is the most reliable for directions. Citymapper is a good second opinion, often with more walking, and it includes the University of Chicago shuttles.
Divvy has bikes, e-bikes and scooters across the city. Single rides can be quite expensive, but an e-bike along the Lakefront Trail on a nice day is one of my most enjoyed experiences in Chicago – and can be one of yours too!
From O'Hare, the Blue Line reaches the Loop in about 45 minutes. From Midway, the Orange Line takes about 25.