SOLO Trip to Chicago

My solo trip to Chicago. The day of my trip the person I was supposed to be traveling with decided not to come and to go on another trip during the same time frame.Being that I was already in Chicago when finding out my travel buddy was no longer coming I decided to make this the best trip ever.

Chicago is a nice city a lot to see and do. My trip was planned to do a lot of sightseeing and exploring and I believe I did just that. I saw light bugs which are the firefly that have little green lights on their butts this was my first time ever seeing one and let’s just say I was super excited about seeing them. The architecture downtown is unique and definitely worth seeing. The people were pretty friendly and helpful when I needed help. I did not get to party but there was this one club that is open on Friday PERSONA I’m not sure if they do it every Friday but they have random free drink hour so would recommend someone check it out when they go. One thing I didn’t get to do was visit the WILLIS TOWER. Everything else I did was all that I wanted to do. Food everything was amazing no complaints there.

Listed is my itinerary and some things that I learned on my Solo Trip to Chicago.


Day 1:

Uber from Airport –Airbnb– Sight Seeing (Crown Fountain, The Bean, Millenium Park, Jay Pritzker Pavilion, and Chicago Theatre, Chicago Water Tower, Navy Pier, Mr. Browns Lounge)–Uber– Airbnb– Walk to Liquor store– Airbnb– Night in

  • All of these sights were literally in walking distance of each other I walked 16,518 steps. I started at the Crown Fountain and made my way through Millenium Park to see the Bean and Jay Pritzker Pavilion. Also, walked through the Lurie Garden which had some beautiful flowers. I then decided to venture out after looking at all of those spots I worked up an appetite. On a search for food, I was able to see the Chicago Theatre (they offer tours before 1pm, and it was about 3 so I was unable to get a tour). The food options were wide but limited, a lot of fast food and steak houses neither was what I wanted, so I just kept walking until I saw a restaurant that piqued my interest, this is when I came across Mr. Browns Lounge a nice Jamaican restaurant. The food was amazing I usually don’t eat all of my food but here I ate the majority of it the portion was huge. I got the MBL Island Jerk Chicken came with a side of red beans and rice, cabbage and plantains, I don’t eat plantains so I got extra cabbage and a side of macaroni. They also had happy hour at 5pm offering $7 Rum punch. I was very much full and needed to walk some of the food off and finish my sightseeing. I then ventured the city some more and walked to the Chicago Water Tower, which isn’t actually a water tower, it seems more like an older church that you were able to walk in a view the history of the are. There were different cow paintings in the surrounding area, that was really nice depicting different views of the animal. Not wanting to end my day I made a 22 min walk to Navy Pier. Navy Pier has a children’s museum, restaurants, bars, a small water fountain for children to play in, an amusement park with a Ferris wheel and other rides. They also offer boat rides for sightseeing and helicopter tours. The boat rides range from $30-50 and the helicopter tour started at $99. This concluded my sightseeing for the day, I later took an uber back to my Airbnb and walked to the liquor store which wasn’t far and decided to have a night in rather than going out.


Day 2:

Uber–Batter and Berries– Bike Ride–360 Chicago Observatory–Oak Street Beach– Artichecture Tour boat ride-Uber–The Angry Crab— Uber– Airbnb

