Drinks with Ghosts in Chicago

July 18, 2022

When looking for a hotel to stay in Chicago, I focused on location and decent price. That’s how I found the Congress Plaza Hotel which is located across from Grant Park for a lower price (about $174 a night) than most of the surrounding hotels. Unbeknownst to me, I didn’t realize why it was cheaper until after my fiancé, sister, and I were checked into our room and my sister told me. Apparently, the Congress Plaza Hotel is one of the most haunted hotels in the Midwest. There are several stories linked to past deaths that took place in the hotel including a woman who jumped off the 12th story with her two children and the theory that Al Capone tortured/killed people at the hotel. Fun. Naturally, my sister and I immediately took to wandering around. 

Congress Hotel lobby

The hotel is definitely creepy. If you believe in ghosts, you can tell with certain parts of the hotel that something is just off. In summary, I could not relax one bit in that place. The oddest thing was that the whole place feels like a maze with staircases that just end in dead ends or hallways that aren’t even in use. While we were on our way to the lobby, we found this third floor hallway that gave us the heebie jeebies. We weren’t brave enough to walk down it. 

Third floor hallway where several ghosts probably live…

While we didn’t have any firm ghost sightings, our first night there I did have a dream about a child asking me for help from “the gangsters”. So, that was fun. Needless to say, I struggled to fall asleep the rest of our time there. If you’re into staying at haunted hotels and walking down hallways that make your skin crawl, I would suggest a stay at the Congress. Otherwise, I will probably never stay there again despite the affordable price. But that’s me and I’m a weenie…

Pretty on the outside, ghostly on the inside

On a happier note, the bars were incredible in Chicago. What’s so great is how walkable the city is. The three of us arrived early Thursday morning and decided to spend the day at Navy Pier. It was a 45 minute walk to the Pier but the path was along the lake and very pretty. When we got to the Pier, we hopped on a Seadog extreme thrill ride. It was a pretty fun ride, sort of similar to a mild roller coaster. We sat at the front of the boat so we only got soaked once. It was an expensive ticket at $42 a person to ride but a once in a lifetime experience. I recommend it! After the ride, we walked around the Pier before heading back to the hotel to change for our friends’ arrivals. 

About a ten minute walk from the hotel, we grabbed dinner at Miller’s Pub. The Pub has a very British inspired ambiance and is a neat little spot to hang out. Their impossible burger was delicious! 10/10 recommend. We ended on a good note by calling it a night after Miller’s. 

Friday morning, my fiancé grabbed us Krispy Kreme donuts (not accessible to us in the Quad Cities) and we ate in the hotel lobby. While I’m a die hard Shipley's girl, Krispy Kreme was not bad. Shipley’s is better but Krispy Kreme can have second place. After we had eaten, we walked to the field museum (about a 20 minute walk). The museum was neat albeit a bit overwhelming. There was so much to see! Unfortunately, we only covered the third floor exhibits before we were hungry and ready to leave. But one exhibit was the dinosaur Sue, so a day well spent. 

My sister working on her modelling career.

By the time we finished at the museum, it was raining so we elected to uber to the restaurant. Lunch was a stop called Taco Maya. Their chips and salsa were delicious. I ordered their cheese enchiladas (my go-to). They were a little small but filling and yummy! 

Lunch put us all into a food coma so we returned to the hotel for a quick nap and reconvened that evening. Since we were meeting friends that night, we ubered to the Northside bars of Chicago. Our first stop, and probably my favorite, was Headquarters Beercade. This bar has arcade games including pinball and racing games, most of which were free. Drink prices are higher at $12 a cocktail, but it was a pretty cool spot and I recommend checking it out. 

Headquarters Beercade

We stayed at the arcade for only an hour because we got hungry again so we walked over to Brehon Pub where we met up with additional friends. The pub was a nice spot, their mac and cheese and mozzarella sticks were delicious! 

