Chicago, my favourite city in the world.
If only it were possible to move there tomorrow, I’d be straight to the nearest Jeep dealer, eyeing up my Lincoln Park apartment and securing my Cubs season ticket. It’s leafy and chilled, where old meets new, there are rooftop bars, volleyball on the beach and comedy shows, but you’re never too far away from some jogging, pram pushing mommies chatting about how they’re so glad they moved here from New York over their tall, soya, iced lattes.
I headed to Chicago last September, very spontaneously after a couple of crazy days at Oktoberfest in Munich, where I was lucky enough to be able to stay with a friend who lives there. I flew American Airlines who are by far my favourite airline, but maybe that’s just because they gave my severely hungover self 3 seats to myself to spread out on. With a 5-hour stop over in Philadelphia first, I arrived in Chicago just before midnight ready to try and figure out the subway (it’s 24-7, take note LDN!) and find my friend’s apartment.
My first day, the weather was super hot so i put my list of things of what I wanted to do and how to get there away and decided to just walk and see where it took me. I was staying in Lincoln Park so I headed towards the park and had a wander around Lincoln Park conservatory and zoo. The bridge in Lincoln Park provided me with my first awesome view of the city. I wandered over the N Lake shore drive bridge and along North Avenue Beach.
On recommendation I made the short walk over to Elaine’s Coffee Call for an iced americano and grilled cheese. This was a really nice chilled spot to just grab a quick lunch before moving on for a wander through Old Town. I was happily surprised to just wander across The Second City. Bill Murray is literally my favourite person in the world and having watched a lot of the early SNL stuff, seeing the place where some of my heroes first started out was pretty cool. This is also where actors and comedians like Tina Fey, Amy Poehler and Steve Carell launched their careers. The theatre is also pretty beautiful.
The next stop was the amazing city views from The Signature Room on the 95th floor of the John Hancock tower. I loved this because it wasn’t busy at all, I was able to just buy my ticket and head straight up with no queuing. Theres a great bar and phone charging facilities up there too so you’re able to spend a lot of time without the worry of running out of battery for photos!
I spent the rest of the afternoon wandering down Magnificent Mile and Michigan Avenue and shopping before grabbing dinner and cheesecake at the very original Cheesecake Factory.
My second day was by far the best day of my trip. I had been waiting for this moment for a very very long time and could not be more excited. I woke up early, excited, so headed out to the Starbucks at the end of the road for breakfast. I was soon on first name terms with the Barista thanks to my British accent (love this city so much). Then we headed to WRIGLEY FIELD FOR MY FIRST EVER CUBS GAME! The atmosphere was insane and unlike any other sports event i’ve ever been too. The fact that all the fans sit together peacefully, no matter who they support, was definitely nothing like i’ve seen in the UK and I loved it. We grabbed some Bud Lights and some nachos and headed to our seats just in time for the second inning against the Cardinals. At this point I wasn’t completely in tune with the rules or what the hell was going on so I had to keep up with the emotions of other Cubs fans to find out when to cheer etc. A few more beers and a hot dog later and I was singing ‘take me out to the ball game’ at the top of my lungs (I had to learn the hard way that in Chicago it is criminal to put ketchup on your hot dog) . The Cubs won the game and once again I was singing, ‘go cubs go’ like i’d been doing it my whole life.
After the game we headed over the road to Sluggers Sports Bar for drinks and the batting cages. We soon made friends, the British accent helping again, and I ended up being pushed straight to the front of the queue. My first attempt at hitting softballs did not go well. But I was made to try again against my will by an ever growing crowd of Americans and that’s when my competitive side came out. I downed a fireball and to their shock chose to hit baseballs and this time smashed them all! I ended up with free shots for the rest of the night and we moved around the Wrigley bars, clubs and pizza places with our new Texan friends before grabbing some Mexican takeout and passing out on the sofa. Best. Day. Ever.
After a very long lay-in we ventured to this amazing bagel place for brunch called the Chicago Bagel Authority. Definitely be prepared when you get there, the Bagel choices are endless and I needed a recommendation. There’s a really cute courtyard, it was absolutely delicious and helped to curing that jelly shot hangover. I had a lot of sightseeing planned in for today and so I headed straight down to Millennium Park to check out ‘the Bean’. There was a big food and drink festival going on on this day so the park was super busy.
I decided to escape the craziness and head over to the Art Institute of Chicago where I bought a ticket for the galleries as well as for the Willis Tower later that day. It worked out cheaper to do it like this. I took in the sights including the Buckingham Fountain and then walked back along the harbour and Chicago Riverwalk.
That evening I chose to head to the Willis Tower for sunset at the SkyDeck on the 103rd floor. I was so happy I decided to get here early because unlike the Hancock Tower, I had to queue for hours. Luckily I got to the top just in time for sunset. The views up here are insane and you can see for miles and miles on a clear day. I definitely recommend going here but do some research for the best times so you don’t have to queue for as long and it isn’t so difficult to get the photos you want when you get to the top.
My last full day in Chicago was spent at Navy Pier and much to my happiness an evening Cubs game! Navy Pier was pretty cool and I had great weather to walk to the end of it. There are plenty of restaurants and bars and pop up art installations so there’s always something cool to stumble across.
That evening the Cubs beat the Cardinals once again and in even better seats and actually understanding the game the end of my trip was coming to a brilliant close. I just wish I could have ketchup on my hot dog without having to explain i’m British.
On my last day before heading home I fit in a trip to the Shedd Aquarium (this place has everything) and a walk over to Soldier Field, the home of the Bears. I spent the afternoon with a long walk back to Millennium Park for some pics of ‘the Bean’ on a quieter day, some shopping and then Tapas at Café Ba-Ba-Reeba (omg so delicious) back in Lincoln Park before heading to the airport. This evening was also the evening of the Presidential Debate so I capped off my trip with some real American airport lounge atmosphere!