Weekend Wanderlust in Chicago

by - 12:52 PM

While planning a winter getaway to Chicago seems a little risky, don't let the threat of freezing temps and high winds scare you. I recently spent a long weekend visiting friends in Chicago and the city did not disappoint.

My childhood (and adult) best friend Ashley has family in the city and when she and her husband decided to make a trip after the holidays, I knew I had to tag along. Luckily, they agreed to let me and our friend Pam join the fun.

The weekend was heavily focused around food, drink and family and I was definitely on board with the plan.

We had a delayed flight and started off the trip with some late-night burgers at Kumas Corner. It's a heavy metal kind of place with crazy toppings stacked high between pretzel buns. And luckily for me, you can substitute any beef patty with grilled chicken or a garden burger. I don't have a picture because it was so dark, but the restaurant definitely deserves a mention.

Saturday morning brunch at Cindy's Rooftop may have been my favorite part of the weekend. The family-style menu including chilaquiles and Nutella pancakes was everything I could've hoped for. Aside from good food, the main attraction of Cindy's is the rooftop view of Millennium Park and Lake Michigan.


Cindy's is a great spot to visit because, after brunch, you can head right down to Millenium Park to see the infamous Chicago bean. 


We then popped in the London House to steal another rooftop view and catch a glimpse of the icy Chicago River. We opted out of pricey cocktails at the LH Rooftop and instead went to warm up in Rossi's Liquors, possibly the darkest, dive-iest dive bar I've ever been to. And of course, I loved it.


We continued the weekend brunching (I highly recommend the Fried Egg Sandwich and Avocado Toast at Bernie's Lunch and Supper) and exploring different neighborhoods while stopping in every appealing bar we came across.

Another favorite of the weekend was Green Street Smoked Meats. Luckily we had Ashley's dad as our resident tour guide or else we may not have found this place at the back of an alley with an unmarked door. With long, wooden benches, rough brick walls and string lights hung across the entire beam ceiling, the place was perfect. I also like the mix of people - some working on computers with lattes, others grabbing lunch with the family, and then those of us sitting at the bar.

The barbecue looked and smelled delicious, but we were still full from and just came for a drink. The beer selection was impressive, but my Paloma cocktail did not disappoint.


And possibly the most important part of visiting Chicago is the pizza. After some debate, we decided to go to Pequod's to fulfill our deep dish cravings. The sauce was tangy and the cheese was plenty, but the real winner was the caramelized corn-meal crust. There's no doubt that I will be dreaming of this pizza until I can make it back to Chicago.


My Chicago weekend of brunching and barhopping was perfect, but I'm hoping to make it back for a weekend in warmer weather. Have any suggestions for places to see or food to try for my next visit? Let me know in the comments!

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