November departures from Dallas/Fort Worth (All Airports) (DFWA) to Chicago O'Hare International Airport (ORD) combine off-peak savings with occasional holiday surges. Early November tends to offer lower round-trip fares and more nonstop options, while the mid-to-late month spike around Thanksgiving increases prices and reduces seat availability. Typical carriers include American Airlines at Dallas/Fort Worth International and Southwest at Dallas Love Field; compare schedules and book 21–60 days ahead for the best November deals. Consider alternative nearby cities (Fort Worth, Arlington, Plano) when searching to increase low-fare options.
Arriving at Chicago O'Hare International Airport (ORD) in November means transitioning from Dallas warmth to crisp Midwestern air. Early November arrivals often find comfortable travel conditions, but late-November travelers — especially around Thanksgiving — should prepare for colder temps, possible snow, and increased passenger volume. The CTA Blue Line and multiple shuttle options provide reliable access to downtown Chicago and nearby suburbs including Evanston, Naperville, and Oak Park. For best results, pre-book airport transfers and confirm baggage services to streamline your November arrival.
November in Chicago features seasonal highlights that often affect travel volume at Chicago O'Hare International Airport (ORD). Key events include the Magnificent Mile Lights Festival (typically late November), the opening weeks of the Christkindlmarket (mid-November through December), and NFL home games for the Chicago Bears which can increase hotel and flight demand on game weekends. These events coincide with Thanksgiving travel and can push fares and local occupancy higher. Travelers should book accommodations and transport early if visiting for a specific event.
The best time to fly DFWA to ORD in November is early in the month when demand is lower and fare sales are common. For Thanksgiving travel, book at least 60–90 days out to avoid high fares and limited seat availability. Tuesdays and Wednesdays are often the cheapest travel days for November, while the Wednesday before Thanksgiving and the Sunday after are the most expensive. Use flexible date searches and midweek departures to maximize savings.
Nonstop flights reduce travel time and connection risk—typical nonstop flights from DFW to ORD take about 2 hours and are ideal for short November trips or business travel. Connecting flights can be cheaper, especially if you’re flexible on travel time; however, they increase the chance of missed connections during holiday weather events or air traffic delays. If traveling around Thanksgiving, prioritize nonstop itineraries to minimize disruption; for early-November leisure travel, consider connecting flights to access lower fares.
American Airlines offers the most nonstop capacity from Dallas/Fort Worth International to Chicago O'Hare and is often the best choice for frequent flyer benefits and late schedule options. Southwest, operating primarily from Dallas Love Field, provides competitive fares and free checked bags but routes to Chicago Midway more often than O'Hare, so confirm arrival airport. United and Delta may offer one-stop options with competitive pricing, especially for travelers using loyalty programs or looking for specific schedule times. Evaluate total cost (including baggage and seat selection) and loyalty benefits when choosing a carrier for November travel.
November requires flexible planning: early-November travelers enjoy better fares, while late-November (Thanksgiving period) sees higher prices and crowded airports. Pack layers for Chicago’s colder climate, bring a carry-on with essentials in case of checked baggage delays, and enroll in airline notifications for gate and delay updates. Allow additional transfer time between terminals at DFW and factor in extra taxi/rideshare wait times at ORD during event weekends. Consider travel insurance or refundable fares if flying during the Thanksgiving peak.
Nonstop flights between Dallas/Fort Worth (All Airports) (DFWA) and Chicago O'Hare International Airport (ORD) usually take about 1 hour 50 minutes to 2 hours and 15 minutes block time. In November, airlines maintain multiple daily flights—early morning departures (6–9 AM) and evening red-eye options (8–11 PM) are common. Frequency increases slightly on weekends and near holidays, but be mindful of Thanksgiving travel spikes which consolidate schedules and reduce flexibility.
To find cheap flights from Dallas/Fort Worth (All Airports) (DFWA) to Chicago O'Hare (ORD) in November, use flexible date searches and price alerts 3–8 weeks before departure. Early November typically offers the lowest fares; avoid the Thanksgiving peak (the Wednesday before Thanksgiving and Sunday after) when fares spike. Compare multi-airport searches (DFW and DAL) and consider low-cost carriers like Southwest at Love Field plus sale fares on American from DFW. Use weekday departures (Tuesday–Thursday) when possible and consider late-evening flights for additional savings.