Chicago

Chicago skyline viewed from the North Avenue Beach Pier on Lake Michigan

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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.