Road Trip to Chicago

This trip happened almost completely on a whim. My friends mentioned they had a few days off for the 4th of July and wanted to get TF out of town. Of course, I was game!! We planned to go to Panama City Beach, FL first, but our Airbnb reservation fell through. So we switched gears. We had been talking about Chicago for awhile because tickets got down to $39 round trip in March, but we were all too busy to take advantage at the time. Chicago is a 7-8 hour drive from Nashville, so we decided to take a good ole road trip!

We left on a Wednesday after my friends got off work. I was happy to be in my favorite seat in the car; the back seat. I spread out and got comfortable and was sleep before we hit I-65N. I woke up a few hours later, still stuck in bumper to bumper traffic. I had no idea where we were but I didn’t care cause: VACATION! We arrived in Indianapolis around 11pm and stopped to get some food before heading to a friends house where we stayed the night.

The next morning we got up and got dressed for the beach. We couldn’t check into our airbnb until 3pm, so we just decided to get an early start. We were in Chicago by 12 and on the beach by 1pm. The water was cold, the sun was hot and the weather was great! We spent a few hours lounging on the beach before we went to Harold’s Chicken.

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I eat a mostly vegetarian diet now, but I occasionally eat fish. The fish was cool or whatever, but I coveted my friends order of wings. The food struggle is real! We headed back to the airbnb to eat and make a grocery list. Then we went back out to grab some food to eat on at the house. Tip: This is a huge money saver. We didn’t eat out as much because we had food and drinks at the house. Plus in the mornings we didn’t have to rush out of the house to get food, because we had fruit and snacks to hold us over. 

Our plan for the next morning was to have brunch at The Bongo Room in Wicker Park, then check out the Chicago Architectural River Cruise. But we walked outside to find a ticket on our rental car. The tags expired June 30, 2016 and the date was July 1, 2016. Before I even get started on how much of a fail it is for Payless Car Rental to give us a car with expiring tags, I have to commend the City of Chicago for not missing a fucking beat. I could never live here cause I’m the queen of riding dirty on expired tags. lol So now we have to make our way towards Midway airport in traffic to trade out our car.  😐 When we got there we continue to have a bad experience dealing with Payless, like it was somehow our fault we got a car with expired tags. But now I know to check in the future!


At this point our entire plan for the day is shot, but we were determined to make the most of it. So we decided to head to Navy Pier to eat at Giordano’s; which made everything okay again! lol After eating we walked to Michigan Ave to shop for a jacket because the temperature was steadily dropping. We bundled up then took an Uber to Sears Tower to watch the sunset from the Skydeck which I absolutely recommend!

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Saturday we started at Millennium Park. We saw The Bean and walked through Grant Park and a few other places. Honestly we got lost for awhile and just wandered around the city. We grabbed a late lunch at Riva Crabhouse, which was delicious! After we ate we rented some bikes and rode along the shore for awhile. We found ourselves back at Grant park where there was a live orchestra giving a free concert.

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Since we were so determined to take the architectural cruise, we got tickets the night before for the 12pm tour. So we get to the place to find out that the boat is having mechanical issues and has been canceled. But the captain worked something out with a competitor that allowed us to jump on the tour they had leaving at 12:30. This is how you accommodate your customers, Payless Car Rental. Even if it means taking an L. Bravo Chicago Architectural River Cruise!!


We met a cool couple when we got in the new line. Honestly, this is my favorite part of traveling: finding your people. Surprisingly, “your people” don’t always look like you; they may be older or younger and definitely have a different background, but that’s what makes it so interesting. Mark and Sandy are from Maine. Mark is a truck driver who was involved in an accident and helped by a reliable California truck accident lawyer. Consequently, he and his wife now travel extensively. Moreover, when facing legal hurdles, you can rely on a Sacramento, CA personal injury lawyer for guidance with integrity and expertise. People who got injured in vehicular accidents in Mesquite, TX may call a personal injury attorney from Fielding Law. In addition, you may also contact Bakersfield, CA personal injury lawyers for guidance that can help you throughout the process.

They were stopping in Chicago on their way to Massachusetts, then home and yes, they’ve been to Nashville!  😉 We got separated when we were boarding due to some ticket confusion, but when we got on the boat, we found our friends saving the seats we had our eyes on. They were so clutch! lol We spent the rest of the tour drinking, cutting up and laughing at the parents trying to subdue their children. Observation: Children 12 and under don’t GAF about an architectural cruise! 

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At the end of the weekend we were all happy when we realized we had a great time without spending too much money. I listed some of the expenses from the trip below.
Airbnb: $500 for 2 bedrooms/3 nights
Car: $166 for 5 days
Skydeck: $22
Chicago Architectural Cruise: $42.60 – 90 mins
Bike Rental: $9.95
Groceries: $50

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