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Going on a solo trip was something that I fancied for so long. It was on my bucket list for years but I never actually made strides to go on the adventure. I also always wanted to visit Chicago, The Windy City. I was fascinated by all the beautiful landmarks and views. I wanted to see “the bean” in real life.

Special thanks to my trip planner/assistant: my sister. She helped me book my flight, hotel, restaurants, museums, etc. I spent a total of three full days in Chicago. I knew that traveling solo was going to be an amazing experience but I made sure to pack my schedule so that I always felt productive.

Before I give you the ins and outs of my itinerary, I wanted to share that although I am very resilient and outgoing, I am also very reserved and get nervous pretty easily. I get intimidated by maps and feel lost when I feel like I’m not prepared. However, I knew that doing this was something I would always remember so I went in with an open mind.


It’s so important to PREPARE and PLAN. Be sure to do your research ahead of time. Being prepared will make your trip much more rewarding. These are some of the logistics I took into consideration when planning.

  • Weather: The weather in Chicago was in the high 80s to mid 90s the weekend that I went. I got lucky with perfect weather but at times it got ridiculously hot and humid.
  • Safety: For the most part, I felt extremely safe in Chicago. I took Uber/Lyft, I walked, and I even cycled. Try to have someone you can call when you are taking long walks, especially when it starts getting dark outside.
  • Perks: Businesses are VERY accommodating for people traveling alone. I was able to get seated quickly at restaurants. I was also able to make changes to the itinerary due to the weather because it was just one person. Overall, there are so many perks to going somewhere alone. You will definitely get great and quick service.

My favorite places in the windy city

Lovely view from Cerise Rooftop

I made a reservation ahead of time but there also weren’t a lot of people when I got there. The food and drinks were fantastic and the service was great. They have indoor and outdoor seating and the view looks amazing from any angle. This rooftop is the top floor of the Virgin Mobile building for reference point.

Perfect hangout spot @ Recess

Recess is exactly that; a mostly-outdoor place with games, music, food and drinks where you are in for a good time. If I was a local, this would be the place I would go with friends for brunch.

Beer and games at Emporium Fulton Market

I found this spot walking around the Fulton Market Area back to my hotel. This place was a barcade. It was pretty packed and fun with most people in groups. They have a great selection of beers in bottle and draft. You need tokens to play games. Pretty chill spot to go with friends.

Must-have Lou Malnati’s Pizzeria*

Hands down the place to go if you’re looking for traditional Chicago pizza. This is not a quick, to-go spot. You need to allocate at least 45 minutes your pizza to be ready. The atmosphere is calm and perfect for a date night or big group. There’s tons to order in their menu but definitely try the deep dish pizza. All of them are delicious and worth the wait.

Millennium Park in Cloud Gate

The bean was obviously such a great and fun visit. Due to COVID, there were gates around it but I was still able to get some nice photos. I would definitely recommend planning at least 1.5 hours to walk around Millennium Park. There’s a lot of great photo ops in the vicinity.

Beach Day in the Windy City – Oak Street Beach

Going to the beach in Chicago wasn’t originally in my itinerary but I had my bathing suit ready for the hotel’s pool. However, the weather was absolutely beautiful so I decided to add it to the schedule. The beach was amazing especially because it was surrounded by many buildings. The city feel and beach vibe was the perfect combination to keep me refreshed on a hot day.

La Michoacana Premium in Pilsen*

If you’re interested in fresh fruit ice cream, popsicles, and sweets, this place is delicious. A bit farther from all of the other places featured in this blog but totally worth it. They have the best mangonada which is a Mexican dessert made of mango sorbet and chamoy topped with chili powder.

Museum of Science and Industry, Chicago

This museum has been on my must-visit list for so long. I had a great time walking through this very informative and fun museum. The exhibits were great and I even got to watch the Michael Jordan to the Max film at the museum. I would recommend this for anyone interested in taking a pause from all the tourist things. They have a great museum shop where I was able to get some great souvenirs to bring back home.

Soldier Field Tour

This tour was so much fun and a dream come true. Growing up, I was a huge football fan and would always cheer on the Chicago Bears. Touring the stadium and literally stepping foot on their home field was such a fun experience. Definitely recommend it. You don’t have to be a sports fan to feel intrigued by the history.

SkyDeck Chicago at Willis Tower

The Ledge was closed when I visited but I was still able to get a magnificent view from the 103rd floor of the Willis Tower. This is a classic, oversaturated Chicago must-do.

Don’t skip the Wendella Architecture Boat Tour

Last but certainly not least, this is a MUST DO! Going on the Architecture Tour close to sunset was such a beautiful experience. The history behind the city of Chicago and the views of the sunset among the skyscrapers was absolutely breathtaking. I would definitely do this tour again when I go back to Chicago.

My solo trip to Chicago will always be one to remember. I did so much in only a few days. I got the opportunity to connect with myself and reflect on how proud I was of myself for completing two big bucket list items. I wish you the best of luck in your travels and hope you check out some of these spots in Chicago! Feel free to share your travel experience with me here.

*added from my second visit to Chicago