The Windy City Travel Guide

One of my favorite things about living on the East Coast is that you can travel anywhere so fast. On the West, you can drive to AZ (Which I do love) in 5 hrs, but over here, in Boston in that time you can go to many different states!

So from Boston to Chicago, which hint hint, will be what I’m telling you about is about a 2 hour flight. SO EASY for a perfect weekend getaway. I had always wanted to go to Chicago, and once we were here it was only a matter of time before the windy city called our names.

I had no idea what to expect, I had heard GREAT, AMAZING, and UNBELIEVABLE things about Chicago, but on the other hand I heard “ehhh” so I had no idea what to think.  But I was pleasantly surprised. San Diego has amazing food and people were like wait til you get to Boston, and Boston has amazing food too, but Chicago. Wow it’s like a food tour is necessary. And I’m a firm believer that calories don’t count on vacation. 

We ate a lot, which I can’t complain. Eating in review you ask? Fine. I’ll divulge, but you have to promise not to judge. And there were even places on my list I wanted to go to and couldn’t. This picture describes all my eating: #eatwithoutregret

Lou Malnati’s: Deep dish. They’re pretty much everywhere, honestly when I look at deep dish, I don’t think it looks good. You can’t see the cheese, all you see is sauce, and who likes that part really of the pizza? Then you cut it and the cheesy goodness is exposed.

Garrett’s: Popcorn. It’s a classic, “Garrett Popcorn” and you get cheddar and caramel, gross right? NO!

Cupitol: For the coffee. Best. Pumpkin. Latte. We started everyday with a cup.

Eataly: Get some cheese, meats, and crackers for a little snack.

Public house: I got avocado toast, so you know now I’ll never be able to afford a house. (Sorry I’m trying to adult over here.)

M. Henry: BRUNCH! It was featured on a food network show- #1 best brunch in the U.S., so yes of course I had to try. (Look at that florentine shrimp and crab cake bennie on the left and cinnamon roll french toast right in the middle).

Old Town Pour House: They have every appetizer you could ever want. And I think our eyes were bigger than our bellies, but it was all so good. That was a reoccurring theme of the food though.

P.S. There are soooo many rooftop bars, with amazing views of the city that are a must.

We walked a lot (and took the L). Pro tip: we bought a 3 day pass for $25 which gave us unlimited rides. The most tourist spots? Okay, I’ll share. (Here’s a sneak peek of the pics version of them.)


Architecture Tour – I’ll be the first to admit, I thought this would be cheesy, but multiple people told me it was a must do. It’s crazy to go through the city and see all the buildings and learn about the history, and even what they have planned and how perfectly it all fits into each other. Did Chicago really burn down because of a cow?

Willis Tower –  1,453 feet tall with an observation area, called the SkyDeck, on the 103rd floor, 1,353 feet above the ground. I heard about it on the architecture tour and knew we had to go. D wasn’t thrilled at all, but me? Couldn’t wait.

Millennium Park/The bean – Your classic picture, it’s as big as you think it would be. They have concerts, a perfect picnic spot,

Navy Pier – Right on Lake Michigan, I found it so amazing that the lake is soooo blue. Like Caribbean waters. If it wasn’t cold and windy, this mermaid would have jumped right in. There’s a huge ferris wheel, and places to eat.

Michigan Avenue and the Magnificent Mile – all the shopping you could possibly want. Every store, big and small. Plus a huge mall!

Buckingham Fountain– If you know the Balboa Park fountain, then it reminds me a lot of that. It’s a huge fountain, with the city in the background.

SPORTS! Yes, we watched them, c’mon you think Danny would go and not? So the Kings (hockey) as always is intense, and it’s not far from the city! We got a box seat with unlimited food, which was most certainly a problem. And the Cubs, we watched a game from across the street on top of some apartments. Definitely different, and definitely fun. But Wrigley Field is one of the oldest baseball fields, and hey, they just won the world series!

Overall: LOVED CHICAGO! It’s one of the most photogenic cities, with the most amazing food, and of course, the most fun!

~ XOXO, the wanderlust struck, Amanda

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Hey there!

I’m Amanda, the blonde behind the blog a twenty-something year old with a love of wine, weekends, and traveling. You’ll find bits of my life, travel guides, beauty, food & of course, my pup Gatsby. I’m so happy you’re here & I hope you enjoy the blog as much I as I enjoy creating it! Cheers!


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