Metro Chicago and Southern Wisconsin Vacation Ideas Metro Chicago and Southern Wisconsin - Road Trip Planner

Getting to Chicago, Illinois, Milwaukee, Wisconsin Dells, Madison - Bus, Train Distance

Things to do / Travel Guide

A metropolitan area, metro Chicago and southern Wisconsin is easy to get to from points of origin across the country. Whether by track, by air, by bus, or by automobile - this region is only a hop, skip, or a jump away.

Chicago Airports

By far the most common way to enter the metro Chicago and southern Wisconsin region is by plane to either Chicago or Milwaukee. Chicago sports one of the largest and busiest airports in the nation, and indeed the world, in O' Hare International Airport (ORD), located 17 miles northwest of the Loop and serving practically every airline imaginable arriving from almost every major world destination.
Notably, O' Hare is a major hub for American, Continental, and United Airlines. Pretty much the only downside of O' Hare is that due to the immense air traffic it's the nations worst in terms of flight cancellations.

Your other option for flying into Chicago is Midway Airport (MID), located just 10 miles away from the Loop and southwest of the city, also known for serving budget carriers. To get between the two Chicago airports, take the hourly Omega shuttle. Both airports offer the Continental Airport Express that will take you straight to the Loop. Of course, both are served by the EL, with access to most of Chicago and some close suburbs.

Madison and Milwaukee, Wisconsin Airports

If you prefer to fly into southern Wisconsin, Mitchell International Airport (MKE) in Milwaukee serves the major airlines, to most popular US destinations. Dane County Regional Airport (MSN) in Madison serve mainly commuter airlines, with non-stop service as far west as Denver, and to main hubs such as New York, DC, Dallas, Atlanta. Short-haul destinations include Chicago and Milwaukee.. Call the Milwaukee County Shuttle Service to get from Mitchell Airport to various places in Milwaukee, or just take a taxi into town. Dane County Airport offers cab services, and various airport hotels offer complimentary shuttle service. All airports in the region offer car rental services.

Flying into the southern Wisconsin airports is generally more expensive than flying into Chicago, and Dane County is more expensive than Mitchell, but often it's worth the few bucks if southern Wisconsin is your final destination, so you don't have to drive an extra 100 miles north after you land.

Train to Chicago

Chicago is a major hub for Amtrak, and fully 12 train lines reach the city: from Boston, New York City, Washington, D.C., Cincinnati, New Orleans, St. Louis, Cleveland, Detroit, Kansas City, Los Angeles, San Antonio, and Milwaukee.

From New York or Boston, take the Lake Shore Limited, which departs afternoons, daily. The train takes about 18 hours to get to Chicago from New York; Buffalo, New York, a tad less than 10 hours; and from Toledo, Ohio, four hours.

From San Francisco, take the California Zephyr, which departs mornings, daily; it takes about two days to reach Chicago from California; 20 hours from Denver, or 9.5 hours from Omaha, Nebraska.

Chicago's Union Station is centrally located, on Canal Street, and it's a fantastic Beaux-Arts masterpiece with a 100-foot-high Great Hall.

Bus to Chicago and Wisconsin

Greyhound Bus Lines, whose Chicago station is on West Harrison Street in Near West Side, offers rides to Chicago from many U.S. cities. Milwaukee and Madison are also major bus station stops and hubs. From Omaha to Chicago, for instance, a bus ride can take anywhere from 10 hours to 14 hours. That's about the same from Buffalo to Chicago.

Chicago Driving Directions

Chicago is the meeting point for a number of different interstates, and you can reach the city directly from a number of other cities of central U.S.
  • I-94 follows Lake Michigan to the south and around into Michigan, and terminates soon after Detroit.
  • Heading north, I-94 runs through Milwaukee and Madison, then turns northwest to Minneapolis-St. Paul.
  • I-57 travels south to the southern tip of Illinois.
  • I-55 heads straight to St. Louis and Memphis, down to New Orleans.
  • I-80 goes west to Omaha, Cheyenne, Salt Lake City and eventually, San Francisco's Golden Gate Bridge. Going east, it passes Cleveland and winds up in New York City.
  • I-90 terminates in the west becomes the North – West Tollway and terminates near Rockford, IL. In the east it heads all the way to Boston, after passing through Cleveland and Buffalo.
  • I-88 heads west, meeting up with I-80 at Davenport.
  • I-43 passes through Milwaukee, after originating in Green Bay, Wisconsin.
  • I-39 serves Madison, and extends from Northern Wisconsin to Central Illinois.

Driving Distance to Chicago

  • Distance from New York to Chicago: 790 miles, 12 hours and 45 minutes
  • Distance from Washington, D.C to Chicago: 700 miles, 11 hours and 10 minutes
  • Distance from Detroit to Chicago: 280 miles, 4 hours and 20 minutes
  • Distance from Indianapolis to Chicago: 180 miles, 3 hours
  • Distance from St. Louis to Chicago: 300 miles, 4 hours and 45 minutes
  • Distance from Minneapolis to Chicago: 410 miles, 6 hours and 40 minutes
  • Distance from Denver to Chicago: 1005 miles, 15 hours

Airports Serving Chicago, Illinois, Milwaukee, Wisconsin Dells, Madison

Sort By: Rating | Name
Austin-Straubel Field Airport (GRB)
General Mitchell Field Airport (MKE)
Michiana Regional Airport (SBN)
Midway Airport (MDW)
O'Hare International Airport (ORD)
Truax Field Airport (MSN)