Best Flights starting from
No flights found for this route.
Other Options for This Route
Other Destinations
Chicago (MDW) to Phoenix (PHX) in December from $144
From $144
Chicago (MDW) to Fort Lauderdale (Any) in December from $170
From $170
Chicago (MDW) to Fort Lauderdale (FLL) in December from $180
From $180
Chicago (MDW) to Phoenix (PHX) in December from $271
From $271
Chicago (MDW) to Jacksonville (JAX) in December from $314
From $314
Chicago (MDW) to Gainesville (GNV) in December from $407
From $407
Flights from Other Cities
Chicago (ORD) to Tampa (TPA) in December from $44
From $44
Chicago (Any) to Tampa (TPA) in December from $65
From $65
Chicago (ORD) to Tampa (TPA) in December from $72
From $72
Cleveland (CLE) to Tampa (TPA) in December from $98
From $98
Hayden (HDN) to Tampa (TPA) in December from $125
From $125
Rochester (ROC) to Tampa (TPA) in December from $128
From $128
✈️ Flight Guide: Chicago (MDW) → Tampa (TPA)
Complete travel information for your December journey
December brings high demand and winter-weather risks for departures at Chicago Midway International Airport (MDW). Travelers heading to Tampa (All Airports) (TPA) should book early for holiday dates, target early-December midweek flights for lower fares, and sign up for airline alerts. Expect multiple daily nonstops (primarily operated by Southwest) with an average flight time of 2 hours 20–40 minutes. Parking fills faster during holidays — reserve ahead — and leave 90–120 minutes before departure to accommodate security lines and possible de-icing operations. CTA Orange Line, ride-shares and terminal shuttles provide reliable ground access; bring winter layers for Chicago and lighter clothing for Tampa. Search fares now and set price alerts to catch MDW to TPA December deals.
Departing from Chicago (MDW) FAQs
In December, especially during holiday weeks, arrive 90–120 minutes before a domestic flight at Chicago Midway International Airport (MDW). Winter weather and increased traveler volume for Christmas and New Year can add security and traffic delays, so plan extra time for parking, shuttle transfers and possible de-icing. Use mobile boarding passes and TSA PreCheck if available to speed through screening.
Yes — Southwest Airlines typically operates nonstop MDW to TPA flights year-round, including December, with multiple daily departures. Nonstop flight time is about 2 hours 20 minutes to 2 hours 40 minutes; check airline schedules for exact times and holiday service adjustments. Booking early for December holiday travel secures better times and fares.
December in Chicago brings a higher likelihood of snow, ice and gusty winds that can cause flight delays or cancellations at Chicago Midway International Airport (MDW). Airlines may preemptively rebook or consolidate flights; check the airline's winter-weather policies, sign up for alerts, and allow extra connection time if your itinerary includes a layover. Consider travel insurance or flexible fares during peak holiday weeks.
In December you can use the CTA Orange Line train to downtown Chicago for an affordable and reliable option, or ride-share services and taxis for quicker door-to-door transfers. Allow extra travel time on icy roads; Midway parking and on-site car rental counters are open year-round if you prefer to drive and return your car before the flight.
For December savings, search flexible dates, early December midweek departures, and set fare alerts on comparison sites like Google Flights, Kayak and airline sites. Consider flying early in the week, avoiding peak holiday days (around Dec 22–26 and Dec 29–Jan 2) and checking Southwest promotions for discounted MDW to TPA fares. Book round-trips or refundable fares if your dates might change during the holidays.
Pack for both cold Chicago mornings and warm Tampa afternoons — layer clothing and check airline carry-on and checked baggage allowances before arriving at Chicago Midway International Airport (MDW). December holiday flights are busy so check in online, print or download your boarding pass, and arrive early to avoid checked-bag lines. If flying Southwest from MDW, note their open seating policy and boarding groups.
December arrivals at Tampa (All Airports) (TPA) enjoy mild temperatures, busy tourist activity and frequent access to Clearwater Beach, St. Petersburg, Ybor City and Sarasota. Expect higher ride-share demand around popular holiday events, so pre-book transfers or allow extra time for shuttles. Rental cars are available but reserve early for holiday weekends. For families, December offers outdoor attractions and light displays; for travelers from Chicago Midway International Airport (MDW), pack layers to transition from colder departures to Florida warmth. Use airline apps for baggage tracking and real-time arrival updates to streamline your December visit to Tampa.
Arriving at Tampa (TPA) FAQs
Arrivals at Tampa (All Airports) (TPA) are generally smooth in December, with mild winter weather and efficient passenger processing at Tampa International Airport. Expect a short walk or shuttle to ground transportation areas; rental car counters and ride-share pick-ups are well signed. December sees higher tourist volume around beaches and holiday events, so plan for slightly busier ground-transport queues on weekends.
From Tampa (All Airports) (TPA) you have convenient access to Clearwater Beach, St. Petersburg, Sarasota, Ybor City and Orlando attractions; many are within a 30–90 minute drive. December weather is ideal for beach walks, holiday light festivals and outdoor activities in the greater Tampa Bay region. Consider renting a car for flexible day trips and sightseeing around the bay area.
Yes — December features holiday boat parades, light displays and festive markets in Tampa Bay that can increase local traffic around evenings and weekends. Events like the Tampa Riverwalk holiday light displays and Holiday Lighted Boat Parades in nearby Clearwater and St. Petersburg may cause higher ride-share demand at arrival times. Arrive with flexible ground plans and consider pre-booking transfers if you land during major events.
