Where To Go In Chicago

Hello, dolls! Hello, weekend!! Soooo I thought August was going to be crazy, but it seems like September is shaping up to be crazier. I will be spending each day planning our big trip in October, I am starting the month by going to an awesome blogging opportunity here in Maryland, and I will be hugging two of my favorite girls that I haven’t seen in almost a year! So yeah, it is a very exciting and eventful month.

Anyway, here’s the continuation of my Chicago series. A and I decided to go to Chicago for our 4 year anniversary. Truthfully, it was an out-of-the-blue decision. I was at work doing computer tasks and I saw an e-mail from Southwest so I started looking at flights. We were in Chicago for 3 nights and 3 days — we left Baltimore at 7pm and got there around 9ish. It was a very spontaneous trip because we just listed down a couple of restaurants and food we must try   As for the places to go to, I just knew we have to take a picture with “the bean” so that was the only thing I remember putting on our list. The rest of the spots we went to were unplanned but definitely made our Chicago trip a really memorable one.


So where do you go when on a long weekend in Chicago?


1. Michigan Avenue

Shopping is something that I can’t miss doing when traveling, I wasn’t planning to splurge in Chicago since sales tax is so high I believe it was around 10% so I figured if I really wanted something I can order it online and have it shipped in Maryland. Anyway, A and I only wanted to visit 1 store during our trip, and that is…..



When we found out there’s a big Topman/Topshop store in Chicago, we made sure that we will find time to go and shop! There were numerous stores around the area too like Nordstrom Rack (which I really loved) and great restaurants too!



2. Wells Street Bridge

I can’t remember how A and I ended up at this bridge but I know for sure it was from one of our “walkathons” after a great meal.


It easily became one of my favorite spots in Chicago because of the view and how it connects to different areas of Chicago that are worth seeing. it just depends how far you are willing to walk 😛 




Aside from the beautiful buildings (which we do not have a lot of in Baltimore), I loved the view of the water. I wasn’t able to plan a lot for our Chicago trip but I am definitely going to try this sightseeing cruise next time!



The best thing about this bridge? It doesn’t get too crowded. When we went there were only commuters passing by but not a lot. I think my gazillion pictures on this bridge can prove that 😛


Before I learned how to use Adobe Lightroom 😛 


They don’t call Chicago Windy City for nothing! My dress kept on blowing away! Weirdly enough the cold did not even last 24 hours. The day before I felt unprepared for not bringing enough “layers” with us. The day that we went to Wells Bridge was the perfect Spring day in Chicago 🙂


3. Skydeck (Willis Tower)

This was the best spur-of-the-moment decision we made that day. A and I are both afraid of heights so I did not really look into this prior to our trip. However, when we realized we were in the area after our “mini session” at Wells Bridge, we decided to go and experience one of the best observatories in the world! — I truly believe it because where else can you go and see 4 states in America??




The Willis Tower observation deck is on the 103rd floor of the building. It was great to see Chicago from above and feel the wind when we were standing on the “ledge”.




I did not expect A to be THAT scared. He was literally on the ledge for less than 2 minutes — just enough time for us to take a decent picture together. After I saw his face, I started to get scared too but I was so determined to get decent pictures…at least.

P.S. This was me conquering my fear of heights. I couldn’t stand up because I felt like I was going to fall any minute LOL




There has only been one incident on the ledge since Willis Tower opened it to the public in 2009. There were no injuries, just a tiny crack on the glass! No incidents have been reported since 2014 so I felt confident that A and I will survive 2 minutes standing there.


Who would think we are afraid of heights?


The $27 ticket price is super worth it! It’s more or less half the price of Empire State Building’s entrance ticket.



I honestly enjoyed Skydeck more than the Empire State Building in New York. Skydeck is waaay more organized and less crowded, at least when we went. You can take great pictures from above too because of the glass walls and be “weatherproof” since its indoor.



The NFL draft happened 4 days after our trip. Pretty awesome to see Chicago prepare for it!


4. The Art Institue of Chicago

One of the largest and oldest art museums in the US. A and I did not go in since we felt like we won’t have enough time at the Millennium Park then go to dinner. But really, if I am being honest, we are just not “museum people” 😛 So it has never been our priority to visit museums. 


There were food trucks right outside the Millennium park the day that we went. I definitely felt like a locale!




5. Millenium Park

Last but not least on my list (see what I did there? 😛 ). Definitely, the biggest park I’ve been to (so far). There are plenty of spots for everyone! I enjoyed watching people relax or do “work” on their computers as I ate my deep dish pizza with A.

The feeling of being in the moment at a place I’ve never been before felt liberating. I was reminded that life is not just about my career, that I deserve to step back once in a while to feel the air and appreciate whatever is in front of me. 



This spot is giving me major NYC feels. the columns are so traditional and the background is the modern city. What a great background to have!




It took us a while to get close to the bean since it was really crowded. We got there in the afternoon so of course, that was the time all the tourists were there!


Rule # 1 For great pictures when traveling — wake up early so you can get to the “spot” before the tour bus rolls up!



Mandatory “bean” selfie :p




A and I LOVE Chicago. From someone who is not from the US, my only knowledge about Chicago is the basketball team “Chicago Bulls” (LOL). I did not expect it to be so versatile! There are places to go to for everyone.


This picture reminded me that I’ve been intending to take pictures with A for the longest time, but it seems like we can never get the chance because I am always about family photos now! How do couples do it when they have a toddler with them?? Baby A has been my favorite subject for 2 years now but I want/need updated pictures with A for our memory box.


Happiest when traveling <3


R <3

4 thoughts on “Where To Go In Chicago

  1. You guys look good together. Looks like you had so much fun on your chicago trip.Thanks for sharing taking the time to post this ♥️ ♥️ By any chance you are interested on doing collaborations, you can check out the collaborations portal of Phlanx.com and connect with amazing brands!


Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.