West side meets South side

Updated: Sep 12, 2018

Girl's weekend in Chicago - all the must see's, must do's and how to incorporate "Shameless" innuendos in 48 hours.

As you prepare for a girls weekend, be sure you have someone who will make a to-do list of must-see's, doesn't care if they are one of two adults (you are the other one) petting sting rays and can celebrate each day with a charcuterrie platter.

Meet Jill or "J-Studd". Our friendship started circa de 2002 thanks to high school cheerleading. Our friendship was built on laughter and good jokes. And we decided to have a girl's weekend in the midwest.

Be familiar with your travel route

After two days in Indy and multiple visits to Patachou (, we headed to Chicago, or as we like to say "Chi." If you are familiar with the route from Indy to Chi, you know you will pass Gary, IN.

Gary, IN is a detoriated industrial town that has been hit with endless economic problems and high crime rates. When talking about Gary or this route, one may say "stay safe" or "there is nothing to see" which leads two chicks from New Haven county curious.

When you think of CT maybe Yale University or a bed and breakfast come to mind? As a CT native, we think of club raids, drug deals and violence. What does Gary, IN have on New Haven, CT? Really good geofilters.

Almost there

As hardcore Shameless fans, we really wanted to stop by the Gallagher house or even Sheila's. We fantasized about the pictures and envy we would get from friends. Our minds changed when a peer told us ubers do not go down there. So we made a commitment to experience things from the show, like the Alibi.

Night One

Our air b&b (around $130 a night) was located in Hyde Park. We were two blocks over from a Dunkin' Donuts and an inexpensive uber ride to happening Chi places.

We started with appetizers and drinks at The Promontory ( - happy hour special included jerk chicken wings and chickpea fries - awesome!

Drink recommendation - The Promontory dreamsicle


The night was young, it was literally 6 p.m., so we had to find out next adventure - a cigar shop ( The fashionable cigar selling lady gave us the 411 on the blends, flavors and proper way to smoke a cigar (don't inhale). I wanted to feel like Al Paccino, so I settled on mint chocolate chip and kahlua flavors.

After walking up and down the streets of Hyde Park, we spontaneously took an uber to a speakeasy karaoke bar where Jill enjoyed a drink called "throwing shade" and I channeled my inner Al for a cigar. Of course, we ended the night with champagne and a charcuterie platter. Could life get any better?

Riding the L after dark

We needed to commit to channeling "Shameless" so we hopped on the L for $2.50 and decided to get off at a stop that seemed popular among travelers. We found our Alibi, local dive bar, where people couldn't formulate sentences due to intoxication levels. I couldn't finish my glass of wine because it tasted like frog piss, but I took in the atmosphere and we were able to check it off our list. Oh ya, don't take the L after 8 p.m.

Our only full day

Every New Englander must start their day with coffee, specifically Dunkin'.

We headed to Shedd Aquarium ( where we were encouraged to buy our tickets online instead of waiting in line. Sounds great? No. The website kept going offline after we typed in our credit card information. Jill was charged twice. Detour to reimbursements. Must sees at Shedd: Sting Rays. We were in the area laughing and squealing as sting rays came near us and touched our hands. If you are like me, and don't follow directions, I may have accidentally poked a sting ray... So we left.

What tourists do - pose with the peace sign at the bean.

Lunch: Giordano's ( It was worth the 45 minute wait. You can also get a personal sized pizza too!

One of the many buildings during the tour.

Your Chicago trip will only count if you take the architecture tour on Navy Pier. The tour is about $50. The views and the history are worth every penny. I want to experience this again.

Navy Pier ( on a Saturday in the summer is poppin'. We grabbed Chicago hot dogs at a counter service restaurant ($10 dinner) and walked around inside and outside of the building. Navy Pier is filled with really cute shops. If you want to buy Chicago gear, hold out until you get to the pier!

I sadly didn't take a picture. Got this on google.

Oh yah the rainbow ice cream cone ( My life changed for the better since eating this. The night ended with the best fireworks show I have ever seen. Seriously, the best fireworks.

We headed back to Hyde Park. Ate charcuterie and went to bed.

I had a medium hot coffee with skim milk, French Vanilla and three equal from Dunkin'. Made to perfection, thanks Chi.


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