Chicago Guide Downtown, neighborhoods, dining, and the lakefront

Arrival

Getting to Chicago

Most visitors arrive through one of two airports — O'Hare International (ORD) on the far northwest side, or Midway International (MDW) on the southwest side — while Amtrak trains from across the country pull into Union Station and drivers come in on the interstates. Both airports have a direct CTA train downtown, which is often the fastest and cheapest way in.

Last checked July 12, 2026

Flying into O'Hare (ORD) and Midway (MDW)

O'Hare International Airport, on the city's far Northwest Side, is one of the world's busiest airports and the main gateway for long-haul and international flights. The CTA Blue Line runs 24 hours a day from the station in the terminal core's lower level to the Loop in 40 to 45 minutes; boarding at O'Hare carries a $5 premium fare (riders with unlimited-ride passes board at no extra charge), which still undercuts a taxi many times over.

Midway International Airport, on the Southwest Side and considerably closer to downtown, handles mostly domestic flights, the bulk of them on Southwest Airlines. The CTA Orange Line connects Midway to the Loop in 20 to 25 minutes for the standard $2.50 fare, though it does not run overnight, when the N62 Archer bus fills in. Both airports are run by the Chicago Department of Aviation; confirm your terminal and the current Blue or Orange Line status before you travel.

Arriving by train at Union Station

Chicago is the hub of the national Amtrak network, and long-distance trains from the East and West Coasts, the South, and across the Midwest arrive at Union Station, just west of the Chicago River at the western edge of the Loop. The station's Beaux-Arts Great Hall is a landmark in its own right.

Union Station is also the terminal for many Metra commuter lines serving the suburbs. From the station it is a short walk or a quick bus or rideshare to Loop and West Loop hotels; the nearest CTA train stations are a few blocks away at Clinton and Quincy.

Driving in

Several interstates converge on Chicago: I-90 and I-94 (the Kennedy and Dan Ryan Expressways) run through the city, I-55 (the Stevenson) comes up from the southwest, and I-290 (the Eisenhower) feeds in from the western suburbs. Rush-hour congestion on all of them is heavy. The expressways within the city are toll-free, but the Illinois Tollway routes ringing the region are cashless: pay with an I-PASS or E-ZPass transponder, or online via Pay By Plate within 14 days of travel.

Downtown parking is expensive and street parking is metered and tightly enforced, so many visitors staying in the center park the car in a garage and rely on transit and walking. Check the Illinois Tollway and city sources for current tolling and any construction before you drive in.

Sources

Reviewed source trail