Day Two in Chicago—walk, breakfast, TOUR, hotdog, TOUR, dinner

by Jim Bellomo | Sep 29, 2026 | 4 comments

Yes, it does seem like all we do is eat, doesn't it? Well, our first full day in the Windy City (we found out it isn't named that because it is windy here; it has to do with politicians making a lot of wind with their speeches) was an all-tour day. We had booked a Chicago Overview Tour with Johanna through Tours by Locals, a company I have highly recommended for quite a while now. Their guides never disappoint. Johanna was no exception. But more about that later. But first, my early morning walk.

The absolute best thing about our Airbnb is its location. For visitors, the city center is Millennium Park. It is the one with the big BEAN art installation in the middle, and it is next door to the Chicago Art Institute. The park has so much more to see, and right now I am looking out the window of our 23rd-story Airbnb and staring directly at the park. That meant there were lots of places to walk to when I wanted to take early-morning photos. So I was up and out at 5:30 to make sure I got my full golden hour and was there for the sunrise at 6:34 am. Here are the photos from that walk.

 

When Kathleen and I were here in 2013 to visit my brother John, we went to breakfast at Wildberry and loved it. Since then, they have added a really nice, rather large patio with lots of tables. And believe it or not, in late September we were really happy to be seated out there. It was beautiful and warm. Our breakfast was also pretty much AMAZING. Check out the pics and my captions, and try not to get hungry.

After breakfast, we were headed out for our tour with Johanna. She got held up on the other side of a motorcade for the leader of the free world (snort), who was in town to present an award at a golf tournament. I am not going to get political here, but seriously…

Johanna finally arrived, and we headed out. Our day was full of quick stops where we would jump out, take photos, jump back in, and head somewhere else. We saw bridges, churches, skyscrapers, neighborhoods, great views, and so much more. And all along the way, Johanna kept us fully informed about what we were seeing, as well as Chicago's history and geography. She is a true local, having grown up here, and she knew a lot of information. We went to a bunch of places, and these are the before-lunch shots.

Last night we had our first iconic Chicago dish—deep dish pizza. Today our lunch would be the second iconic Chicago food, a Chicago hot dog. Before we left, we knew we wanted to try one, but all we knew about them was that you NEVER asked for ketchup on them. EVER! And I will admit that when it comes to hot dogs, I am a ketchup guy. But once I tried the Chicago dog, I may never go back. If you are unfamiliar with a traditional Chicago hot dog, it has an all-beef dog with tomatoes, pickle relish, mustard, a pickle spear, and small piquant peppers, all on a poppy seed bun. DELICIOUS! See the pics. We loved them. One made a super lunch, since we had that big breakfast and were going out later that night.

After lunch, we were back in the car for the second half of our tour. See the afternoon photos below. Around 4:00 pm, Johanna dropped us off at our Airbnb, and we said a fond farewell. I would recommend her to anyone for a fact-filled, fun day. Photos from the afternoon are below.

We were back at the AirBnB for about 90 minutes, and then we had reservations at Frontera Grill, one of Ricky Bayless’ Mexican restaurants here in Chicago. We had been to his “higher-end” place (Topolobampo) when we were here in 2013, and although it has a Michelin star, we weren’t impressed. I don’t understand the whole “foam as food” thing. It was four people for more than $400 (in 2013!!!), and we all left hungry. Last night at Frontera was not like that. The Eater website (where I find a lot of restaurant recommendations) said it was “not the pretentious food you would find at Topolobampo.” Thank the gods, it wasn’t. It was a delicious meal.

And that was enough for our day. We were all wiped out, and we had an early meeting with an architectural tour the next morning.

“It’s the finest hot dog on the planet, the one they make in Chicago. I said it, and I meant it!” —Anthony Bourdain

4 Comments

  1. Anonymous

    as usual, looks like you’re having a great time!

  2. Anonymous

    Thanks Jim for the great Chicago pics. Love “the BEAN!” I have visited ,and wandered around Chicago during my working days when I traveled there for conferences. So glad I took advantage of the time I was there. It was fun! Wish I had tried their hot dog!!! Your weather looked perfect!!!
    Continue to enjoy and stay safe…

  3. Bob

    Well the lake pics still make it look windy in a real way. Love to have that dog. Your pic looks so much better having taken your course.. (couple in the square) and no tripod. lol. You are also seen in a high category of Mikes favs. Great weather hope it holds. BON Voyage

  4. Eileen Anderson

    Jim, you had me laughing from the get go. Thank you for lightning up my afternoon while I hide in the house to avoid the heat. I’ve never been to Chicago and after seeing all these photos, I think I need to go. starting with that breakfast of yours, the Chicago hot dog, the Chicago pizza you had the night before and ending with this restaurant. I’ve never heard of I learned so much from one of your posts. The photos were just incredible, Kathleen and you look amazing, Judy and Mike are having a Judy and Mike are having a great time with and you captured a beautiful day.

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from our team.

You have Successfully Subscribed!