Traveling Smitty's took on the Windy City in 2022. The Windy City is basically our back yard, we are 90 min north of it, but we only go there for solid reasoning. As nice as it is to hang out in Chicago, there are some elements that make it a little less appealing. We do, however, love to go there for a purpose and have a blast when we can. This particular visit was for a concert, and we had an amazing time there. We got a hotel for this visit since it was only a one night stay. You will notice that we like to get AirBnB when we can for longer stays, but with the fees and stuff sometimes it is cheaper to just get a hotel. This was absolutely one of those times. The hotel we stayed at was the Kinzie Hotel in the River North district. Honestly, we could not have chosen a better hotel for what we needed. The entire trip was based around a Dorothy concert at the House of Blues and the Kinzie hotel was literally just around the corner from that. We drove down with very little excitement or incident, which is saying something for a weekend on I-94. The hotel check in process was super simple, and as soon as we had dropped our bags, we were ready to hit the streets and see what we could find. Our initial plans included hitting up one of my favorite places Ramen-San for some amazing ramen. We had a 3 pm reservation and we were a little early. As we walked to the restaurant, we passed a bar that had a sandwich board advertising a Bacon Whiskey and Pickle Back. Since we had the extra 17 min and the temptation of something new, we went back and tried that shot out. The bar was O'Callaghan's Pub on Hubbard. It was a super quaint bar. Basically, that is nice speak for "just enough room to drink at the bar", but that is all you need in a good bar. The whiskey was called Ol' Major Bacon Bourbon and you can find it at a lot of places, but I wasn't able to find a website for the actual distillery. The shot came with a pickle back, which is fancy speak for a shot of pickle juice chaser for anyone that didn't know. All in though, that was a pretty damned tasty combo, so if you ever end up with a bottle of that stuff and some pickle juice, you won't be in a bad space. The topper of the bottle was cool too, it was a pig head. You can find those online as well. After O'Callaghan's we went to hit our reservations at Ramen-San. That place has been one of my favorites since I first tried their Fried Chicken and Kimchi Ramen. The combo of flavors is everything I could ever ask for. I had never physically eaten there though, so this was a new experience. We had some beers with our food and loved every option and flavor provided to us. It was a great all around experience since they played some old school rap and the atmosphere was super cozy. The food was, and literally always is, super good and worth any travel you have to make to get there. Just check Yelp! and see the reviews. We finished up at Ramen-San and moved over to Rossi's bar. The outside looks divey as all get out, but honestly the bar is amazing. You walk in to a limited seating area and there are coolers you just walk up and pick your beer from. Then you walk to the bartender and have them opened and pay for them. It is a super great system and the bartenders were amazing to us. We hung out there for a few hours before the concert we were heading to and met a group of people out for a 21st birthday. We had so much fun I cannot imagine us not going back to hang out there again in the future. Next stop was the House of Blues. The HOB isn't everyone's taste, but it is a great venue for a show. We went to see Dorothy, but ended up loving all of the bands that played. So much fun. The cost of beers and shots creates a huge sticker shock for someone from Wisconsin where we get alcohol super cheap, but if you live in that area you are used to it. The building is gorgeous and the acoustics were great. It was a lot of fun and the place deserves top marks besides the drink prices. After that we stopped and grabbed a few slices of pizza at Dough Bros Pizzeria & Sub Shop. The pizza was amazing and just what we needed after a night of hanging out, drinking, and dancing. After the pizza and a full night we decided it was time for us to pack it in, so we did just that so we could still get up and get some breakfast before checkout. The next morning we got out to an Einstein's Bagels for some breakfast before checking out and leaving. So there you have it, the fun that can be had when you roll in with a flexible plan and the willingness to get into something new. The funnest part of travel is being able to get out there and experience new stuff. We take that seriously and make it a point to get out of our comfort zone as often as we can. If you aren't willing to do that, you are wasting your time traveling. In order to enjoy a new city, you have to experience the real parts of the city that most people avoid. So that is our trip to the Windy City. We could take 300 of these and have new experiences every time in the Windy City. If you need help planning your trip, just send a message and we can help you figure it all out. Enjoy your travels, we always do!