The lowest price for a flight from Pueblo to Chicago is currently $266. There are no direct flights from Pueblo, Colorado to Chicago, Illinois. The closest airport to Pueblo is Colorado Springs Airport (COS). The closest airport to Chicago is Midway Airport (MDW). As of March 2021, the only commercial flight option available is a one-stop flight via Phoenix Sky Harbor International Airport (PHX) operated by American Airlines. This flight operates twice a week on Mondays and Fridays. The best time to fly from Pueblo to Chicago is typically in the late morning or early afternoon, as this will minimize the amount of time spent in the air. You will also have the best chance of avoiding traffic delays, as well as arriving at your destination at the most convenient time. There are currently no commercial flight options available for direct flights from Pueblo to Chicago. The closest option for travelers is to take a direct flight from Pueblo Memorial Airport (PUB) to Denver International Airport (DEN) and then take a connecting flight from DEN to Chicago O'Hare International Airport (ORD). Yes, if you are not a US citizen or a permanent resident, you will likely need to obtain a visa in order to travel from Pueblo to Chicago. You should check the visa requirements of your destination country before traveling. 1. United Airlines
2. American Airlines
3. Delta Air Lines
4. Frontier Airlines
5. Allegiant Air American Airlines, United Airlines, and Air Canada all offer nonstop flights from Pueblo to Chicago.
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