This summer I did a brief weekend trip to Chicago, Illinois. If you know me, you know I’m from there originally. We tried so much food and got to witness the yearly Airshow event. So much packed into three days, let’s get started!

The first evening we ended up at a cocktail fine dining restaurant called Sophia Steak. We ordered the “Cucumber Cooler” made with gin, yellow chartreuse, cucumber, basil, and agave syrup. My friend ordered the “Cherry Moscow Mule” made with blue ash farm Wisconsin cherry vodka, lime, ginger beer, lime wheel, and mint. Both were 10/10!! I’m not going to lie, I definitely didn’t need another after realizing how strong these were!

The next day we headed to the city! We made a pit stop for lunch at Time Out Market Chicago. If you can imagine a giant food hall where you can just go pick food around the world then you get the idea.

I ended up deciding on a Mexican type of cuisine while my friend made it to an all raw bar section ( sorry no images to show on those). My dish was AMAZING, entailing quinoa, steak, arugula, pickled onions, and an amazing cilantro lime sauce. They also offer a side of potatoes ( also amazing) with a Mexican flare. Let’s just say, I now try to recreate this dish at home all the time for an easy lunch!

Our next stop ended up being my friend’s top recommendation and must-have while we were in town. She raves specifically about their bambolino donuts. So we popped around the corner at Bar Siena and gave them a try and they were great! They come with four different sauces, my favorite being the fruit jam.

I also tried their Limcello Mojito since I needed an afternoon pick-me-up after all this food. Also was amazing!

We ended up stopping at our hotel to take a break and get settled in before dinner. We stayed at 21 C Museum Hotel Chicago. Great location if you want to be downtown and has easy walking access. All accommodations were well attended to and great service.

For dinner, we got a reservation for the outdoor patio at Bar Avec in Chicago. I’ll do a full blog post on this dinner since we tried so much. Overall the drinks and food were amazing. Not going to lie, from the online menu I was not expecting this place to be great or anything and I was quite wrong. And who doesn’t love an amazing view of the city?!

The drinks we ordered were the Titos mule and mine was the “Livin La Vinho Verde” which consists of cucumber, mint ooh vodka, Ameal vinho verde, basil, and lemon. Both are refreshing but I will say their drinks are not very strong if that’s what you’re looking for!

After dinner, we had a late-night reservation at Three Dots and a Dash in Chicago Downtown. If you can imagine a speakeasy tiki tropical-style bar then you get the idea. Drinks here are very expensive but all come with a theme. We ordered the “Clarevoyant Missionary” which has missionary milk punch, Zafra 21-year-old Panama rum, lime, pineapple, mint,peche, and mint chartreuse pineapple soas (left green drink). I ordered the “Frappe” which has Appleton estate 15-year-old Jamaican run, riesetbaur raspberry eau de vie, amontillado sherry lime, pineapple, pedro ximenez, and prerry lava flow. Phew, that was a mouthful. As much as they are expensive, they are strong so you get your money’s worth.

The next day we walked around downtown and watched the yearly Chicago airshow. The popular lakefront event features a wide variety of military and civilian performers and aerial demonstration teams with world-class pilots performing their aerobatic maneuvers along Chicago’s lakefront. We also ended up hopping onto one of the Chicago waterfront architecture tours. If you are ever in town, it’s a must-see and never gets old, even to locals.

Lastly, we ended the night at Celeste for dinner. Which is a three-story bar including a rooftop. Each floor has a different theme. The first floor is a cocktail lounge, the second floor is an all-disco bar (the floor even lights up), and the third is an outdoor rooftop lounge. Of course, we had to end our night with dancing at Vig, which is Old Town Chicago’s premier 1950s sports theme bar.