We’d never taken Amtrak before. We weren’t sure how the logistics would work, whether we’d regret not driving, or if getting around Chicago without a car would be a hassle.
By the time we got home, we were already talking about doing it again.
Tom and I, Andi and Elsie — four of us on a train from St. Louis to Chicago for a few days we’d been looking forward to for a while. We were a little anxious about the logistics going in. It ended up being one of the better trips we’ve taken.
What Made This a Great Chicago Trip: Getting There by Train
We planned ahead and kept it simple — backpacks instead of suitcases. No checking bags, no hauling luggage through a city. We stepped out of Union Station into warm July air and started the mile-and-a-quarter walk to our hotel. Backpacks instead of suitcases meant we could just go.
That walk set the tone for the whole trip. We weren’t tourists trying to see everything. We were just moving through a city with nowhere urgent to be.
We stayed at the Hilton Garden Inn on the Riverwalk. After checking in, we walked over to Chicago Brewhouse Riverwalk for lunch — right on the water, a good start.
The Architecture Tour
Next we headed to Shoreline Sightseeing for the architecture boat tour. It was hot and we’d already been outside in the sun for a while, so we sat on the lower deck and took the breeze off the water while the city went by.
Do the architecture tour. We weren’t sure we’d care that much about architecture, but it ended up being one of the highlights of the trip. Seeing the city from the river changes your perspective..
We were glad we went that day. Thursday, the smoke from the Canadian wildfires had made it to Chicago. The sky was grey and hazy. We got lucky with the timing.
Thursday — Shedd and the Bean
Breakfast at the hotel, then an Uber to the Shedd Aquarium. We spent the morning there and really enjoyed it — the kind of place that’s easy to spend more time than you planned.
Sharks are Elsie’s favorite, and she knows a lot about them. The Shedd has some species you don’t see at most aquariums, which made it worth the visit even if you’ve been to aquariums before. I could watch sharks swim for hours. There’s something about the way they move through the water that just holds your attention.
After the Shedd we caught an Uber to Millennium Park for the obligatory stop at Cloud Gate. We walked underneath the Bean, looked up, took the photo, and checked another Chicago classic off the list.
Then we walked to Coco Bar, a Mexican restaurant just across from the hotel, for lunch. It was still hot, but the patio had plenty of shade. The sky was grey and hazy from the wildfire smoke, but we sat outside anyway.
After lunch we went back to the hotel to rest before the concert.
The Rush Fifty Something Tour
We took an Uber to United Center — our driver was on his fourth car, which explained a lot about the ride. We knew we were getting close when we saw a parade of mostly older white guys all heading in the same direction. The only concert I’ve ever attended where there was a long line for the men’s room and none for the ladies.
The concert was incredible. Rush has always been about more than the music—the musicianship, the lyrics, and the band’s history. There was a beautiful tribute to Neil Peart and a classy nod to John Rutsey during Working Man. The crowd knew every word to every song.
We ended up talking to a couple seated behind us from Scotland. Same story you hear from every Rush fan—they found the band as young teens and never stopped listening. We heard stories like that all night.
Tom sent a message to Rush on Instagram after the concert that night. The next morning they had reposted it in their stories. We have the screenshot. That was a good morning.
Getting home from the concert was a little stressful. We found the Uber pickup lot, had our ride cancelled while we were waiting, but Tom was on it. He’d handled all of our Uber rides during the trip, and within a minute another driver who was already in the lot picked us up. In the end, it was easier than we’d expected.
Friday — The Field Museum and Home
Breakfast again at the hotel, then we grabbed snacks for the train, packed up, and Ubered to the Field Museum. We rented a locker for our bags and spent a couple of hours before heading to Union Station.
The Field Museum was genuinely interesting. You walk through different time periods and the exhibits pull you in further than you expect. We went through the gems and minerals, the taxidermy, and the dinosaur section. I’m a rad tech, and Andi is a nurse, so one dinosaur skeleton led to a discussion about anatomy. We looked up how dinosaur vertebrae are numbered, learned that T. rex had anterior and posterior ribs rather than a circular ribcage like humans, and even looked up how many bones were in dinosaur feet.
Bones look different when you spend your days looking at them. Apparently that doesn’t stop when they’re 66 million years old.
The gems and minerals are worth more time than we gave them. That’s on the list for next time.
Chicago Without a Car
By the end of the trip, we’d hardly thought about not having a car. Between walking and Uber, we got everywhere we wanted to go without any trouble. Chicago turned out to be one of the easiest cities we’ve visited without a car.
The Train Home
The train was two and a half hours late coming home. We’d arrived at the station an hour early, and since there were no assigned seats, the four of us couldn’t even sit together on the ride back.
None of it really mattered.
The delays, the cancelled Uber, and not sitting together on the train home weren’t the things we talked about afterward. We talked about the architecture tour, Rush, Sue the T. rex, and how easy Chicago turned out to be without a car. Those are the parts we’ll remember.
A Few Things We’d Know Going In
Take Amtrak. If you’re coming from St. Louis, we’d do it again. No airport security, no parking downtown, and you arrive right in the middle of the city.
Bring a backpack instead of a suitcase. It made walking from Union Station to the hotel—and everywhere else—a lot easier..
Download entertainment before you leave. The Amtrak Wi-Fi never connected for us, but cell service was reliable. I’d still download a movie, podcast, or book before you leave.
Do the architecture tour. We weren’t sure we’d care that much about architecture, but it ended up being one of the highlights of the trip. Seeing the city from the river gives you a completely different view of it.
Have a plan for getting home after the concert. We eventually figured out the Uber pickup area, which is in Lot E, but it took some trial and error. Knowing where it is ahead of time would have made getting out much easier.
We grabbed snacks at the hotel before heading to Union Station and were glad we did — the café car had limited choices and sold out of things quickly.
We’d go back just for the Lake Michigan cruise and the summer fireworks.
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