Thursday February 28th - Saturday March 7 - Wisconsin and Chicago

Our flight from Seattle got in on time at the very end of Wednesday night, almost Thursday midnight.  We got our luggage quickly after a very long walk through O’Hare airport.  Then we had to navigate getting to the rental car center.  Normally that’s an airport transportation system ride from any terminal out to the rental car center but that was being maintained when we arrived.  So, after finding the correct door to wait outside, we waited in a chaotic line for 2 different buses that were substituting while the train was down.  It was misty and cold and not very well organized so it felt like forever.  Then the bus took us on a long meandering trip through the many access roads around the airport and eventually let us off at the rental car center.  There was nobody on the ground floor at the Enterprise counter so we went up to the 3rd level where the ‘other’ Enterprise desk was.  Thankfully we ended up being first served out of the clump of people who were waiting at the same time.  Enterprise employee Hunter lead us out to a variety of nice cars to choose from and ultimately recommended a Hyundai Genesis G70.  The tank wasn’t full which is an issue since I took the ‘prepaid’ option where I paid for a very full tank of gas in return for being able to return it as empty as possible.  The guy at the gate tried several times to adjust the fuel charge but ultimately didn’t succeed.  Then we headed out for our 2 hour drive through dense for up to Elkhorn Wisconsin.  

When we arrived to the hotel at 2:30 am, the front desk person struggled for 20 minutes to get us checked in since, by the computer’s logic, we were a no-show and our reservation had cancelled.  It was an exhausting end to a very long travel day. The next morning we had lunch (sort of breakfast for us) at Culver’s and then headed up to a hike I had picked out earlier.  The hike was 4 miles through a forested peaceful area with some gentle hills.  The trail was still pretty wet in spots but overall it was nice having a peaceful activity after the day before’s travels.

The drive to Madison was nice and we arrived just about the right time to check-in.  Our room was gorgeous with an absolutely perfect up-close view of the capitol building filling our window.

Though it wasn’t THE reason we came back to Madison after just being there back in October of 2025, the bar ‘Woofs’ was a big part of it.  Even though there were only about 3 people in the bar the last time we were in town, the bartender, Sam, was very entertaining and we spent about 2 hours talking to the one person that was there as a customer.  She is a theater tech who works in the community theater scene and I think had done professional work in other cities in the past if I remember correctly.  We also had (on the last trip) some amazing snacks (fried rice balls and wings?) from D’Vino next door to Woofs and owned by the same person or people. Naturally we had to try the full D’Vino experience this time and it was amazing.  Kind of a fine dining Italian menu with a huge wine and cocktail list.  The desert of dual lava cakes and a house made cherry almond ice cream was especially nice.  After dinner we went next door to Woofs and it was again the same woman and Sam the bartender and not much else going on that Thursday evening.

Friday we headed out on a 2 legged rainy scenic drive west of Madison and then went to the Ho Chuck casino in Wisconsin Dells.  We didn’t make MUCH at the casino but compared to most casino trips we did come out a little ahead and enjoyed an indulgently long day of gaming along with a tasty Chinese lunch at one of the casino restaurants.  Sam said that Friday would for sure be a lot more lively and that anybody who came in shirtless got a discount on drinks so we headed back to the hotel just in time to get to Woofs before 9 pm.  It really was much busier and it was wonderfully festive.  We talked to SO many people including a man from Germany with ambitious plans for a multi-disciplinary graduate degree and another from Ireland who was very fun to talk to.  And our shirts came off for at least the last 30 minutes or so.  It was a rare night for us but seems like the kind of thing that isn’t that rare in Madison.  When we walked the 4 blocks back to the hotel there were a ton of people out in the streets having fun.  It felt very safe and festive and reinforced our warm feelings for Madison.

Saturday was basically entirely gobbled up getting to Chicago and checking into the hotel.  Since we had a lot of bags we opted to take the hit on the drive time and go directly to the hotel in Lakeview BEFORE backtracking to O’Hare to return the car.  The drive from Madison until we exited I-90 was VERY fast and smooth.  The city driving to the hotel was agonizingly slow but probably ‘normal’ by local standards.  We couldn’t check into the hotel (it was only 11 am) but we unloaded all our stuff then ground our way back to O’Hare with a lunch at Portillo’s along the way.  Drew at the Enterprise return area quickly and graciously gave us a credit to cover the missing gas from when we picked the car up.  The airport train was working so getting back to Terminal 2 to take the long tunnel walk to the CTA Blue line train was relatively easy.

