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Cheap Flights from Tampa (TPA) to Chicago (MDW)

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      Travellers and cabin class, 1 Adult, Economy
      Southwest Airlines

      Compare Tampa International to Chicago Midway flight deals

      Find the cheapest month or even day of the year to fly to Chicago Midway

      Book the best Chicago Midway fare with no extra fees

      Flight deals from Tampa International to Chicago Midway

      Looking for a cheap last-minute deal or the best return flight from Tampa International Airport to Chicago Midway Airport? If you want to travel next month, return fares start from $271. Find the lowest prices on one-way and return tickets right here.
      Chicago.$271 per passenger.Departing Sat, 7 Nov, returning Tue, 10 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Tampa International on Sat, 7 Nov, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 10 Nov, arriving in Tampa International.Price includes taxes and charges.From $271, select.
      Chicago.$271 per passenger.Departing Tue, 6 Oct, returning Tue, 13 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Tampa International on Tue, 6 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 13 Oct, arriving in Tampa International.Price includes taxes and charges.From $271, select.
      Chicago.$305 per passenger.Departing Wed, 30 Sep, returning Wed, 7 Oct.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Tampa International on Wed, 30 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 7 Oct, arriving in Tampa International.Price includes taxes and charges.From $305, select.
      Chicago.$306 per passenger.Departing Fri, 25 Sep, returning Sat, 26 Sep.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Tampa International on Fri, 25 Sep, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Sat, 26 Sep, arriving in Tampa International.Price includes taxes and charges.From $306, select.
      Chicago.$311 per passenger.Departing Thu, 29 Oct, returning Mon, 2 Nov.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Tampa International on Thu, 29 Oct, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Mon, 2 Nov, arriving in Tampa International.Price includes taxes and charges.From $311, select.
      Chicago.$330 per passenger.Departing Sat, 5 Dec, returning Tue, 8 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Tampa International on Sat, 5 Dec, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Tue, 8 Dec, arriving in Tampa International.Price includes taxes and charges.From $330, select.
      Chicago.$363 per passenger.Departing Wed, 14 Oct, returning Sat, 17 Oct.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tampa International on Wed, 14 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sat, 17 Oct, arriving in Tampa International.Price includes taxes and charges.From $363, select.
      Chicago.$364 per passenger.Departing Tue, 17 Nov, returning Wed, 18 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tampa International on Tue, 17 Nov, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 18 Nov, arriving in Tampa International.Price includes taxes and charges.From $364, select.
      Chicago.$383 per passenger.Departing Wed, 26 May, returning Sun, 30 May.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tampa International on Wed, 26 May, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 30 May, arriving in Tampa International.Price includes taxes and charges.From $383, select.
      Chicago.$384 per passenger.Departing Sat, 31 Oct, returning Mon, 2 Nov.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tampa International on Sat, 31 Oct, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Mon, 2 Nov, arriving in Tampa International.Price includes taxes and charges.From $384, select.
      Chicago.$384 per passenger.Departing Mon, 21 Dec, returning Tue, 5 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tampa International on Mon, 21 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 5 Jan, arriving in Tampa International.Price includes taxes and charges.From $384, select.
      Chicago.$384 per passenger.Departing Fri, 19 Feb, returning Tue, 23 Feb.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tampa International on Fri, 19 Feb, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Tue, 23 Feb, arriving in Tampa International.Price includes taxes and charges.From $384, select.
      Chicago.$385 per passenger.Departing Fri, 4 Dec, returning Wed, 9 Dec.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tampa International on Fri, 4 Dec, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Wed, 9 Dec, arriving in Tampa International.Price includes taxes and charges.From $385, select.
      Chicago.$390 per passenger.Departing Wed, 26 May, returning Tue, 1 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Tampa International on Wed, 26 May, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 1 Jun, arriving in Tampa International.Price includes taxes and charges.From $390, select.
      Chicago.$405 per passenger.Departing Fri, 8 Jan, returning Sun, 10 Jan.Return flight with Southwest Airlines.Outbound direct flight with Southwest Airlines departs from Tampa International on Fri, 8 Jan, arriving in Chicago Midway.Inbound direct flight with Southwest Airlines departs from Chicago Midway on Sun, 10 Jan, arriving in Tampa International.Price includes taxes and charges.From $405, select.
      Chicago.$406 per passenger.Departing Fri, 20 Nov, returning Wed, 30 Dec.Return flight with Frontier Airlines.Outbound indirect flight with Frontier Airlines, departs from Tampa International on Fri, 20 Nov, arriving in Chicago Midway.Inbound indirect flight with Frontier Airlines, departs from Chicago Midway on Wed, 30 Dec, arriving in Tampa International.Price includes taxes and charges.From $406, select.
      How did we find these deals? The deals you see here are the lowest prices for flight tickets from Tampa International to Chicago Midway found in the last 4 days, and are subject to change and availability.