December in Tampa (All Airports) (TPA) is typically mild and pleasant with daytime highs in the mid-60s to mid-70s°F (18–24°C) and cooler evenings. Pack light layers, a windbreaker for breezy beach conditions and a swimsuit for sunny afternoons. Since you’re flying from Chicago Midway International Airport (MDW), bring adaptable clothing to transition from winter in Chicago to comfortable Florida weather.
Upon arrival at Tampa (All Airports) (TPA), choose between rental cars, ride-share services, taxis, airport shuttles and public buses; rental car lines are often busy during holiday season so book in advance. For short trips to downtown Tampa, Clearwater or St. Petersburg, ride-shares offer door-to-door convenience while public transit serves budget-conscious travelers. Check any special event schedules that could affect transit times during December weekends.
For domestic arrivals from Chicago Midway International Airport (MDW), baggage claim at Tampa (All Airports) (TPA) is straightforward with local carousels and efficient retrieval; customs is not required for domestic U.S. flights. If you’re connecting to an international flight out of Tampa, allow extra time to re-check bags and clear international screening. Track your bag on airline apps and report issues promptly at the airline baggage office in the terminal.
1.0.2512.11
December Events & Festivals Near MDW and TPA | Holiday Travel Highlights
In December, Chicago visitors departing from Chicago Midway International Airport (MDW) may enjoy Christkindlmarket, holiday theater performances and illuminated displays along Chicago River and Navy Pier — expect increased airport and transit usage on festival weekends. Tampa (All Airports) (TPA) hosts holiday boat parades, the Tampa Riverwalk lights and seasonal markets in Ybor City; nearby Clearwater and St. Petersburg stage popular lighted-boat events that can increase evening arrival traffic. Plan transfers and ride-share pickups around event schedules and consider midweek travel to avoid crowds. CTA: Check local event calendars before booking MDW→TPA December travel.
Best Time to Fly MDW to TPA in December | Save Money & Avoid Delays
The best time to fly MDW to TPA in December is typically early-December midweek (Tuesday or Wednesday) for lower fares and fewer crowds. Early morning flights reduce the risk of weather-related delays at Chicago Midway International Airport (MDW). Avoid travel windows immediately before Christmas Eve and New Year’s Eve for better prices and smoother airport experiences. If you must travel during the holidays, aim to book flexible fares and check-in online to save time. CTA: Search midweek MDW→TPA flights for the best December deals.
Direct vs Connecting Flights: MDW to TPA in December
Direct (nonstop) flights from Chicago Midway International Airport (MDW) to Tampa (All Airports) (TPA) offer the fastest, most predictable travel (about 2h20–2h40) and reduce the risk of missed connections during December winter weather. Connecting flights can be cheaper or more available outside nonstop schedules but add layover time and vulnerability to delays at connecting hubs. For December holiday travel, choose nonstop where possible for reliability; for maximum savings and flexible dates, consider a single-connection itinerary but allow at least 90–120 minutes for layovers during winter months. CTA: Compare nonstop and one-stop options for MDW→TPA today.
Airline Comparison: MDW to TPA Carriers & December Policies
Southwest Airlines dominates Chicago Midway International Airport (MDW) schedules and frequently offers multiple nonstop MDW→TPA flights daily, with generous two-free-checked-bags policy that can save families money during December holiday trips. American and United may offer connecting options through their hubs with different loyalty benefits but narrower nonstop availability at MDW. For December travel, compare total trip cost including baggage and seat selection fees; Southwest often provides the most convenient nonstop schedules from MDW to Tampa (All Airports) (TPA). Look for airline holiday flexibility waivers and book refundable or changeable fares if your plans are uncertain. CTA: Compare carrier fares and baggage costs for your December trip.
Seasonal Travel Tips for December: MDW to TPA
Pack in layers to move comfortably from winter conditions at Chicago Midway International Airport (MDW) to warm days in Tampa (All Airports) (TPA). Expect de-icing and snow-related delays departing MDW — build buffer time and consider travel insurance or flexible tickets for holiday travel. Reserve parking and rental cars in advance, use mobile check-in, and sign up for airline and airport alerts to stay updated on schedule changes. For the best December experience, fly midweek, consider nonstop flights for reliability, and confirm event-related transportation availability at your Tampa arrival destination. CTA: Prepare for MDW→TPA December travel — check flights, pack smart, and set alerts now.
Flight Time & Schedules: Chicago Midway International Airport (MDW) to Tampa (All Airports) (TPA) in December
Nonstop flights from Chicago Midway International Airport (MDW) to Tampa (All Airports) (TPA) generally fly 2 hours 20 minutes to 2 hours 40 minutes depending on winds and routing. In December, expect multiple daily departures: early morning windows (6–9 AM CST), mid-day (11 AM–2 PM CST) and evening options (5–9 PM CST), with an hourly time change (CST to EST). Holiday schedules may add extra flights or adjust times; check airline timetables close to your travel date. For connecting itineraries, common hubs include Atlanta (ATL) and Charlotte (CLT), which add typical total travel times of 4–6+ hours including layovers.
Cheap Flights MDW to TPA in December | Deals & Strategies
To find cheap MDW to TPA flights in December, search flexible dates across early December weekdays and avoid the busiest holiday travel windows (Dec 22–26 and Dec 29–Jan 2). Set price alerts on Google Flights and Kayak and compare round-trip vs one-way pricing. Southwest often posts sale fares from Chicago Midway International Airport (MDW) to Tampa (All Airports) (TPA); join airline newsletters and loyalty programs for targeted deals. Consider red-eye or early-morning departures, and be flexible about return dates — shifting by one or two days can reduce fares significantly. CTA: Compare MDW→TPA fares now and set alerts to lock in December savings.