A Weekend in the Windy City

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?

xx

LC

My Solo, Impromptu trip to Chicago

As a habitual planner I am always trying to work on my spontaneity in life: reservations don't always have to be made, days don't need to be planned out to the last detail and if things don't work out you don't have to take responsibility for the failed plans' shortcomings. Life should be lived more on the no-plan plan which is something I'm constantly working on. I have had some glimpses of spontaneity over the past few years, but probably the one I get the most reaction from is the trip I booked to Chicago on 6 hours notice... BY MYSELF! 

I'd recently been on the job hunt and was looking to change my career. The whole process was emotionally draining and I still wasn't particularly sure I was on the right career path, but despite my uncertainties I had found a job and signed the offer to start on Monday. Before I entered into this new phase of my life I felt like I needed to both de-stress and have a change of scenery before embarking on this new journey.

It's Wednesday night and I'm searching Expedia and Kayak for travel deals that would have me on the beach by Thursday morning. With my friends unable to pick up and go from their jobs and lives, I made the decision to take the trip alone. Limited funds and lack of last minute deals killed my beach dreams, so I started looking at some cities I've always wanted to visit and Chicago came on my radar. The windy city: home to the Chicago Bulls and Cubs, the Magnificent Mile and who could forget Ferris Bueller's famous day off. I was sold and a few hours later at the airport. 

I always appreciate a city with easy commute options from the airport. The CTA train takes you from O'Hare Airport right downtown, and it wasn't more than an hour later I was standing on the Magnificent Mile looking at a tree lined lit street that gave me the Christmas feels (and I'm not even a Christmas person!). I'll mention my trip happened in the middle of December and coming from the west coast I found the windy city to be also quite chilly. The trip I booked had me staying at the Hyatt Chicago Magnificent Mile: a beautiful hotel, perfect location for walking distances to museums and attractions along with a king size bed that Kevin McCallister from Home Alone would be stoked to jump on and snuggle up in. I had no time to plan this trip so I hit up the concierge for some tips to start my first night (and the following nights) in the city. 

First stop led me to the John Hancock building, iconic to the Chicago skyline standing 1,000 feet above the ground. I was in time to catch the sunset and received a tip that rather than spending the money on the observation deck, head to the 96th floor bar for the same view to be enjoyed with a cocktail in hand. A seat for 1 is no trouble to find and I ended up with an incredible view and met my doppelgänger on the same trip as me. She happened to be starting a job on Monday as well and went on a last minute trip herself! I will recommend checking out the bathrooms at this bar as they have a floor to ceiling window. Needless to say my selfie didn't turn out but still a cool view! 

Dinner, for 1. The common misconception when you see someone dining alone is they'd been stood up or are at the wrong restaurant and their 3 friends are next door. My quick research on the restaurant scene led me to The Girl & The Goat, the executive chef had recently won Top Chef so naturally I wanted to see what the hype was about. The concierge politely informed me there was no way I was getting a table there. She recommended Beatrix instead and I couldn't have been more pleased! I opted to sit at the bar where I was confused for a nice man's blind date - it was all going well until the girl showed up 45 minutes late and I basically third wheeled their date and made menu suggestions. I'd recommend the Straight "A" Salad which I re-create at home and the meatloaf (a restaurant fave!). 

Three Dots and a Dash: one of the coolest bars I've ever been to. Another recommendation from the concierge, she basically told me to walk down a dark alley for 10 minutes and when you see a torch you'll know you're at the right place. A bit unnerving but I was game! You're escorted downstairs to this room and you're immediately immersed in the feels of a beach side bar on a tropical island. Drinks literally the size of the table and more umbrella drinks than you could imagine. The room is filled with a mix of men in suits and tourists but the vibe is intoxicating. I traded in my usual neat scotch drink for the "house" drink of rum, all spice and something citrus. It was heaven and I was drunk 3 sips in. 

Museums! I love visiting museums in new cities, I was lucky enough that the David Bowie exhibit was on at The Museum of Contemporary Art. The man was a legend you really saw how ahead of his time he was, from his persona Ziggy Stardust to his elaborate costumes and music videos. David Bowie changed music and his iconic forward thinking approach to the artistic side of it all paved the way for artists to be able to express themselves through so much more than their music but rather display what music meant to them as artists and how they connect with their audience. The Art Institute of Chicago was another highlight and one I could keep coming back to to fully absorb the monstrosity that is this museum - it is one of the oldest and largest museums in the United States in fact. I won't pretend to know too much about art but I do enjoy wandering the different rooms and era's, noteworthy mentions would be Monet, Picasso portraits, Andy Warhol and the painting that captured Cameron's attention in Ferris Bueller, exhibit A below. 

Architecture Boat Tour: A friend had recommended after doing in the summer and I was pleasantly surprised that it was still running in December. We were welcomed with coffee and baileys to keep us warm on the river as we cruised through the city. The architecture was incredible to learn about and the view from the boat offered a different perspective than walking by it. My favourite building was the London Guarantee that stands tall beside the Michigan Avenue Bridge. 

Chicago Bulls Game: How could you not go and watch the Bulls play, I mean Michael Jordan played on the same court... a $50 ticket got me a seat at literally the very last row in nose bleeds but it was one of the most fun times I had at a sporting event. I don't think it was a very important game against the Portland Trailblazers that night but the crowd made it feel like it was a game 7 in the play offs. I appreciated the gentleman sitting beside who told me the full history of the Chicago Bull's history as he'd been a season's ticket holder for 25 years. Best. Fans. Ever. 

I obviously couldn't leave without a cliche solo photo in front of the giant bean! I'd definitely visit Chicago again as I feel like I just tipped the iceberg with all the fun things to do in this city, next time I want to catch a show at Second City and a Cubs game! 

Has anyone else done a solo trip? Where did you go? Would you do it again??

xx

LC