Chicago Brunching at Cindy’s Rooftop

Feb 9, 2016

mimosa brunch

Who isn’t up for some fabulous Chicago brunching every now & again. I know I had mentioned last week I was headed to Cindy’s on the Rooftop on instagram and I am happy to report it didn’t disappoint. It’s so hard to muster up the courage during Chicago winters to get out in the cold and make it somewhere but I was so happy to sneak some much needed girl time in with some of my favorite ladies. Kelly was so sweet to organize everything for us and easily booked our reservation through the DINE app. If you haven’t used it, it’s kind of amazing and let’s you in on the good spots to grab a bite to eat while allowing you the option to pick a reservation at the same time.

Cindy’s is at the top of The Chicago Athletic Association and I had never ventured down there before. It’s right behind Millennium Park and The Bean and the rooftop restaurant is stunning. I was hoping the food lived up to the ambiance and it definitely did. They have an amazing deck that has couches surrounding fire pits and would be the perfect happy hour spot during the summer.

We dove right in and ordered almost every indulgence on the menu. The plates are all for 3-4 people so it’s perfect to share and get a little taste of everything. I am more of a savory breakfast person than sweet but I loved having a bite of the french toast at the end. The drinks were equally as good and since I was off Whole 30 I indulged in a mimosa but the spicy bloody mary looked equally as yum! As far as food here are a few of my favorites:

Salt & Pepper Biscuits: I can NOT stop dreaming of these biscuits. I don’t know if it was because it was my first taste of butter and carbs in a month but I will be back just for these! They came with a side of homemade jams and butter that were to die for.

Cast Iron Chilaquiles: A spicy take on a breakfast food that is always one of my favorites. I especially loved the salsa verde they had on top!

Cinnamon Raisin Brioche French Toast: So yum! I am a huge fan of cinnamon raisin toast – my mom used to make it for us all the time as kids so this tasted just like home to me.

We stayed and enjoyed the atmosphere all afternoon and I highly suggest a visit here! The next time we have friends and family in town we will be back – it’s the perfect place for people to enjoy downtown without being at a stuffy high scale restaurant you would usually find in River North! Let me know if you try it and any other good spots you know of downtown, I am always at a loss down there!

PS: don’t forget today is the last day to enter the giveaway for your own Terracotta NY scarf – details here!

cindy's rooftop

cindy's rooftop restaurant

craft cocktail

homemade biscuits

bloody mary

homemade biscuits


french toast



cindy's rooftop


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  1. Sed Bona says:

    Oh it all looks so good! I STILL haven’t been here for brunch despite being here many times for cocktails in the evening. Must go if only for the kombucha menu!


    Ashley || Sed Bona

  2. Ianne Cabangon says:

    Must try this, we are planning a trip to chicago next month. Thanks for sharing!
    Xo, Christianne

  3. Anna Baun says:

    I’ve been meaning to give Cindy’s a try! The food looks amazing and the view is perfection! So glad you girls had a great time! XO

    A Lily Love Affair

  4. What a gorgeous restaurant! I’m going to tell my Chicago friends to try it.