Getting in
Arrive at Union Station if you are coming from Milwaukee, St. Louis, or Detroit: the walk to most Loop hotels is under 15 minutes. Flying into O'Hare, the Blue Line is faster than a car during any weekday afternoon.
Day one: the Loop and the river
Start at the Art Institute early, walk north on Michigan Avenue, and take an architecture cruise in the late afternoon when the light hits the west facades. Dinner in the West Loop is a 20 minute walk or a short ride.
Day two: lakefront and neighborhoods
Rent a bike and ride the Lakefront Trail north to Lincoln Park. In the afternoon, take the Pink Line to Pilsen for murals and tacos. If the Cubs are home, build the evening around Wrigley.
Where to stay
The Loop for rail arrivals and quiet weekends, River North to walk to dinner, Logan Square for cheaper rooms and better food.
Common questions
Do I need a car in Chicago?
No. The L reaches both airports and nearly every neighborhood a visitor wants, and downtown parking runs $45 to $75 per night.