chicago explorations and the best places for deep dish pizza

After wrapping up our time in Milwaukee we headed back to Chicago yet again. Part of the reason we went back to Chicago was because getting flights from Rochester to Chicago was much cheaper than flying into a smaller airport like Milwaukee’s. The car rental was only $50 a day and for each drive to the different cities we did same-day pick-up and drop off. Not the most convenient since we had to go through the pick-up/drop-off process twice but in the end, it gave us some savings. Another reminder to get creative with your travel plans if you’re traveling on a budget!


This time while staying in Chicago we stayed downtown right on South Michigan Ave. It was being in this area that we truly felt like we were experiencing all that Chicago has to offer. We were within walking distance to Millenium Park, many restaurants, the Shedd Aquarium, Field Museum and more. We stayed at The Hilton and I definitely recommend it! The rooms were large and modern. A few tips on saving time and money when booking places to stay in an expensive city like Chicago:

1. The nice Air BnB’s were just as expensive as the hotels so I factored in location to my pricing. When staying at the Hilton because of our great location we walked everywhere and had no Uber/Lyft costs. Comparatively, when staying in Lincoln Park we were spending $30-$50 a day on transportation. The cheaper accommodations may seem like a great deal but there will always be “while you are there cost” you have to factor in!

2. During check-in at Hilton there was an extremely long line. We’re not sure why the line was so long but I had downloaded the Hilton Honors app and could check-in directly on my phone. The app gave me a virtual key so we were able to do everything with a few clicks of a button, including getting into our room. When traveling remember to always download helpful apps before you get there to save time.

Once we were refreshed and ready to start exploring there were some unexpected rain showers. We ended up getting soaked when searching for a place to eat! Luckily it cleared up quickly and we made our first stop to Millenium Park.

To our surprise, there was a jazz festival in the park that weekend so it was packed with musicians, locals, and tourists. The buzz of energy in the area was really exciting to be a part of.


After spending time in the park we set-off walking without a clear purpose but wanting to continue to explore. We ended up making our way to the water and seeing dozens of boats anchored. We saw signs for Navy Pier which was another spot I had found during my research and was eager to explore it. It was a bit of a hike but we made it to the pier which was also pulsing with people and energy. Navy Pier has countless restaurants and shops inside and then a beautiful Ferris wheel outside. You can also catch architecture boat tours out on the dock. We had considered taking a tour (which I’ve heard are amazing) but were having more fun enjoying the day at our own pace so we decided to skip it.


After Navy Pier we were exhausted from all the traveling for the week and walking from the day and decided to relax in our King bed at the hotel. We had one major thing we had yet to experience though that Chicago is famous for… deep dish pizza!

I had done my share of pizza research (arguably the best kind of research) which included asking friends who live in the area and online searches of the best places to get a deep dish pizza. We also chatted with locals we met while in Chicago and asked where their favorite pizza places are. Here’s the list we gathered:

1. Giordano’s

2. Lou Malnati’s

3. Gino’s

4. Pequods

We decided to go with Lou Malnati’s and get it delivered to our hotel because we were so tired! I have to admit that this pizza was the best pizza I’ve ever had in my entire life. Although we didn’t get to try pizza from all of the places listed above, I promise that you can’t go wrong with Lou Malnati’s.


With the pizza sauce coursing through our veins we caught a second wind and decided to take a final stroll. We took a leisurely walk around Buckingham Fountain and grabbed some gelato to snack on. It was the perfect way to end our time in what quickly became one of our favorite cities.


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