Friday, May 29, 2026

Let's Go Places: Chicago and Austin Madness!

 


Friends, we have things to talk about! Buckle in and let me tell you about my latest trip.  It started with a single day event in Chicago, and from there it morphed into a 10 day trip that included a train and Texas.  As if that wasn't enough, I scored big time on the travel hacking front.

Where?  What???

One day each year the Frank Lloyd Wright Trust hosts an event called Wright Plus.  It is held in Oak Park, the Chicago suburb where FLW lived, and for that day only a handful of private residences are open for tours.

I live six hours away from Chicago, and if I was still working, I would probably have driven to CHI on Fri, done the event on Saturday, and come home on Sunday.

Now that I'm retired I have more options.  Anytime that I go somewhere I try to add in additional places to make the travel time worth while.  I know that you understand that, but you're probably wondering how doing a few extra things in CHI includes going to Texas.

Well, what going to CHI has to do with going to Texas is that I've had an overnight train trip on my bucket list for a while.  My intention was to take Amtrak from where I live all the way to the West Coast, which would mean a 3:00 AM departure and two nights on the train.  The 3:00 AM departure was the dealbreaker, since that pretty much guaranteed a night with no sleep and feeling crappy the next day.  The next issue is that I was pretty sure that I would like train travel, but not 100% sure, and that's a long time to be stuck on a train if it turned out that I didn't like it.

A few months ago I saw this video on YouTube about a train trip from Chicago to Austin, Texas.  Oh hey now!!!  Leaving from Chicago meant leaving during the day, the travel time is 30 hours, so there was only one overnight, and Austin is on my travel list.  Yes please!

The plan came together:

  • Thursday, May 14: head toward CHI, but stop at the Michigan City lighthouse and Indiana Dunes on the way.  Spend the night in Hammond, Indiana.
  • Friday, May 15: go to CHI, visit the Charnley-Persky House (FLW thing), do CHI stuff, go to hotel in Oak Brook (a 'burb about 20 minutes away from Oak Park).
  • Saturday, May 16: Go to Oak Park for Wright Plus
  • Sunday, May 17: Hop up to Wisconsin and see my blogging buddies!
  • Monday, May 18: Tour the Rookery (another FLW thing), get on the train!
  • Tuesday, May 19: arrive Austin in the evening
  • Wednesday, May 20: do Austin stuff
  • Thursday, May 21: get back on the train!
  • Friday, May 22: arrive in Chicago in the afternoon, do CHI stuff
  • Saturday, May 23: come home

There were two things that I needed to solve to make the trip possible:

  • Find somewhere to stay in CHI that didn't cost a fortune.  All told I was spending four nights in CHI, and my early searches indicated that meant big bucks.
  • Find somewhere to leave my car in CHI that didn't cost a fortune.
In the end I paid $0 for the four nights, and $132 to park my car from Monday to Saturday, which I felt was a very fair price.  The free nights required a little bit of thinking about how best to use credit card points, and the car part was easy - Millennium Garages are convenient for downtown, not too awful to drive to, and have good rates as long as you reserve parking online in advance.  As an added bonus you can access your car whenever you want, leave and come back to the garage anytime, and it feels reasonably safe.

A Travel Hacking Brag

Travel hacking deets are either fascinating or deadly boring depending on your POV.  Feel free to skip if this is not your jam!

This trip would have been quite expensive if I was paying street prices.  I let my stash of Chase, Hyatt, and Amtrak points do the lifting for this one.


  • Indiana hotel: $150 per night is my target hotel price, and the Holiday Inn in Hammond fit the bill.  Naturally I paid with my IHG credit card to get more points.
  • Oak Brook hotel: I stayed at the Hyatt House in Oak Brook, which is about 20 minutes away from Oak Park.  The cost for three nights was $795 (not including taxes, so the actual price would have been more), but points were 8,000 to 9,500 for those nights for a total of 27,000 points.  I used the remainder of my Hyatt sign up bonus and transferred 10,000 points from Chase to Hyatt.  As a added perk, the hotel had free parking.
  • Austin Hotel: lol, another Hyatt house.  The cost was close to my target of $150/night, so I happily paid and got more Hyatt points.
  • Chicago Hotel: this was the big splurge.  I stayed at the Hyatt Centric at the Magnificent Mile.  I didn't write down the exact price, but it was over $500.  I used my annual free night certificate from my Hyatt credit card to make it $0.  From what I've seen, the price for this hotel varies wildly.  Some nights it's less than $300 but some nights it is over $700.
  • Amtrak!!!  The price to go from CHI to Austin was $435, but the price to come back on Thursday was $784.  On Friday it was back down to $435, but I didn't want to stay in Austin that long and I would have had to pay for a hotel, meals, and activities to stay an extra night, so I wasn't coming out that far ahead..  The points were higher to come back on Thursday vs Friday as well, but in the end I decided that "free is free" and went for it.
Thursday - Road Trip!!!

My life is a little more complicated now that I'm living on my own.  I used to just have a packing list for me, and now I have a packing list for Doggo and a checklist of things that I need to do before leaving the house (such as taking out the trash and turning the heat down).  On Thursday morning I checked off all of the checklists and was out the door soon enough.  I dropped Doggo off with Hubs and hit the road.

Mid afternoon I arrived in Michigan City, and went to check out their lighthouse.  It's been on my radar for a while, but this was the first chance that I had to go.




Next up I went to the Indiana Dunes visitor's center.  I saw a flyer for the Three Dune Challenge, which seemed hard but not insane, so I figured it was a good way to use up the rest of the afternoon.  Just a note for anyone playing along at home, Indiana Dunes NP and Indiana Dunes SP are separate institutions with separate admissions fees.  The Three Dune Challenge is at the SP.


