When it comes to the Midwest, enjoying your time here is often season-dependent.
But what’s not up for debate are the region’s 2 most beautiful cities.
No offense to Nebraska and Iowa, but you guys have some work to do…

If a genie granted you 2 guesses, chances are you’d pick Chicago as one of them.
The other?
It’s a vibrant capital split between Lake Mendota and Lake Monona — and it’s a foodie’s dream.
Who would ever turn down endless helpings of cheese? Not us…
Amtrak may be the most reliable name for U.S. train travel, but there’s long been one glaring omission on its route map.
That’s set to change with Amtrak’s latest announcement that these 2 gorgeous Midwest cities will now be directly connected, saving travelers from TSA headaches, annoying rail transfers, and a longer-than-necessary road trip with Chicago’s snail-paced traffic.
Introducing Amtrak’s Most Exciting New Route In Years

Flight routes come in hot and heavy, but train routes, especially stateside? Not so much.
Despite train travel making an LL Cool J-sized comeback, America’s rail network still doesn’t hold a candle to that of Europe and Asia, which makes the news of anything new feel like striking gold in the travelverse.
Of course, Amtrak did have a highly successful revival last year in more ways than one, with record ridership and the revamped return of their Mardi Gras route, traversing some southern stunners, including New Orleans and numerous Mississippi beach towns.

There have been rave reviews ever since about ‘Mardi Gras’. As such, Amtrak expects the same result with its next grand venture:
A game-changing route between Chicago and Madison.
Why this is a game-changer:
- Madison currently lacks direct Amtrak rail service, making this a major upgrade
- Easier downtown-to-downtown connection
- No airport hassle
- No congested roadways (train will be faster than current drive time)
- No more hitching a ride from Columbus, WI (the nearest stop to Amtrak’s current route)
Is Madison Really Worth Visiting?

When we say Madison is ‘beautiful’ — we mean it!
Upon arrival, you’re welcomed with arguably the prettiest domed Capitol building in all of America, surrounded by a glimmering isthmus of lakes, leafy parks, and vibrant neighborhoods.
As a 3-season destination (winters are gnarly), there are few bad times to visit, making the city’s 600+ restaurants more enticing to grab a patio seat to absorb the views and soak up the views, and savor everything from cheese curds and bratwurst washed down with a local brew.
Not to be cheesy, but Wisconsin’s capital lives up to every bite. Plus, there’s an array of surprising attractions, including free museums.

But the truth is, Madison is a place to arrive hungry and leave happy, whether perusing bustling farmers’ markets or drinking your way through ample breweries, giving nearby Milwaukee a run for their money.
Does Chicago Live Up To The Hype?
We’ve all been somewhere major where we leave wondering to ourselves, “why on Earth would anyone ever come here?”
The proof is in the pudding deep-dish pizza that Chicago does indeed live up to the hype, and then some.
In fact, Chicago is more popular than ever. As the Midwest’s only true metropolis, travelers come in droves for world-class food, mesmerizing architecture, and lakefront thrills (just don’t tell Dave Matthews).

Chicago truly has it all. No matter what type of traveler you are, you’ll find your niche. Plus, it’s often considered more affordable and less crowded than New York City, despite channeling the megacity aura brimming with urban delights.
Amtrak’s Full Route & Launch Date
Amtrak currently runs direct service from Chicago to Milwaukee, and the expanded route would continue on to Madison with a handful of underrated stops along the way.
Our local source claims the following will be Amtrak’s full route once launched at an undisclosed date in 2030:

- Chicago
- Milwaukee
- Pewaukee
- Watertown
- Madison
This route is expected to operate twice daily.
As federal funding remains an obstacle, exact stations have not been decided. 2030 remains the best estimate for full operation as Amtrak spokesperson Marc Magliari was quoted as saying this exciting new route “aims to start the line as early in the 2030s as possible”.
Additionally, Amtrak is undergoing a fleet overhaul, so you can expect a more modern onboard experience when it comes time to book your ticket.
