Chicago, Illinois

Travel Diary: 24 Hours in Chicago

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If you view my Instagram stories then you’d know that I was just in Chicago a little over a week ago!

My sister, Katherine, had originally planned to spend some time in Chicago with her friend and when her friend couldn’t make it, I jumped in last minute! So though it was short and sweet (just about 24 hours), you’d be surprised at all we were able to pack in!

This is not my first, second, or even third time going to Chicago so this isn’t a great guide for newbies or first timers as I’m not going to cover anything “typical” like the pier or the bean, but it was still a fun mini trip that I’d like to share and maybe you’ll pick up some new places to go to your next time there!

Chicago winters, like midwest winters in general, are cold. So definitely dress for warmth! I didn’t feel too bad in my boots, sweater, coat, scarf, hat, and gloves, but there was one time I went to Chicago in just a light wrap coat and tennis shoes and I was freezing. But then again, I hate being cold! Related: Traveling in the Winter? Here’s How to Look Chic and Stay Warm!


Drink/Play: Starbucks Reserve Roastery

646 Michigan Ave, Chicago, IL

This was the first place we went to and let me tell you, this place is definitely making coffee consumption an experience. It’s 4 levels of food, drinking, and coffee-related shopping. Plus, the atmosphere is just so cool and it definitely gave me coffee-in-the-future-hipster-vibes. Go to look around, stay for the coffee…if you dare to wait in a crazy long line and overpay on coffee! 😉 But for real, it’s cool to see.

Eat: Shake Shack

This was my first time eating at Shake Shack and man oh man, those burgers are gooooddd! That’s really all I’ve got to say about that.

shake shack chicago il

Eat/Drink/Play: Eataly

43 E Ohio St, Chicago, IL

Eataly is one of my favorite places and I never get tired of it. I just love the whole atmosphere and it reminds me of one of my favorite places on earth! I come back every time because whether you like Italian restaurants, specialty grocery stores, coffee/dessert, or to just be reminded about Italy in general, this place is for you! No surprise that I took the most pictures here!

coat | hat

Shop/Play: Nordstroms

Would you believe this was my first time at a Nordstroms? I know, I know, appalling for a fashion blogger. There just aren’t any near me in smallish town Iowa! It was cool to see some of my favorite designer pieces in person though. And nope, I didn’t get anything. Well, unless you count the free Hermes ribbon that the perfume lady gave me…ha!

Eat/Drink: Stan’s Donuts

It was a little chilly walking up and down the Magnificent Mile, so Stan’s Donuts made a great place to warm up and get a coffee + a doughnut! It’s a really cute place too!

Stan's Donuts Chicago, Il

Eat/Drink: Giordano’s

1340 S Michigan Ave, Chicago, IL

Did you really go to Chicago if you didn’t eat at Giordano’s? Usually, I get the deep crust (what they’re famous for) but I tried the thin crust this time for dinner. It wasn’t terrible, but I’d say just go for the deep dish if you do come here!


Goddess and the Baker

44 East Grand Avenue, Chicago, IL

Give me a good cafe in the morning (or really any time) and I’m happy. Especially when it involves black coffee, avocado toast, and a warm croissant! Mmmmm. Cute atmosphere? Icing on the cake! Or should I say creamer on the coffee? Hardy har har!

Next stop after the cafe? Home. And that concludes my 24 hours in Chicago! Don’t think I didn’t realize that most of it was just eating at different restaurants haha. #noshame #notevenalittle

Chicago, Illinois

Have you spent at least 24 hours in Chicago before? Is it a place you want to go?

If so, then you’re going to want to know about the 5 chicest cafes there

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24 hours in chicago


Founder and editor of My Chic Obsession, Carolyn is your trusted fashion maven. Carolyn's drive to help others achieve a classic and timeless wardrobe fuels her posts, making a go-to resource for style seekers worldwide. Beyond the wardrobe, she resides in the heartland of the Midwest, dreaming up new ideas and raising her two lively boys - her biggest fashion critics.