KAT'S Hometown Guide to ChicagoGrowing up in Chicago meant a lot of exploring downtown... There is so much more to see and do beyond this list, but these are a few of my iconic favorites and hidden gems along the way! Authorskatherinebeard
DestinationsChicagoItinerary

Stays

The Royal Sonesta Chicago Downtown
An elegant, modern hotel right on the Riverwalk with decorative nods to Chicago history and an onsite restaurant, Hoyt’s. Give their watermelon feta salad a try. Book their Fitness Suite for spacious, luxury accommodations (complete with a personal gym setup!!)
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Hoyt's Chicago
Connected to the Royal Sonesta, this restaurant serves upscale “American” cuisine. Try their watermelon feta salad in the summer!
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Loews Chicago Hotel
A luxe stay right on the river, the Loews has everything you need onsite from sleek rooms, to a coffee shop, fine dining restaurants, and more!
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For Five Coffee Roasters
Just one of the three onsite restaurants, this spot makes delicious coffee! It’s perfect for guests on the go who need a quick pick me up ☕️
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Streeterville Social
This rooftop (part of the Loews Hotel) has laidback vibes, perfect for a nice day in Chicago. Try their Lime in the Coconut cocktail or grab a happy hour frose 🍹
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Hampton Inn & Suites Chicago-Downtown
A family-oriented stay just blocks from downtown! Complete with free breakfast, an onsite pool, fitness area, and connecting rooms, you’ll be all set for a trip to Chicago with their amenities and super friendly & helpful staff.
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OLIO E PIÙ
Connected to the Hampton Inn and Suites, this onsite restaurant is dreamy from its elegant decor to its fresh pesto gnocchi.
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Warwick Allerton - Chicago
Right on Mag Mile, this stay is super convenient for exploring the city or a shopping trip! Their Petite Classic room is small, but perfect for solo travelers or couples.
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Eats & Drinks

J.P. Graziano Grocery
if you’re looking for a lunch spot that will get you in and out this is it! Try their Italian sandwich and make sure to ask for the giardiniera 🤌🏻 and pair it with a fresh cannoli!
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Bavette's Bar & Boeuf
Arguably one of the best steakhouses in Chicago, this spot is absolutely swanky and feels very high class. Their fattier ribeye cuts are packed with flavor! If you’re a cocktail person, try their perle blanche 🍸
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Pops for Champagne
This iconic champagne bar is perfect for any celebration! 🎉 They have a host of champagnes by the glass, half, and full bottles 🍾
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Garrett Popcorn Shops
An iconic Chicago bite… Get the Garrett’s Mix here, the perfect combination of sweet carmel corn with cheesy popcorn. Perfect for an afternoon snack!
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Firecakes Donuts
My favorite doughnut spot in Chicago! Their glazed is so light and fluffy 🍩
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Fairgrounds Craft Coffee and Tea
Using locally sourced beans, this coffee shop is the perfect spot for a pick me up!
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Philz Coffee
Started in LA, but with cafes in Chicago now, they have one of my favorite coffees on the go. Each cup is brewed to your liking!
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Aba
One of my favorite spots for ~fancy~ drinks and dinner. They have a delicious Mediterranean inspired menu. The Hugo Spritz is one of their amazing, delicious, refreshing cocktails 🍸 or get an espresso martini to end the night.
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Streeterville Social
This rooftop (part of the Loews Hotel) has laidback vibes, perfect for a nice day in Chicago. Try their Lime in the Coconut cocktail or grab a happy hour frose 🍹
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Beatrix
Beatrix is a coffee shop, restaurant, bar, and market all in one! It’s everyone’s favorite local spot for a meeting, date, or catch up with a friend!
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Portillo's & Barnelli's Chicago
Make sure to grab yourself a true Chicago hot DAWG… no ketchup allowed here 🥫
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m.henry
Just outside downtown, this is one of my favorite brunch spots! It has a homey interior and the portions here are HUGE and SO yum. Order their French Toast for a real morning treat!
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Erie Cafe
A classic Chicago style supper club with a huge selection of wines and steak cuts. Get ready for a filling meal here!
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Hannah's Bretzel
Quick and easy lunch spot for on the go sandwiches. They use pretzel buns here 🥨 The seasonal sandwiches are 🤤
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Things to See & Do

