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IntroductionI made a last-minute decision to come to Chicago because there was an international conference for one of the clubs I did when I was in college. The time frame fit perfectly in my schedule, so I told myself what the heck and decided to take the leap. After spending a week in Chicago, I realized that coming here was the right choice. There's just so much to do and see, and different areas of Chicago brought a different flavor to my experience. I made a lot of memories when I was in Chicago, and I would definitely visit again!
Day 0I flew into O'Hare International Airport, which is one of the main airport in Chicago. My flight arrived at around 12:30am and there weren't many people at the airport. I opted to take the L (Chicago's subway system) to my Airbnb, which was a little far from the city center. The good thing is that the L runs 24/7, so it's very easy to get to anywhere in Chicago. If you're arriving during the daytime, the L is easily the most cost-effective option. However, if you arrive as late as I did and you feel unsafe, I would recommend taking an Uber as any area outside downtown can feel a little dicey. If I were to do this again, I would had taken an Uber, which you'll see why in a second.
I went to one of the machines and bought myself a 7-day Ventra Card, which came out to around $33 USD. This included the fee for the card itself and unlimited rides on Chicago's public transportation system for 7 days. I bought this pass because I was staying a week, and it was a good investment - I definitely made the cost worth it. Even if you choose not to get a pass, I would still recommend getting a Ventra card and loading a few rides on it because you'll probably end up taking the L or the bus at some point. I took the Blue Line to my Airbnb and the 1.5 hour subway ride there was quite an experience that I don't think I want to repeat. Nothing bad happened to me, and I wasn't in any real danger, but there were a a few homeless people in the train car. At one point during the ride, I'm pretty sure there was a guy that was high out of his mind and a girl that had no pants on. Towards the end, I was praying that the train would go faster so I could just go to sleep and get out of the subway. It was a 10-minute walk to my Airbnb after I got off the subway, and I would not recommend walking around in the middle of the night out in the suburbs. There was no one around me but you could just feel something odd going on. By the time I got to my Airbnb it was around 2:30am and I was dead tired, so I fell asleep almost instantly.
Day 1I woke up pretty late because I got into my Airbnb so late. After getting ready and doing some research, I decided to set out for the day since this would be one of the only full days I have before the conference starts. To start off the day, I went to Yolk, which is a brunch place my friend recommended to me. Brunch is one of my favorite meals and it did not disappoint - I was really happy with my entire experience. I got an egg white skillet, which was absolutely amazing. The gravy they gave me was a very nice touch. Also, the place is also decorated in a very cute way. I would definitely recommend giving this place a visit!
After brunch, I decided to take a walk through Grant Park and pass by Museum Campus and the Alder Planetarium. The walk was very peaceful, and you could see kids with the families, as well as people using segways as part of a tour. The area between Museum Campus and the planetarium gives you a good view of the city.
Then, I took the L to south Chicago to see The University of Chicago. The campus reminded me of a cross between Columbia and Harvard, and it was quite lively despite it being summer. I went from North Campus to the south, while stopping at the Booth School of Business to take a break from all the walking I've done so far. As I was walking through the campus, all I could think was how the campus was so beautiful - UCSB and the UCs really need to step up their game (yes, I know UCSB has a beach).
After walking through the campus, I walked through the area of Hyde Park and began to work my way uptown via Jackson Park to go uptown. If I wasn't feeling so tired, I would have walked through more of Jackson Park because there wasn't a lot of people and that it was very peaceful - I was the only person there. For a moment, I forgot that I was in the city because it was so pretty. Then, I decided to head to Dimo's Pizza for dinner but I had to make a bus transfer near Millennium Park. There was an unusually large number of people, so I decided to check it out. It turns out that the city does a summer film series during the summer. Hundreds of people were just sitting on the lawn with picnic baskets, wine, food, and chairs while watching the movie. I loved this concept because it seems like an easy way to invite some friends to hang out or to take someone on a date! I wish more events like this in SoCal. My hunger eventually got the better of me and I went to Dimo's Pizza, which was amazing! I came here because of a recommendation my friend made, and it was definitely a good choice. The slices are HUGE and they have some very unique pizza toppings - I wanted to try their elote pizza but unfortunately they ran out. I decided to opt for more basic flavors instead, which was still a good decision. I left very satisfied and I would want to come back again someday to try some more unique pizza toppings. After I finished, I took the bus back to my Airbnb to get some rest - the conference was supposed to start tomorrow!
