WebChicago Airports. When youíre looking to book flights to Chicago, Illinois, there are two airports that serve the Windy City. O'Hare International Airport is the main one, while … WebOctober. $259. November. $300. December. $257. January is currently the cheapest month to fly to O'Hare Intl. At this moment in time June is the most expensive month. These prices are determined by multiple factors and booking in advance can help keep costs down if your schedule is not as flexible.
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