Chicago Travel Guide: Best Food Spots, Things to Do & Instagram-Worthy Outfits

Chicago has a way of pulling you in from the very first visit. I first experienced the city on a quick day trip and, in just 24 hours, I was hooked. So when my best friend’s birthday rolled around, we knew it was the perfect excuse to go back—this time with more time to explore, eat, and celebrate. From its rich mix of cultures to its endless food options and iconic sights, Chicago is a city that never runs out of things to offer. In this post, I’ll take you through some of the best spots we discovered—foodie finds, must-see attractions, and hidden gems you’ll want to add to your own itinerary.”

Places To Eat

🍴 Of course, we had to kick things off with food—y’all know I’m a true foodie at heart. This trip was definitely filled with some hits (and a miss), but let’s talk about one of my favorites first: Cleo’s Southern Cuisine in Hyde Park. The name says it all—soul food with that comforting, down-home vibe, created in honor of a grandmother’s southern cooking. We tried the mac ’n’ cheese fried chicken sandwich, fried catfish, and the lobster mac ’n’ cheese, and let me tell you… every single bite was pure joy. 10/10 recommend! If you’re in Chicago and craving soulful flavors that taste like love on a plate, Cleo’s is a must-visit.

Friday night, we kept the celebration going at Hacienda Calavera—and wow, talk about an Instagram-worthy spot. The atmosphere was vibrant, with lively music and even a special on-stage celebration for all the birthday girls (such a fun touch!). I ordered the ‘Los 3 Huastecos,’ a flavorful combo of skirt steak, shrimp, and octopus that did not disappoint. Between the festive vibes and the delicious food, I’d give this place a solid 10/10. If you’re looking for a spot in Chicago that knows how to turn dinner into a party—especially for birthdays—Hacienda Calavera is the place to be.

By Saturday morning, we were ready to brunch it up, so my girls and I headed to Toast It Iz, a Black-owned restaurant that’s been getting some buzz. I went for the lamb and sweet potato waffles with eggs and a side of red beans & rice. The lamb and waffle combo? Amazing. But the red beans and rice… not so much—definitely lacking seasoning. One of my friends ordered the oxtails and grits, and unfortunately, that dish was also a letdown, especially considering the price. So while the vibes were good, the food was a bit hit-or-miss for us.

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☕ After a few foodie ups and downs, Sunday totally redeemed itself with a stop at the Starbucks Reserve Roastery—and let me tell you, this was hands-down the most unique food spot of the entire trip. Imagine a Starbucks on steroids: five floors, each with different menus and experiences, all wrapped up in the ultimate Instagram-worthy setting. I ordered the Fig Walnut Ricotta Toast and the Pistachio & Rose Twice-Baked Cornetto (basically a fancy croissant), and wow… that cornetto might just be the best I’ve ever had. Between the flavors, the aesthetic, the vibe, and the incredible service, this place was a 10/10 across the board. If you’re in Chicago, this is a must.

For Sunday night dinner, we checked out Kitchen + Kocktails downtown. I’d been to their D.C. location before and loved it, so I was excited to try the Chicago spot. But honestly? It didn’t quite live up to the hype. The vibe wasn’t as strong, the service was just okay, and my seafood gumbo was way too salty—plus they barely gave me enough rice to balance it out. The sweet potatoes, on the other hand, were incredible. Overall though, the experience was a bit underwhelming.

Thankfully, Monday morning made up for it in a BIG way with HoneyBear Café—hands down my favorite brunch spot of the entire trip. We split the French Toast Trio (amazing!) and I ordered the Stuffed Cajun Cheesesteak Biscuit, which was absolutely next-level. Every single bite had me in food heaven. Honestly, I wish you could taste the food through the screen because baby… it was that good. Add in the great music and laid-back vibe, and I’d give HoneyBear a 10000/10 without hesitation.

After brunch, we wandered over to Chinatown and stumbled upon Molly Tea—and oh my goodness, this place was a gem. I call myself a tea connoisseur, but I’d never tried a cream or milk tea before. I ordered the Premium Jasmine Oat Milk Tea with coconut milk, and let’s just say… life changed. Smooth, flavorful, perfectly balanced—I was in tea heaven all over again. If you’re a tea lover (or even if you’re not), Molly Tea is a must-try.

Things to Do

Chicago is a city that knows how to keep you busy—whether you’re into food, shopping, sightseeing, or just vibing with the locals. Here are some of the highlights from my trip that you’ll definitely want to add to your own itinerary:

Starbucks Reserve Roastery – This place deserves to be mentioned twice because it’s not just about the food (though the pastries are unforgettable). With five levels of coffee experiences, it’s part café, part museum, and part Instagram dream. Even if you’re not a die-hard coffee lover, the sheer creativity and vibe make it a must.

Alice + Wonder Custom Hats – If you love a good statement piece, head over to Alice + Wonder for custom trucker hats. You get to design your own with fun patches and words, making it the perfect personalized souvenir. Mine definitely became one of my favorite keepsakes from the trip.

R&B Boat Tour – One of the highlights of our weekend was cruising the Chicago River on an R&B boat tour. The music was unmatched, the skyline views were stunning, and the vibes were all the way up. If you want to turn your sightseeing into a full-blown party, this is it.

Chalet Chicago – For a chill night out, we popped into Chalet Chicago, a bar that’s all about the vibes. Think cozy yet trendy, with music and energy that makes it a perfect spot to wind down (or turn up, depending on the crowd).

The Bean (Cloud Gate) – A Chicago classic that you just have to see. Yes, it’s touristy, yes, it’s crowded—but snapping that mirrored skyline reflection is a rite of passage.

Fruit Cup Street Vendor – Sometimes the simplest things end up being the most memorable. We grabbed fresh fruit cups from a street vendor, and it was honestly one of the best little refreshers between all the sightseeing.

360 CHICAGO Tilt Experience – If you want a dose of adrenaline, head to 360 Chicago and try “The Tilt.” You literally lean out over the city skyline from a glass window—it’s terrifying but so worth it for the view and the rush.

Chinatown – Beyond just the amazing food (hello, Molly Tea!), Chicago’s Chinatown is full of culture, shops, and little discoveries. Take your time walking around, exploring murals, and popping into bakeries or tea houses.

Perfume Making at The Aroma Workshop – For something unique, we booked a session at The Aroma Workshop, where you create your own custom perfume. It’s such a fun, creative experience and a perfect way to take home a scent memory from the trip.

Shop My Looks

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Here's a closer look at all of my outfits from this Chicago trip. You can shop these looks on my LTK here.

Thank you so much for taking your time to visit CRMstyles and reading about my trip to Chicago. I hope you enjoyed it, and I hope you found a spot to add to your itinerary for your next Chicago trip. Let me know in the comments below if there's a place I should visit next time I return.

Until next time!

XOXO