✈️ Flight Guide: Chicago (ORD) → Tampa (TPA)

May brings a vibrant events calendar to Tampa Bay — expect food festivals, pop-up concerts, and waterfront events in Clearwater and St. Petersburg that draw travelers from Chicago. In Chicago, May also has major outdoor festivals and sports events that can increase departures from Chicago O'Hare International Airport (ORD). Plan ahead for hotel and car rental bookings in Tampa during festival weekends, and check local event calendars to align your itinerary. CTA: Browse local event listings in Tampa and book flights early if your dates overlap with large festivals.

The best time to fly from Chicago O'Hare International Airport (ORD) to Tampa (All Airports) (TPA) in May is midweek (Tuesday–Thursday) and early mornings to avoid heavier weekend demand and airport congestion. Avoid Memorial Day weekend if seeking the lowest prices; if you must travel then, book as early as possible. Use fare calendars to compare week-to-week prices and consider red-eye or late-night flights for potential savings.

Nonstop flights from Chicago O'Hare International Airport (ORD) to Tampa (All Airports) (TPA) provide the fastest travel time (about 2 hours 40–3 hours) and reduce the risk of missed connections. Connecting flights may be cheaper, particularly midweek or with alternative carriers, but add at least 60–120 minutes of travel time and connection risk. In May, weigh the value of time vs price: for short stays in Tampa Bay, a nonstop often yields more usable time on arrival and less travel stress. CTA: Filter search results for nonstop ORD→TPA to compare time savings versus cost.

United, American, Delta, and Southwest all typically serve the Chicago O'Hare International Airport (ORD) to Tampa (All Airports) (TPA) route in May. United often offers multiple daily nonstops with strong loyalty benefits for MileagePlus members. American provides extensive connectivity for passengers connecting through hubs and competitive fares. Delta offers solid schedule options with Delta Comfort upgrades for added legroom. Southwest can be a value play with two free checked bags and flexible ticketing but may require early check-in for preferred boarding. Compare total trip price including baggage and seat fees to determine the best carrier for your May trip. CTA: Check each carrier's May schedules and price-match to secure your preferred flight.

Pack lightweight layers for travel from Chicago O'Hare International Airport (ORD) to Tampa (All Airports) (TPA) in May: cool mornings in Chicago, warm and humid afternoons in Tampa, and an afternoon shower is possible. Bring sunscreen and a reusable water bottle for Tampa Bay activities, and a compact umbrella for spring storms. At ORD, wear easy-to-remove shoes for security and allow extra time during busy Thursday–Sunday travel windows. CTA: Check weather forecasts 48 hours before departure and adjust packing accordingly.

Nonstop flight times from Chicago O'Hare International Airport (ORD) to Tampa (All Airports) (TPA) average 2 hours 40 minutes to 3 hours. Airlines often schedule early morning and late afternoon nonstops to accommodate business travelers and weekenders; weekend frequency increases in May. For connections, allow 60–90 minutes at ORD for domestic transfers. Remember the one-hour timezone difference (Central to Eastern) when viewing schedules. Check airline apps the day before departure for gate changes or delays.

To score cheap flights from Chicago O'Hare International Airport (ORD) to Tampa (All Airports) (TPA) in May, search 3–8 weeks before travel and be flexible with weekday departures. Use incognito mode and fare trackers on Google Flights or Skyscanner, compare low-cost carriers like Southwest with legacy carriers for bundled benefits, and consider nearby alternate airports such as Midway (MDW) for additional savings. Set price alerts for both nonstop and 1-stop options, and book as soon as you see a fare dip — Memorial Day weekend often raises prices, so plan accordingly. CTA: Start a price alert now to lock in cheap ORD→TPA fares for May.