North America, States, Travel

Chicago, Illinois

May 2017

Chicago was lit. Aside from what the city had to offer, it was just an overall amazing trip. I somehow had three guy friends, my cousin and a co-worker come together and explore what Chi-town had to offer. Five of us met up at Miami International Airport, and right there was the first time my cousin met my three guy friends. So far, so good. Mostly because we made it through security and onto the plane in MIA. For the record, I hate MIA, every flight I have missed out of Florida, has been because of that airport. But we made it on board and were set to go.


Once we landed in Chicago, we took the train straight from the airport to the hotel. This trip, we stayed at La Quinta Inn & Suites Chicago Downtown, off south Franklin Street. This was definitely one of my pricier hotels I’ve stayed at while on a group trip, but it was centrally located and basically within walking distance to everything. Disclaimer: it was still cold and windy, so we did end up ubering more than one would normally uber.


After check-in, we set off to get food. One of the guys cousins had recommended to us: Au Cheval on 800 West Randolph, saying their burgers were the best he’d had and he was a chef. So we took his word, and headed over, to find an hour+ wait. We put our names on the list, then decided to go diagonally across the street to, Haymarket Pub & Brewary. What can I say, we were starving. At Haymarket we just ordered some flights, to try some local craft beers along with a few appetizers to share among the table. Perfect timing, because right when we were done at Haymarket our table at Au Cheval was ready. At Au Cheval we all got the same thing basically, which was a burger. Some of the guys opted to go big and got the double, and others just got the single. But we had fries and mashed potatoes, and some drinks. Like I said, we were hungry. All the food at both places were reallllly good, I highly recommend them both.

After food, we just started checking out some places by walking around, and made a quick stop at Macy’s, then headed back to the hotel until my co-worker arrived. If you have time, go to that Macy’s! It’s HUGE! Like 8 full floors, huge.

That night was Cinco de Mayo, one of my favorite holidays, but we ended up just staying in for the night and ordering like 30 tacos off ubereats. Honestly, they weren’t horrible, until we spilled the complimentary horchata on one of the beds. At least we semi-got to celebrate.


The next morning all six of us got up and ready to officially start our day, with one of my sorority sisters meeting us at the hotel for the day. We made our way to Willis Tower – SkyDeck and then grabbed some pizza at Giordano’s. After lunch, Alder Planetarium was up on the list, followed by Shedd Aquarium. Of course, between each destination, we stopped for pictures and whenever we could, food. Following these stops, we continued through town on the Big Bus Tour. On that ride, we saw infamous buildings like NBC and Trump. The big bus tour was included in our Go City Pass, along with all the other stops on our trip. Honestly, the Go City Pass was awesome! I loved the experience so much, I’ve since used it in other cities I’ve visited. It was great to know that you have options, and don’t have to pay out of pocket more than the ticket amount, to see a cities top attractions.

We then said good bye to my sister and headed to see The Bean! While we were seeing the bean, the sunset approached, so we got to get pre-sunset and post-sunset pictures there. Our last stop site seeing of the day was, Tilt.

360 Chicago View

That night for dinner, we tried to have ramen at High Five Ramen, but the restaurant only had like 10 seats total. Two of us stayed there, and the rest of us went upstairs for some BBQ at Green Street Meats. Green Street did not disappoint, but if you want to pick from the full menu, make sure to get there earlier, as the menu items go away once the days batch finish.


The next morning, and our last, we just had Starbucks for breakfast after checking our bags in with the hotel concierge. Since Starbucks was across the street from the hotel, we walked there, then ubered to Navy Pier.


Last on our Sunday list was, Wrigley Field. Unfortunately, our trip didn’t give us enough time to watch an actual game, but we still had fun and explored everything surrounding the field. We stopped by the store, saw the fire station, and the entrance where the players were walking into. Yes, we even got to see them walking in, then we ended up at Cubby Bear for lunch and drinks. From there we only had enough time to get our bags from the hotel, and make it to the airport. My coworker had a flight that was 30 minutes before ours, and she almost missed it. The TSA lines were extreme, so maybe plan accordingly if you’re heading back home through O’Hare International Airport.


Another eventful weekend, in a new city. Thank you, Chicago!

<3 idkjac 

Interested in planning a trip but don’t know where to start or just don’t have the time? Contact me – I can plan all the details for you at no cost to you! Jacklyn Adventures – Independant Travel Agency

My Cousin – Main Photographer

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