You all know how much I love to talk, borderline brag about living in San Diego. I couldn’t ever go back to the cold, but the city of Chicago and my recent weekend of bloody marys and brunch sure makes it very tempting. Having been once before in the summer, and now in the fall, I am so in love with this city! I love the energy and electricity of a big diverse city like Chicago!

Recently, I traveled to Chicago with my bloody mary bestie, Shelley from The Drunken Tomato to meet up with our other bloody amigo, Jason from Eat, Drink, and Bloody Mary! We embarked on an epic bloody mary adventure getting #brunchfaced at four bloody mary and brunch spots on Saturday and then getting tomato tipsy at the Chicago Bloody Mary Festival on Sunday! The trip wasn’t without a few hiccups but overall got some great content, met some awesome people and had hella fun with my bloody mary amigos! 

Here is the full recap:

Day One

I arrived in the Windy City on Thursday evening, expecting my bloody bestie to have landed, only to find out her flight was canceled. Boo. So, I called a Lyft and headed to our Airbnb. I’ll spare you the details, but it was a bit of a crisis and I ended up packing my bags and high tailing it out of there before I even unpacked!

Crisis averted, and I landed in the gorgeous neighborhood of Gold Coast in Chicago at the Ambassador Hotel. Thank goodness for Hoteltonight.com and thank goodness to Hotel Ambassador for having a bar/restaurant still open, since I hadn’t eaten anything since I was in San Diego! I may have downed two vodka sodas in the search for stress relief after the whole ordeal, or maybe I didn’t.

Day 2

I woke up in the beautiful Chicago hotel with some work to do, so I decided to treat myself and order some room service and stay in bed since checkout wasn’t until 12! It was one of the best “workdays” I’ve ever had!

Still waiting for Shelley to arrive, I wanted to explore the beautiful Gold Coast neighborhood of Chicago and found my way to Blue Door Kitchen, on recommendation from Jason. Blue Door Kitchen was the most adorable farm chic restaurant and my first Chicago bloody mary! What a way to start off! Blue Door Kitchen’s bloody mary is spicy, fresh, and full of garlic and dill! I couldn’t ask for anything more in a bloody mary!

Finally, after delayed flights and long travels, my bloody bestie Shelley arrived in Chicago. I only had one night at the Hotel Ambassador so Friday night we stayed at the Loews Hotel, which was absolutely gorgeous!

We made a few stops at the Broken Shaker and Three Dots and a Dash, both of which are popular craft cocktail hot spots in Chicago, for some celebratory cocktails! Heading back to the Loews we had dinner at their restaurant, ETA (got the prime rib) and I highly recommend it. We had a nightcap at the lobby bar and met the bartender Bobby who actually creates their bloody mary mix from scratch! He let us have a taste, so we knew we had to grab breakfast and bloody in the morning.

Day 3

Bobby’s bloody mary in the morning did not disappoint. Although the breakfast was super rushed because we were meeting up with Jason for our epic bloody crawl, I’m glad we got to try Bobby’s sweet, spicy, and smokey bloody mary. You’d be surprised how many hotels have amazing bloodys!

 Bright-eyed and bushy-tailed, we headed out to meet up with Jason to begin our epic Bloody Mary crawl!

First Stop

Our first stop on the bloody mary crawl was Highline Bar + Lounge on Kinzie Street. We were absolutely blown away by their brunch buffet and build your own bloody mary bar and frankly didn’t know where to start. With several bottled mixed options, I chose Chicago’s own Zing Zang.

Feeling like a kid in a candy store, we grabbed a tray and gathered all the garnishes from the brunch buffet. Choices like Chicago dogs, fried chicken sliders, CBD donuts, Poptarts, chicken wings, pizza, and pretzels, (just to name a few) and then finished off with all the familiar toppings. Building your bloody mary at Highline is like bloody mary arts and crafts and the possibilities are endless! Bonus: all of the garnish aka entire brunch meal is absolutely delicious!

Second Stop

What might have been the last 70-degree day in Chicago, the tres amigos hit the streets and headed to our next bloody mary destination; Sunda New Asian on W Illinois St. Their Sumo Mary has been on my bucket list for years when I first saw the bloody on Pinterest.

The Sumo Mary did not let us down! Served in a 32oz mason jar and topped with so many unique (for a bloody mary) Asian goodies. The garnishes include tocino grilled cheese, steamed duck bao bun, crab handroll, and crispy pork belly, just to name a few. Not only is the garnish out of this world, but the mix is also yummy. Full of hearty umami flavor and the perfect amount of tang and spices, it was an awesome moment to finally have the Sumo Mary!

Third Stop

Last, but certainly not least, was the hip The Smith on N. Clark St. With locations in NYC, DC, and Chicago The Smith does brunch and bloody marys right! The Smith gave us Bloody Mary experts that thought-provoking question that Shelley always asks, what is a Bloody Mary?

The Smith has their classic hair of the dog bloody mary that was bold and full of flavor, but they also have two cocktails that made us scratch our heads and wonder…could this be? The Dirty Jane with vodka and a pickled green tomato and the What’s Up Doc? carrot concoction had us almost convinced, but we decided, although delicious and able to cure a hangover, not a bloody mary.

The brunch food at The Smith is incredibly bomb and there is such a variety of different foods! You’ll be incredibly #brunchfaced after trying their Italian Baked Eggs, Mac and Cheese, Churros Waffles or their signature dish, Spicy Salmon Tartare (so so good).

Conclusion

Chicago is such an amazing city for so many reasons, but they really go hard when it comes to bloody marys and brunch……move over deep dish pizza! I know we barely scratched the surface but I’m not sad about it. That only means I have to go back again (after winter) and try the rest of them! Thanks to Jason for hosting us and thank you Day 4 was the unforgettable Chicago Bloody Mary Fest and I’ll be recapping that soon!