Chicago Food Guide: Where to eat and drink in Chi-Town!

My Chicago-Denver trip was my final and biggest trip of the year. After 2 months of non-stop travel, I ended it with a week long getaway to Chi-town and then to Denver. I spent 2.5 days in Chi-town and covered a TON of ground. My favorite part was that I had ZERO plans and asked for recommendations just via Instagram and from locals. It took me to places that weren’t super touristy and I loved it. To save you from an endless post of pictures, I’m breaking up my Chicago trip into multiple posts and I’m sharing just where to eat and drink today! Check it out:

DropShot Coffee and Snack Bar inside FieldHouse Jones

All my days must start with some hot beverage. I dropped into DropShot Coffee inside a newly renovated hotel. I was told it used to be a basketball court and the cafe was adorable. There was cool art and repurposed furniture to create a unique look. It was only open for a week when I stumbled in.

Lunchin’ at Left Coast in River North

First of all, this place is SO darling. I had to exert self-control from geeking out over the decor. It was soo pretty. The food was delicious and I ordered the Montecito Hash. Lots of healthy options and a patio to die for.

Big and Little’s Restaurant in River North

I asked for a hole in the wall and my friend Jeana delivered! Big and Little’s is an inconspicuous, off-the-beaten path eatery that really hits the spot. You’d easily walk past this place without a second glance. They offer a variety of tacos, burgers, fried fish, wraps, sandwiches and more. It’s a cash-only joint and there are 3 locations.

Green Street Smoked Meats for Texas BBQ in West Loop/Fulton Market

I’m not a BBQ connoisseur, but I was definitely hesitant about trying “Texas-BBQ” outside of Texas. I tried to hit the ramen spot next door, but with an hour and a half wait, I opted to check out Green Street Smoked Meats in Fulton Market/ since everyone was suggesting it. Once inside, I got the Warren Moon which is a pulled pork sandwich with a split link on top and added sweet pickles to it and I really enjoyed it. The meat was flavorful and moist. It didn’t disappoint.

Bombobar for dessert in West Loop/Fulton Market

Just a short walk away from Green Street Smoked Meats is this walk-up donut bar. It’s attached to Bar Siena and is so cute and fun. I actually started my night with dessert when I opted out of taking a spin class. #NoRegrets. I ordered the nutella cream donut and it was delicious! You squeeze the nutella into the center of the donut and it just oozes out when you bite your way into the center. I also spotted ice cream/gelato donut concoctions and other delicious flavors. I was just sad that I only had so much room in my stomach.

Grab a juice at Real Good Juice Co. in Wicker Park

I like a fresh juice every now and then and I grabbed this one simply because it was pretty. It ended up being really delicious and reminded me of an Asian soy milk dessert. You can order juices made there or grab a bottle like this one and head out. A little on the pricey side with juices around $10 bucks.

Mahalo for Poke Bowls in Wicker Park

If you’re in the trendy Wicker Park, Mahalo is a great spot for something light and fresh. I ordered the poke bowl of the day which included yellowtail. You need to check out their Instagram, which is what I use to scope out what I want to eat. There are some beautiful dishes and drinks. I specifically want that pineapple drink.

  Big Shoulders Coffee in River West

I had a fun coffee date here at this itty bitty coffee shop. I LOVE their marshmallow latte. It was excellent and the marshmallows are home made. The shop isn’t much for aesthetics, but the coffee is good and this is worth the stop.

Apogee Rooftop Lounge inside the Dana Hotel (River North)

You can’t go to Chicago without hitting up a rooftop bar. It’s almost a rite of passage. A friend and I dropped into the new Apogee Rooftop Lounge for a pitcher of sangria. Gorgeous bar and gorgeous views. What else can you ask for?

Three Dots and a Dash in River North

From rooftop to underground bar I went! A short walk from Apogee Lounge, we ended up walking into a basement and into a very cool Tiki Bar. It was still early in the night and the place was already packed. I’d recommend going early or staring your night here. The drinks are delicious and there are so many to choose from. Such a fun spot!

Live music and beer at Bub City (River North)

For a friend’s birthday, I checked out Bub City which is a Western themed pub that features live bands, BBQ, and a hefty list of beers and whiskeys. If you’re feeling a little home sick, this definitely reminded me of Dallas.

Grab a Chicago Dog and Italian Beef Sub at Portillo’s

So my night out in Chicago ended with a Chicago dog at Portillo’s. I know I’m definitely adulting when it’s a win that my night ended before midnight with a hot dog. LOL. Portillo’s closes at midnight. After a few cocktails, we ended up grabbing some food before grabbing a cab home. Apparently you are not allowed to eat a Chicago dog with ketchup otherwise you’ll be shunned! It was delicious. I didn’t get to try the Italian beef but it was looked amazing.

I’d say I definitely ate and drank my way through the city and hit up a bunch of different spots. I just wished I had more room in my stomach for more! Hope this Chicago food guide is helpful if you’re planning on visiting the Windy City. Let me know what some of your favorite Chicago eateries are and I’ll save them for my next trip!

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