A Perfect Weekend in Chicago by a LocalChicago is FILLED with amazing sights to see, unique neighborhoods to check out, and even after 20 years of calling it home I still have spots to explore. Here is how to make the most of your next weekend trip in Chicago, according to my "local expertise." Authorskatherinebeard
DestinationsChicagoItinerary

Friday

Loews Chicago Hotel
Check into one of my favorite Chicago stays, right on the Riverwalk, complete with inhouse restaurants (yes, plural). I am obsessed with their on-site coffee shop: For Five Roasters.
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Warwick Allerton - Chicago
A more budget-friendly stay located right on the Magnificent Mile, making exploring by foot and public transport super easy.
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Wildberry Pancakes & Cafe
For a quick lunch or brunch, this is THE Chicago pancake spot. They whip up delicious biscuits and gravy, along with traditional, fluffy pancakes.
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The Chicago Theatre
You have to stop by this photo-op on your way to dinner!
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Bavette's Bar & Boeuf
Head to (IMO) the BEST steakhouse in Chicago. Their steak frites & ribeye cuts are divine!
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Saturday

Firecakes Donuts
Start your Saturday by fueling up at Firecakes. Right now they have doughnuts inspired by "The Bear!"
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Oak Street Beach
Head to the beach! In the summer this is a great spot to roast under the sun, take a cool dip, and enjoy skyline views... In the winter, the lake often creates what I like to call "icebergs" along the shore!
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Portillo's & Barnelli's Chicago
I always need to make a pit-stop at Portillo's when I am home for a slice of their deliciuos chocolate cake. They also serve TRUE Chicago hot dogs!
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Lake Michigan Sunset Cruise in Chicago
Book the Sunset Lake Cruise along Chicago shores using this link!
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Wendella West Docks (3 & 4)
One of my favorite ways to see the city! Book a Sunset Lake Cruise through the Viator link above^
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Pops for Champagne
A Chicago staple, this champagne bar has been a favorite for 40 years now. Grab a glass of champagne and side of oysters to celebrate your stay!
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TAO Chicago
If you want a taste of nightlife, head to the TAO shows and club. Make sure to dress accordingly.
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Sunday

Fairgrounds Craft Coffee and Tea
Start your day with locally brewed coffees, right across the street from the Bean and Millenium Park.
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Cloud Gate
No trip is complete without a selfie in the Bean, more formally known as the "Cloud Gate."
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Millennium Park
Wander around Millenium Park, exploring the Lurie Gardens, Amphitheatre, and skyline views for the afternoon.
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Cindy's Rooftop
Come up to Cindy's for rooftop views overlooking Millenium Park and a delicious lunch service.
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Nichols Bridgeway
Head up the Nichols Bridgeway for views of Michigan Avenue. This is one of my favorite sneaky photo spots and it leads right up to The Art Institute.
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The Art Institute of Chicago
Admire famous paintings, check out limited exhibits, and wander around one of the most famous art museums in the country. Growing up in Chicago, this has always been one of my favorite spots for a taste of culture!
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The Dearborn
A short walk from the Art Institute, this spot has modern American fare and craft cocktails. I LOVE their burgers! It is a relaxed way to end your weekend in Chicago!
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