Trains Milwaukee, WI to Chicago, IL: Times, Prices and Tickets

The route from Milwaukee, WI to Chicago, IL

The train journey from Milwaukee to Chicago is a swift and convenient trip covering 86 miles. Operated by Amtrak, the Hiawatha service runs parallel with Lake Michigan southward, terminating at Chicago. It’s Amtrak’s shortest running service line and among the most stress-free means to travel between the two cities. The first incarnation of this service launched in the 1930s when it utilized Hiawatha trains running north to Minneapolis. These were once among the fastest trains in the world.

Today’s Hiawatha service is the same only in name. It departs from Milwaukee Intermodal Station, the city’s main transport hub located in the heart of Downtown. It’s the second-busiest station in the Midwest after Chicago and is linked through the city by buses and streetcars. Be sure to arrive at least 30 minutes before departing to find your train and seat in good time. After leaving Milwaukee, you can expect to make the following stops:

• General Mitchell International Airport Station
• Sturtevant Station
• Glenview Station
• Chicago Union Station

Departing Milwaukee

Your train heads south from Milwaukee’s glass-clad 60s station, crossing the Milwaukee River. To your left, you’ll find the city’s scenic Harbor View area, passing warehouses and carriers as you depart the waterfront. From here, your train heads to Milwaukee’s airport, General Mitchell International Airport. It doesn’t take long to leave the surrounding suburbs for open fields and farmland.

The southern reaches of Wisconsin are largely rural, passing Racine and Kenosha counties. It’s a journey through manicured villages like Somers and small farms. The bulk of industry and more urban towns are located further east along the coast. It’s a sleepy journey south as you head across the Illinois border, crossing via Russel.

Into Illinois

Your introduction to Illinois is via Van Patten Woods Forest Preserve. This serene 975-acre park is home to rich oak forests and a small lake. Pretty meandering rivers and forest views continue south as you pass County Forest Preserve. It’s a scenic trip through Illinois’ protected natural parklands and agricultural heartland. The first major stop in Illinois is Glenview, a pretty town renowned for its golfing.

It’s now a short train ride south into Chicago through the city’s suburbs and satellite villages. You skirt around Humboldt Park via Western Avenue, pulling into Chicago Union Station. This iconic station is Amtrak's fourth-busiest station. Built in an impressive Beaux-Arts style, it's a testament to the city's strong architectural heritage. It connects with the wider city via Metra, local rail, and bus services.

Discover Chicago, IL – the Windy City of beloved architecture and sports

Chicago has absolutely everything you could want from a fine city break. Appealing architecture, excellent museums, and a first-rate dining scene mean you're never stuck for fun options. Add to that a spectacular lakeside location, and you have endless waterfront activities and excursions.

Stunning art and architecture

Chicago is renowned for its steely skyscrapers. Roughly 100 of these monoliths line the Chicago skyline. Some of these architectural feats date from the 1920s, with elegant Art Deco and Beaux-Art designs. The Willis Tower is the tallest in the city, offering hair-raising panoramic views from its observation deck. To get the most out of Chicago’s architecture, head to the Chicago Architecture Center. This establishment hosts tours and talks on Chicago’s premier buildings. The scenic river tours, in particular, are delightful.

Chicago also boasts some impressive art organizations. The Art Institute of Chicago, in particular, houses an impressive collection of European masterpieces. You'll also find American classics like Edward Hopper's Nighthawks and Grant Wood's American Gothic here. For something fun and funky, head to Millennium Park. Here, you'll find an exciting collection of outdoor public artworks, including Anish Kapoor's iconic Cloud Gate. Following the waterfront south, you'll discover Museum Campus, a charming park containing 3 of the city's top museums.

A rollicking sports and music heritage

If there’s one thing Chicago goes crazy for, it’s sports. Whether you catch a tournament in person or head to a local bar, Downtown bursts to life during a Bears game. Baseball, too, is a much-loved institution. For the best experience, head north to Wrigley's Field. This iconic stadium is sure to charm with its nostalgic neon signs and hand-turned scoreboard. Even if you can't catch a game, take a tour of these legendary grounds and eat some local chicken tenders.

Chicagoans love the blues. Blues Brothers was set here, and the city has launched everyone from Muddy Waters to Howlin' Wolf. The tradition is still alive today with vibrant blues bars and rock n’ roll venues. If you try just one, head to Buddy Guy's Legends. While Guy only performs a few times a year, acts still get his prestigious stamp of approval. For a deeper dive into the world of Chicago blues, head to Rosa’s Lounge, Blue Chicago, or Kingston Mines.

Chow down in Chicago

Bring an appetite for your trip to Chicago because this city knows how to eat. To get started, hunt down the city's eponymous deep-dish pizza. Among the best places to try these controversial staples is Lou Malnati's. Other local Italian classics to look out for include beef sandwiches. Chicago even has its own hot dog, an all-beef sausage topped with mustard and relish on a poppy seed bun.

Chicago isn’t all junk food. The city boasts an impressively versatile restaurant scene that spans continents and styles. There are 23 Michelin-starred restaurants in the city, offering contemporary American, French and Japanese flavors. For the most inventive food in the city, head to Randolph Street or Division Street.