A Weekend in Chicago with Wore Out's Caitlin

This is part of a dual post with the fabulous Caitlin Pierce of Wore Out: A Burlingtonian Style Blog.  I've had the pleasure of reading her blog since I started blogging, and her support of my blog has been invaluable to me.  Not to mention she's super stylish and a great writer!  Head here to check out her tour of her lovely New England home!

Hello all! There is a heck of a lot to do in Chicago, but I’m going to give you my weekend tour, which is heavy on the eating and light on the touristing.  In my opinion, that’s the best way to see a new place and get a feel for how the locals live!  You may not know it, but Chicago has some of the best damn food in the country (and that’s coming from someone who insists that everything is better on the East Coast).

Let’s get started on your weekend tour!

Friday:

You’re tired. Your flight was probably delayed, because you were flying into Chicago (hey, just keeping it real).  What you really want is some delicious, hearty food, and a relaxing drink.  Enter: DMK Burger Bar.

Located just off the Wellington stop on the Brown Line, here you’ll findmany a fine burger, as well as a ridiculously long beer list and a cocktailmenu full of new things to try. True, you will see a lot of plaid, but there’s already plenty of that in New England, right?  You must be used to it by now.  The hipster factor is well worth the experience, and the soundtrack ranges from high school pop-punk to the Black Keys without a skip. 

My favorite: I change my mind every time when it comes to the burgers, but you must not leave without sampling the fries, preferably all of them.

Look at those delicious, waistline destroying fries...ahhh.  On to the next!

Saturday:
Because you're doing this my way, we sleep in.  Yeah, you work a regular job that requires you to get up early in the morning, and so you wake up a couple of hours earlier than me, but whatever.  When we're finally all prepped and ready, we head down the the Armitage El stop and swing into Glazed and Infused in the lovely environs of Lincoln Park, home of some of the most delicious doughnuts I have ever tasted.  If we're in luck, they'll have a glazed blood orange doughnut (or six or seven) available.  After enjoying those on the shore of beautiful Lake Michigan, straight east of that doughnut haven, we'll head back to my neck of the woods for a quick rest.

After our restful moment, we can head out to grab a quick bite at Café Tola on Southport Avenue, home to some of the most delicious empanadas I've ever eaten.  My personal favorite is the goat cheese, plantain, and black bean empanada.  Eat a couple of those and you'll be perfectly ready for a night out on the town (drinking, I'm talking about drinking).

Then, we get dolled up and hit the town!  There are so many great (and crappy) bars in Lakeview and Lincoln Park that it's impossible to single them out, but my favorite way to get out on a Saturday night is to start in Lakeview and just see where the night takes you.  It's the way to be, and as long as you're with friends, the North Side is nothing but a good time.

Sunday:
Because it was the cheapest flight, you unfortunately have to head towards the train on the early side.  Because I'm me, I say, let me make you breakfast!  My new favorite breakfast is just a simple soft-boiled egg on a slice of toast smeared with a lemon herb aioli.  My current staple is from Stonewall Kitchen, which I pick up at Southport Grocery and Café.  It's just about my favorite thing to put on EVERYTHING.  And you'll love it, too.

I hope you all enjoyed your weekend with me, and if you're in the Chicago area, I suggest trying this itinerary yourself.