What made the hike hard is that most of it was loose sand, and as promised, there was quite a bit of up and down.  What made the hike worth it was the "hard but doable" aspect plus the views.






After the hike, I drove on to the hotel.  There was a Buffalo Wild Wings next door, so I did not overthink where to have dinner after a tough hike and a tough hike appetite.

Friday - FLW and a Willis Tower Fake Out

On Friday morning I headed into the city.  I've said this before, but I am comfortable driving TO Chicago but not comfortable driving IN Chicago, so the #1 goal is always to ditch the car ASAP.  It was too early for the hotel, so I parked at Millennium Garage for $13 and walked from there.




My first destination was the Charney-Persky house.


The house was designed by architect Louis Sullivan, with an assist from his young staff architect Frank Lloyd Wright.  Who did what is unclear: Sullivan said that Sullivan did all of the work with a few tasks delegated to Wright, and Wright said that Wright did everything and Sullivan put his name on it.


Plan A was to build another house right behind it, hence the lack of design.  There was no Plan B for when Plan A didn't happen.



After the tour, I had enough time to do something else.  One thought that came to mind was going to the top of Willis Tower.  You know, the tallest building in Chicago, the one that's near the hotel that we usually stay at in the Magnificent Mile.



Even though I knew where it was and had walked past it on my way to Charnley-Persky, for whatever reason I decided to map it on my phone.  It said that it was two miles away, which couldn't be right.  Huh, GPS can get weird in CHI.

I walked to "Willis Tower" which is how I learned that the building at 875 N Michigan Avenue is not Willis Tower.  Today it's just called 875 North Michigan, and formerly it was called the John Hancock Center.



I went up to the observation tower, and had a look at Real Willis Tower...I mean, they are not dissimilar.


I texted Hubs to say that I felt silly for thinking that the big black building in the Magnificent Mile was Willis Tower for all these years, and felt better when he responded, "What is it if not Willis?"  Apparently the whole family thought that it was Willis.

After my "Willis" adventure, I sucked it up and drove for an hour in nasty traffic out to Oak Brook.  I was upgraded from a "kinda suite" to a full suite. 


The only oddity was that you had to use your key to enable the light switches.  That's a first, at least for me.



Saturday - FLW in the House!

On Saturday I headed into Oak Park for a day of FLW Madness.


There are a lot of rules when there is a one day a year tour of someone else's house.


There were eight houses in total available to tour plus the Wright Home and Studio and Unity Temple, which I had already been to.  I made it to seven of the eight houses.  There were a lot of people there, and it was a very hot, very physical day.


I don't want to write too much about the houses, since they are people's homes, but the day was basically an exercise in seeing how rich people live in historic homes, and it was fabulous.  Even though it was a tiring trek, 10/10 would Wright Again.

You can buy a boxed lunch with your ticket, but I don't know why anyone would do that when the locations are so close to the Oak Park restaurants.  I walked down the street and went into the first place that called my name.


That night I went with my standard "I am exhausted" road dinner, which was to stop by Whole Foods and get a slice of pizza, a salad, and an ice cream sandwich.

Sunday - Let's Hang Out With People!

Thanks to blogging, I have a lot of friends in Wisconsin, and when the driving distance was only two hours, there was no way that I was not going to see them.


There was a big storm that morning, so we planned an indoor activity.  Anne and I went to Engie's house!!!

There was an admission fee.  Engie and Hannah met us on the steps, and Engie threw us a container of chicken to feed to Hannah.  Once Hannah had the goods, she approved Anne and me for entry into the house.


I had to laugh since I now have my own reactive dog, and anyone coming to my house has to buy their way in with treats.  The difference is that Doggo demands a continuous stream of treats in order to feel comfortable with visitors.

Zelda also made a brief appearance.  I failed to take a picture, since she is Queen Zelda and one does not take a picture of the Queen, but she is a lovely kitty.

We had a lovely day of puzzling and chatting, and then I went back to the Big City.

Monday - Let's Get One Last FLW Hit Before Getting Out of Dodge

On Monday, I checked out of the Hyatt, drove back into the city, and parked my car for the week.  I had one more stop to make before getting on the train.


That was a tour of the Rookery, which was the last word in 1880s office design.  FLW had an office there and updated the interior.



The big draw of the Rookery was that in the 1880s it was tough to get good light in an office building.  In order to help with that, the architects kept the center of the building open so that there were windows on all sides and the ground floor had a light court. It was cloudy and raining when I visited, and the building was still full of light.  What works in the 1880s to get more light into a building still works in the 2020s.

With that, my next move was back to the car for my luggage and then a taxi to Union Station.  But this post is getting long, so we'll talk about the train trip next time.  Let's skip from Monday to Friday, when I came back to CHI.

Friday - Let's Close out the Chicago Madness

When I got back to CHI on Friday, I hopped right into a cab and went to my hotel, the very posh Hyatt Centric in the Magnificent Mile.


I had one more "standard Chicago touristy thing that I've never done" item on the agenda.


Yep, I went to Navy Pier and hopped on the Ferris Wheel.


There were no bad views, and it was not "one and done".  The wheel spins you around at least three times - mind you I wasn't counting so it might have been more.



With that I got dinner and crashed in my very posh hotel room into the most comfortable hotel bed that I have ever known for a long and deep night of sleep.

The next day I came home from my epic adventure.  But that's a story for another day.

Who has been to any of these places?  Anyone else get faked out by "Little Willis Tower"?  

Next Time: We're taking the train!!!

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