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Refined and Enhanced

To give you the most unique and exciting travel experiences, the Utrip team curates each destination with a combination of human expertise and artificial intelligence. We’ve done the heavy lifting and sorted through thousands of activities, restaurants, and nightlife so that you don’t have to. Our Refined & Enhanced destinations include original content and local recommendations, providing a special touch so that you can plan your perfect trip. Learn more about the Utrip process.

Overview

Chicago is a titanic city. Its history is laced with an astounding mix of upstarts, extravagance, and moxie. From its roots as a trading town, Chicago emerged as  the cultural hub of the Midwest, and despite historic hardships like the Great Chicago Fire and the gang violence of the Prohibition Era, Chicago is a city that’s always managed to come out on top. Now, it brandishes some of the most exquisite fine dining, the most revered museums, and architecture it actually wrote the book on, Chicago has established its own greatness. It’s a city that refuses to sit still, and is a city with so many places to uncover.

Chicago’s always been at a crossroads—which, admittedly, comes in handy when playing the blues. It’s arguably the greatest railroad hub in the United States, and with this crossing of cultures, Chicago has become one of the world’s great urban icons. While the Roaring Twenties and the Great Chicago Fire pockmark Chicago’s past, it’s a city that’s awash with astounding artistic and cultural contributions; from the Chicago School of architecture (responsible for the first skyscraper) to Chicago blues, there are so many things The Windy City has bestowed on the world. Hoping to explore the city for yourself? Walk around one of the 77 neighborhoods and explore. Just don’t forget to check out the amazing museums, art galleries, parks, and local haunts while you’re at it. And if that’s not your scene, try something else! You can always kayak, drop into a brewery, or even ogle over the amazing public art that’s all over town. 

Let’s face it: there are plenty of stones to overturn looking through Chicago, and you’re bound to work up an appetite doing so. Thankfully, you’re in good hands—culinarily speaking, of course. Whether you’re looking for ultra-modern restaurants brandishing three Michelin stars, or you want some of the best street food you can find anywhere (Italian beef sandwich anyone?), Chicago has the cuisine that will most delight you—and maybe expand your gastronomic horizons. And when you’re done sampling, duck in somewhere and hole up for the evening; catch a show, be enhanced by the world-class performing arts, or laugh your way to a six pack at one of the many comedy clubs in town. And whether you’re looking for a rowdy dance club, a laid-back wine bar, a speakeasy, or even an 80s-themed, arcade-adorned nightspot, Chicago’s a town that doesn’t mind you staying out for a nightcap. So go ahead: indulge!

There are great cities, and then there’s Chicago. This lakeside icon has grown from humble roots into a metropolitan iconoclast. It’s a city with its own rules, and a city that has defined and redefined itself generation after generation. Dive into its history and see what’s made this place so legendary; immerse yourself in its art, discover it’s astonishing cuisine, and find your own niche while you’re here. Before long, you may just realize that Chicago is both an amalgam of iconic Americana and international greatness; it’s an all-American city, and a city for the world.

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Pilsen Latin American Cuisine

Hub for Authentic Latin American Fare

Wrigley Field

Historic Ivy-Covered Home of the Chicago Cubs

Yvolina’s Tamales

Restaurant

The Corned Beef Factory Sandwich Shop

The Corned Beef Factory Sandwich Shop

Willis Tower

Famous Chicago Skyscraper

Pollo Express

Pollo Express

Cuba 312

Cuba 312

J.P. Graziano Grocery

J.P. Graziano Grocery

The Art Institute of Chicago

A World-Class Art Museum in the Heart of Chicago

The Jibarito Stop

The Jibarito Stop
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