I’ve had my eyes set on Chicago for at least a year now, but it wasn’t until a few months ago when I finally got some friends on board to go explore the Windy City and thankfully Southwest was having a sale.
Friday morning Tricia drives down to Charlotte from Raleigh to meet me, so we can fly out of Charlotte-Douglas Airport later in the afternoon. Our flight takes off at 5pm and thanks to the time change, after 2 hours we touch down at Midway Airport at 6pm. We take a Lyft into the city to get to our hotel, the W Hotel-Lakeshore, and meet up with our friend Michelle who flew in from Washington, DC earlier. This hotel is stunning and in a perfect location right across the street from Navy Pier and in walking distance to almost everything we wanted to do for the weekend. I wouldn’t stay here again, but for the weekend it worked for us. From the lack of free wifi, overpriced room service and drinks, and slacking service, I would recommend finding a different hotel but in the same location. There are plenty to choose from! I originally wanted us to stay at the Sheraton close by, but we didn’t move quickly enough and it was all booked up by the time we were looking for a place to stay.
We drop off our bags, get changed out of our airport clothes and head over to Navy Pier to find some food. We end up stopping at The Billy Goat Tavern and enjoy some Hamborgers which are very thin patties on a kaiser roll but very delicious and enough to hold us over for the long night ahead of us. We head back to the room to get ready to go out. The nice thing about our hotel is that the lobby area turns into a very fun bar at night fully equipped with a DJ. Downside: The drinks are $15. Plus side: They’re very strong. But we only stay for one drink and set off to start our night. Tricia wants to close all of her rings on her Apple Watch so we walk a mile to get to the bar of choice for the night, Joy District. While we are wandering around downtown Chicago trying to find this bar, we run into two guys, Drew and Todd, who tag along with us since they are struggling to find the bars as well. Joy District turns out to be a super cool bar that plays all throwback rap songs with the music videos playing on all the TVs. It is like being back at all of our cheesy middle school dances and we are loving every second of it! When we were getting our IDs checked we were asked if we wanted to go to the bar or club. The bar was obviously our answer but we start to notice more and more people walking upstairs to the club area so we decide to figure out how to get up there. The club is free for girls and $20 for guys. Drew and Todd pay to get in and we head up to the super crowded but very fun club. We make our way to the dance floor/DJ area to enjoy the night but there are people everywhere so we barely have room to move. Remember from the Wilmington trip how I said my friends love to spend money? Well Tricia goes up to the bouncer to find out how to buy bottle service so we can get away from everyone and have our own VIP space to enjoy. They take us over to a huge couch and table area followed by a bottle of Grey Goose being brought our direction and lots of sparklers. Once we get our first drinks poured, one of the bottle service girls comes back and starts apologizing to us explain that they already reserved this area for a different party, but they can move us to a different couch area and throw in a free bottle of champagne, if we don’t mind. Free champagne? Of course we don’t mind! They move us back down to the dance floor but this time we have our own roped off area equipped with our own bouncer and a new couch to dance on. We are having the time of our lives until they turn all of the lights on around 1:30am and we have to make our way downstairs. We get outside and get offered a ride in a limo with random people we met while trying to order an uber back to our hotel. We almost take them up on the offer until we look near us and see a guy sitting on the side of the building throwing up. The bouncers are trying to call the cops on him so Tricia jumps into nurse mode and tries to take care of him instead and puts him in and uber that she and Drew also get into and take off. I have no idea what our justification for letting Tricia leave with two strangers and putting all of our trust into Drew was, but we did, and Michelle, Todd and I start walking back towards the hotel. We didn’t get far before we were stopped by a homeless man who was telling us about his wife who had died and his daughters he hadn’t seen in a long time. We end up standing on the side of the road in the middle of downtown Chicago and say a prayer for this man and his family. He seems very kind so I take him into a seven eleven to buy him groceries. While we were checking out he ended up just wanting money, which we didn’t give him, so we called our Uber and headed for the hotel and Tricia. Somehow we all make it safely to the hotel and we set our alarms so we can get a quick nap in before we have to get up in the morning.
7am comes too early for us to get up and get ready but it’s game day! Michelle feels the best out of all of us so she gets us coffee while we get ready to head to Wrigleyville. Originally we were thinking about taking the L to get to the game but we go down to the lobby and start talking to one of the bellmen to get directions and after a lot of confusion on our end he tells us that Uber will be quicker and easier so we don’t argue with him. We hop in our Uber and head to the stadium area. After we do some shopping we start wandering around to find a good bar to stop at. We hear a man yelling about $3 Jell-O shots, so we decide that it sounds like a good place to explore. We have ended up in the Dugout Sports Bar and Grill and enjoy $2 tall boys while we wait for my friends Erica and Eric to get to the area. Once they get near the stadium, we take off to meet them at the next bar, The Cubby Bear. The Cubby Bear is a must go to bar and is directly across from the stadium. Drew and Todd meet back up with us here, but we don’t have long to enjoy the bar before it’s time to go into the game.