Day 2To start off the day, I packed up all of my things and checked out of my Airbnb. All conference attendees were required to stay at the Chicago Marriott Downtown Magnificent Mile, which was right in the heart of downtown. The conference didn't start until around 4pm and I didn't want to lug my bags around all day, so I went to the hotel to drop off my bags with the concierge to pick up later.
First off, when I travel, I almost never stay at hotels because they're just simply too expensive for my budget. But after staying there for a good 5 days, I can see the appeal of such a nice hotel. When I arrived, I was sweating and out of breath from walking with my heavy backpack. I couldn't find the concierge right away, so I waited in line to ask the check-in staff and the lady was incredibly nice! She told me who to talk to and offered me some water - obviously she could tell that I was winded! Before talking to the concierge, I took my Hydroflask to one of their water dispensers but one of the staff immediately came to me and told me he would personally bring a few bottles of water for me. I was obviously struggling to fit my 40 oz container under the spout, so I really appreciated that. The service I received in the span of 15 minutes was very impressive, and I instantly understood the appeal of nice hotels. However, staying in major hotel chains when I travel will have to wait when I'm older and have more of an income! After I dropped off my bags, I went to Beatrix to eat brunch. My friend raved about how good it was, so I was excited to try it. There was a huge crowd in front of the restaurant, so I was worried that there was going to be a long wait. However, when I told the staff it was just me, they seated me at the bar right away (one of the many perks of solo traveling!). I was initially overwhelmed by the menu because everything just sounded so good. After lots of thinking, I decided to get the egg white omelet with a side of the chicken sausage. Once I got my meal, I instantly knew I made the right decision as every part of the meal was very tasty. The chicken sausage seemed to just taste perfectly right, and the omelet itself was delicious - the spreads and the add-ons were a good touch. 
In order to make it back by 3pm to take care of a few things before the conference, I decided to head uptown to Montrose Beach and then rent a bike and then head down Lake Shore Drive, which borders Lake Michigan. I was very excited for the bike ride because my other friend said the ride was very pretty.
I started off by taking the bus uptown and then walked to Montrose Beach, which was a great experience! I've been to nicer beaches, but I really enjoyed the atmosphere. When I went, it was the 4th of July. So, You could see lots of families and groups of friends just relaxing on the beach and at the fields just before the beach. For the past years, my 4th of July usually consists of work or going with my family to the community pool to eat some free El Pollo Loco. However, I was awed by what I saw. People brought canopies, tents, BBQs, ice chests, volleyball nets, chairs, and lots and lots of food. It almost seemed like a summer camp for all ages as you could see kids playing in the water while their family was having a great time. I feel like people in Chicago go all out for the 4th of July and it was very interesting to see! After walking on the beach and the nearby grassy fields, I decided to look for a bike rental machine. This was easier than I expected as there was one really close to the beach! Renting a bike only costs $3 for 30 minutes, or $15 for unlimited 3-hour rides over 24 hours. Since I knew I had to be back by a certain time, I decided to not get the unlimited pass, which saved me money. Initially, it was very hard to find the defined bike path, but after some guesswork I found it and I started to head down south to downtown.
Now, throughout the bike ride, I was so glad I decided to do this because the views you see are absolutely beautiful. It was easily one of the favorite parts of my trip! It's not too intimidating as the path is clearly defined for you and just stay to the right if you're going a little slow. You pass by various beaches and grassy areas, and I definitely stopped a few times to just take pictures and to take it all in. In my opinion, the best part was when I got closer and closer to downtown (around North Avenue Beach). You could see the beach coastline along with the skyscrapers of downtown, which makes for a good picture! Then, I ended my ride at around Ohio Street Beach, and then went back to the hotel. After I went back to the hotel and attended the conference for the day, my district and I went to eat dinner at Lou Malnati's Pizzeria, which was also a place my friend recommended to me. We all wanted to try the deep dish pizza, so we ordered a few large pizzas to share. The pizza too a while to come to the table, but it was all worth it in the end. The pizza tasted very good, and I managed to eat 3 slices even though it was very filling. A couple of people and I had to sit in a booth because the table wasn't big enough to seat all of us, and I appreciated the fact that the server made sure to check up on us too. He also cut and gave out the slices of pizza to everyone! After a delicious meal, we all started to head back to the hotel.
