TicketScanner Discover Travel

Flights · United States

Cheap Flights to Chicago

Country
United States
Airport code
ORD
Nonstop from
19 cities
Route guides
24 cities
Chicago skyline viewed from the North Avenue Beach Pier on Lake Michigan

Chicago sits on the shore of Lake Michigan, and that lake shapes nearly everything about visiting, from the skyline views to the wind that gave the city its nickname. Two airports serve the city: O’Hare International, one of the busiest hubs in the country roughly 17 miles from downtown, and Midway, smaller and often cheaper, about 10 miles southwest.

Two Airports Means More Ways to Save

Because O’Hare and Midway compete for the same routes, comparing both airports on the same trip dates can turn up a meaningfully cheaper fare, especially on domestic routes where budget carriers lean toward Midway. The Blue Line (from O’Hare) and Orange Line (from Midway) both run directly into the Loop on Chicago’s elevated train, the L.

Lake Effect Weather, Both Ways

Lake Michigan moderates summer heat near the shoreline but adds a real bite to winter wind, which is a large part of why Chicago earned the Windy City name. July and August bring peak lakefront season and the highest fares, tied to festivals like Lollapalooza and Taste of Chicago, while January and February regularly bring the cheapest tickets of the year for travelers prepared for genuine cold.

Once You Land

The L connects both airports directly to downtown, and most of the Loop, Millennium Park, and the Museum Campus are walkable once you’re there. Many visitors handle a Chicago trip entirely on transit and on foot.

Search live fares to both O’Hare and Midway above and compare which airport gets you the better deal on your dates.

FAQ

Chicago flights, answered

Is there a direct flight to Chicago?

Yes. Nonstop routes exist from Atlanta, Boston, Calgary, Detroit, Dublin, Halifax, IAH, Las Vegas, London, Mexico City, Minneapolis, Montreal, Paris, Quebec, Salt Lake City, SAN, San Francisco, Toronto, Winnipeg. Other cities may also fly direct; search above to check from your own airport.

When's the best time to visit Chicago?

Month-by-month guide to flying to Chicago: cold, windy winters and lake-cooled summers, the festivals, marathon and conventions that drive hotel prices, the cheapest and busiest windows, and how to get downtown from O’Hare and Midway.

Do I need a rental car in Chicago?

Whether to rent a car in Chicago or rely on the ‘L’, buses, Metra and Divvy: how the city grid works, CTA fares and the 24-hour trains from O’Hare, what driving, tolls and parking really cost, when a car is worth it for Midwest road trips, and a decision table by trip type.

Which airports serve Chicago?

Chicago is served by O’Hare International Airport (ORD). Our airport guides cover terminals, ground transport, and parking for each.

Where can I fly to Chicago from?

You can search flights to Chicago from any airport. We also have route guides from 24 cities, including Atlanta, Boston, Cancun, Dallas, Denver, and Detroit, each with a live search and recent fares where available.

Can I also compare hotels in Chicago and car rentals in Chicago?

Yes. Our hotels and car rentals pages for Chicago each have a live search, so you can plan the whole trip in one place.