  • Day 2 was less busy but just as eventful. I originally was supposed to take the train but thought it was going to take too long now reflecting back I should have just took the train. Started my day going to Batter and Berries, which had an hour wait, during this time I decided to walk the neighborhood and see what else the city had to offer since I was in a different area than before. The houses here look like the buildings on monopoly they are really tall and long in length. After walking around for 45 min it was finally my time to taste the food that everyone recommended I try. I got the French Toast flight which consisted of a sample of 4 different flavored french toast, with a side of cheesy hashbrowns and bacon. Let’s just say I was very satisfied with the recommendations provided the food was amazing and filling. Instead of taking an uber to my next destination, I rented a bike for 30 min for $3.00. This was actually really fun I haven’t ridden a bike in a while and when I did it wasn’t to get me from Point A to B it was simply for fun, but being able to navigate myself in traffic on a bike was very exciting. The Chicago 360 Observatory was the best view ever costing $25 and the have a ride the “Tilt” that’s an additional $8. Well worth the money you go up to the 94th floor and get to look all over Chicago North, South and West they don’t have an Eastside because that’s where the water is I believe. (don’t quote me on this) You get a view of the whole city from all aspects it is breathtaking. The Tilt ride is where you get into these window panes and it tilts you 30 degrees down for you to see below. It seemed scary watching others do it but once on the ride it wasn’t that bad. My goal after leaving the Observatory was to ride the bike to Navy Pier for my Artichecture tour but I visited 2 bike stands and they were out of bikes so I had to walk. On my walk I passed through Oak Street Beach, the water was beautiful nice clear blue no seaweed truly a beautiful beach. There were different boat ride tours but I wanted to see the architecture that Chicago has this tour was 75 min and about $46 with tax. After the Tour, I took an uber to the Angry Crab which was another recommendation. The prices for seafood here were way more expensive than what I am used to in Texas. Since prices were higher than normal I got 2 pounds of shrimp 3 corn, spicy with their season blend mix and it was worth, I even had some food left over. Before eating I had the intentions of going out I even found a club that offered free shots, but I was exhausted when I made it to the Airbnb so I enjoyed another night in.


Day 3:

Train–Taste of Chicago— Uber–Oak Street Beach— Train– Airbnb

  • I started this day late intentionally since it wasn’t a lot that I had planned and wanted to get some sleep in. I used google to help me figure out what train to take and what stop to get off at. The train ride was $5.50 for one way and the ride was about 40 min. Lucky for me the train stopped right in front of the taste of Chicago. This food festival is ultimately what I came for but waited until my last day to indulge. There were over 100 different food vendors so many options to choose from, some places offered full portions while some offered samples. The tickets ranged from 7-20 for a single item at certain spots. Tickets were sold by a strip of 14 for $10 I started with 2 strips and that went by fast so I got 2 more totaling $40 and 56 tickets. I had rib tips, 2 bottles of water, cookies, popsicle, pizza, and elote. I spent about 3.5 hours here, I ate walked around sat down let my food digest got more food. It was pretty fun they had sort of a concert going on at one end, door dash had an area called camp door dash that was a resting and recharging area. It also rained for like 30 min while at the festival definitely wasn’t in the forecast but everyone kept walking around as if it wasn’t even raining. After here I headed to the beach to relax and enjoy the nice blue water, I couldn’t find the train that I was supposed to take to get there so I took a uber to the beach. The beach was pretty full, but I picked a spot laid my stuff out and headed for the water which was extremely cold even though it was about 90 degrees the water was super chilly, my body adjusted to temperature after being in it for a while. After about an hour in the water, I decided to lay out and sunbathe this was very refreshing listening to the water crashes and other people talking I drifted off until a nice little nap. After my time at the beach, I headed back to the Airbnb to clean up and prepare for my departure the next day. I ate my leftover shrimp for dinner along with some cookies for dessert.


Things I wish I knew in the beginning:

  • Ubers are expensive and time-consuming, I used the uber pool since that was the less expensive route and if you don’t know in uber pool people can be added to your route if you are going in the same direction or coming from the same area. It was nice to meet others but put me off track some times since the ride would add 30 extra minutes due to another passenger.

  • I should have followed my first instinct and took public transportation from the beginning could have definitely saved some money on transportation.

  • Plan your trip daily and by distance. Everything luckily for me was in the same area, but a couple things I had planned were farther out than expected.

  • Use Eventbrite for local events going on in the area.

  • Airbnb- $278.08

  • Transportation (uber, bike, Train) – $170.61

  • Eating -$147.13

  • Entertainment -$121.84

  • Flight -$181.61

TOTAL: $899.27

The Airbnb and Flight were paid for before the actual trip. My goal was to spend $300 on the trip, but I spent $438 which isn’t bad considering I didn’t split transportation with anyone as planned.

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