I love Chicago.
I love Chicago the way I love Nutella. I just really can’t get enough of it and I like it in so many ways that it would take posts on posts to explain it properly.
This past weekend was my fourth time going to Chicago. I went once with my best friend, another time to get my mind together after a breakup and a third time to go to the NFL Draft. This time I took my boyfriend on a little baecation for the weekend because I wanted him to have an awesome 30th birthday and also for him to see how incredible the windy city is.
Friday, March 31st – Arrival
On Friday we went to Billy Bishop Airport and took a Porter Airlines flight to Midway. Flying from Billy Bishop is so much better than Pearson because as a downtown dweller it means less time spent traveling to the airport and more time enjoying the free snacks and water bottles at the airport (picture below). I also love flying with Porter! The people who work for them are always so nice and you get to drink and have snacks on the airplane at no additional cost. Also, their complimentary shuttle from downtown to the airport comes in handy. After much beer, wine and chips – we landed at Midway.
The subway system in Chicago may be a bit dated, however, I would choose their system over Toronto’s ANY DAY. I love the 3-day unlimited rides pass for $20 and I also love that both of their airports are connected to the subway. No extra fees or needing to take a special subway or bus, you just hop on the subway lines and can make your way downtown so easily.
As we boarded the subway to our destination, we were accompanied by some gentlemen we had met on the Porter flight who were heading to Chicago for a wedding. We mentioned that it was my boyfriends birthday, at which time they handed him a bottle of Crown Royal to start drinking on the subway. I will neither confirm nor deny if this happened, as that may be considered lewd behaviour – to some. Not me.
We arrived to our hotel for the weekend, the Millennium Knickerbocker. This is an old school looking hotel in downtown Chicago. I loved everything about it. I booked the king room which was a nice size for the two of us and came with complimentary Wi-Fi and a very nice bathroom. In their lobby they even had a jazz band playing by the bar on the Friday evening which gave us the real feel of the history in the hotel.
After relaxing for a little while in our room it was time to take my boyfriend to eat the most important meal in Chicago – deep dish pizza. I love deep dish pizza. I LOVE IT MORE THAN THAT THIN CRUST THING THEY SERVE YOU IN NEW YORK. Yes, I said it. I prefer Chicago deep dish pizza to that thin stuff in New York. We went to the closest Giordano’s we could find via Google maps. Upon arriving there was a bit of a wait, however, you can pre-order your pizza which takes 45 minutes to make anyways so it was at least being worked on while we waited for a table.
I realize between Gino’s East, Lou Malnati’s and Giordano’s everyone has their own favourite pizzerias in Chicago and you can stick to whichever one you like best. For proximity and the massive screens they had both NBA and NHL on, Giordano’s was very good for us. This was the perfect meal to send us into a food coma and sleep to prepare for our busy Saturday.
Saturday, April 1st – Birthday
I thought I was going to sleep in on this weekend getaway, but as someone who has been waking up at 6am on weekends for the past three years – no chance. My boyfriend was still asleep and since it was officially his birthday I took a stroll to the hotels lobby to get some breakfast for us. Let me say this, holy shit breakfast at hotels is expensive. I know I should have just assumed that and maybe planned better, but I didn’t want to be gone long so I could surprise him as he woke up. I purchased the two breakfasts and made my way back up to the room and surprised him. The food was OK, not the worst breakfast I’ve ever had nor the best. At least the miniature jars of jam that it came with were really cute.
After lounging around for a little bit more, we started our walk to Navy Pier. The scenic route along Chicago’s Lake Shore Drive is always something to be delighted about, especially on a day where it was sunny and 15 degrees. My next birthday gift was a lunch boat cruise on the Spirit of Chicago. All I can say is WOW about the whole experience. The staff (shout out to our waitress Nicky) and the ambiance was incredible. The cruise came with a buffet lunch and a two hour ride on the water. I purchased some extras for our ride like the shrimp cocktail and also a window seat. Another thing we decided to purchase while on the boat was a 45-ounce rum punch drink. Yes, you read that right, 45 ounces. It didn’t even matter than we had a massive buffet lunch, once that rum punch hit we were both wavy.
There was a DJ on the boat playing some music and people did dance, we saw some get down real hard to the Cupid Shuffle. Many people aboard were either celebrating birthdays or anniversaries and ALSO drinking that 45-ounce rum punch – very jubilant crowd.
As we disembarked from the cruise we were also handed freshly baked cookies by the staff and I was able to take my 45-ounce glass with me home as a souvenir. Overjoyed, and birthday boy was having a great day.
The plan after the cruise was to go shopping, that definitely did not happen. Due to the large consumption of alcohol we fell asleep in our hotel room for almost four hours. Wasted the afternoon, literally. When we woke up and realized it was evening and that the NCAA Final Four games were on, we decided to just order some food and watch those.
Now it was time to party. I had read about there being a reggae lounge called The Wild Hare with live bands and a Twitter follower of mine had sent me a flyer for a hip hop club named The Evil Olive that also had a dancehall/afrobeats/soca room in the back. At the reggae lounge the cover was $10 and the crowd was definitely there for the vibes and food, not so much dancing. We stayed there for about 30-45 minutes taking in the wonderful singing on stage but we decided that we wanted to go dance and not just observe that evening. At this point we left for the hip hop club.
Cover for me was $10 but for my boyfriend it was $20, also, he had a light sweater that he had to put in ‘mandatory coat check’ – odd. I was a bouncer for five years and had never witnessed a mandatory coat check, especially of a light sweater. This place was booming. The front had a large dancefloor with an elevated area for the DJ and many strobe lights. I hoped to walk through and hear Faneto, that did not happen. We went to the tiny room in the back that was designated for dancehall instead.
This room was so small and the people were not even dancing. I loathe that there are so many people (men and women) who spend all this money to go out and look nice but do not dance and just spend the whole night Snapchatting themselves pretending to have fun. It was a strange thing to see as my boyfriend and I came there for the sole purpose of dancing. The DJ was OK, his choice of dancehall songs to mix was very odd. I would say he was maybe a notch above the dancehall selections top 40 clubs in Toronto play. Eventually some people began dancing (3am) but by 4am we were ready to leave and go to sleep.
Sunday, April 2nd – Departure
On our final day in Chicago, I took my boyfriend to my favourite brunch place there called Yolk. I had been there numerous times on my previous trips and their red velvet french toast stuffed with cream cheese was calling my name. The place was very busy and we were eventually seated. The french toast was delicious and so was the raspberry lemonade that felt like it was being served by the liter.
Following this large brunch we walked over to Millennium Park to do some touristy Chicago things. The Bean, the stage, the walkway to the Art Institute of Chicago and the front entrance of it. I wanted my boyfriend to see all the wonderful architecture that Chicago has to offer that is not inundated solely by glass structures of condos on condos on condos. (Sorry, Toronto)
Sadly it was time to return to Midway for our flight back to Toronto. I love that our hotel had a bag hold for no extra charge so we didn’t have to spend the day carrying our luggage around while sightseeing. After picking our bags up we hopped back on the Red Line and then the Orange Line to be on time for our 7:30 pm Porter flight.
Overall, this was an awesome weekend getaway for both of us. He got to celebrate his birthday being inebriated on a boat and I got to eat more pizza. Most importantly, this was another person I had converted to loving Chicago. To understanding that there is more to Chicago than just media headlines. I hope to be back in July for my 5th time, so I can attend the Taste of Chicago!