October 27th -29th 2026 - Fall travels to Chicago and Wisconsin - Amtrak and Chicago - 20+ miles of urban walking, no elevation gain

This trip has been on the calendar for so long it seemed like it would never get here.  We booked the train and the 2 Chicago and Madison hotels back in April when we last saw our friend Jim in Saratoga Springs.  As it turns out the timing is pretty great since we’re preparing to move (to someplace with worse Amtrak connections) and fall is our favorite time to travel in general.

Jim arrived Monday afternoon so we had all of Tuesday to hang out before our train left at 11:30 pm.  Brian had to work but Jim shopped for CDs in Rochester in the morning and I did some more packing and cleaning at the apartment.  Later in the afternoon we had just enough time to watch ‘Who’s Afraid of Virginia Woolf’ which was a very challenging and long movie to take in.  At 5:30 we  had a lovely dinner in Fairport at Bocaccinis with Jim’s other Rochester friends.  We watched another movie (this one with Brian) at home before taking Uber to the Amtrak station.  Hairspray (2007) was really entertaining and fast paced.  It’s not a deep thought provoking movie but it was fun and breezy.

The Uber trip into Rochester for the train station started a long chain of good logistics events that, at least as I write this on Friday, has continued throughout our trip.  We put in out request for a ride and was very skeptical when it said our driver was nearby and would arrive in 2 minutes.  Living in car dependent suburbia there aren’t usually a lot of ride-share people cruising around.  Our driver showed up literally in 2 minutes so we were a little frantic as we grabbed our luggage, skipped saying goodbye to the cat and got on our way.  The drive into Rochester was smooth and easy.  The train arrived to Rochester on-time and got into Chicago on-time Wednesday morning.  The train ride was good and Brian and I slept better than we maybe ever have on the train.  That isn’t a high bar to clear but I actually felt reasonably rested when we got into Union station. Jim seemed to enjoy his train trip but he did not share in our restful sleep as much.  I enjoyed my ‘train shower’ and even our breakfast was pretty good and very relaxing while we watched Indiana roll by.

We had a lot of luggage so we ended up taking Lyft to our hotel and our driver was awesome, there was zero traffic and the whole trip (in an XL vehicle) only cost about 35 dollars including tip.  Then, despite arriving at 11 am, 5 hours before check-in, we were invited to check into both our rooms right away, a very rare treat.  That gave us a place and time to get settled before we started out Chicago adventures.  We had lunch at the super-nice front desk guy’s recommended Devil Dawgs right next to the hotel.  It was delicious, very Chicago and not expensive.  It was also the first of several places that didn’t accept cash, something I noticed last time we were in Chicago.  We bought a gift card for the front desk guy’s who was so helpful and let us check in early. 

Next up was the Chicago History Museum, someplace I’d never gone to.  In terms of being a nice facility and covering a lot of topics, this was a fine museum but…. I really felt like they compromised on the quality of exhibits by having a one-sided political tilt in several ways.  

First, one of the largest temporary exhibit areas was entirely bi-lingual. Every interpretive sign was split horizontally into English and Spanish.  As a result, almost none of the signs had more than 3 short paragraphs on them.  Many of them had just 2 or 3 sentences.  I’m a reader and I would have appreciated more text to ingest.  If they used QR codes on each of the signs they could provide a link to translations of each of the interpretive displays and not just in Spanish but in 3 or 4 languages.  All without compromising on the depth of the information provided.

Also, they would do well to have at least 1 advisor or consulting professor that isn’t left of Bernie Sanders.  Nearly every area of the museum focused on the under-represented anarchists, the unfairly oppressed union laborers, the courageous activists that fought every factory, highway or building anybody tried to build in the last 100 years.  On balance, it is probably appropriate to focus on the communities that paid disproportionately for the modern conveniences and opportunities Chicago has come to have but if you are going to talk about all the difficulties faced by steel workers trying to unionize, you might want to acknowledge the reality that part of the reason there were 180 thousand steel workers in 1930 and only 6000 now includes increased costs and decreased productivity unions fought for.  There were other topics where their messaging was similarly one-sided.  And of course they had the ‘land recognition’ plaque acknowledging that the museum grounds were once Native American lands.  I find these land acknowledgement signs to be so trite and silly but if there are any Native American representatives who read my blog who want to express how grateful they are for these signs, I’m open to the correction.  I honestly think we should just include tribal acknowledgments on road signs.  ‘Welcome to New York, historically of the x y and z tribes’ .  

Thursday we started off by going to Buckingham Fountain which has been on my Chicago to-do list for a while now.  I don’t know how I lived in suburban Chicago for several years and never made it to this iconic landmark.  We walked around Grant park afterwards and admired some of the skyline from that vantage.  It wasn’t clear what we should do with the rest of our afternoon.  We were close to the Art Institute which I’m sure is lovely but Brian and I aren’t really artsy enough to appreciate several hours (and 34 dollars) worth of art the day after going to the history museum.  We’ve all been to the top of the Sears tower and unless somebody really felt the NEED to go, I’m happy possibly dying having never made it to Navy pier.  Then, as we were heading to the L station, Brian noticed a ‘Paris Baguette’ and we had a nice break and I had an early lunch while Brian and Jim had treats.  While there I decided that the Lincoln Park Zoo would be our next destination and that it would be a ‘secret’ destination.  I’d never been to the zoo here and it’s free so it seemed like a good fit.  It’s lovely that the zoo is free and so accessible.  Personally, I would prefer a bit more of a ‘start here and follow this path to see it all’ type layout.  Lincoln Park Zoo has many entrance points and the majority of the exhibits are arranged along looping walkways.  There were maps here and there but since the zoo is free they aren’t eager to hand-out paper maps and signage on the ground was very thin, mostly just pointing you to the closest major exhibit building.  Highlights of our zoo visit were the Meerkats, the Zebras and the penguins.  One of the lions was very close to the glass wall in the lion building which was cool.  

Dinner Thursday, after much contemplation, ended up being an Asian fusion place close to our hotel. It was delicious, just adventurous enough and very friendly and welcoming.  We returned back to the hotel briefly before heading out for a final drink in Chicago.  We ended up at Sidetrack’s because Roscoe’s was very crowded.  Jim enjoyed seeing a different bar and the bartender who served us was really good and quite interesting to watch work.

It’s early Friday as I write this and we’re preparing to head to O’Haree to pick up the rental car.  Honestly, so far, EVERY piece of our trip has been beyond my expectations.  All the logistics have gone swimmingly well, the CTA has been clean and lovely and mostly on-time, every single person we interacted with related to Amtrak was as nice as they could possibly be.  The waiters and Lyft drivers and various other people we’ve interacted with have all been great.  Will Madison continue this winning streak?