The Windy City. Chi-Town. Chicago. 



My mom was sent to Chicago for a training so when she told me she was going, I said I’d tag along. We had never been to Chicago before and we had never done a mother/daughter trip so this was something we were pretty excited about. Below you’ll see some pictures from the trip, an itinerary of what we did and you’ll find a few helpful tips for your next trip to the Windy City.

Day One

After a 2.5 hour flight, a 1-hour drive from the airport and finally checking-in to the hotel, it was safe to say we were starving. The Hampton Inn at E. Wacker & Michigan gave us a free appetizer coupon to a nearby restaurant and we headed straight there.

Emerald Loop Bar & Grill

This Irish Pub is located in the heart of Downtown Chicago in the old “Jewelers Building.” A cozy little spot that seemed to be as local as it got in the heart of the city. It didn’t take us long to agree on that free appetizer. No questions asked, we ordered the muscles. These were probably the 2nd best muscles I’ve had. If you’re curious, my 1st choice are the muscles at Vino Vino in Austin. For lunch we ordered sandwiches and of course, homemade kettle chips.

Architecture River Cruises

After lunch we walked down to the river walk to catch an architecture cruise. Before leaving to Chicago I purchased Chicago explorer passes for $75 each that included admission to 3 attractions, tours or activities. There are multiple architecture cruises but not all take the explorer pass. Remember that Shoreline Sightseeing will accept your pass. Important note: the cruises that depart from Michigan Ave have a bar on the lower level.



We ended our first night with a quick Walgreens run for chocolate and wine and watched Law & Order the rest of the night.

Day Two

Now it’s day two. First on the itinerary was breakfast of course.  We indulged in eggs benedict and crepes at Wildberry Pancakes & Cafe. If you enjoy a good brunch like me, this is your place. Fair warning: there is typically a wait but very much worth it. We put our names down and crossed the street to Millennium Park. Yep – Millennium park is just across the street. We took advantage of the hour wait to knock out our pictures at Cloud Gate a.k.a The Bean. After checking it out, wen found a cozy bench in the shade and waited for our table. The restaurant sends you text and gives you 5 minutes to claim your table. Take advantage of the beautiful park across the street if you have to put your name down for more than 45 minutes. IMG_6691IMG_6700

The Art Institute of Chicago


After our breakfast, we walked about half a mile to the famous art museum Ferris Bueller visits on his Day Off. This museum is large so prioritize the exhibits you want to see before you go. So where is the famous painting from movie? Cameron is seen standing in front of George Seurat’s painting, A Sunday Afternoon on the Island of La Grande Jatte. You can find this painting on the 2nd level of the museum in the Impressionism section. My favorite part of the museum was the photography exhibit located on the lower level. You’ll notice that the pictures in the introductory slideshow are in black & white. I was inspired to do this after seeing the numerous beautiful black & white photographs in the museum. If you’re a photography junkie and love admiring other people’s work, this exhibit is the place to visit.

Skydeck at Willis Tower



From the Art Institute we took a cab to the Sears Tower, now known as the Willis Tower to get to the famous Skydeck. On a weekend afternoon, plan to spend at least an hour and a half waiting to get up the elevator, through security and up another elevator just to get to the top floor. Once you are up here, keep in mind that to get the famous photo in the glass box, you’ll need to wait in yet ANOTHER line. By the time we made it up to the very top, my mom and I were sooo over waiting in lines that we just walked along the glass windows and enjoyed the view from there. So once we finally got our fix of the Chicago skyline, we turned the corner to take the elevator back down and guess what? Yep – another line. Long story short, if you are dedicated to your Instagram feed and you think the lines are worth your time, this is definitely a place you want to visit. Especially if you are willing to wait in the last line for the ledge photos.

Helpful tip: Purchasing the Chicago City Pass gets you through all of the lines much faster except the line for photos on the ledge.

IMG_7671When we finally made it back outside, we took a cab over to the Navy Pier. As soon as we got there, we got stuck in short rain storm but were lucky enough to find a spot at the bar to have a beer while the rain passed. Once it did, we walked to Beer Garden for some live music. If you’re from Austin like me and expect to see a live band at every other restaurant, this is the place to go to get your live music fix.

We ended our night at Portillo’s Hot Dogs (YUM). We waited out another short rain and then headed back to the hotel.


Day Three

We had breakfast at the hotel that morning and sipped on some coffee before a relative of a relative picked us up for some more sight seeing. They took us to what is known as La Villita or Little Village for some delicious tacos al pastor and an ice cold michelada (with Negra Modelo of course).



We drove around the village that reminded me so much of a small pueblitos you see in Mexico. We then drove through China town and finally ended our time with them along Lake Shore Dr. where the city meets Lake Michigan.

We had plans to have pizza for dinner at Giordano’s but we were so stuffed from the tacos that we just couldn’t make our way there. We ended up at the hotel bar for some cocktails and planned to have the famous pizza for lunch the next day before I headed home.

Day Four 

My last day in Chicago and I’ll have to say that I think I went out with a bang. We woke up early, had our coffee and walked over to the Giordano’s on Michigan Ave & Randolph. We got there before they opened so we would have plenty of time to indulge in our pizza before having to catch my flight. 5 minutes before they opened, a sea of people lined up behind us at the door. Once the doors opened, we snuck through the crowd and made our way to the bar. The bartender was kind enough to ring our order in right at 11 a.m. While we waited for our pizza, we sipped on mimosas and watched the line at the host stand get longer and longer. Before we knew it, our pizza was out in front of us. I now understand the use of the word “pie” when people refer to pizzas. This deliciously stuffed pie (sausage, pepperoni and bell peppers) could only be handled with knife and fork.



Helpful tip: If you ever visit Chicago or if you have before but have never been to Giordano’s, be sure you arrive about 15 minutes before they open (especially on the weekend) and try to skip the wait line by heading to the bar. These deep dish pizzas take an average of 45 minutes so be ready to wait. When it comes to all the lines and waits we had to experience on this trip, the 45 minute pizza was definitely worth the wait.

So I finally made it back home on a Sunday evening and I’m back on the office grind. My next trip before the year is over is TBD but I can’t wait to tell you all about my trip to Guatemala in January of next year!

If you’ve been to Chicago, comment below and tell me what your favorite things to do are! If you haven’t been to Chicago, what are your favorite travel destinations?


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