One thing you must do in Chicago is try a hot dog. I can’t explain what it is about the hot dogs here, but they are so much better than any other hot dog I’ve ever had! We all get a hot dog and beer and head up to our seats to enjoy the game. This is the first MLB game I have ever been to and Wrigley blew me away! It was definitely an experience of a lifetime! The stadium is huge, and the energy is incredible, especially in the final inning of the game. Unfortunately, the Cubs end up losing this game to the Cardinals but won the series overall and it was still a great time. After the game, we are exhausted. We go our separate ways from Eric and Erica and head back to our hotel to finally get some sleep.
On our way back to the hotel we were fully expecting to take naps, wake up, and be ready to take on another Chicago night. That is not at all what happened. We woke up totally hungover and starving, but we didn’t want to go anywhere so thank goodness for room service. $100 later we each have a meal brought up to the room. I am not lucky enough to get to enjoy my plate of spaghetti because my head is stuck in the toilet all night, but Michelle and Tricia enjoy their meals. Needless to say, we do not make it out like we had originally planned.
Sunday morning, we wake up bright and early, and thankfully not hungover because we have a full day ahead of us. We head out of our hotel to make our 10am Architecture River Cruise. This cruise is, in my opinion, the best way to see the city. We get to see all different areas of Chicago while learning all about the history of the city, and there is a lot! It seems like every building has its own unique story. Also, the views are incredible! Everywhere we look we are surrounded by more and more cool buildings. Once the tour is over, we head back to our hotel room to pack up our things and check out. Thankfully the hotel lets us leave our bags downstairs because we have late flights and more of the city to explore. We head about a mile down the road to go to lunch at The Hampton Social. This restaurant is totally Instagram worthy. The nautical decorations are so intricate, and you can tell that a lot of thought went into this place. There is also live music to make for an even better dining experience. On top of that, the food is to die for!
After lunch, we walk another mile to get to the Willis Tower, formerly known as the Sears Tower. On our walk we end up passing the Flamingo statue which is located outside of the post office building. We obviously stop to take pictures and then continue on to Willis Tower. Once we get inside we wait in line for probably about 30 minutes before we get on to the elevator that takes us to the Skydeck at the top. I should preface this with telling you that Michelle is terrified of heights, so she is freaking out the entire time. When we get to the top, the views are breathtaking! It is an overcast day, so you can’t see as far as normally but you can still see for miles and it is amazing. We get in line for one of the four glass boxes that jets out from the building, so you can experience views of Chicago all around you. This absolutely terrifies Michelle. She is basically having a mental breakdown while we are waiting in line. When it becomes our turn, Tricia and I have to hold her hands as she walks out on to the ledge. Don’t let the pictures fool you because there were many tears shed as we made our way back out of the glass box, but she did it! We get in line to take the elevator back downstairs to head to our next stop, The Bean.
We walk a little over another mile and find the Crown Fountain in Millennium Park. These are interactive fountains and if you’re lucky enough like we were, you will see someone get sprayed with the water that comes out of the mouth. Up the stairs a little ways past the fountains, we turn the corner and there it is- The Cloud Gate. The Bean is a pretty awesome sight to take in but it’s also hard to do because there are people everywhere. We take our obligatory pictures and then head back down to the fountains to get away from the mass amounts of people and to finally sit down to rest our feet. We look up how far Lincoln Park Zoo is, as our potential next stop, but it’s a few miles away and we are tired of walking around so instead we decide to Uber back to Navy Pier for some famous deep dish pizza. Thank goodness we get to Giordano’s with plenty of time to spare because it is a 45-minute wait to be seated. They have the option to order your pizza ahead of time with cash. We decided not to do this but should’ve because it takes about 30 minutes for them to make the deep dish pizza, which we didn’t realize at the time. Once we get seated we each order our own meals and a pizza to split. Our meals were decent, but the pizza was to die for! I have gotten mixed reviews leading up to this trip, but I am absolutely in love with deep dish pizza.
Once we settle into our food comas and finish up at Giordano’s, we head back to the hotel to get our bags and say our final goodbyes ☹ Tricia and I get in our Uber to Midway, and Michelle heads to O’Hare. Thanks to the time change we touch back down in Charlotte around 12:30am and have to face reality of going back to work in a few hours. The trip was completely worth the exhaustion.
Chicago, we fell in love with you.