So the last time I visited Chicago in March of 2022, I was suggested by my future in-laws to check out Pinstripes. My friends and I enjoyed it so much, we went back the next day. Determined to eat there again, I booked a reservation for our group Saturday morning. Their food is DELICIOUS. I love eggs Benedict, and I hate to say it, but theirs is better than my mom’s homemade Benedict. Sorry, Ma! Pinstripes also has bottomless mimosas for $24 a person, which let’s be honest, you won’t beat that price in Chicago. While there is a time limit on the mimosas, each time we’ve gone we have had a wonderful server who didn’t enforce this limit. We all definitely put the bottomless drinks to good use. 

My fiancé (left) and friend, about three pitchers in at Pinstripes. 

After brunch, we visited the Medieval Torture Museum. I love the Medieval time period and history in general, so I personally thought this was a pretty neat museum if not a little creepy. There are interactives and wax statues for several torture devices, and although I’m a nerd and knew most of the information, I still found it informative. If you’re into that time period, I’d say go check it out! It’s definitely a unique museum. 

Following the museum, we napped at the hotel again. We are big on necessary naps. Since I was craving another impossible burger, we decided to check out the Burger Bar of Chicago. My friends all reported that their burgers were delicious, but as a vegetarian, I hated mine. They have the option to customize the burger, but the kitchen forgot half my items and left the paper backings of the cheese on! So when I first bit into my meal, I got a mouthful of paper. I was pretty irritated, and even more so when I saw that they up-charged my bill for each item that I ordered but didn’t even receive. This put me in a pretty foul mood for the evening that was luckily reconciled by the King of Cups bar. Again, Medieval nerd. 

The King of Cups was a neat place. It’s a pretty small bar but we were able to be seated by the window at a round table. The decorations of this place were enough to have me grinning from ear to ear because it felt like we stepped back in time. There were screens on the walls that rotated portraits of old kings and chandeliers hanging from the ceilings. What was even cooler was most of their cocktails get lit on fire before being served. It was awesome! Expensive at $16 a drink, and once in a lifetime place, but awesome! I was happy to end our night there. 

One of the images in rotation on the bar’s screens. I want this portrait but can’t find it anywhere! 

Unfortunately, Sunday I woke up feeling sick so the day was a blur. We grabbed brunch (I freaking love brunch) at Grant Park Bistro. I ordered their Land Benedict which was served with bearnaise sauce instead of hollandaise. Honestly, it wasn't my favorite but I’m a Benedict stickler. It has to be pretty close to my mother’s Benedict to impress me, hence Pinstripes. 

Following brunch, we went to Elephant and Castle, another British inspired pub. Their Irish coffees were incredible and I ordered their garlic roasted tomatoes with whipped feta. Y’all…so good. I’m going to need to learn how to make it because it was pretty simple yet I was obsessed! I swear, it brought me back to life. 

After our late lunch, we walked around Grant Park. The one thing about Chicago that kept taking my breath away was the architecture. The buildings are old and beautiful. I love old things and it felt so well preserved. On the walk to our hotel, we could spot huge lantern lights and archaic designs that I never grew tired of looking at. 

My sister, wearing a skirt I’m probably going to steal, and the Chicago skyline.

I’d love to have these outside my house, unfortunately they’re not on Amazon

Old buildings make me happy.

We had our last meal for the day back at Miller’s Pub. I really just wanted their burger again. It was delicious and I needed to redeem my Impossible burger taste buds from the overcharged paper burger the night before. Following dinner, we walked to a bar called Twenty 2 Twenty. It was a cute spot with darts and some arcade basketball games. My sister and fiancé enjoyed darts and, according to him, the cheapest beers in the city, while my friend and I walked back to the hotel and called it a night. 

By Monday morning, I woke up with a fever. We dropped my sister off at the airport and drove back to the Quad Cities. I slept the entire three hour ride. When we got home, I tested positive for Covid. 

Although my eyes did bulge a little when I saw the damage to our bank account due to my lack of self control to stop after just one $16 cocktail…

Worth it? Totally.