Travel Diary: A Weekend in Chicago, IL

A girl’s trip is a necessity in life and should be done as often as possible.  For most, they’ll do an annual girl’s trip so that they can get together with their favorite gal pals.  Girl’s trips are good for the soul, and I will highly recommend doing a trip with your girls, at least once in your lifetime.  So, stop reading now and plan your next girl’s trip with your favorite girls- and then come back to this post!

Anyway, getting together with my girlfriends was my plan for my recent trip to Chicago, IL.  While it wasn’t an annual girl’s trip, it was an overdue girl’s trip with my amazing college gal pals, and I’ll remember this trip for life.  We had such a blast from the amazing food that we ate to the heartfelt conversations that we had, and we hope to look forward to another girl’s trip in the future.

Anyway, enough of my summary of a girl’s trip weekend.  Without further ado, check out my recent travel diary of a weekend away in Chicago, IL.

Day #1:  Acting like a Tourist

I didn’t get to do much touring in Chicago as my girlfriends and I mainly wanted to focus on spending quality time together.  However, I did not want to leave Chicago without seeing The Bean at Millennium Park.  So, once I landed in Chicago (at 7 am) and got my nap in, the girls and I headed over to Cindy’s Rooftop for brunch and to get some nice views of The Bean.  When we were done with our lattes at Cindy’s, we headed over to get a glimpse of the famous Chicago Bean.  It was like a dream come true for me at that moment.  The Bean in Chicago was always on my bucket list, so I was glad I finally got to check that off my list.

Once we were done at The Bean, we headed to get some classic Chicago deep-dish pizza.  I would be lying if I said that I didn’t enjoy that delicious deep-dish pizza.  It’s something to try at least once in your lifetime. Lastly, for our night time activity, we went to an Indian restaurant and saw a Comedy show at the famous Second City Comedy Club. If you don’t know, Second City is where most of the SNL casts starts or gets discovered. So it’s a great experience to be in the presence of the future of SNL!

Ready for a girls dinner & comedy club!
The famous Second City Comedy Club!

Day #2:  All the Good Food

On the second day of our trip, my girlfriends and I had more of a relaxed time.  We focused this day mainly on the Chicago food culture and the Chicago speakeasy culture.  If you weren’t aware, Chicago still has the original speakeasy locations from the Prohibition era, with drinks still made the same- however, they are fully renovated and modern looking on the inside.  The great thing about the speakeasys’ in Chicago is that you must search for them as they are hidden in plain sight.  This was fun for my girlfriends and me as we got to experience the speakeasy culture from the 1920s. 

Anyway, since we had the classic Chicago deep-dish pizza the day before, we wanted to have other types of food on this day.  We enjoyed a classic brunch and an extravagant dinner at some amazing spots.  Check out the pictures below for the amazing food and restaurants that we visited.

Enjoying the Chicago rooftop views.

Day #3:  Local Brunch & Shopping

Saving the best for last- the relaxation day.  On this day, me and another one of the girls were flying back to our current cities.  So, we kept this day even more relaxed than the previous day.  One of the girls had to leave by 7 am to catch her flight so we bid our farewells early to her.  My flight left in the afternoon, so I had the morning to spend with our lovely friend who hosted us.  We walked over to an amazing whole-in-the-wall brunch spot that was near my friend’s place.  We didn’t even make any reservations- just hoped that they would be able to seat us. 

Afterward, we walked a bit in downtown Chicago, so that we could digest our brunch and explore the city a little more.  I love walking and had wanted to walk a bit before I had to get on my flight and sit for hours.  Once the walk was done, I had to head back to my friend’s place and do some final packing before my flight.  Then I hopped into an Uber and ended the amazing girl’s trip.

Saying my final good-bye to Chi-town!


Chicago has many hotels and AirBnb that you can stay in throughout the city.  Most of the hotels are in safe and good areas of Downtown Chicago.  If you are to stay anywhere in Chicago, I would recommend staying in Downtown Chicago as you’ll get to experience the Downtown Chicago vibes at a closer distance.  You want to be walking (or a short Uber ride) distance away from most of the touring or good restaurants in Downtown Chicago.

Lucky for me, I was fortunate enough to be hosted by one of my friends who was living in Chicago at the time.  While I don’t want to give away my friends’ location, I’ll just mention that we were near the River North area in Downtown Chicago.  We felt safe staying there and the neighborhood itself is quite quaint.  It’s also away from the Tourist parts of town so it feels cozier even though we were stills staying in Downtown Chicago.

Chicago city views from my Stay.


As mentioned above, this trip focused a lot on the food culture in Chicago.  I believe I gained some weight from this trip but well worth it.  As they say, vacation calories don’t count- right?  Anyway, we tried everything from deep-dish pizza to Indian food, to Italian food, to the brunch scene.  We didn’t have any bad experiences or dislike any of the food in Chicago.  If you’re going to Chicago for the food scene, then it is well worth it.  Just make sure to make your restaurant reservations at least a month in advance. 

Well, there you have it for my travel diary for the short and fun girl’s trip weekend to Chicago, IL!  I hope you enjoyed the highlights of my trip, mentioned in the post above.  What is your favorite weekend trip that you have done recently??  Let me know in the comments below!

Much Love,

8 thoughts on “Travel Diary: A Weekend in Chicago, IL

  1. How fun! I haven’t been to Chicago since I was a little girl. I would love to go back and experience it as an adult. It seems like there are a lot of fun things to do. I enjoyed your post!

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