Economy Roundtrip to Chicago (MCO-MDW) in Nov from Orlando

November travel from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) blends mild Florida weather on departure with early-winter conditions in Chicago on arrival. This month sees steady demand from holiday travelers and event-goers; early- and mid-November often offers lower fares and smaller crowds than late-November Thanksgiving travel. Use targeted fare searches and flexible dates to find the best nonstop options.

Departing from Orlando (MCO) FAQs

Orlando International Airport (MCO) typically sees moderate traffic in November, with a noticeable spike around Thanksgiving week. Early and mid-November are often less crowded than summer or December holiday periods, making it a good month for lower crowds and more reliable check-in times. Book parking and airport shuttles in advance if you travel during the Thanksgiving window.

Yes — multiple airlines operate nonstop service between Orlando International Airport (MCO) and Chicago Midway International Airport (MDW) in November, with Southwest Airlines often providing the most frequent nonstop options. Nonstop schedules increase flexibility; compare prices and book early, especially for holiday travel around late November.

The easiest options to reach Orlando International Airport (MCO) from downtown are taxi, rideshare (Uber/Lyft), airport shuttle, or driving and using long-term parking; travel times average 20–35 minutes depending on traffic. In November, midweek mornings and late evenings usually have lighter traffic — consider allowing extra time during special events or early holiday travelers.

Weather delays at Orlando International Airport (MCO) in November are less common than in winter months, but flights to Chicago Midway (MDW) can be delayed due to cold-fronts or early-season snow near Chicago. Always check both origin and destination forecasts, sign up for airline alerts, and consider travel protection for November travel during potential Thanksgiving weather disruptions.

TSA security wait times at Orlando International Airport (MCO) in November vary: midweek mornings tend to be quieter, while peak holiday days like the Tuesday-Wednesday before Thanksgiving see longer lines. Enroll in TSA PreCheck, arrive at least 90 minutes for domestic flights during busy travel days, and check live MCO wait time tools for the most accurate updates.

November often brings competitive fares and Black Friday sales on the Orlando (MCO) to Chicago Midway (MDW) route, particularly early in the month or around airline promotional days. For the best deals, monitor fare alerts, compare budget carriers and legacy airlines, and book weekday departures or red-eye flights where available.

Arriving at Chicago Midway International Airport (MDW) in November means entering early-winter conditions, with popular seasonal events and holiday travel affecting transit and accommodation availability. MDW's proximity to downtown Chicago and efficient CTA Orange Line service make city access simple, but travelers should pack warm clothing and prepare for occasional weather-related disruptions.

Arriving at Chicago (MDW) FAQs

Chicago Midway International Airport (MDW) offers the CTA Orange Line direct to downtown Chicago (The Loop), plus taxis, rideshare services, and rental cars. In November, trains and rideshares remain reliable, but allow extra time during large events or holiday weekends when demand can increase.

Expect cool to cold temperatures upon arrival at Chicago Midway International Airport (MDW) in November, with average highs in the 40s°F (4–10°C) and the possibility of windy conditions or early season snow showers. Pack insulated outerwear and plan for potential weather-related delays during transit or flights.

Travel time from Chicago Midway (MDW) to Naperville or Schaumburg varies: expect roughly 40–70 minutes by car depending on traffic and weather, while public transit options require transfers and longer travel times. During November, allow extra time for potential slowdowns from rain, wind, or early snow.

Yes — November events such as the Magnificent Mile Lights Festival and Christkindlmarket (late November into December) can increase passenger volume and ground transportation demand near Chicago Midway International Airport (MDW). Book accommodations and airport transfers in advance and monitor local event calendars for peak days.

Chicago Midway International Airport (MDW) offers baggage services, dining options that may include seasonal menu items in November, rental car counters, and ground transportation desks. Many concessions adjust hours for seasonal demand; check terminal maps and service hours before arrival and consider pre-booking ground transport during holiday weekends.

Late November, especially around Thanksgiving, often brings increased delays and higher passenger volumes at Chicago Midway International Airport (MDW) due to weather systems moving into the Midwest and peak holiday travel. Arrive prepared with flexible plans, check in with your airline for alerts, and allow buffer time for connections and ground transportation.

