✈️ Flight Guide: Denver (DEN) → Chicago (ORD)

November features several events that can affect DEN–ORD travel. In Denver, the Denver Film Festival generally runs in early November and ski areas near Aspen and Vail may begin limited operations, driving demand for airport transfers. In Chicago, the Magnificent Mile Lights Festival and the seasonal Christkindlmarket often occur in mid-to-late November, increasing hotel and airport demand. These events drive spikes in fares and ground-transport demand—book flights and local transfers early and allow extra time for arrivals and departures.

The best time to fly DEN to ORD in November is early in the month or midweek (Tuesday–Thursday) when fares and crowds are lower. Avoid the Wednesday before Thanksgiving and the Sunday after Thanksgiving if you want to minimize delays and high prices. Early-morning flights reduce the risk of cascading weather-related delays, while late-night red-eyes can offer lower fares but may be less convenient for travelers connecting to local ground transport.

On the relatively short DEN–ORD route, nonstop flights are usually the best choice in November: they save time, reduce the risk of missed connections during winter weather, and are often competitively priced. Connecting flights can be cheaper on some dates but add travel time and increase the chance of delays during snow or de-icing operations. If you are using loyalty benefits or traveling to secondary destinations beyond ORD, a connecting flight might make sense—otherwise opt for nonstop service whenever possible.

United Airlines offers multiple daily nonstop flights between Denver International Airport (DEN) and O'Hare International Airport (ORD) with strong connectivity at ORD and comprehensive loyalty benefits. Southwest provides flexible fares, two free checked bags and frequent daily frequencies, making it attractive for budget-conscious travelers. American Airlines offers competitive schedules via ORD with extensive domestic connections, and Delta may offer one-stop options via Minneapolis or Salt Lake City. Evaluate total cost including bag fees, seat selection and change policies when choosing an airline in November.

November travel between Denver and Chicago requires preparation for colder temperatures, variable mountain weather and holiday crowds. Dress in layers for Denver altitude changes and carry a warm coat for Chicago wind chill. Keep carry-on essentials (meds, chargers, warm layers) in case of short delays or gate holds, and verify baggage policies to avoid last-minute fees. For Thanksgiving travel, allow extra time for TSA and airport transfers and consider travel insurance or flexible tickets.

Nonstop flight time from Denver International Airport (DEN) to O'Hare International Airport (ORD) averages 2 hours 20 minutes to 2 hours 40 minutes depending on winds and routing. Multiple daily nonstop options are available year-round with peak frequencies during morning and evening waves; in November, carriers often add extra flights around Thanksgiving. Typical carriers include United Airlines (hub at ORD), Southwest Airlines (high-frequency), and American Airlines; schedule updates are common during winter operations, so confirm times before travel.

To find cheap DEN to ORD flights in November, search early in the month for midweek departures (Tuesday–Thursday) and avoid the week of Thanksgiving when fares spike. Use flexible date tools, set fare alerts, and compare nonstop vs one-stop itineraries—nonstop flights are often competitively priced on this short domestic route. Consider early-morning or red-eye flights for the best value and take advantage of airline sales and mileage redemptions for additional savings.