Home Food & Beverage A Whirlwind 50 Hour Trip to Chicago – Day 2

A Whirlwind 50 Hour Trip to Chicago – Day 2

by joeheg

This is Part 2 of our Chicago trip report. Click here to see part 1!

For the second day of our Chicago trip we got an early start. Well, at least it was an early start for us when we’re on vacation. We had a bunch of things we wanted to do, thanks to all of your wonderful suggestions. We decided the first thing we’d do was the one activity that left on a schedule – the Chicago Architecture Foundation River Cruise. As we approached the river and Wacker Drive, the crowd increased tremendously. We then noticed marching bands and many people from all different ethnic groups gathered together. It turned out there was a parade that day to celebrate the 100th Anniversary of the Lions Club, who were founded in 1917 in Chicago. This also may have been the reason that hotel rooms were really expensive for the weekend. We finally made it down to the riverwalk and the dock for the boat.

Chicago Architecture Foundation River Cruise

We had booked our tickets the day before for the 10:30am sailing.


Chicago Architecture River Cruise

The 90 minute trip started by going inland and to the North Branch, and then the South Branch of the Chicago River. We then returned back down the Main Branch, right up to Lake Michigan. We had a very knowledgeable guide who told us about the buildings, what made them important and pretty much a beginners’ class in different architectural styles. All of the guides for this tour are volunteers with the Chicago Architecture Foundation (our guide’s wife was standing on shore waving to him when we passed their building). So while every tour would be a little different, the guides do have a passion for Chicago and its architecture.

The views of Chicago from the river are really stunning. We sat out on the front part of the boat and took in the views. The weather was beautiful but it was a little warmer and sunnier than we had planned for so I ended up with a nice sunburn on my face for the next day or so. Note that they do have a snack bar on the boat that sells small snacks, drinks and alcoholic beverages, so if the tour is not your speed you can pretend you are on your own little party boat.


After our cruise, it was around noon and we were getting hungry. I planned our day so that we would be hungry for lunch when we were close to Portillo’s.


I admit that I had never heard of this place before doing some research on where to eat in Chicago, b ut this sounded like a perfect place for us. We love to try “local” places that have really good, simple food. Wow, did this place fit the bill!


Portillo’s @ Clark and Ontario

Several suggestions were for us to try the hot dogs but we also were told that they had really great sandwiches along with shakes. We did the best we could for a first visit. Sharon ordered a hot dog with everything and french fries and I got an combo beef & char-grilled sausage sandwich. We just went with sodas to wash it down and thought we might get a chocolate cake shake for dessert.


Lunch at Portillo’s

After the hot dog and sandwich (Sharon said I won because my food was better, but she’s really a fan of ” just mustard & sauerkraut” on her hot dogs), we didn’t have room for any more food so the shake will have to wait until next time. We left lunch and headed north to the John Hancock Building, home of 360 Chicago and Tilt!

360 Chicago and TILT!


John Hancock Building

This was one of the only activities we knew we wanted to do while in Chicago for this trip and it turned out we had such a great time that it earned its own post that you can read here. We spent a little over an hour at the observation deck looking out over the Chicago skyline and we had a wonderful, clear day to do so. By this time, it was getting to late afternoon and we still have several stops to make to finish seeing “all the things.”

Millennium Park and The Art Institute

Since we were now the furthest north of our planned activities, we decided to get a ride back to our next stop, Millennium Park. We make a quick stop at Garrett Popcorn Shop and picked up some Caramel Cashew Popcorn. After eating most of the bag we brought home with us, we wish we had purchased a bigger bag. (Note from Sharon: Next trip!)


The next few stops were mainly to get some touristy photos for our yearly wall calendar. We always make a calendar with pictures from the past year and we always need some good shots from where we went.


We eventually managed to get a decent selfie in front of “The Bean” (it took about a dozen tries)


One of the Lions from in front of the Art Institute (and Sharon)

Unfortunately it was already past 5 PM so all of the museums and other touristy places were closed. It didn’t matter much as we were wiped out from sitting in the sun on a boat, tired from walking several miles and still suffering from lack of sleep the night before. We decided that it was time to relax so we headed to the Palmer House Hotel.

We almost stayed here, as rates were quite reasonable when I looked several months before our trip. However by the time I went to book, the rates had skyrocketed. It’s still an old hotel though, and that’s something we are always willing to look at.

Palmer House

The hotel lobby was quite crowded as it appeared that several weddings were going on that night, as well as the members of the Lions returning to their hotel. We managed to grab two seats at the end of the lobby bar and settled down to relax. What a grand room the lobby is. The bar area is off to the left in the top picture.


Lobby area of the Palmer House


View of the lobby and painted ceiling (check in desks are to the right)

We enjoyed some properly chilled adult beverages and caught up on our Facebook posts for the day. After an hour or so we went around to look at the lobby and take some more pictures. We got some dinner suggestions and decided to eat at the restaurant located next to our hotel (a hotel restaurant wouldn’t usually be a first choice for us but it was recommended by a friend and we didn’t feel like exploring much more. Thanks, T.J.!).

After dinner, it was around 9PM. Time for bed. I know there was so much more we could do in Chicago on a Saturday night. I wanted to go out and see the 11PM show at Second City. We could have gone back to see if we were still “cool” with the doorman at Three Dots and a Dash. Nope, we went up to our room and packed our stuff and laid down in the really comfortable bed (We normally don’t like the beds when we travel because we have a Tempurpedic at home but the bed as the Kimpton Allegro was really good).

So that’s the end of the trip. Well, except for breakfast the next morning at Cochon Volant where I got a wonderful Duck, Bacon and Cheddar Omelette.


I’m not one for food pictures but this was a darn good breakfast

That’s how we spent 50 hours in Chicago. By no means did we see everything but, thankfully, we will be heading back in November for a Frequent Traveler University and we just added on an extra day so we can play tourists again. We know the weather won’t be the same but we’ll have some more time to do things we had to pass up this trip because to time restraints. We really want to go see inside the Art Institute and we also want to see a place we walked past this trip called the Driehaus Museum and a return trip to Portillo’s (Note from Sharon: And another trip to Three Dots & A Dash, please and thank-you!).

This was Part 2 of our Chicago trip report.  Click here to see part 1!

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Diane July 6, 2017 - 4:09 pm

The Dreihaus Museum is wonderful! The building itself is a treasure and the poster show they have on display right now is beautiful.

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