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Chicago Itinerary

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As a chicago lover, here is a perfectly curated list of things to do and places to eat and drink. I’ve been to many of these and I plan on going to more.
Map
Sections
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Restaurants

 
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You have to get the focaccia bread to start or the flaming burrata! I got the ricotta pillows for dinner along with a glass of wine! The vibes are impeccable!
etta | Neighborhood Italian Dining
 
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Their brunch menu is amazing! The italian benedict or swedish pancakes are so good, get a bellini or mimosa to wash it all down!
3 Arts Club Cafe at RH Chicago
 
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Try the arancini for dinner and affogato for dessert! They are to die for!
Acanto
 
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Try the momo royale, raspberry passion dessert and matcha cocktail! I highly recommend!
Momotaro
 
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You have to get the spritz purse and eat on the river! It’s a once in a lifetime experience!
Pizzeria Portofino
 
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They have really good brunch options such as chilaquiles, french toast and even chicken and waffles but even better dinner options! This restaurant is also on the river!
River Roast
 
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If you like seafood, this is the perfect place for you! They have so many options
RPM Seafood
 
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Cute place on the river for pictures! I absolutely love the vibes! They definitely have a variety of food! I really like the avocado hummus and cheeseburger!
Beatnik On The River
 
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You HAVE to try the prosciutto and egg pizza (I know it sounds weird but trust me it’s good)
Summer House Santa Monica
 
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You gotta get the truffle fries along with the calamari or dynamite shrimp to start! Get the lobster roll next genuinely one of the best menu items!
The Hampton Social - River North
 
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Best italian food in all of chicago! As a pasta lover, the vodka rigatoni was so good! Make sure you get the sticky date cake!
Trivoli Tavern
 
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Cute city view and good italian good! Again as a pasta lover, I loved this place! They have so many amazing options
Tre Dita
 
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Nice little mexican restuarant so cute! Their drinks are so good along with their appetizers! Perfect for a night out
Tzuco
 
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Best breakfast sandwiches in chicago! You need to try this place!
Doma Cafe
 
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You have to get the chicago dog, its a staple
Portillo's
 
Castaways Beach Club | 1603 North Lake Shore Drive, Chicago IL ...
 
Dimmi Dimmi | Italian Restaurant in Chicago, IL
 
Caché - Chicago's Most Exclusive Hideaway
 
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Get the banana espresso martini, so good!
DJ's Great Room | Neighborhood Bar & Restaurant in Chicago, IL
 
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Get the “girl dinner”, comes with your choice of martini, pasta, salad and fries!
Augie's
 
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My favorites are the avocado crispy rice, grilled avocado and japanese cucumber! Wash it all down with a lychee martini!
Miru - Miru Restaurant
 
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The chile-honey soppressata pizza is hands down the best pizza ever
Zazas Pizzeria | Chicago IL - Facebook
 
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The chimichangas, guava martini and mojito flight are my favorites
Havana Grill - Chicago

Drinks/Rooftops

 
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Overlooks Millenium Park and the bean
Cindy's Rooftop
 
Upstairs at The Gwen
 
Offshore Rooftop
 
Rooftop at Nobu Hotel Chicago
 
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If you go in the winter, they have a christmas pop up!
LH Rooftop bar - LondonHouse Chicago
 
 
The Aviary
 
HIDE+SEEK
 
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Cute little bar, they have a photobooth!
Gilt Bar
 
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Cutest place for cocktails and pics!
Crying Tiger
 
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If you're looking for some clubbing
Beauty Bar Chicago

Coffee shops

 
Nomad-Chicago
 
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Perfect little coffee shop! They also have pastries and breakfast options for on the go!
Goddess and the Baker, 33 S Wabash-Millennium Park
 
Happy Monday Coffee - Loop
 
Blue Bottle Coffee
 
Bad Owl Coffee Roasters
 
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The famous starbucks reserve is a must try if you’re in Chicago!
Starbucks Reserve Roastery
 
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BEST bagels in Chicago!
Gotham Bagels - Gold Coast
 
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Just like NYC, Chicago also has a Ralph’s coffee and it’s super cute!
Ralph's Coffee
 
Noble Fat (@noblefat) · Chicago, IL - Instagram

Things to do

 
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Looking for something to do? Look no further! Alice + Wonder has a hat patch bar where you ca pick your hat and patches to put on it!
Alice & Wonder - Webster
 
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Want to workout? Here’s a fun and cute idea! Rooftop yoga is one of my favorite things!
Deep House Yoga Experiences
 
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DIY face mask
Scratch Goods
 
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The most adorable yoga class!
Puppy Sphere | Puppy Yoga (West Town)
 
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So much fun in the summer! I’ve been to many classes and they never disappoint
Beach Yoga Chicago
 
The Playpen Chicago
 
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In the summer, rent a daybed and bring friends! The drinks and apps here are amazing and it feels like you’re on an island
Shore Club Chicago
 
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Looking for a spa day? AIRE ancient baths is an amazing option!
AIRE Ancient Baths Chicago
 
Millennium Park Ice Rink
 
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Get all your shopping done on the Mag Mile!
Magnificent Mile
 
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Fun club! They play all the throwback hits!
Joy District
 
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Such a fun club!!
Galería Chicago | Art-Inspired Nightlife & Events

Hotels

 
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Ive stayed here so many times, it has the best views!
Hotel in Chicago Downtown | Holiday Inn Chicago Dwtn-Wolf Point