Day 3-5During the next 3 days, I was attending the conference so I didn't really have time to do any sightseeing. However, instead of boring you with all the details, I would recommend going to these places:
Joe's Seafood, Prime Steak, and Stone Crab - This place was absolutely AMAZING. I chose to get the salmon because that's what I was in the mood for. Everything from the service to the food was really good, but it is definitely on the pricey side - expect to spend around $30 for a main dish. It was way pricier than what I would usually eat, but I thought that I should treat myself - after all, when was I going to be in Chicago again? Hing Kee - A tasty dim sum place in Chinatown (with some American elements?). Overall pretty good, but I wouldn't go out of my way for this place. Kung Fu Tea - I got some milk tea with boba from this place, and I thought it was worth my money because the cup they give you is quite big! Jake Melnick's Corner Tap - This place kind of has a bar vibe, but they serve INSANELY good chicken wings - we got a combination of a few wing flavors and some fries which made for a good meal. Buckingham Fountain - Initially it seems like it's just a fountain, but it's still pretty cool to see. The Bean - One of the major icons in Chicago and definitely worth a visit! However, you don't need to stay there too long - just snap a few pictures and move on. It's very crowded and the bean itself is filled with handprints. Navy Pier - Another major icon in Chicago, also worth a visit but you don't need to spend too much time here. To be honest, I thought it was a little underwhelming. It's basically a small mall-like building which leads to a mini amusement park. Behind the Ferris Wheel is a view of the harbor near the pier, which is nice for pictures. Chicago Riverwalk - It's a very nice area to walk through. I did the walk at night, which allowed us to see the city skyline at night. However, I feel like it would be very nice to visit during sunset. Millennium Park - It's a very nice park to walk through, and it has the Bean along with other things to see. Michael Jordan's Steakhouse - My friends and I mostly went to try the 23-layer chocolate cake, which was REALLY good. I would say it's definitely worth stopping by. However, if you want anything else, it's very expensive for a steak and other items. I also got duck fried rice, which was very tasty. Pizzeria Due - Also a very tasty pizza place. Don't get something too large because the pizzas are quite big! Also got the veggie dip, which was good but it was definitely something I could have just made at home. Xoco - I got the Carnitas tacos, which were a very good value for the price. Very tasty and filling. They also had a guacamole bar, which looked promising. Bangers & Lace - Great Chicago style hot dogs with a chill vibe. Roti - a chain serving the Mediterranean equivalent of a Chipotle - very tasty! Lito's Empanadas - very affordable if you're looking for something quick.
Day 6My friends and I woke up somewhat early to get brunch with our district administrator and a few other people that stayed in Chicago a few days after the conference. We went to Wildberry Cafe, which was one of the places I had bookmarked. I was very excited to try the restaurant because it looked very good. I got the Garden Skillet with pancakes which was really good! However, I wasn't able to fully enjoy the skillet because I had a huge headache during the entire brunch, which was frustrating. In the end, I just took it to-go to eat later. I would definitely recommend paying the extra amount to get specialty pancakes, because they have very interesting toppings and they all looked delicious.
After the brunch, I went back to the hotel to take a nap because of my headache. When I woke up, I rested for a little and decided to go to the John Hancock Center to see the Chicago skyline. I chose this over the Willis Tower because the John Hancock Center has a tilting attraction, where you pay a little extra to have the experience of tilting over the building to see the skyline - I definitely recommend doing this as it was a very unreal experience. However, I would pass if you're scared of heights. Overall, I really enjoyed the views. It costed me about $33 to go to the top of the tower and for the tilt attraction. Then, I headed towards the Riverwalk to take an architectural tour by Wendella Boats. I would definitely recommend the tour, especially if you're into architecture. During the tour, we went up and down the Chicago River, while our tour guide gave an extremely detailed summary of various buildings as we passed them - it was a really great experience! Also, it was very scenic and relaxing. Overall, the tour lasted about an hour and a half.
After the tour, I decided to head towards Giordano's to try some more deep-dish pizza as my last meal in Chicago. The pizza itself was pretty good, but I made the mistake of going to the one near Millennium Park because it was super crowded. I got seated right away, but it took me almost an hour and a half to get my pizza and by then I was starving. I didn't have the best experience but I would go to a location that's not in central downtown.
Afterwards, I went back to the hotel and packed to head back to SoCal because I had a 5:30am flight the next day! Overall, I had a great time in Chicago and I can't wait to visit again. If you have the time, I would also recommend going to the Art Institute! |
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