October is a smart month to fly from Midway International Airport (MDW) to Tampa (All Airports) (TPA) for mild Florida weather and often lower-than-summer fares. Nonstop flights generally take about 2.5 to 3 hours gate-to-gate; Southwest provides the largest number of daily nonstop options. For the best prices, target midweek travel and book 3–6 weeks in advance, and keep an eye on Tampa events (college football, Lowry Park Zoo 'Boo at the Zoo') which can increase demand. Remember hurricane-season advisories in early October — subscribe to flight alerts and consider flexible fares when possible. Nearby major destinations accessible from Midway include downtown Chicago, O'Hare International Airport, Milwaukee, and Indianapolis, while Tampa serves as a gateway to Clearwater, St. Petersburg, Sarasota, and Orlando. Book now for October deals and compare MDW to TPA flight times to secure the best schedule and fare.
Arriving at Tampa (All Airports) (TPA) in October offers warm weather and easier access to Gulf Coast beaches such as Clearwater and St. Petersburg. Expect quick arrivals with streamlined domestic procedures and multiple transit options including rental cars, shuttle services, rideshare, and local buses. October sees family-oriented festivals and college football events that can affect hotel rates and ground transport demand, so plan transfers in advance. Tampa is also a practical hub for day trips to Sarasota, Orlando, and even Miami for longer itineraries. Use airport ride apps or reserve rental cars online to save time after arrival and take advantage of lower fall-season room rates.