Welcome to Chicago: 11 Things You Must See and Do in the Windy City

'The Golden Girl' blogger Jess Keys gives us the local lowdown for your trip to Chi-Town.

Welcome to Chicago: 11 Things You Must See and Do in The Windy City

Looking for a place to getaway to this Spring? Chicago has got all the food and fun you could possibly pack in a vacay! We caught up with local Chicagoan and the face behind The Golden Girl blog, Jess Keys, and she filled us in on the best places to hang out when the weather turns warm and the wind subdues in Chi-Town.  

1. Best Chicago hotdog:

That would definitely have to be Portillo's! They're famous for their Chicago dog's and Italian Beef (both Chi-Town staples!) You also can't leave without getting the cheese fries. They're to-die for. However, if you're wanting more of an "experience" you'll definitely want to check out Wiener Circle. Just.. trust me on that one. [Editor's note: if you find yourself at Wiener Circle, you must ask for a chocolate milkshake.]

2. Best brunch in town:

That is a VERY tough question. It seems like there's a new brunch spot popping up every week. I really love Cindy's Rooftop when the weather is nice, because the views and the patio are absolutely stunning! Summer House Santa Monica is a pretty close second! Also, if you love BBQ, Smoke Daddy has a ridiculous brunch for BBQ lovers! (Pulled pork Eggs Benedict? It's heaven.)

3. Must-see museum:

The Art Institute is a no-brainer. It's the best way to spend a rainy day, ending it with a glass of wine at the cafe in the modern wing, overlooking Millennium Park! It's my favorite day-date activity with my boyfriend, Neal!

4. Best hotel + favorite hotel bar:

The Park Hyatt and their bar NoMI are really great, especially for lunch - NoMI has beautiful views of Water Tower and also a big patio that is great when the weather is nice. The Waldorf and The Langham are must-do's if you're wanting to splurge, they both have incredible spas as well.

Then there's Hotel Lincoln in Lincoln Park, I always recommend it for my friends who have been to Chicago several times - staying out of the Loop and in Lincoln Park is always a breath of fresh air, and it's still a quick cab ride downtown. Their hotel bar is one of my favorites, and has one of the prettiest views of the lake and the skyline!

5. Best patio for day drinking on a sunny day:

I think any Chicagoan would argue that margaritas on the patio at Big Star are a must-do! (They're cash only, so come prepared!) 

During the summer, Castaways is really fun, it's a boat-shaped bar on the beach!

6. Favorite off-the-radar spot:

A casual cuban spot called 90 Miles Cuban Cafe. It's BYOB, and has an awesome patio! (They enclose it during the winter months, so you can go all year round!) It was also on Diners, Drive-ins and Dives but surprisingly, a lot of people have never heard of it!

7. Best after-hours spot:

This might not be where the coolest cool kids hang out (I am WAY too old for clubs) but at 2 AM you can often find me a 24-hour Mexican restaurant called El Taco Veloz. They have karaoke... and it may or may not only be available spanish.

8. Favorite local coffee shop + your drink of choice:

I've been loving Caffe Streets lately because of their (you guessed it) patio! I always order the Thai iced coffee and work on my laptop outside. (It's equally as cute inside, you know, for the winter months.)

I also love Lovely Bake Shop, it's quiet, charming, and they have some amazing sweets!

9. Best spa to indulge at:

If you're looking for a massage, head to The Four Seasons. For an indulgent pedicure, you can't beat Cowshed at Soho House, and for a facial definitely get the oxygen facial at Bliss Spa at the W!

10. Best kept "locals only" secret:

Pilsen! A south side neighborhood that rarely sees tourists, but its one of my favorite neighborhoods in the city. Amazing local shops, and my favorite bar/concert venue called Thalia Hall. They have several bars within it, Punch House is my favorite, it's a basement bar with several kinds of punch on tap, decked out in amazing 70's decor. You also MUST have tacos if you're in Pilsen! Los Camales is a great spot, and if you're up for it, Taqueria Iguala, a legitimate hole in the wall with the best tacos I've ever had. (Can you tell I like tacos? I think I've already referenced Mexican food like 4 times.)

11. If someone is only in town for 1 night, they absolutely cannot miss:

A comedy show at Second City - Chicago, famous for it's amazing comedy scene! The world's best comedians all got their start at Second City.

Did we miss any of your favorites spots in Chicago? Let us know below!

Fashion, beauty and lifestyle editor at Livingly. Miami Hurricane obsessed, forever Miami Heat loyal, Food Network junkie. You can reach me anytime at alison.higgins@livingly.com.
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