Chicago, IL

Best time to visit Chicago

• Spring (April to June): Ideal for nature lovers as parks and gardens burst into life.
• Summer (July to August): Chicago’s festival season with numerous concerts and events. It’s also peak tourist season, so expect larger crowds and higher demand for hotels.
• Fall (September to November): Cooler temperatures, colorful trees and events like Chicago Gourmet and the Chicago International Film Festival.
• Winter (December to March): Chicago transforms into a holiday wonderland, perfect for ice skating at Millennium Park. Snow and cool temperatures may mean some attractions are less accessible, so be sure to plan ahead.

How many days to spend in Chicago

Spend two to three days in Chicago and you’ll have time to take in the top attractions and enjoy a river cruise. Extend your stay to five to seven days to explore Evanston’s lakefront or head to Oak Park for its historical charm and architectural tours. Additionally, consider a day trip to Lake Geneva for watersports, boutique shopping and local dining.

The vibe of Chicago

Chicago natives are known for their mix of grit and generosity, blending urban sophistication with a homespun charm. Locals are welcoming and take pride in their rich cultural heritage and neighborhoods, so be prepared to make new friends. Chicagoans are passionate sports fans with a deep love for teams like the Chicago Cubs (MLB), Bulls (NBA), Bears (NFL) and Blackhawks (NHL). Game days in this city are special, so book tickets to an iconic sports ground like Wrigley Field or simply head to the nearest sports bar to experience Chicago at its fun-loving best. These places get seriously busy, so even if you’re not a big drinker, if you're settling in for a few hours for the game, make sure to tip accordingly.

What is Chicago famous for?

Chicago is famous for being the backdrop of several blockbuster movies, from Ferris Bueller’s Day Off to Home Alone, so many streets and neighborhoods may feel familiar for first-time visitors. Take a Downtown T.V. and Movie Sites Walking Tour and visit iconic locations from some of the hundreds of movies and television shows that have been filmed here. The city’s influence on popular culture also extends to music, from the birth of Chicago Blues, with legends like Muddy Waters and Bo Diddley, to the present-day hip-hop scene which keeps the city on the musical map. Jazz and blues clubs draw old-school music lovers from all over the world, while huge outdoor festivals like Lollapalooza keep things fresh for younger audiences.

Events in Chicago

This fun-loving city features a jam-packed calendar, so why not time your vacation with a Chicago event, festival or parade? Each summer, music lovers pour into the city for the Chicago Blues Festival (June), Chicago Jazz Festival (August) and Lollapalooza (August). Love a parade? Don’t miss the dazzling display of green at the St. Patrick’s Day Parade (March), where the city goes all out with festive floats and the dyeing of the Chicago River. Chicago Pride (June) turns the streets into a river of rainbows, while the Thanksgiving Parade (November) features giant inflatables and marching bands. Foodies can savor Chicago Gourmet (September), while film buffs are spoiled for choice at the Chicago International Film Festival the following month.

Food in Chicago

You will not go hungry in Chicago. The city’s food scene ranges from old-school favorites to avant-garde gastronomic adventures. Chicago has a knack for taking classics to the next level, whether it be the humble doughnut, hot dog or Italian beef sandwich. However, the best example has to be pizza, which has been supercharged into the city’s go-to meal – deep-dish pizza. Generations of immigrants have helped shape the city’s food scene, so expect everything from Puerto Rican jibarito (a type of sandwich), succulent Irish corned beef and Swedish cinnamon rolls. One of the best ways to lift the lid on Chicago’s food scene is to take one of the city’s walking food tours which, as you’d expect, come in a mouthwatering variety of themes and flavors.

Nightlife in Chicago

Chicago has had a great nightlife scene ever since the ragtime dance craze exploded in the 1890s, and today it’s still a scene-setter when it comes to nights out. At clubs like the House of Blues, The Bassment and Kingston Mines, discover why no place plays the blues quite like Chicago. Bar hopping more your thing? Follow the cool hunters to Wicker Park for chic lounges, indie venues and friendly dive bars. For LGBTQ+ vibes, Northalsted serves up drag shows and DJs in an inclusive, welcoming atmosphere. Whether you’re looking for speakeasies, rooftop bars, jazz clubs or house music parties, the Windy City won’t disappoint. Grab an entertainment guide on arrival to plan your late-night adventures.

Shopping in Chicago

Pack light, because Chicago is a shopper’s paradise mixing high-end, designer and one-of-a-kind finds. State Street’s historic shopping district features flagship stores like Macy’s as well as local independents. For luxury brands, head to Oak Street and The Magnificent Mile on Michigan Avenue. For a more eclectic experience, explore the shops in Lincoln Park and Wicker Park, where you’ll find vintage boutiques and record shops galore. Foodies will love the French Market for gourmet treats and artisanal goods. And, when it comes to souvenirs, nothing says Chicago like a jersey or merch from one of the city’s iconic sporting teams.