• Laura B

My Chicago Weekend

Updated: Feb 3

by Laura Bissessar

I'm going to admit it here like I admitted to my husband when we went on this trip: I knew absolutely nothing about Chicago before going. I knew they had the Bulls, da Bears (ha), and some pizza, but that was about it. So I have to say, I'm pretty dang proud that I managed to research and plan a weekend in the unknown city that became one of my favorite trips. Here's what I did...


This mystery kid is cooler than all of us.

Research Public Transportation

One of the first things I do when looking for a place to visit is find out what that city's public transportation is like. Even when you add cost of trains, buses, and the occasional Lyft ride, it's more cost effective than renting a car. 


Chicago has the CTA (Chicago Transit Authority), which includes the 40 minute train ride (the "L") to and from O'Hare International Airport and an efficient bus system. Visitors can purchase a multi-day pass at the airport for their time in the city. 


Research Things To Do

This may be obvious advice, but I was flying blind as I was realizing that they don't call it the Sears tower anymore. What I found was nothing short of a golden nugget of traveling. It's called the Go City Card, and it's available in multiple cities for various activities. I purchased a 3-activity card, which allowed me to select three activities at a discount from a wide selection.


It was well worth it for the Sears, I mean, the Willis Tower and the Art Institute of Chicago admissions, where we got to skip the lines and get our tickets to go through security right away. If you don't think that sounds like a big deal, you will when you see lines that extend down the block and around the corner. Nothing makes a traveler more smug than when they get to cut everyone in a long line! Get this card, and see stuff like this...



Picasso's "The Old Guitarist" just right there, unobstructed.

Research the Tips... and Follow Them!

Speaking of the Willis Tower, every single website says to visit early. And I thought, "Yea yea, everyone is gonna be there early, so how much difference is it really gonna make?" Turns out, it was the difference between walking right into the building and waiting, well, down the block and around the corner. We got there shortly after they opened on Sunday morning, and was out of there and onto brunch in an hour.



Note that time. I. was. not. playing.

Research the Food

I ate my share of Chicago-style hotdogs and deep dish pizza, but we also enjoyed incredible upscale Italian food and went to an Eastern European-fusion restaurant (can't get that at home). Quick tip - before you get back to your hotel or apartment rental, order your pizza to be delivered there, and skip the hour-long wait just to get a seat at Lou Malnati's.

FTW, short-rib pierogies and deep-dish-pizza-in-bed.


Leave Room for the Random Stuff.  

You can't research everything, and part of the fun of traveling is being spontaneous. I didn't know what our third Go Pass activity was going to be, and it wound up being my favorite part of my entire summer - an architecture river tour.


It was a close second to the Art Institute, and while I got to see the city from above, the view from below enabled me to absorb all of the fascinating history of every work of art in the form of a building, and it was amazing.



Breathtaking architecture has left me sarcasm-free


Other Things You Should Do

- See a professional sports game or a show.

- Bring a sweater in the summer. That Chicago wind is no joke.

- See Navy Pier, but I'm warning you, it's a tourist trap.

- Go to a rooftop event in the summer, but book it as soon as summer begins

- For free stuff to do: the beaches along Lake Michigan, Millenium Park, and the Chicago Cultural Center.

- Enjoy these last pics!



Twist Ending - This trip happened pre big haircut



All photos and content is original by Laura Bissessar.

Please do not use without my written consent. Or I will find you. Thank you!


I am not endorsed or affiliated with any of the companies on this post. Although if they would like to pay me, I wouldn't be opposed.


#travel #weekendtravel #Chicago #Chi-town #Searstower #Willistower #LakeMichigan #NavyPier #HancockTower #MilleniumPark #ChicagoCulturalCenter #TheLoop #theL #ConcreteBeach #architecture





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