Flights to Chicago, United States of America

Located in the state of Illinois in the American Midwest, Chicago is an international hub for commerce, finance, technology, telecommunications and transportation. Undoubtedly a global city, its cosmopolitan metropolis is buzzing with life and inclusivity.

Chicago is fairly easy to navigate. Right by Lake Michigan in the east is the downtown area, also known as the Loop. Surrounding it are the North, South and West Sides. Most famous travel sights are agglomerated in downtown, including signature buildings by Ludwig Mies van der Rohe and Louis Henri Sullivan.

Millennium Park is a different kind of town square, where you’ll find state-of-the art architecture, landscape design and art that provides the backdrop for a medley of cultural and family programs. The huge bean-shaped structure you see is Cloud Gate, known affectionately as ‘The Bean’. Dine in one of the Michelin-rated restaurants, pop into the Chicago Cultural centre to an amazing range of performance and visual arts, or simply shop till you drop on the retail paradise of State Street.

On the Northside are eclectic mix of neighbourhoods and one of the largest LGBT communities in America. Watch a baseball game in Wrigleyville, or boutique shop in Wicker Park and Bucktown. North Side is also brimming with bars and pubs, where you can enjoy live music nightly. In the Far North Side are many ethnic neighbourhoods where you can truly taste the cultural diversity of Chicago, as well as endless cuisines.

West side is generally known as the rougher part of town, although it makes for a worthy exploration if you are looking to sink your teeth in the real Chicago. Notable is the hipster enclave of Wicker Park. South Lawndale is practically a little Mexico, where you can enjoy sometaquerías amidst music and smiles on 26th Street.

South Side is where you’ll find the real Chicago blues. The creation of part-time street musicians from the 20th century migrant black community, the Chicago blues has travelled far beyond the boundaries of its hometown through the well-known likes of Muddy Waters and Koko Taylor. Pay homage to this genre at the Ruby Lee Gatewood’s Tavern, or ‘The Gates’ where virtually every big name played in the 1930s.

Overall, whether you’re looking to enjoy a few key attractions or really get into the heart of the city, Chicago is a good place to be. Just go with the pulse of the city, and, like everyone else who lives there, make it your own.

Getting around

The grid-like system of Chicago makes it easy to navigate, with avenues generally running north-south, and streets east-west. Avoid driving; the CTA operates an extensive and comprehensible system of trains and buses that will virtually take you anywhere you need to go. You can even track the bus schedule on the CTA Bus Tracker, which used a GPS to tell you when exactly you can expect your ride.

Getting to Chicago

The two international airports serving Chicago are O’Hare and Midway International Airport. The latter is less crowded, less notorious for delays and significantly closer to downtown. It is served by Air Tran, Delta, FlyFrontier, Porter, Public Charters, Southwest, Sun Country and Volaris. From here, the CTA Orange Line train takes you directly downtown in half an hour.

Flexible where you fly? Search nearby airports for bigger savings.

Airports near Chicago

Frequently asked questions

There are 4 airports in Chicago: Chicago O'Hare International, Chicago Midway, Chicago Rockford, and Chicago Dupage County.
Gulf Air, Norwegian, GoJet Airlines, Azul Airlines, Thai Airways, Avianca, Austrian Airlines and Frontier Airlines all fly direct to Chicago.
The cheapest month to fly to Chicago is November.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.