36 Hours in Chicago

July 21, 2016

For those of you that don’t know, I actually grew up outside of Chicago. Aside from a short stint in London from ’94-’96, my childhood was spent in the beautiful suburbs of the great Windy City.

That being said, my parents moved to Colorado over two years ago and therefore I hadn’t been home in nearly three years until recently! Over Memorial Day weekend I had the chance to head home and see one of my closest high school friends get married and I soaked up a very short but sweet weekend in the city I love so dearly.

Today I wanted to share some of my must-not-miss spots for Chicago. I’m already hoping I can return soon so if you have recommendations for my next visit, I’d love to hear them in the comments.

How to Spend 36 Hours in Chicago

Where to Stay:

If you want to stay in the most ideal location to be central, book your room at The Westin Michigan Avenue. I loved that I was in walking distance from the beach along Lake Shore Drive, good shopping (hello, Nordstrom!! We don’t have one in NYC if you can believe it…) and some of my favorite sites (more on that below!) I always love the service provided at the Westin Hotels (they delivered me New Balances to head to a nearby Soulcycle class so I didn’t have to take up precious space in my suitcase packing sneakers!) and am personally a big fan of the Heavenly Beds. (Remember my delightful stay in Boston?) Never a bad experience so a major thanks to Westin for the stay (and the gorgeous view as seen above!)

The Westin Michigan Avenue Chicago

What to Do:

Chicago has no shortage of things to do but this time around I did a mix of old favorites and new spots I was curious to try. That being said I’ve sprinkled in a few things below that I didn’t do this time around but always recommend visitors to Chicago look into.

36 Hours in Chicago

Architectural Boat Tour: Hands down my favorite activity in Chicago. It doesn’t matter if you’ve done it a half dozen times, this boat tour along the Chicago River is just so fun. A wonderful ambiance with a sprinkle of historical fun facts, you’ll get to know so much about the city on one of these tours.

Chicago's Cultural Center

The Art Institute: I have such fond memories of trips into Chicago for field trips or with my mom to visit this gorgeous museum. I love it in particular because of its impressionist collection but the building itself is beautiful and always worth wandering in. Be sure not to miss the collection of dollhouse miniatures in the basement. It was (and remains) a favorite little piece of Chicago for me.

Chicago's millennium park

Millennium Park: I distinctly remember when Millennium Park was revamped and re-established as a place to visit in the city. The Bean was installed, the concert venue arrived and all of a sudden the Southern part of the Magnificent Mile had a new sparkle to it. I personally love the novelty of the Bean. I also have lovely memories from my summers in Chicago seeing concerts or movies in this park.

Spending 36 Hours in Chicago

Where to Eat & Drink:

Man, does this town know its food. From Chicago style hot dogs to brunch done right, I love Chicago’s food scene. My friend Angie in particular always knows the best spots and takes me to some stellar meals when I visit her. (She and I met when I was a little ol’ intern in Chicago the summer after my sophomore year in college! We worked at a very, very small ad agency and became fast friends and to this day remain close!)

Cindy's Rooftop

Cindy’s Rooftop: I had seen Cindy’s all over Instagram and can definitely see why given both A) their food and B) more importantly, their view! (See above). This spot has a great vibe up on the roof, is super light and airy and the outdoor terrace really cannot be beat. The menu features several “platters” meant to be shared and we dined on awesome French Toast and Chilaquiles.

Sweet Mandy B’s: This spot is home to my favorite Chicago cupcakes. They are so, so good! Imagine my delight when Katherine & Matt featured a dessert bar from this local bakery at their wedding #winwin. It is in one of my favorite neighborhoods in the city perfect for walking around and shopping. And while I’m partial to the cupcakes, I also love the lemon bars and cookies here. (I try really hard not to discriminate against desserts ;))

Bittersweet: This spot is a long-standing Donovan family go-to spot. We’d drive into the city and eat here before heading to spend an afternoon exploring together. The lunches are somewhat light (think salads and quiches) but as my mom has previously pointed out the only reason one lunches at Bittersweet is so you can have dessert immediately following. AKA: The French-inspired pastries are not to be missed.

Southport Grocery & Cafe: Early bird gets the food here. The lines get insane at this spot but man is their brunch to die for! The bread pudding pancakes are truly worth waiting for and I love the cozy ambiance in this place. I also really love to walk off brunch in the surrounding hood looking at all the beautiful homes.

Maple + Ash in Chicago

Maple + Ash: Angie and I dined at this spot which is new on the scene and we had such a great meal. The space is multiple floors and visually stunning. It reminds me of The Great Gatsby a little bit, in fact. The most memorable things we ate were the above dessert featuring whiskey bananas and rich chocolate (brb..drooling remembering it…) and the baked and loaded potato situation which I can’t even describe properly but just know it was out of this world. When upon leaving it was pouring outside we happily saddled up to the bar for another glass of rose. Twist our arms…

And if you have more time, I always love a drink at The Signature Room, lunch or dinner at RL Restaurant and breakfast at Milk + Honey.

Chicago, you are the best and I can’t wait to return soon! 

p.s. a guide to Nantucket and a New York staycation.

[All photography by Meghan Donovan]

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