Navy Pier
one of my absolute favorite summer spots to admire the lake and grab a slice of pizza
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The Chicago Theatre
An iconic Chi Town photo spot 📸
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Nichols Bridgeway
My favorite photo spot in all of downtown! Such a hidden gem.
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Riverwalk
The Riverwalk is a great spot for a morning walk/run, evening happy hour, or picnic lunch during the summer! During the wintertime stand atop Monroe Bridge to watch the ice chunks float on the blue-ish-green waters.
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Millennium Park
A green space and hub in downtown Chicago complete with live music, the Bean, gardens, and more! It’s a great spot to explore during any season.
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Cloud Gate
More commonly known as "the bean" by locals, this sculpture/installation is an iconic, must-visit. Make sure to take a selfie in the mirrored surface with the skyline in the background. Pro tip: get up and go early (8:00 a.m. or earlier) to avoid large crowds.
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Wrigley Field
Going to a Cubs game is the real way to see Chicago pride! Pro tip: sit in the bleachers for great energy and views of the game!
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Sports World
If you forgot your Cubs gear, don't fret! This spot has all the gear you've ever dreamed of... Pick up a personalized jersey or a cap for the game. Pro tip: check out their sale section for great caps 🧢
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Gin Alley
This is a hidden gem in the Fulton Market District! Grab drinks or a meal at Trivoli or Green Market Meats.
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Harold Washington Library Center, Chicago Public Library
Head to the 9th floor to see the "Winter Garden" here.
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North Avenue Beach
One of my favorite photo spots in all of the city. Head here on a clear morning for saturated sunrises, morning dips, picnic lunch, or an evening stroll. Walk out onto the "ledge" area for amazing photos of the skyscrapers!
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Lake Michigan Sunset Cruise in Chicago
One of the best ways to see the Chicago skyline is on the sunset cruise through Lake Michigan. Sit in the back left (or right) corner of the rooftop boat area for some of the best views and photo-ops.
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Wendella West Docks (3 & 4)
Book this tour with the link above! It’s such a fun evening activity in the city before a late dinner. Watch as the lights come on in all of the skyscrapers 🌃
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Lincoln Park
A favorite running spot and lush park just outside of downtown. Lincoln Park has a beautiful architectural structure overlooking the skyline and manicured landscaping all year long. There are amazing restaurants and coffee shops around here too!
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Lincoln Park Zoo
One of 3 FREE zoos in the country, Lincoln Park Zoo is great at any time of year. During the summer, soak up the sunshine or in the winter admire the twinkling holiday lights here ✨
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Oak Street Beach
Morning dips here can’t be beat! Oak Street is a great spot to beat the Chicago heat in the summer or admire the floating “icebergs” of Lake Michigan in the winter. There are even beach volleyball courts.
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Fulton Market District Gateway
Fulton Market is the trendiest neighborhood in Chicago right now! It is home to so many great restaurants and bars: Aba, Beatrix, JP Graziano’s, Levain, and more!
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Flamingo - Alexander Calder
One of my favorite photo spots! The red from Calder’s Flamingo is such a pop of color amidst the city streets.
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Magnificent Mile
The best place to pick up essentials in Chicago… it has all of the shops from Nordstrom, Aritzia, and Brandy, to the cool new Converse pop up!
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The Art Institute of Chicago
One of the most extensive art collections in the world, the Art Institue is always a favorite when I am back home! Check out their featured exhibits during your next visit.
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The Salt Shed
The best new, outdoor venue for concerts in the city.
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Crown Fountain
Splash in the waters here during the summer or admire the portraits during the winter. This iconic & interactive art installation is a must-see when in Chicago.
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Lurie Garden
Inside of Millenium Park, this garden area is an oasis from the skyscrapers of downtown anytime of year. They plant seasonally, so come enjoy a stroll or a well-deserved seat amidst the vegetation here.
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