✈️ Flight Guide: Chicago (Any) → Washington, D.C. (Any)

December in Washington is filled with seasonal events like the National Christmas Tree lighting, the Downtown Holiday Market, seasonal concerts at the Kennedy Center, and museum holiday exhibits. These draw visitors and can increase traffic near Reagan National (DCA) and downtown, so schedule additional transfer time if attending major events. Consider visiting nearby Annapolis and Baltimore holiday markets for less-crowded experiences.

The best times to fly in December are midweek (Tuesday–Wednesday) and early mornings. These slots typically offer lower fares and fewer weather-related delays. If you must travel over the holidays, aim to depart before December 20th or after December 27th to avoid the busiest periods and premium fares.

Direct nonstop flights between Chicago and Washington are usually faster and reduce the risk of missed connections during December storms. Connecting flights can be cheaper, especially on low-cost carriers or when using MDW and BWI, but they increase vulnerability to delays. For December travel, prioritize nonstop flights if your schedule is tight; if you need to save money, allow longer connection buffers.

Major carriers like American, United, and Delta typically provide multiple daily nonstops from ORD to DCA/IAD and have robust winter operations and rebooking policies. Southwest often serves MDW→BWI/DCA with attractive checked-bag policies and competitive fares but fewer nonstops. Low-cost carriers can offer the cheapest tickets from MDW to BWI, but factor in baggage and change fees. For December travel, prioritize carriers with strong irregular operations teams and flexible rebooking policies.

Prepare for winter travel by packing layers, carrying essential medications and chargers in your carry-on, and checking weather forecasts 72 hours before departure. Opt for refundable or flexible fares if traveling near major holiday dates, confirm ground-transfers in advance, and arrive at the airport earlier than usual due to increased security lines and holiday crowds. Travel insurance or airline waivers can provide extra protection against storm-related cancellations in December.

Nonstop flight time between Chicago and the Washington area is generally 1 hour 45 minutes to 2 hours depending on winds and routing. ORD↔DCA/IAD/BWI typically offer multiple daily nonstop options; MDW tends to have fewer nonstop flights and more budget-carrier schedules with possible connections. In December, airlines may add or reduce frequencies based on holiday demand—expect more evening and red-eye options around the holidays to accommodate increased passenger loads.

To find cheap flights in December, use these tactics: be flexible with dates (midweek travel tends to be cheaper), compare all three Washington airports (DCA, IAD, BWI) and both Chicago airports (ORD, MDW), set fare alerts, and consider early-morning or red-eye departures. Low-cost carriers often serve MDW→BWI routes at discounted prices, while legacy carriers may run promotions for ORD→DCA. Use multi-airport search queries and book 6–10 weeks in advance to lock in the best holiday airfare.

Tips

• Set fare alerts 8–10 weeks before travel and track price drops.
• Search ‘+/- 3 days’ on flexible-date calendars to find midweek savings.
• Compare total door-to-door cost (airport transfers, baggage fees) not just ticket price.