There are a few cities that I keep in my travel roster and Chicago is definitely one of them. It’s a place that stays relevant with its architecture, food, museums, and sports teams. While it does remind me of New York in many ways, it has it’s own charm that makes it a destination you can visit year round.
I’ve had the opportunity of doing some travel for work as of late and I’m one of those people that usually likes to tack on some pleasure with business and find ways to extend a trip if I can. I found myself in Lafayette, Indiana and when I realized Chicago was a short 2 hour drive I felt I had to celebrate my birthday in the windy city. DISCLAIMER: the drive was NOT 2 hours and for a person who does love driving, big city traffic is enough to make anyone mad. Tack on navigating an O’Hare Airport pick up may be so frustrating to end a relationship or just leave the person there all together - luckily my friend is one of the most patient souls and waited for a very delayed pick up. Uber or the L train is the way to go.
Having been to Chicago once before and it being the first time for my friend, we checked out a few staples but managed to get in lots of new spots.
Where we Stayed
We opted for an Air BnB in Uptown, home to the famous jazz club ‘The Green Mile’ where you’ll find the drinks to be strong and the jazz to continue to 4am. The Air BnB was in an iconic building that had a coffee shop and bar in the lobby, a gym with a full boxing ring and a roof top lounge. With the city filled with so many pocket neighborhoods I was excited to see what Uptown could offer, and we were only about 25 minutes from city center.
Where we ate
Avec: Where birthday celebrations started. A spot I found doing some blog research and it didn’t disappoint - the place was packed on a Thursday (always a good first sign) and boasted everyone from the suits to young families and a bachelor party. Our waiter was quick to offer suggestions and the highlights were definitely the chorizo medjool stuffed dates.
The Girl and the Goat: As soon as I found out I’d be in Chicago I tried to get a reservation here without any luck - this place has been on my radar since my last Chicago trip 3 years agao. It has earned a reputation with the chef, Stephanie Izard, earning the title of Top Chef in 2008. Found on the infamous Randolph Street, home to every cuisine to man kind, we lucked out and got a seat at the bar and had a great time. The ambiance was incredible: dim lighting and big windows with a huge open kitchen, the drinks were strong and delicious and the food didn’t disappoint: we loved the empanadas and kohlrabi salad. There was also a wedding proposal in our presence so love was really in the air.
Lula Cafe: Cutest brunch spot found in Logan Square - it’s not new and had a local feel as you walked in, even better you weren’t greeted with a block long wait for a table (I hate being hangry anytime but especially at brunch). With the menu constantly changing depending on the season, it will keep you coming back to see what new items has been cooked up. I opted for the Tofu Veg Scramble and it was perfect fuel for exploring the murals and boutique shops in the area.
Other notable mentions:
Lou Malnatis for deep dish (not my favourite but you know, when in Chicago) - plan for a 30 minute line up.
The Hampton Social for eggs benny and an instgram moment.
The Publican for brunch, not to be confused with the Publican Market across the street.
What we saw
The Chicago White Sox: Naturally, my usual MO is going to a sporting event whenever in a new city - I was disappointed to not visit the infamous Wrigley Field but had a great time watching the White Sox dominate the Cubs, even Kanye and Saint showed up! I’ll meet the Green Monster one day…
Architectural Boat Tour: This was my second time doing this tour and I’d do it a third time. It was a beautiful day (opposite to my December sailing last time) and the guides truly make it so engaging - you always leave learning something new about the city. The attention to detail on these builidings is incredible; the marble from the finishing on the old post office mirrors the new build across the river which captures the reflection perfectly complimented with the colour of the water and sky (or something like that). You won’t regret it!
Second CIty: Home to where oh so many SNL stars made their big break, it’s definitely worth checking out. It’s the perfect size to feel like you’re part of the show but can sit far enough back that you won’t get picked on (for some reason - always a fear at improv!). They offer early bird and late night shows to appease all people; we ended up at an 11pm show that I actually stayed awake for which is a feat in itself and clearly entertaining.
Chicago Murals: Can be found all over the city and we ended up on an impromptu walking tour of some famous ones in the Logan Square area. It’s evident the city takes so much pride in its art - just another element of character to the city.
Union Station: What can I say - I come from an era of Gossip Girl and I’ve got a thing for airports and train stations; perhaps just always keen for an adventure. Union Station is beautiful, found in the heart of downtown with all the pillars, windows and vaulted ceilings. Take a stroll through… XOXO GG
What to leave with
Garrett’s Popcorn: Didn’t know about this til a co-worker told me about it. Garrett’s is the OG Chicago mix. And if you’re lucky to find someone in your life that likes the sweet as much as you like the salty then you’re set - the caramel and cheddar mix. This place has numerous locations and usually always a line up. Plane friendly - grab some at the airport and make someone’s day.
To sum up, Chicago will keep me coming back for a 3rd and 4th time. It’s a great spot to go and for a weekend whether it’s a birthday, stag or mid November. Keep in mind, it is WINDY - that’s not just a saying. If you and your friend get really frustrated with your long hair blowing madly in the wind every time you step outside and decide on an impromptu haircut at Floyd’s “we sometimes do girls’ hair” Barber Shop - take a walk around the block and think it through again. It’s ok - it evened out.
Where’s your repeat travel spot?