You're standing on the platform at the historic La Crosse station, coffee in hand, watching the fog roll off the Mississippi. Or maybe you're staring at your GPS in a driveway on the south side of town, dreading the 280-mile slog down I-90. We've all been there. Choosing how to get from La Crosse to Chicago isn't just a matter of miles; it’s a choice between two very different types of stress.
Honestly, the drive is a classic Midwestern gauntlet. You start with that beautiful driftless scenery, but by the time you hit Janesville or Beloit, the charm wears off. Then comes the Illinois border. Tolls. Construction. The inevitable realization that "The Loop" is still ninety minutes away even though you’re technically in the suburbs.
But there’s a reason people keep doing it. Speed. Sorta.
The Reality of the Drive
If you leave La Crosse at 4:00 AM, you can make it to O'Hare in about four hours. Maybe four and a half if you stop for a bathroom break in Rockford. It’s a straight shot down I-90 East. You pass the Wisconsin Dells—which, let's be real, looks a lot less magical at 70 mph—and then you just cruise.
But let’s talk about the "Chicago factor."
Once you hit the Elgin toll plaza, your ETA becomes a suggestion rather than a fact. I’ve seen that last 30-mile stretch take longer than the entire trek from La Crosse to Madison. If there’s a Cubs game, a light drizzle, or just a Tuesday, the Kennedy Expressway will eat your afternoon. Parking in the city? Expect to pay $40 to $70 a day at a downtown garage like the Millennium Park Garage or anything near Navy Pier. It’s a racket.
Why the Empire Builder is a Cult Classic
Most people looking at La Crosse to Chicago options eventually land on Amtrak. Specifically, the Empire Builder.
This isn't just a commuter train. This is a long-distance legend that starts all the way back in Seattle and Portland. By the time it pulls into the La Crosse station (usually around 10:00 or 11:00 in the morning, though freight interference can nudge that), it’s on the final leg of its journey to Chicago Union Station.
There is something deeply satisfying about sitting in the Sightseer Lounge car with a Grain Belt or a soda, watching the river bluffs fade away as you roll through Wisconsin. You aren't white-knuckling a steering wheel through a construction zone in Beloit. You’re reading a book. Or napping.
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The downside? Reliability. Because the Empire Builder travels thousands of miles before it gets to us in the Coulee Region, it can be late. I’ve seen it run like a Swiss watch, and I’ve seen it show up three hours behind because of a blizzard in North Dakota. Check the Amtrak app before you leave your house. Seriously.
The Borealis: The Real Game Changer
For years, we only had that one train. If you missed the morning Empire Builder, you were driving. But the transit landscape changed recently with the introduction of the Borealis.
Sponsored by the Wisconsin and Minnesota DOTs, the Borealis runs a daily round trip between St. Paul and Chicago. For folks in La Crosse, this is huge. It usually hits our station in the early afternoon. Unlike the Empire Builder, it doesn't come from the West Coast, so it’s much more likely to be on time. It feels like a "normal" train. Reliable. Predictable. Clean.
The ride takes about 4 hours and 45 minutes. You arrive at Union Station right in the heart of the city. You walk out the doors, and you’re a five-minute Uber from basically anywhere in the West Loop or a short walk to the Willis Tower. No parking fees. No traffic rage.
Cost Comparison: The Brutal Math
Let’s get nerdy for a second.
- Driving: 280 miles. At 25 mpg, that’s roughly 11 gallons of gas. At current prices, maybe $35-$45. Add $10-$15 for Illinois tolls (the I-90 tolls are no joke if you don’t have an I-PASS). Then add the $50 for parking. You’re looking at over $100 just to get the car into a stall downtown.
- Train: A coach seat on the Borealis or Empire Builder can go for as low as $30 if you book a few weeks out. Even last-minute tickets usually hover around $50-$70. Even for a couple, the train often wins on price once you factor in the "Chicago Tax" of parking and tolls.
Small Town Stops and Hidden Perks
Traveling from La Crosse to Chicago isn't just A to B. If you’re driving, you have the option to hit the "Hidden Gems."
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Ever stopped in New Glarus? It’s a bit of a detour, but the brewery is world-class. Or maybe you want to stop at the Mars Cheese Castle in Kenosha (though that’s getting pretty far off the I-90 path).
If you take the train, the stops are fixed. Tomah. Wisconsin Dells. Portage. Columbus. Milwaukee. The Milwaukee stop is actually pretty great because you pull right into the Intermodal Station. If you have friends in MKE, it’s an easy place to meet up for a quick coffee during the 15-minute dwell time.
The Winter Factor
Do not underestimate a Wisconsin winter.
Driving I-90 during a January lake-effect snowstorm is a nightmare. The stretch between Madison and Janesville gets notoriously slick. The train, meanwhile, just plows through. There is something incredibly cozy about being in a heated railcar with a massive window while a blizzard rages outside. It’s peak "hygge," if you're into that sort of thing.
Navigating Chicago Once You Arrive
Whether you drive or take the train, you eventually have to deal with the city.
If you took the train to Union Station, you are at 225 South Canal Street.
You can catch the "L" (the CTA trains) easily from there. The Quincy stop (Brown, Orange, Pink, Purple lines) is just a few blocks east. Or just grab a Divvy bike. Chicago is surprisingly bikeable if you stay off the main arteries.
If you drove, God speed. My advice? Find a "SpotHero" parking space before you arrive. Do not just pull into the first garage you see. You will pay double. Use the app, find a spot near where you're staying, and leave the car there for the duration of your trip. Use public transit or walk once you're in the city limits. Driving inside Chicago is a sport, and if you aren't used to it, it’s an expensive one.
The Verdict
So, which way is better?
It depends on your "why."
If you’re moving a kid into a dorm at DePaul or Loyola, you’re driving. You need the trunk space. If you’re heading down for a solo weekend to see a show at the Chicago Theatre or catch a game at Wrigley, take the train. The La Crosse to Chicago rail corridor is one of the best-served routes in the Midwest right now.
There’s a freedom in not being responsible for a ton of metal on a six-lane highway. There’s a freedom in knowing that your biggest worry is whether the snack car has those little hummus cups left.
Actionable Steps for Your Trip
To make the most of this trek, keep these practical tips in mind:
- Book the Borealis, not the Builder: If you want to arrive on time, the Borealis is the smarter bet. It starts in St. Paul, so there's less "lag time" for delays to stack up.
- Check the "Track a Train" tool: Amtrak has a live map. If you're picking someone up or heading to the station, use it. It's much more accurate than the printed schedule.
- The I-PASS Hack: If you’re driving, get an I-PASS or use your E-ZPass. Illinois has moved largely to all-electronic tolling. If you don't have a transponder, you have to go online within 14 days to pay your tolls manually, or they’ll mail you a bill with a "service fee" that’ll make your eyes water.
- Avoid "The Junction": If you're driving, try to avoid hitting the I-90/I-94 junction (the Jane Byrne Interchange) between 3:00 PM and 6:30 PM. It is consistently ranked as one of the worst traffic bottlenecks in the United States. If you're going to arrive then, stop in Schaumburg for dinner and wait it out.
- The South Loop Parking Secret: If you must drive and need "cheap" parking, look for lots in the South Loop or near the Roosevelt "L" stop. It’s a bit of a hike from the Magnificent Mile, but you’ll save enough for a nice dinner.
The trip between the Mississippi River and Lake Michigan is a rite of passage for Wisconsinites. Whether you choose the rail or the road, the transition from the quiet bluffs to the roaring skyline never gets old. Just remember to pack your patience—and maybe a portable charger.