Unfortunately, our train ground to an extended stop just a few stations from the airport.  Somebody in the very next car had a medical emergency and had to be removed from the train.  For whatever reason they kept us held at that station until paramedics could arrive and even then another 10 minutes for a total of about 25 minutes stuck.   When we got off the train to change to the Red Line I heard a CTA person yelling something about the Red Line not running its normal route and decided that it might be a sign to take some time and do something fun instead of rushing back to the hotel.  So we followed the ‘Pedway’ all the way till it came out at street level near Millenium Park.  We had a snack at Starbuck’s along the way.

Millenium Park is the home of the very popular ‘Bean’ which I had only been to once, many years ago.  After the obligatory photo near the Bean we explored some other parts of the park including the video walls and then finally headed back to the L which was running the Red Line on the famous elevated square that winds around the inner prat of downtown instead of its normal, faster route underground.  There was a very persistent panhandler on the train and 1 car smelled more like a bong than an actual bong but we did eventually get to Belmont and figure out how to walk the last 3/4 of a mile to the hotel which we could now check into.

The air conditioner split HVAC thing in our room wasn’t working and though 2 groups of hotel employees tried, they couldn’t get it to turn on either.  By the time they were done trying it was rapidly cooling off outside and I had cooled off after all the walking etc that had my heated up in the first place so it didn’t seem that important by then.  We had a fantastic dinner at ‘Larks’ on Halsted then an ice cream desert from ‘Drip’ a little farther down the street before retiring to our room to watch an episode of ‘Yes, Chef’ which we are enjoying.

While mostly enjoyable, we seemed to be having a less well-polished Chicago experience than any of my last several visits to the city.

Sunday started off with an expensive but fun breakfast at 'The Bagel Restaurant'.  Our server Brenda was VERY funny and sassy, full of personality.  We then headed to the relatively new '606' trail which is an elevated rail trail that goes 2.7 miles weaving through a lot of quiet side sections of neighborhoods.  The trail was very busy even at 10 am but the vibe was very pleasant with joggers and dog walkers etc.  The trail is well designed with controlled exit points and was very clean.  

They built a little spiral walkway to the top of a very small hill at one end of the trail and called it an observatory.  There was one strangely placed bar chair at the top of the hill so I took a picture of Brian there.

When we got to the end we looked at the map and realized that, like the other end we started on, this end wasn't at all near an L station so we back tracked part way then took a bus to get to the L.  At that point we either needed to head back to the hotel (with the 2 train rides and 3/4 of a mile off walking that entails) or switch gears and go onto the next activity.

I've always heard that Evanston is a nice college town with a walkable downtown and though we came close last time we were in Chicago, I didn't think we actually got to Evanston.  So we took the weird walk through a mall to get from the Blue line to the elevated traks where the Red line was running during the track maintenance.  Luckily there was a CTA employee who was just getting off work who also needed to get to the Red line so we followed her through the maze off walkways and escalators to get through the underground tunnels and out to Washington street.  The ride on the red line was pretty long but when we arrived at the last station (Howard), we were able to walk across the platform to board the waiting Purple line train that would take us to Evanston.  In downtown Evanston we had a fast-food lunch at a local burger place called Epic Burger.

I looked up the 'things to see' at Northwestern University and we headed through campus to get to their lakefront section with sweeping views of Lake Michigan and the distant Chicago skyline.  It was at this point that we realized that, while we hadn't gone to downtown Evanston, we had absolutely been to Northwestern on our last Chicago visit.  We laughed pretty good at that so I think 'I'd like to finally get up to Evanston' will be a recurring joke on future visits to Chicago.  Still, the views and fresh lake air were great, especially since it was very warm and brilliantly sunny for a March day.  Brian was kind of walked-out since we'd walked a full 10 miles already that day, mostly from the 606 and the lengthy connections required to get to and from it.  I told Brian if we could explore Northwestern that we could take Lyft back to the hotel instead of the lengthy walk back to the Purple line and then the long Red line ride back to Belmont station.  Our ride showed up very quikly and he was very entertaining and full of energy.

Our energy level was pretty low at this point so Brian had a bath in our room's wonderful Jacuzzi tub and I used the shared hotel hot tub which was wonderful also.  We finished our evening with 1 last walk into the heart of Boystown to have a light dinner at 'Drews'.  

There were unfortunately a lot of noisy people outside the hotel as we tried to fall asleep.  Not sure what was so part worthy on a Sunday evening but eventually they moved on or we fell asleep in spite of them.

Monday (at 9:30 pm) we head home on Amtrak.   I'll cover Monday and our return to home in the next post.