Chicago is commonly known as the “Windy City” but I think a better nickname would be “the best weekend getaway city”. Back in April, that is exactly what we did!

We flew out of Tulsa on an early Saturday flight, with a stroller and a single checked bag. No car seat for Nolan, meaning that we were committed to a trip using only public transportation to get around. This was to be a quick getaway trip and enjoy all that the city life had to offer; train, subways, and buses included. We had just over 72 hours in Chicago and it was the perfect amount of time to experience a little bit of everything. These are just a couple of things that stood out and made our trip that much better!

The flight was a breeze, a quick 1.5 hours. Just enough time to get comfortable and keep Nolan entertained without it being unbearable for him. Easy snacks like applesauce pouches and puffs along with suction-type toys were all that we needed. Once we landed, O’Hare was so easy to navigate to baggage claim and then to the train. We opted to buy the unlimited 3-day pass for a MetroCard, for only $15. Two of these passes were cheaper than a single Uber ride from the airport to the hotel. We had already done our research and found that this would cover all trips on the train, L, and buses if needed, and then that way we didn’t have to worry about reloading a balance after reaching a certain limit of swipes. Once we bought our passes, we settled on the train and headed into the heart of downtown. I would say that the only downside of this plan was that it took time. The train ride was about an hour long. Even though we left Tulsa early and the flight was short, we still didn’t start our day in the city until about 1 pm after dropping our bags off at the hotel.

We met up with a group of friends and stayed at the Hilton DoubleTree on the Magnificent Mile, Downtown. This hotel was in the best location, close to public transportation stops, just around the corner from Navy Pier and all the great restaurants and shops.

Our main purpose for going up there for the weekend was to attend a White Sox baseball game. This was a stadium that neither Collin nor myself have been to before so we were stoked to knock it off of our list. We got tickets for seats in the outfield, just a couple of rows up from the wall. Last year we went to a Cubs game and I have to admit that the surrounding area around the Cubs stadium was much better. There were countless souvenir stores, bars, and restaurants. Where the White Sox stadium is south of the city and right off the highway. I could see how this is more of a benefit for anyone that might have to drive in for the game but it is just the stadium itself.

As much as I preferred the stadium location and surrounding area of the Cubs, the atmosphere, fans, and food for the White Sox were completely unmatched. An absolute blast of a time. Coming into this series, the Sox were 4 and 25 meaning that they were the worst team in the league. But you not have had any clue of this by how committed the fans and season ticket holders that were seated around us. The game would end up going into extra innings and the White Sox would end up taking the win with a home run. When I say that the crowd went crazy, I truly mean it. The crowd erupted and you couldn’t help but feel the love for the team, even if this was only their 5th win of the entire year. Highly recommend attending a game out here. It was a fantastic experience for us and we will be visiting again in the future.

Sunday morning we went to breakfast before our friends headed out on their way back home. We ate at the Egg Harbor Cafe which was delicious. The staff was so nice and the service was super fast getting us seated and served, even as a table of 6 plus a high chair. After that, we walked down to the Starbucks Reserve Roastery to visit and see why it is claimed to be the largest Starbucks store in the US. Before entering, I assumed that the Reserve Roastery locations would be an interactive museum experience similar to what Collin and I have done at the Guinness Factory in Dublin. A multiple-level, interactive, inside look at how their famous coffee and beans are processed and made. I might have been setting myself up to have too high of expectations but it was the only thing similar in my brain to what I thought it would be. Unfortunately, it was not like this. It was still a cool store with multiple floors to see, but it was not an educational tour but rather just different avenues of business. One floor was their bakery and lux coffee bar, another was an actual liquor bar along with a rooftop and gift shop. The decor in the store was incredible but I wish it would have been a bit more interactive of an experience.

Sunday afternoon, after our friends had headed out, we ventured over to Navy Pier and ended up doing a guided tour of the coast of Lake Michigan. It was about 45 minutes and we learned about the history of Lake Michigan and also the city itself. This was a great, quick adventure to see a brief overview of the layout and structure of the town. The company offered 2 different options of tours. One that stayed in the harbor and another that went up the river and into downtown. As we had already completed a bit of walking around downtown and by the river, we opted just for the one in the harbor. Next time we visit, we plan on doing a dinner cruise around Lake Michigan.

After we finished the boat tour, we headed over to do the 360 Chicago and Tilt. We timed it perfectly and booked a reservation for 8 pm which was right after the sun had set. We were able to see the city with the beautiful, golden glow as the sun was fully setting and then with all of the beautiful city lights after it went completely dark. The Tilt attraction was something beyond words could describe. It offered a great view of the city that almost felt unnatural and stolen to see. If you are severely afraid of heights then it might be hard to appreciate it but if there is any way that you can push through, I highly recommend it. Truly remarkable, especially at night.

Monday was our last day in the city and we decided to head over to Soldier Field and see the Shedd Aquarium. I had pretty high expectations considering it is one of the top 5 largest aquariums in the US by tank volume but unfortunately, I was a bit underwhelmed. I think a lot of this had to do with the chaos of children that seemed to have been there from multiple school field trips but also because it was a very compact design. The aquarium featured 3 main, large holding tanks where the sea lions, dolphins, and beluga whales would rotate doing educational shows. This made up the majority of the facility space. 3 different floors had both viewing windows and also interactive pieces but unfortunately, it just felt pretty crammed.

After we finished the aquarium, we walked down the pier to the planetarium where we saw that they had special hours during the school year where they were closed 2 days a week for school trips. I think that this would be a great practice for the aquarium to adapt to help eliminate any frustrations due to the limited size of the facility and large attendance. Overall, the exhibits were great and the staff was all super nice and informative, I just wish that there was a bit more space.

On our way back to our hotel to grab our bags before heading to the airport, we stopped at a taco truck to have a quick lunch. Mr. QuilesMexican Food truck and it was the best food of the entire trip! I got 4 tacos, 2 carne asada and 2 al pastor, while Collin got 3 queso birria tacos. The meat was tender and full of flavor and the salsas were the perfect level of heat. 10/10 would highly recommend it if anyone is in town and craving some amazing food!

After lunch, we grabbed our bags from the hotel and hopped back on the bus for one last time. We took the bus west to the entrance of the Blue Line where we would transfer to the train that would take us into the airport. This transportation was honestly the easiest we have experienced in all of our years of traveling to bigger cities. In my opinion, it was better than NYC, London, and Boston. We checked a single bag and our stroller and then were able to go through the family option of security which took less than 10 minutes total. You can tell that the city of Chicago has put time and thought into how to make it the smoothest experience for anyone coming to visit.

Chicago started as just a city with a couple of baseball stadiums on our list to visit but has become one of my favorite places to visit, especially with a young family. If you don’t want to deal with the hassle of traveling with a car seat that needs to be loaded into every taxi, Uber, or rideshare, I recommend leaving it behind and fully committing to using the CTA. They have made it so simple for tourists and as long as you plan ahead of time for given wait and travel times, it is cost-effective and gives you a different view of city life.

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