Train Trip to Chicago on a Whim

Every so often, when life gets really crazy, you need to just get the heck out of Dodge for a weekend. A few weeks ago Becki and I had to do just that. All the craziness of work, blogging and wedding planning was wearing us thin, so on Friday we decided to wake up early Saturday morning and take the train down to Chicago.

Chicago theatre district

We took the Hiawatha from Downtown Milwaukee to Chicago’s huge Union Station. It’s always exciting to see Union Station – the railroads really made Chicago what it is today, and there are still tons of people heading out across the country in every direction from Chicago. There’s been a Hiawatha line in operation in one form or another for over 70 years, and riding on it always makes me feel like I’m stepping back in time.

Becki and I are big fans of train travel. There’s something about it that pulls you into a bygone era, when traveling was more than just a destination. Nowadays most people only see their routes from 30,000 feet, and only the longest flights take more than a few hours. It doesn’t give you the same feeling of the traverse – of actually covering a vast distance, letting you know that you’ve actually gone somewhere and that your destination will probably be nothing like where you came from.

Okay, that last line might not exactly be true of the Hiawatha (Milwaukee to Chicago isn’t exactly Milwaukee to Santa Fe), but long-distance train or boat travel – or just a good old fashioned road-trip – gives you so much more feeling of having truly gone somewhere.

Tons to do While Staying in Downtown Chicago

And so we did truly go somewhere. We booked a hotel right on the Chicago River, hopped on a train, and put all our cares behind us.

Chicago River at night

Sweet view from our baller hotel room :)

For those that have been following along, we’ve been dabbling in travel hacking so that we can go, see and do more things without breaking the bank. It just so happened that I have tons of Marriott points saved up, so I called them up to see what was available.

Downtown Chicago is not a cheap place to stay – even for just one night – and bringing your car down is prohibitively expensive as well, so going on this trip hinged upon getting a free night someplace in walking distance to all the attractions. Luckily there was a reward night room available at the Renaissance Downtown, so we booked it and made our plans.

This may come as a shocker, but I’ve never really done the Chicago thing. Technically speaking I’ve been there before, sure – visiting friends, supporting my Dad when he ran the Chicago Marathon, etc. But I’ve never really just cruised around Downtown, never been to any of the attractions…never even had Chicago deep-dish pizza while in Chicago! So we put together a military-siege-style itinerary, synchronized our watches, stormed the city, and then…

We Only Made It Through Half Our Plans

…which is exactly what I thought might happen. We went round and round about whether we should buy the city pass card or not. Sure, it is a great deal if you get to all of those attractions, but we were only staying one night, so that was a pretty big if.

After hoofing it from the train to the hotel, and then from the hotel to the Field Museum, I learned that my walking shoes were in a desolate state. They still looked good from the outside, so I was unaware that they’d been infested with thousands of tiny goblins living inside them, waiting to rub my heels raw with 100 grit sandpaper.

Field Museum in Chicago, IL

Becki didn’t fair much better, but as a kindness to her we’ll leave her feet out of the limelight ;)

The museum was lots of fun, and much more open and well lit compared to most natural-science museums I’ve been to. We thoroughly enjoyed all the exhibits, had a great time playing on the giant map of the South Pacific (“don’t touch the water, it’s hot lava!”, I shouted to Becki as I jumped from island to island all nimbly-bimbly. Her response to this claim was to push me into the lava and laugh maniacally…), but we especially loved the conservation series.

Did you know that Chicago actually dims its skyline during times of migratory bird travel? It helps prevent them from circling tall buildings until they fall out of the sky from exhaustion. It’s an effort called Lights Out Chicago, and I have to tell you, seeing these Monuments of Greed agree to showboat a little less – in order to help nature – really made an impression on us. This was probably the single biggest thing that warmed my heart to a city I’ve always considered Milwaukee’s metastatic extension to the South.

Not to mention the work the Field Museum is doing to save the rainforest. Help save the rainforest? If it wasn’t on our bucket list before, it is now.

We took a water taxi half from the museum area to Navy Pier to ease our peda-pain. Thoroughly exhausted, we finished our day with some authentic deep-dish pizza and found Lord of the Rings was on TV – bonus!

Navy Pier ferris wheel

Saturday morning came and our feet were still aching, so we hopped the bus back to the museums and fully intended on going to the Shedd Aquarium. However, the Bears were playing and we “somehow” got swept away (read: I missed the spot to pull the cord) to Soldier Field and a manic sea of orange and blue. Fortunately, the bus just went full circle around the stadium and dropped us off right in front of the aquarium.

Like I mentioned above, I’ve never been there before, so I can only imagine the excitement Becki felt getting to show the place off to me. Because, if you didn’t know, the Shedd Aquarium is awesome.

We spent hours and hours here – so long that we ended up taking a later train back to Milwaukee. We especially loved the big aquarium right in the center. We could’ve watched it for hours, especially with that loggerhead turtle playing around in there.

All Great Avoidances of Responsibilities Must Come to an End

At last the time came. We had to go back home to Milwaukee. A total of two train rides, two boat rides, two bus rides, and miles of walking made this feel like a much bigger trip than it was.

Not to mention how well it put all our cares and concerns behind us. And sometimes, beyond all the sights, experiences and culture, that is the best thing you can get from travel, even if only for a weekend.


  1. I wish I had known! I may have been able to get you tickets to the Shedd Aquarium or a potential backstage tour.

  2. I loved Chicago when I went there! It is such a cool place to visit.

  3. Best of luck on your travel adventure!


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