Photo: Songquan Deng/Shutterstock

Chicago has long drawn dreamers, strivers, hustlers, and hard workers from across the country and around the world, all hoping to make it in the Second City. That has created a town where people believe nothing is impossible. Chicagoans made a river run backward, invented the skyscraper, built political machines and notorious bootlegging syndicates, and ended up with a truly wonderful city. Along the way, they also made it a beautiful city set on a brilliant blue lake, with an emerald green river, world-class parks and museums, and a gleaming skyline as nice as you’ll find anywhere. Continuous waves of immigration have established vibrant neighborhoods and brought unique cuisines that change and fuse together as cultures intermingle. This guide to Chicago will set you on the path to discovering that story, the food, the neighborhoods, and the soul of the city.

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introduction

Chicago has long drawn dreamers, strivers, hustlers, and hard workers from across the country and around the world, all hoping to make it in the Second City. That has created a town where people believe nothing is impossible. Chicagoans made a river run backward, invented the skyscraper, built political machines and notorious bootlegging syndicates, and ended up with a truly wonderful city. Along the way, they also made it a beautiful city set on a brilliant blue lake, with an emerald green river, world-class parks and museums, and a gleaming skyline as nice as you’ll find anywhere. Continuous waves of immigration have established vibrant neighborhoods and brought unique cuisines that change and fuse together as cultures intermingle. This guide to Chicago will set you on the path to discovering that story, the food, the neighborhoods, and the soul of the city.

MATADOR GUIDES

General Tips

When to visit

The weather in Chicago is pretty unpredictable, and it’s impossible to say what it will be during any given month. Still, though, there are definitely better and worse times to visit. Summer in the city is when almost every Chicagoan would agree is the best time. From June through mid-September, we emerge from the shock of winter and really embrace the sun and warmth. Summer is when the beaches and lakefront parks are at their most inviting, and when vibrant neighborhood street festivals go down every weekend all around the city. Depending on your luck, summer can mean perfect days with the temperature in the mid-70s or sweltering steam room days in the 90s. 

Fall is probably the second-best season to visit. It’s less rainy than spring, and the city is excited for another (probably disappointing) season of Chicago Bears football. It’s usually still warm enough for most activities, and there are enough parks to see some beautiful fall foliage as well. Spring is hit or miss; the weather might be perfect, but it could also be sweltering hot or even snow as late as the end of April. 

Chicago winters can be brutal. From late January through March most Chicagoans are more likely to be at home with Netflix than out on the town. The holidays are nice though, and the Lincoln Park ZooLights and the holiday decorations and shopping along Michigan Avenue are a big draw.

Language

Chicago is a proudly international city and you can hear dozens of different languages spoken around town. Over 30 percent of the city speaks a foreign language at home, with Spanish and Polish being the most common. Just about everybody speaks English here though, and you won’t need any other language to get by. We definitely have our own slang here, but don’t worry, da Chicago dialect is pretty easy to understand.

Transportation

Chicago is a huge sprawling city but a lot of it is fairly walkable. The main sites downtown are easily reached on foot, and within neighborhoods you can usually get where you need by walking. We also have Divvy Bikes, a bike-sharing program with hundreds of stations around the city. Taxis are everywhere and are similarly priced to Uber and Lyft. 

Chicagoans complain about the CTA (Chicago Transit Authority) as much as we complain about Bears quarterbacks (that’s a lot, in case you don’t know). In reality, we actually have a pretty good public transit system of trains and buses that can get you pretty much anywhere you need in a reasonable amount of time, comfort, and safety. A Ventra card is essential for taking the bus and train, and you can even order one through the mail before your trip, which we recommend. Google Maps (and most other GPS apps) is pretty good about recommending the best way to get from A to B on the “L” or bus.

Safety

Chicago is nowhere near as dangerous as a lot of people like to claim. It’s true that some neighborhoods struggle with gangs and gun violence, but almost no visitor would ever find themselves in those areas unless they tried to get there. The areas where most tourists go are about as safe as can be, and venturing out into most of the more local neighborhoods is also pretty low-risk. If you’re going anywhere to visit a particular museum, bar, restaurant, or concert venue, it won’t be in one of the areas where gang violence is a major problem.

itineraries

Essential Chicago: Day One

Explore the best of downtown Chicago.

Essential Chicago: Day Two

Make time for parks and shopping.

Essential Chicago: Day Three

It's time to get out into the city’s surroundings.

The ultimate LGBTQ guide to Chicago

9 best bars for a late-night drink in Chicago

The 10 most fun things to do on the South Side of Chicago

The 8 best food spots only Chicago locals know about

The 10 best pizza places in Chicago

The 9 best venues for live music in Chicago

The 9 best Irish bars in Chicago

How to get around Chicago like a car-less local

Chicago’s 10 best spots for a picnic

The best coffee shops in Chicago right now

9 amazing things to do in Chicago that you won’t find in a guidebook

7 distilleries making great booze in Chicago

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