Beginner's Guide to Chicago

Chicago can be daunting to first-time visitors. We get it. It's huge, has a long, rich history, and is home to so many great attractions. To help you embark upon your first-time visit to Chicago, we've put together a Beginner's Guide to Chicago, which provides some insider tips and need-to-knows that'll have you walking and talking like a Chicagoan by the time you check in.

chicago transportation guide

Getting Around Chicago

The El (short for the CTA's elevated train, which also includes subway trains) is Chicago's go-to mode of transportation. With seven train lines (not including the Yellow Line) that take riders to every corner of the city, the El offers a quick and inexpensive public transportation option. If you need to get out to the suburbs, Metra Trains from Union, Ogilvie, and La Salle Street stations provide comfortable transportation on a set schedule.

In downtown Chicago, you'll find no shortage of cabs. However, rideshare services like Uber and Lyft will help you help you explore the city with a few simple clicks.

For a more active trip to Chicago, take advantage of Divvy, Chicago's ubiquitous bikeshare service. With stations all across the city, Divvy's convenient bike rental stations make it easy to pick up one of their unmistakable blue bicycles, head towards your destination, and drop your bike at any Divvy station in the city.

Want more information about navigating Chicago? Take a look at our Chicago Transportation Guide for detailed directions from the airports, a step-by-step walkthrough for getting on the El, and other transit tips.

Chicago Transportation Guide

arial view of the chicago loop

Getting to Know Chicago

Architectural Boat Tours

Chicago is a huge city with a lot to offer, but, with a little planning, you can cover a lot of ground in no time. For a scenic, succinct, guided introduction to Chicago, don't pass up a 90-minute architectural boat tour, which provides a great glimpse into the city's history, culture, and atmosphere.

CityPASS Chicago

For an amazing tour of the city's world-class museums and attractions, purchase a Chicago CityPASS, which gives you VIP access to the Field Museum, Sky Deck, Shedd Aquarium, Art Institute, and other iconic destinations.

With a Good Meal

But perhaps the best way to get to know Chicago is with a great meal. Whether you're grabbing a quick Italian beef or indulging at a Michelin star restaurant, you'll find no better expression of Chicago's vibrant, eclectic, and welcoming culture than in the city's restaurants.

guide to the best restaurants in chicago

Eat Like a Local

Deep dish pizza is a right of passage, but Chicago has so much more to offer. While Italian beef sandwiches and Chicago-style hot dogs are essential to an authentic dining experience, the city's farm to table restaurants, amazing taquerias, legendary steakhouses, and creative and eclectic neighborhood spots are the heart and soul of the Chicago dining scene. Take a look at our River North dining guide, treat yourself to some Chicago staples, and experience the city one plate at a time!

River North Dining Guide

best cocktail bar in chicago

Drink Like a Local

Chicago is a city that loves to eat, but it also features some of the country's very best beer, cocktail, and coffee scenes. During your visit, make sure to sample the city's best local liquids.

Locally Roasted Coffee

During your Chicago adventure, kick off your day with freshly-roasted coffee from some of the country's most acclaimed and innovative roasters like Intelligentsia, Dark Matter, and Metropolis.

Chicago Craft Beer

After a jam-packed morning of Chicago sightseeing, duck into a great local bar, get off your feet for an hour, and grab a beer (or two) from one of the city's world-class craft brewers. You can't go wrong with Half Acre's Daisy Cutter, Revolution's Anti-Hero, or Off Color's Apex Predator. If you feel like delving deeper, don't overlook beers from Pipeworks, Three Floyds, or Marz.

A Cocktail Renaissance

Spending a night on the town? Make sure to order a cocktail made with locally distilled spirits. Letherbee Gin is a favorite in these parts, but you can't go wrong with whiskeys from Koval or anything from Few. For a truly singular (and courageous) Chicago drinking experience, order yourself a shot of Jeppson's Malört, Chicago's divisive, love-to-hate, puckeringly bitter wormwood liqueur. You might deplore it, but it's a true Chicago rite of passage.

chicago art and theatre district

A Home for the Arts

Despite its hard-working reputation and passion for food and drink, Chicago is also one of the nation's most eclectic cultural hubs. From Ernest Hemingway to Gwendolyn Brooks, Bill Murray to Chance the Rapper, and Muddy Waters to Wilco, Chicago boasts a storied, eclectic, and inspiring cultural landscape. During your visit, see a play at the Goodman Theatre, attend a performance at the gorgeous Auditorium Theatre, catch a show at local venues like the Hideout or the Empty Bottle, or spend an unforgettable, jazz-filled evening at the legendary Green Mill Cocktail Lounge in Uptown.

chicago cubs at the art institute

Chicago Sports Culture

Chicago loves its hometown teams. The rivalry between the Cubs on the Northside and the Sox on the Southside can get heated, but we all come together for our true love: the Chicago Bears. For a truly Chicago experience, catch a Blackhawks game at the United Center. From the national anthem to the final horn, the Madhouse on Madison boasts an inimitable electricity that'll turn a casual hockey fan into a Blackhawks die-hard.

winter in chicago

Chicago's Weather

How can one talk about Chicago and not mention the weather?

Chicago has developed a reputation for its infamously harsh winters. While they can be cold (and so, so long), they're actually quite manageable with a warm coat and a good pair of boots. On the other hand, Chicago's summers are a thing of beauty. Between its cool lake breezes, amazing street fests, and a vibrant, fun-loving energy, Chicago shines during the summer.

Check Out Our Favorite Autumn Activities

Check Out Our Favorite Winter Activities

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