Chicago by Train

AKA, the easiest way to visit the Windy City (with or without kids).

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Chicago is among America’s most delightful cities, so it’s unfortunate that driving in the town is a hellish dystopia of all-against-all gridlock enlivened by lawless interludes where inexplicable diagonal roads gouge the grid to create impossible intersections. And I grew up driving in New York City! But getting behind the wheel in New York is like the end of a horror movie—it all happens very fast, and then it’s all over and you laugh. In Chicago, it’s more like a Warhol film that goes on forever and tells you about the futility of striving. 

So how can someone from the Twin Cities enjoy the delights of Chicago without the anguish and ordeal of having to drive there? Friends, I am here to extol the magical, life-changing thing I’m admittedly a little late to the game on: the train! Amtrak, specifically. Taking the Amtrak is a little faster than driving, and a lot less stressful. My trip from the renovated and very beautiful Union Depot in downtown St. Paul to downtown Chicago’s Union station took about seven-and-a-half hours. 

Frequent fliers will be happy to know that on Amtrak, your first four pieces of luggage are free. Another crazy fact: There’s no airline security–style situation that requires you to arrive two hours early. Just walk on up to the train and hop on. Once aboard, you never have to turn off your cell!

Tickets vary in price with demand, though there are many discounts for students, seniors, and AAA members. Oh, and two children per adult can ride half-price. My two kids and I traveled round trip for $280. Here’s a recap of our adventure. 

Day One 

I board the train with two kids and an enormous bag of snacks, and promptly cuddle into one corner to read Narnia books out loud. Soon, we tire of Narnia and move to the Observation Car, which has a glass-dome roof. The train is right beside the Mississippi for the first 100 miles after Red Wing, where you’ll see bluffs; gray, fresh water; lacy river islands; and birds. We play Go-Fish. We count bald eagles out the window—22! More Go-Fish. Happily, I discover a snack bar beneath the observation car packed with bloody mary makings, chamomile tea, chocolate bars, chips, and the like. We continue playing Go-Fish while drinking chamomile tea. Eventually, we pack up Go-Fish and find the dining car. We are like Carole Lombard in 20th Century! The food is pretty bad—mac ’n’ cheese for the kids and a dry burger for me. But gosh-darn it, it’s fun to eat at a table on a train. We notice it has started to snow one of those wet snowstorms, and I’m so happy we are not driving. 

After dinner, we head back to our seats to watch The Boxtrolls on the DVD player. Then, suddenly, we’re in Chicago, where there’s a full-on blizzard. The train porter who helps me with my bags tells me the airports are shut down. The highways are snarled. We train people didn’t even know this was anything more than decorative snow. My kids and I taxi to the Swissotel—Chicago’s family-friendly Loop district with a full-size penthouse swimming pool for all. We unpack, swim, and head out for dinner. 

Day 2 

Shedd Aquarium. The hotel concierge gets us a special line-jumper ticket (many of the hotels seem to have these) and we taxi to the Shedd, where lines stretch entirely across the park. We breeze past like we’re the Kardashians or something, and then it’s a blur of face painting, sea star petting, and dolphin show watching. Next up: a taxi to The Publican, the famous restaurant by chef Paul Kahan that serves a limited but still wonderful early menu from 3:30 to 5:30 pm. We get slices of that elite American ham all the chefs love, and then the best roast chicken and frites platter you can imagine. The server couldn’t be nicer, even though some of us are still wearing face paint. 

Day 3 

We walk to the giant silver bean statue at Millennium Park (real name: Cloud Gate), then taxi to John Hancock Center and head up to the observation deck for pics. Then we shop before heading back to the hotel for a fancy dress change. We are going to the Palm Court at the Drake Hotel for afternoon tea! If you have a daughter, this is something you have to do at least once. There’s a harp player, everything is white and gilt—mirrors, flowers, and balloons—and it looks like Princess Diana and Queen Elizabeth might swan in any minute (both had tea there). A waiter in a tailcoat brings my daughter a great number of cream puffs shaped like swans. I took 200 photos of her. My 10-year-old son sat perfectly still, and I believe tried to pretend this was not happening. He liked the cream puffs, though. 

Day 4 

Museum of Science and Industry, followed by a 4 pm dinner at Chicago’s most famed burger spot, Au Cheval. Have you heard about the three-hour waits for these burgers? Not at 4 pm you haven’t. Also: They’re totally worth it. 

Day 5  

We spend the morning at Navy Pier’s Winter Wonderfest, where they fill an indoor area with an ice skating rink, climbing walls, and bouncy castles—everything you want kids to do before a long train ride. At 2 pm we get back on the train headed for St. Paul. We are scheduled to get in around 10 at night, and we’re all tired, so it’s a lot less exciting on the way back. We read Narnia books, play Qwirkle in the observation car, and eat dinner in the dining car. Everyone falls asleep watching a movie in our dark little area with reclining seats. My little one clutches the stuffed penguin she got as a souvenir. She calls him Chicago. “We’ll always have Chicago,” I say as a joke (the penguin got mislaid and found a hundred times on the trip, as toys do). As we go across Wisconsin, Chicago the penguin’s white fur belly catches the station lights of Winona and Red Wing, and I think of that line in The Great Gatsby when Nick recalls “the thrilling returning trains of my youth.” That was this train. Chicago, we’ll always have you, and we’ll be back. 

Mpls.St.Paul Daily Edit

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