Ultimate Weekend Guide to Chicago, IL

September 25, 2018


I've heard a lot of mixed reviews on the city of Chicago, never having personally been there myself. But, when given the opportunity to celebrate a close friends birthday there, I jumped at the chance. And I have to say, I'm in love! The (summer) weather was beautiful, the city was clean, the people were friendly, and there were so many options on what to do. So, I'm going to give you a breakdown on what's what to have the perfect weekend in Chicago.


Where to Stay


River North: This is the place to be! It's close to everything, from shopping, high-end bars, and the navy pier. This is where we stayed during my weekend in Chicago and we were smack dab in the middle of everything (touristy). Nothing we wanted to see or do was more than a mile away. So if you like the hustle and bustle and want to be close to everything there is to see, this is the neighborhood for you.

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Where to Eat


Wow Bao: If I'm being perfectly honest, the food...well the bowls... aren't that good. However, we got a voucher for a free meal, and nothing can beat free; and the restaurant itself was pretty cool. You order from a kiosk and then your name appears on a cubby for you to pick up your order. So if you're going to check it out, I recommend sticking to the baos.


Wildberry Pancakes & Cafe:  Breakfast is the most important meal of the day, and boy does this place know how to do breakfast. They have all sorts of specialty skillets, pancakes, french toasts, and coffees. The best part, it's right across the street from Millennium Park.

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Volare Ristorante Italiano: If you want delicious, authentic Italian food and wine, pay a visit to Volare. It's a cute, quaint little Italian Ristorante in the heart of downtown Chicago. They have everything Italian from homemade ricotta raviolis to veal parmigiana. 

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Where to Drink


LondonHouse: Seeing as we started every night out at LondonHouse, I would say this has to be my favorite bar. The drinks were a little overpriced, but we are in downtown Chicago, after all. But the views from this rooftop bar are breathtaking. You see everything, and all within the confines of a beautiful Victorian bell tower? This is a must see if you're in Chicago, even for a day.

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Untitled Supper Club: This speak-easy turned club is one you can stay entertained all night. They're most known for their whiskey library, which keeps the boys happy, and killer playlist, which keeps the girls happy. You can start the night with dinner and drinks and end it shaking your booty until closing. This place is a one stop shop for all night fun.

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Chicago Riverwalk: Well, this is just fun for the whole family! You have a wide variety of restaurants and bars to choose from while listening to blaring top 40's music and dodging happy hour-ers. But seriously, the riverwalk is very pretty and very fun. Just sitting outside for two minutes we were already approached by new friends.



What to See


Millennium Park: This is a first-timer's must see. You have to visit the fountain, walk through the park, and take a picture with the bean; and if you're lucky, there will be orchestra practice at the Jay Pritzker Pavilion.


John Hancock Center: This is the closest thing you'll get to Disney in Chicago. You get to wait in an hour and half long line, take the scariest elevator ride up 94 floors, and see a 360 view of Chicago, in this magnificent observatory. AND...If you're feeling really adventurous, and willing to fork over $8, you can have the thrill of your life on Tilt. Attached to the observatory is a thrill ride, where you stand in the windowsill and it tilts down toward the street, while you're 94 floors above street level.

Navy Pier: Another first-timer's must see. This is the Santa Monica of Chicago. It has shops, restaurants, a greenhouse? and a variety of bars with a beautiful view. 


Magnificent Mile: If you have time for shopping, this is where online shopping dreams come true. I, personally, hate online shopping! I like to feel fabrics and try things on, and the magnificent mile has a crazy amount of shops that you only see online (or in Chicago, apparently).  

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