Chicago Travel Guide – What to Do, See, and Eat

Chicago Travel Guide - Stylista Esquire - @stylistaesquire

I can honestly say I fell in love with The Windy City! As some of you may have seen through my Instagram stories, I was in Chicago for The Blog Societies Conference.  If you haven’t heard of The Blog Societies, or TBS, it’s a tight-knit network of bloggers started by Cathy and Jessica, who are amazing bloggers!  I’m sure you follow one or both of them already!  They are so talented in what they do, and luckily, they decided to share their knowledge and connections with fellow bloggers.  I’m so thankful for them for introducing me to some wonderful ladies and for giving me an excuse to visit Chicago!  Below, I’m talking about some of the fun things I did in the city, for when you get the chance to spend some time in Chi-Town.

My oh-so amazing roomie for the conference, Lauren, and I met up at O’Hare Airport after our early morning flights. O’Hare is about a 40 minute Uber ride to downtown Chicago, which cost us around $35.  We dropped our bags off at the super lux W Lakeshore, which has THE most amazing view of Lake Michigan.  From there, we grabbed brunch at The Hampton Social, which is that Chicago restaurant you have probably seen all over Instagram. They are famous for their Rosè All Day sign, because duh, it’s so instagrammable!

After brunch, Lauren and I walked through the downtown areas and the Chicago Riverwalk.  Chicago has that big city like NYC because the buildings are super tall, BUT the streets are spaced out much farther apart than the ones in NYC, so I didn’t feel claustrophobic.  Big streets and sidewalks and long blocks also mean lots of walking. I  think it’s so cool that the city has a river that runs through it!  Plus, they have sandy beaches!  Chicago really has it all.  For more touristy things, we went to Millennium Park for pictures at The Bean.  It looks so much bigger in pictures! If we had had more time, I would have loved to explore The Art Institute of Chicago which is right by Millennium Park.

Lauren really wanted to check out The Second City comedy club, so we went to a late show. A lot of comedians come through Second City and make their way to bigger and better things, including SNL.  It was hilarious! I highly recommend it – especially if you are a liberal, or are a conservation who doesn’t mind Trump jokes.  It IS Chicago after all!

Even though we had the conference on Friday and Saturday, we still got to try different restaurants (thanks to some of our sponsors, Vera Bradley and Marc Fisher) and hit up some more Chicago tourist spots.  Thank you to Vera Bradley for throwing us a welcome cocktail party at Sugar Factory and Marc Fisher LTD for treating us to lunch.  Below, I’ll round up the best food and tourist spots were came across.  Plus, I’ll give you a peak and what all the amazing brands gifted us!

Food/Coffee

The Hampton Social – Must have: fried chicken sandwich; lobster roll; frose (it tastes more like a frozen peach bellini!)

Chicago Travel Guide - Stylista Esquire - @stylistaesquire

Dollop Coffee Co. – Adorable coffee shop by The W. Plus, I love the word ‘dollop’!

Chicago Travel Guide - Stylista Esquire - @stylistaesquire

The Boarding House – Marc Fisher LTD treated us to lunch here and it was so good.  The restaurant itself is so beautiful and the short ribs are excellent.

Lou Manlati’s – DEEP DISH PIZZA. The original. So. Good.  As I am writing this, I have a tab open to order a frozen pizza from them…

EATALY Chicago – The famed Italian market/eatery. I found it to be way more confusing than the NYC location, but the cannoli bar was very yummy.

Chicago Travel Guide - Stylista Esquire - @stylistaesquire

Pictured: Ravioli with peas and prosciutto from EATALY Chicago

Chicago Must-See’s

Millennium Park/The Bean – Everyone needs to take a selfie at The Bean!

Chicago Travel Guide - Stylista Esquire - @stylistaesquire

Chicago Riverwalk – The only thing I was sad I did not get to do, was an Architecture River Tour.  That’s on my list for next time!

Navy Pier – They have a ferris wheel, deep dish pizza, and Garrett’s popcorn!

Chicago Travel Guide - Stylista Esquire - @stylistaesquire

Wrigley Field – You can go there and just take a picture outside the famous sign! Also, on my to-do list for next time!

I need to go back ASAP.  Let me know if you’ve ever been and what you love!  If you haven’t visited yet, definitely book a trip out there!  But before it snows…

-Jacqueline

Here are some of the gifts we received from the wonderful brands and sponsors!  All items were received as gifts and were not in exchange for promotion, etc.  All opinions and reviews are my own!

Some photos were shared by my TBS roomie and now, forever-friend, Lauren from Wellesley & King!

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4 comments

  1. I live in Chicago and always feel so proud when other people love Chicago as much as I do!! I hope you enjoyed the city and had fun at the conference. The workshops on Friday were so informative!

    xo, Sarah

    1. Oh my gosh yes! It was such a whirlwind weekend…if you ever find yourself in D.C., let me know and I’d be happy to be a tour guide and introduce you to my hometown!

  2. Yes, you must go back. My new tennis partner and longtime Chicagoan said the two things not to miss are the Architectural river cruise and the art museum. It’s been a few years since I have been there so I’ll have to go again and try your yummy eats suggestions.

    1. Yes, I must go back! Let me know if you ever wind up there and I’ll pop over! 🙂