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A Long Weekend in Chicago
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items Chicago is a stunning city full of great architecture, culture and things to see and do! This list just barely scratches the surface of must visit restaurants with incredible food options, art and major points of interest, and some outfit ideas so yo...
Sections
3
Where to Eat/Drink
What to Wear
Things to See / Do
Where to Eat/Drink
Make sure you get a reservation and enjoy authentic, family style Italian eats! Do not miss the whipped ricotta and porcini risotto
Quartino Chicago - Quartino Ristorante & Wine Bar
This is a true fine dining experience! Oriole is a contemporary-American restaurant located in Chicago’s West Loop neighborhood featuring Executive Chef and Owner Noah Sandoval’s award winning tasting menu. Since Oriole’s opening in 2016, it has repe...
Oriole
After a career in customer service, John (Juan) Zaragoza decided he wanted to bring a bit of his hometown of La Barca. Jalisco to Chicago. After operating an underground restaurant in his empty house, he sold it and in October of 2007, rented out a f...
Birrieria Zaragoza | Home
A strong contender in the Chicago beef scene, this is worth the trip to visit! Bring cash and be prepared to never want Italian beef again unless its from here
Johnnie's Beef | Elmwood Park IL
This is not the deep dish pizza you would expect - instead this is a cracker-thin, tavern-style crust loaded up with all the goodness. Give it a try, I dare say its better than deep dish!
Home | Vito & Nick's Pizzeria Chicago
As one of the first restaurants on Chicago’s famed Restaurant Row in the West Loop, Stephanie Izard’s Girl & the Goat began in 2010 with a goal of serving bold, global flavors to our local community (and visitors!). Since then, our desire to trea...
Menu | Girl & the Goat Chicago | Chef Stephanie Izard
What to Wear
Looking cool and comfortable is the name of the game for visiting Chicago! These sweater pants will have you looking good and feeling like you didn't change out of your pjs
CashSoft Shaker-Stitch Sweater Pants | Gap
This is another pair of super comfy, super trendy pants that you can dres up or down for a day into night look!
Pull-On Straight Pants in Stretch Satin | Madewell
Its not secret that it can be very cold in Chicago! Bundle up in a cute sherpa in the windy city!
Women's Sherpa Jacket
I love the effortless look of these tailored pants. They are flowy and comfortable and would look incredible for a day of site seeing with a chunky sweater
The Harlow Wide-Leg Pant in Drapey Twill | Madewell
I love the little bow details on this sweater! Layer a basic long sleeve under it for a cute and warm look
Trendy Women's Knitwear Collection - Shop Now at SHEIN USA
I love love love the oversized buttons on this cardigan! Quince is high quality and so versatile
100% Organic Cotton Cropped Cardigan
A perfect staple sweater that acts as a blank canvas for accessorizing!
Ribbed Cotton-Blend Sweater | Madewell
A cute and comfy sneaker will go great with everything from dresses, to athleisre to tailored trousers! Your feet will thank you
Gazelle Bold Shoes
Things to See / Do
Take in the stunning city architecture from the rivers of Chicago! This trip is less than 2 hours and is a fun way to experience the gorgeous downtown area
CAC River Cruise aboard First Lady
See some of the most impressive art collections in the world! Dorp in to a sketching or art class, tour limited time exhibitions, and so much more!
Home | The Art Institute of Chicago
Come laugh until it hurts at a world famous club that has hosted the likes of Jimmy Fallon, George Lopez, Kevin Hart and so many more!
Chicago’s Best Stand Up Comedy Club | Laugh Factory
More commonly known as “the bean” the 110-ton elliptical sculpture is forged of a seamless series of highly polished stainless steel plates, which reflect Chicago’s famous skyline and the clouds above. A 12-foot-high arch provides a "gate" to the con...
Cloud Gate in Millennium Park
Test your nerves and fear of heights looking down over the entire city of Chicago from The Skydeck! Dine in the restaurant in the sky too for an even more unforgettable experience!
Skydeck | Things to Do in Chicago, Events, & More