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November Events & Festivals Affecting MCO and MDW

November has notable events that affect travel to Chicago Midway International Airport (MDW) and departures from Orlando International Airport (MCO). Chicago’s Magnificent Mile Lights Festival and the Christkindlmarket (late November) increase hotel and transit demand downtown. Orlando hosts seasonal theme-park events such as Mickey’s Very Merry Christmas Party beginning in November and Epcot Food & Wine overflow events that can influence airport traffic. Plan your flights, book ground transport early, and arrive at the airport with extra buffer time when attending these events.

Best Time to Fly — Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) in November

The best time to fly from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) in November is early-to-mid month on weekdays, or early morning departures to avoid peak delays. Avoid the three days before Thanksgiving and the Sunday after, when fares and crowds peak. Use flexible-date searches and aim for Tuesday–Thursday flights for lower fares and less crowded terminals.

Direct vs Connecting Flights — MCO to MDW in November

Choosing direct flights between Orlando International Airport (MCO) and Chicago Midway International Airport (MDW) reduces total travel time and minimizes the risk of missed connections during November weather. Nonstop flights are generally more convenient, though connecting itineraries can be cheaper or provide better schedule options outside peak days. If cost is a primary concern, consider one-stop options; for time-savings and simplicity, book direct nonstop service.

Airline Comparison — Orlando International Airport (MCO) to Chicago Midway International Airport (MDW)

Compare primary carriers serving Orlando International Airport (MCO) to Chicago Midway International Airport (MDW): Southwest (frequent nonstop service and competitive base fares), American (regional and mainline options, sometimes via O'Hare or hubs), Delta and United (offer variants including connecting options). Consider fare class, baggage policies, and loyalty benefits when selecting—Southwest often includes two free checked bags which can be a decisive savings factor in November holiday travel.

Seasonal Travel Tips — MCO to MDW (November)

November travel between Orlando International Airport (MCO) and Chicago Midway International Airport (MDW) requires flexibility for weather, holiday crowds, and event-driven demand. Pack layers for Chicago chill, confirm transit and rental car reservations, and expect higher demand around Thanksgiving and festival dates. Use early-morning flights, enroll in TSA PreCheck, and allow additional time for baggage claim and ground transport at MDW during peak days.

Flight Time and Schedules — Orlando International Airport (MCO) to Chicago Midway International Airport (MDW)

Nonstop flight time between Orlando International Airport (MCO) and Chicago Midway International Airport (MDW) averages about 2 hours 30–40 minutes gate-to-gate. Time-sensitive planning must account for the one-hour timezone change (ET to CT). In November, airlines typically operate multiple daily nonstop flights, with the highest frequency on major carriers like Southwest and American; schedules increase around holiday travel days, especially the days leading up to Thanksgiving.

Cheap Flights from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) in November

Find cheap flights from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) in November by booking midweek, setting fare alerts, and being flexible with departure dates. Use primary keywords like "cheap MCO to MDW flights November" and LSI phrases such as "discount Orlando to Chicago fares" or "economy flights MCO MDW". Compare budget carriers and legacy airlines, search incognito to avoid dynamic price increases, and consider southwest and other low-cost options for the best base fares. Sign up for airline newsletters and monitor Black Friday/Cyber Monday sales for additional savings.

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✈️ Flight Guide: Orlando (MCO) → Chicago (MDW)

Complete travel information for your November journey

Departing from Orlando (MCO) FAQs

How busy is Orlando International Airport (MCO) in November?

Are there direct flights from Orlando International Airport (MCO) to Chicago Midway International Airport (MDW) in November?

What is the best way to get to Orlando International Airport (MCO) from downtown Orlando in November?

Do weather delays often affect flights from Orlando International Airport (MCO) to Chicago Midway in November?

What TSA and security wait times should I expect at Orlando International Airport (MCO) in November?

Are there November travel deals or airline sales from Orlando International Airport (MCO) to Chicago Midway (MDW)?

Arriving at Chicago (MDW) FAQs

What transportation options are available from Chicago Midway International Airport (MDW) to downtown Chicago in November?

What weather should I expect arriving at Chicago Midway International Airport (MDW) in November?

How long does it take to get from Chicago Midway International Airport (MDW) to Naperville or Schaumburg in November?

Are there November events near Chicago Midway International Airport (MDW) that impact arrival traffic?

What amenities are available at Chicago Midway International Airport (MDW) for arriving passengers in November?

Should I expect more delays arriving at Chicago Midway International Airport (MDW) in late November?