Chicago is monumental to me because it is my first travel destination all by myself. Traveling to a new city, especially on my own, was daunting because I didn’t know the area or neighborhoods, let alone know anyone. I also had to figure out how to get around. I know most people just UBER it nowadays, but I like to get the feel of wherever I am at, so I would prefer walking or using public transportation. Make friends with the hotel staff because they will surely give you tips on what to do and how to navigate wherever you are. The bellhop explained to me how to get downtown.
I was only working in Chicago for 3 days. I had plan of things to do and eats to try to maximize my time here, while taking tips from the hotel staff to add to my agenda. I visited Chicago mid-October. If you have a choice of when to come, I’d suggest coming during the spring and summer, as October nights in Chicago are cold and windy. I guess that’s why it’s called the Windy City (that’s not the real reason. Find out here.) It’s best to dress in layers and bring a coat with you. I had brought a thinner jacket but that wasn’t enough for me (even with layers). Since most of my exploration was taking place during the evening and at night, I splurged on a coat to endure the cold. Lucky me, the Fashion Outlets were across from my hotel.
My hotel accommodations were at the Crowne Plaza in Rosemont, close to O’Hare International Airport. The work I was doing was also taking place at my hotel, so after I finished working at 4:30 p.m., I ran up to my hotel room to change. I walked to the train station, about 15 minutes away. Then, I took the Blue Line to Downtown Chicago, approximately 40 minutes from Rosemont. If you could stay closer or within Downtown Chicago, you’d definitely save yourself some travel time.
Initially I was planning on UBERing it to Downtown Chicago, until I heard that it would cost at least $40 each time. I was on a budget and spending that seemed outrageous. Instead, I spent a little less than $40 by getting a three-day pass and taking the CTA Blue Line. One of the things on my list was Millennium Park. The bellhop explained how to get off at Washington. I used Google Maps to help me navigate the rest of the way. So the first night I went to Millennium Park and then walked to Navy Pier. On the second night, I went to Willis Tower and the last night, I traveled to the Lincoln Park neighborhood to see a comedy show. Because it seemed like I walked everywhere on my first night, mostly because I got lost, I kinda got a lay of the land and had an idea of where the train stations were located.
So if you are in Chicago for a short time like I was, these are your must-dos.
Stroll through Millennium and Grant Park-That’s where “The Bean” is located. It is amazing especially as you come as the sun is setting. The mirrored reflection of the city’s skyline is impressive. You can even even walk underneath it; it has the creative funhouse mirrored effect. If you keep walking through Millennium Park, which is a part of Grant Park, you can see two architectural designs of Frank Gehry (who I only know because of his Tiffany & Co. jewelry collection), the BP Bridge and the Jay Pritzker Pavillon. There is also the Lurie Garden and the Crown Fountain to visit there too. I didn’t get a chance because I had to go to Navy Pier for my boat tour.
Take a boat tour-This is great to do on your first day. It is approximately 75 minutes but it’ll help you get your bearings of the city. I took the Seadog River and Lake architectural boat tour from Navy Pier at night. It was freezing! We started in Lake Michigan. The Chicago Harbor Lock separates the Lake Michigan from the Chicago River. It was pretty cool to see how we start in Lake Michigan and how at the lock, it cycles through the water to bring its level to the level of the Chicago River within approximately 15 minutes. The tour guide amusingly narrates facts, stories about the history, buildings, and bridges along the Chicago River.
Try a Chicagoan hotdog-FYI, in Chicago, you do not put ketchup on your hotdog. Instead, there’s raw onion, mustard, sweet pickle radish, tomato slices, a dill pickle spear, sport peppers, and celery salt. With all of that on it, you really don’t need any ketchup. There are plenty of places to try a Chicagoan hotdog, but I went to Portillo’s.
Visit the Willis Tower Skydeck-If you are scared of heights, I wouldn’t recommend it. I’m one of those people, but I am trying to overcome my fears by doing something I wouldn’t normally do. The Willis Tower, formerly the Sears Tower is the tallest building in Chicago. You can get up to the 103rd floor Skydeck, which offers 360 spectacular views of Chicago. It also has the Ledge, which is a glass balcony extending four feet outside the 103rd floor. Don’t look down. If you must, do it quickly! In actuality, it was pretty awesome to be standing and sitting on top of the city.
Try deep-dish pizza-Since I live in Connecticut, New Haven pizza is all I know. Thin-crust pizza is the clear winner in my book. However, I couldn’t knock deep-dish until I tried it from where it was invented. Chicago gets a lot of attention for its deep-dished pizza. There were several places that were recommended to me: Lou Malnati’s, Giordano’s, Pequod’s, the Art of Pizza, and Gino’s East to name a few. Since I was limited on time and couldn’t visit all those places, I tried Giordano’s (mostly because there was one close to the Willis Tower). Warning: it takes about 45 minutes for your pizza to come out because it needs more cook time since it has thick layers of toppings. So don’t go there when you are at the point of starving and hangry. My personal size meatball deep dish pizza was plenty and more like 3 meals for me. It was like eating a meatball grinder just pizza style. Surprisingly it wasn’t as doughy as I expected. The crust is just deep and creates a bowl for the layers of cheese and whatever topping you choose. It was good, but for me, New Haven pizza is like no other.
Catch a show-Poor planning on my part, I’ve wanted to go see Hamilton in New York City, but its costs stop me from purchasing tickets. Tickets in Chicago are a tad bit cheaper and had I been thoughtful, I would have gotten myself tickets. But don’t despair, Chicago has more than just Broadway. My motto when traveling has always been to venture out beyond the touristy, downtown areas. Check out other neighborhoods. My friend had recommended me to see Second City, located in the Lincoln Park neighborhood. Second City is Chicago’s famous improv and sketch comedy show, known for producing a lot of famous names, like Tina Fey, John Belushi, and Stephen Colbert. Laughter was what I needed. Lucky me, I was in for a special treat. They decided after the original show to extend it by revealing some new sketches.
Visit Wrigley Field-Even if you don’t care for baseball, catch a game at Wrigley Field. So I was hoping I could go see a game while I was in Chicago, but they lost the National League wild-card game. A coworker of mine came here during the spring and said it was an experience to be had and the ballpark was reminiscent of 1914 and really hasn’t changed much. I’ll take her word for it.
I hope I get to visit Chicago again soon to try some more foods, catch a ballgame and try to scout out the film locations of one of my favorite television series is Chicago Fire, Chicago PD, and Chicago Med. Wishing you all happy and safe travels!