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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!
Saturday
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.

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!
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!

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!
Sunday
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

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…


Eataly and Stan’s Donuts sound amazing! I haven’t been to Chicago since I was a child – I need to get back there someday.
We have Eataly in Toronto but I haven’t tried it yet. I would love to see Chicago, it looks like a beautiful city to visit and these fun places to hang out for coffee or a bite to eat! Thanks for sharing this❤️
Isn’t it fun how when you travel somewhere, you basically just eat and drink your way through the place? Haha! I now want to eat ALL THE THINGS thanks to this post. Mostly Shake Shack, which I miss desperately. The closest one to me is like 2.5 hours away so I don’t get it often. Congrats on your first Nordstrom experience! We have one in my city, but it’s like 40 mins away and I just don’t like spending ridiculous amounts of money on clothing, so typically I avoid it unless I really need new Topshop jeans haha! Glad you had a good time in Chicago!
I have eaten at the Eataly in Boston and it was FANTASTIC. I’m glad you got to go.
I wonder if they’re all the same everywhere or not!
I think I need to go to Chicago just for the food! SO many yummy finds in so little time 🙂
-xo, Azanique | https://www.lotsofsass.com
For sure! And I barely scratched the surface on the food!
I’m totally bookmarking this!! I’ve only been to Chicago once and really loved it. I’d love to visit again!
It’d be so fun to meet you in Chicago one day!
I have never been to Chicago but it’s on my travel list! Eataly looks so yummy and your black and white jacket is so cute! I can’t wait to visit Chitown sometime soon
Yes, Chicago should definitely be on your list!
Your giant scarf! Too awesome! Can you provide any tips on where to find one?
Aw thank you! I love it. It’s old and from H&M. I’m linking to their scarves right here because I had a quick look and it looks like they have some other large scarves too!
I would love to visit Chicago one day. I’ve heard Eataly is so good!
It definitely is!
I just pinned this post. I am hope to visit Chicago later this year.
Thanks for pinning!!
I’ve been wanting to go to Chicago for the longest time! love your photos, you did a lot during your 24 hours there. The pizza looks so great!
Give me pizza and I’m a happy girl!
Sadly I’ve only been to Chicago for a funeral years ago and have always wanted to go back for fun!
Sorry that that is what brought you there–you’ll have to go back!