Getting to Chicago

Chicago has been the country's crossroads since the railroads made it one, and that still shows. Two big airports, one of the busiest train stations in the country, and a knot of interstates all meet here. From most of the Midwest you can pick between a train, a bus and your own car. From farther out you'll fly, and you'll have plenty of airlines to choose from.

This page is the overview. The details live on their own pages: flights to Chicago, O'Hare and Midway, and getting between the two airports. Once you're here, our transportation page covers the L, buses and getting around town.

Flying in

O'Hare (ORD) is the big one, 17 miles northwest of the Loop, a hub for both United and American, and one of the busiest airports in the world, with 84.9 million passengers in 2025 (Wikipedia). Midway (MDW) is smaller and closer in on the Southwest Side, and it's Southwest Airlines' town. Southwest carried about nine of every ten passengers who flew through Midway between June 2025 and May 2026 (Wikipedia).

Both airports have a train straight downtown. The Blue Line runs 24 hours from O'Hare and takes about 40 minutes to the Loop. The Orange Line gets you from Midway to the Loop in 20 to 25 minutes. A ride costs $5 when you board at O'Hare and $2.50 everywhere else, including Midway (CTA fares). Search "Chicago (CHI)" rather than a single airport when you shop for fares, since that code covers both. Our airports page has terminals, taxi and rideshare pickup spots, and the rest.

By train

Every Amtrak train into Chicago ends at Union Station, 225 S. Canal St., on the west edge of the Loop. The Great Hall is worth a look even if you're only passing through. From the station, the Blue Line's Clinton stop is a couple of blocks south, and Quincy on the Loop L (Brown, Orange, Pink and Purple lines) is a short walk east across the river. Metra commuter trains share the station too.

The short-haul corridor trains are where Amtrak beats flying outright. You skip the airport run on both ends and arrive downtown. Schedules and fares are on Amtrak.com; book early, since fares climb as trains fill.

• Milwaukee on the Hiawatha, six round trips a day (five on Sunday), with a stop at Milwaukee's airport. The daily Borealis runs the same line on to St. Paul. See getting from Milwaukee to Chicago.
• St. Louis on the Lincoln Service, three round trips a day, about five hours each way (Amtrak). The Texas Eagle uses the same tracks. See getting from St. Louis to Chicago.
• Detroit on the Wolverine, three round trips a day between Chicago and Pontiac by way of Ann Arbor and Detroit. See getting from Detroit to Chicago.
• Elsewhere in Michigan and Illinois: the Blue Water to Port Huron, the Pere Marquette to Grand Rapids, the Illini and Saluki to Champaign and Carbondale (see getting from Champaign), and the Illinois Zephyr and Carl Sandburg to Quincy.

The long-distance trains fan out to both coasts. The Empire Builder goes to Seattle and Portland, the California Zephyr to the Bay Area, and the Southwest Chief to Los Angeles (see getting from Los Angeles). The City of New Orleans runs south, and the Lake Shore Limited runs east to New York and Boston (see New York and Boston). The Floridian, which started in November 2024 as a stopgap merger of the old Capitol Limited and Silver Star, goes to Washington, D.C. and on to Miami. The Cardinal takes the long way to New York through Indianapolis and West Virginia three days a week (see Indianapolis). These trains take a day or two and are about the scenery, not speed. A sleeper on the Zephyr through the Rockies is a trip in its own right.

By bus

Chicago's intercity bus station is the Greyhound terminal at 630 W. Harrison St., a few blocks south of Union Station and close to the Blue Line's Clinton stop. FlixBus, Barons Bus Lines and Burlington Trailways use it too.

FlixBus is usually the cheapest seat into town. Besides the Harrison Street station, its Chicago stops include a curbside stop outside Union Station (currently on the south side of Jackson Boulevard just east of Clinton, moved there because of construction), the Cumberland stop on the Blue Line near O'Hare, and the 95th/Dan Ryan Red Line terminal on the South Side. Check your ticket for the exact stop, because Flix moves them.

Megabus is the name a lot of people still think of, and it started its U.S. network in Chicago in 2006. It isn't the same operation now. Its parent Coach USA went through bankruptcy in 2024 (Wikipedia), and megabus.com's stop list now shows Chicago seats sold on partner lines, such as Jefferson Lines from the Harrison Street station and the Van Galder airport bus from O'Hare. Book through the site and check which carrier and stop your ticket names.

A handful of regional carriers run curbside or airport service instead. Van Galder connects O'Hare with Rockford, Janesville and Madison, and Peoria Charter Coach links Peoria, Normal and Champaign with Union Station, Midway and O'Hare (O'Hare shuttles and buses). See getting from Madison for more.

Driving

Most interstates in the region end up in Chicago. I-94 comes down from Milwaukee and in from Detroit. I-90 arrives from Madison and Rockford in the northwest and from Cleveland in the east, by way of the Indiana Toll Road and the Chicago Skyway (see getting from Cleveland). I-55 is the road from St. Louis, I-57 comes up from southern Illinois, I-65 feeds in from Indianapolis, and I-88 comes in from the west. Locals call the expressways by name, not number: the Kennedy, the Dan Ryan, the Stevenson, the Eisenhower. The traffic reports will make more sense once you know that.

A few things to know before you drive in:

• Illinois tollways don't take cash. An I-PASS or E-ZPass transponder works. Without one, pay online through the Illinois Tollway after your trip so the bill doesn't grow.
• Weekday rush hours run long, and the Kennedy and Dan Ryan back up well outside them. Aim to arrive mid-morning or after 7pm, and avoid a summer Friday afternoon if you can.
• Parking downtown is expensive, and hotel valet more so. Booking a garage ahead with an app like SpotHero usually beats the drive-up rate. Or park once and use the L.

If you'd rather not bring your own car, our car rental page covers the options. And if Chicago is the start of the drive, not the end, Route 66 begins downtown on Adams Street. Our Route 66 page has the details.