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Chicago Must See and Eat
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items My Chicago must-sees and must-eats 🫶 I’ve spent plenty of time exploring the city throughout both my childhood and adult life, and these are some of my personal favorites! Whether you’re looking for the best places to eat in Chicago, Chicago bars an...
Sections
4
Food
Drinks
Activities
Lodging
Food
From Chicago brunch spots and local restaurants to quick bites, sweet treats and dinner favorites, there’s no shortage of incredible food in the city. These are some of my favorite places to eat in Chicago that are worth adding to your list! ✨
If you’ve heard Magnolia Bakery has some of the best banana pudding, I’m here to confirm it’s true 😂 And I do NOT mess around when it comes to banana pudding. If you’re looking for a sweet treat or dessert spot in Chicago, their famous banana puddin...
World-Famous Banana Pudding at Magnolia Bakery
If I’m in Chicago, I will actively go out of my way for an Ann Sather cinnamon roll ✨ They’re seriously some of the best cinnamon rolls in Chicago and an absolute must for me every time I’m in town. Their breakfast and brunch menu is full of plenty o...
Ann Sather Home
A Chicago brunch must! 🤍 Olio E Più is such a good spot if you’re looking for Italian food in Chicago, especially for brunch. We love the mimosas and apps, and the spaghetti carbonara and burrata are two of our absolute favorites. Definitely one to ...
Olio E Piú - Italian Restaurant in NYC, Chicago, Washington D.C.
Easily one of my favorite restaurants in Chicago! 🍽️ If you can, grab a seat at the bar. We got to watch all the food come out while we ate, and the staff was incredible about explaining everything to us along the way. The tuna tartare is a must-ord...
The Purple Pig Restaurant
Drinks
Chicago has no shortage of places to grab a drink, but sometimes the experience is half the fun 🍸 From unique Chicago bars and cocktail spots to creative drinks and memorable atmospheres, these are some of my favorite places to grab a cocktail in Ch...
One of the coolest cocktail experiences in Chicago 🍸 The Berkshire Room is tucked inside ACME Hotel in River North, and their Dealer’s Choice experience is what makes it a must-try. Choose your spirit, flavor profile and glassware, then let the bart...
The Berkshire Room
If you’re looking for creative cocktails in Chicago, Broken Shaker is such a fun River North spot to add to your list 🍹 Tucked inside Freehand Chicago, this cocktail bar serves up unique drinks with house-made syrups, infusions and fresh ingredients...
Broken Shaker at Freehand Chicago: Craft Cocktails and Casual Vibes | Freehand Hotels Chicago
If champagne is your drink of choice, Pops for Champagne needs to be on your Chicago list 🥂 This iconic Chicago champagne bar is such a fun spot for bubbles, cocktails and a night out in the city. Do yourself a favor and order the whipped ricotta wi...
pops for champagne
Activities
There are so many fun things to do in Chicago! From iconic Chicago attractions and must-see sights to museums, experiences and hidden gems, these are some of my favorite activities and places to visit while exploring the city.
Cocktails with one of the best views in Chicago? Yes please. ☁️ CloudBar at 360 CHICAGO sits 94 floors above the Magnificent Mile with incredible views of the Chicago skyline and Lake Michigan. Grab one of their Chicago-inspired cocktails and take in...
CloudBar at 360 CHICAGO: Bar at former John Hancock Center
A Chicago classic for a reason! 🐠 Shedd Aquarium is one of my favorite family-friendly things to do in Chicago, with so much to explore for kids and adults alike. If you love marine life or you’re looking for an iconic Chicago attraction to add to y...
Shedd Aquarium
If you love plants, add the Lincoln Park Conservatory to your Chicago itinerary 🌿 This free Chicago attraction is filled with tropical plants, palms, ferns, orchids and seasonal flowers, making it such a pretty escape in the middle of the city. It’s...
Lincoln Park Conservatory
Lodging
Where you stay can make all the difference on a Chicago trip! 🏨 From Chicago hotels and unique places to stay to convenient spots near some of the city’s best attractions, these are my favorite places to stay in Chicago.
Such a fun option if you’re looking for a unique boutique hotel in Chicago! 🏨 ACME Hotel has a quirky, artsy vibe with everywhere right in River North, just a couple blocks from the Magnificent Mile. Plus, with cocktails at The Berkshire Room and We...
ACME Hotel
One of the most unique hotels in Chicago! 🎨 21c Museum Hotel combines a stay in the heart of the city with an incredible contemporary art museum that’s free and open 24/7. It’s such a fun Chicago hotel if you want your stay to feel like part of the ...
21c Museum Hotels Chicago Museum