      Find the cheapest month to fly from Tampa International to Chicago Midway

      We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Tampa International to Chicago Midway flights are currently cheapest in October.
      Sep
      from $306
      Oct
      from $271
      Nov
      from $271
      Dec
      from $330
      Jan
      from $405
      Feb
      from $384
      Mar
      from $417
      Apr
      Find prices
      May
      from $383
      Jun
      from $709
      Jul
      Find prices
      Aug
      Find prices

      Direct flights from Tampa International to Chicago Midway

      Southwest Airlines

      Tampa International to Chicago Midway: Alternative routes

      Compare routes from Tampa International to Chicago below. You may find an airport to fly into that's cheaper, faster, or easier than Chicago Midway.

      Chicago Midway

      14km from central Chicago
      Closest
      from $271
      Search flights

      Chicago O'Hare International

      25km from central Chicago
      Cheapest
      from $179
      Search flights

      Chicago Rockford

      127km from central Chicago
      Search flights

      Tampa to Chicago: Flight information

      The things to know before you go.
      Cheapest flight found$271
      Cheapest month to flyOctober
      Average flight time2 hrs, 47 mins
      Most popular airlineSouthwest Airlines
      Average flights per week28

      Finding cheap flights from Tampa International to Chicago Midway: Frequently asked questions

      The best price we found for a return flight from Tampa International to Chicago Midway is $271. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
      2 hours and 47 minutes is the average flight time from Tampa International to Chicago Midway.
      Southwest Airlines flies direct from Tampa International to Chicago Midway.
      As of September 2026, there are 28 flights per week flying from Tampa International to Chicago Midway.
      The cheapest month to fly from Tampa International to Chicago Midway is usually October.
      After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Tampa International Airport to Chicago Midway Airport on Tuesday, 6 October 2026.
      Yes – the average flight time is 2 hours and 47 minutes.
      We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago Midway but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

      We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

      Currently, Frontier Airlines and Southwest Airlines offer the cheapest flight tickets to Chicago Midway.

      Travelling from Tampa International Airport (TPA) to Chicago Midway Airport (MDW): what you need to know

      • The average length of a direct flight from Tampa International Airport to Chicago Midway Airport is 2 hours 40 minutes.

      • Chicago's timezone is UTC-6, making Chicago one hour behind Tampa.

      • Take your pick of 17 weekly Tampa International Airport to Chicago Midway Airport flights. The 05:25 departure with Southwest Airlines is the earliest flight available. Southwest Airlines operates the last service of the day at 21:55.

      • Arriving two hours before an international flight and one hour ahead of a domestic departure are travel rules to live by. Be at the airport on time to board your TPA to MDW flight.

      • Travelling during a peak time like April? Major public holidays and other high seasons can result in longer lines and delays at security. Play it safe and get there up to four hours before an international flight and two hours before a domestic departure.

      • Jetting into Chicago (and then discovering more of the United States!) is a breeze with Southwest Airlines. This popular airline has direct flights from Tampa International Airport to Chicago Midway Airport.

      • Most travellers choose to travel with Southwest Airlines on this route.

      • With 78.47% of its services arriving as planned, Southwest Airlines is the most punctual carrier operating TPA to MDW flights.

      How to find the cheapest flights from Tampa International Airport (TPA) to Chicago Midway Airport (MDW)

      • Currently, $136 is the lowest price we've seen for a one-way Tampa International Airport to Chicago Midway Airport flight. The best price for a return plane ticket is $271. Bear in mind that fares can change due to availability at the time of booking.

      • Don't wait until the last minute. You're more likely to get cheap tickets from TPA to MDW if you book ahead. Airlines often offer some amazing early bird rates.

      • May is the cheapest month for flights from Tampa International Airport to Chicago Midway Airport. If you'd like to travel at a different time of year, the 'Whole month' tool will give you the lowest airfares for every month.

      • You won't have to check back in every day to see if fares have dropped when you create a Price Alert. We'll let you know the moment there's a new deal on cheap flights from TPA to MDW.

      • Discover the right flight for you by using the filters. To see the 'Fastest,' 'Best' or 'Cheapest' flights from Tampa International Airport to Chicago Midway Airport, use the 'Sort by' tool. You can also filter by arrival and departure times, airline, and number of stops.

      Handy information about Tampa International Airport (TPA)

      • TPA's address is 5507 West Spruce Street.

      • Of all flights leaving Tampa International Airport, 78% land on schedule at their destination.

      • Central Tampa to Tampa International Airport is around 11 kilometres. Depending on traffic, it'll take about 20 minutes to get there if you're ride-sharing, catching a taxi or driving.

      • You can expect a journey time of roughly 35 minutes on public transport.

      • Taking an early flight from Tampa International Airport to Chicago Midway Airport? Avoid rushing to the terminal (and catch some extra z's) by choosing one of these stays close to TPA:

      Arriving at Chicago Midway Airport (MDW)

      • If you're landing on a late Tampa International Airport to Chicago Midway Airport flight, nothing tops the convenience of being close to the terminal. Grab your bags from the carousel and then be showered and snoozing soon after at one of these accommodation options near MDW:

      • Explore without limits with a Chicago Midway Airport rental car. Pick up a set of wheels from Dollar, Hertz or Budget and see more of Chicago and beyond.

      • Reserving your vehicle from Chicago Midway Airport about four weeks in advance can help you get the lowest rate.

      When to fly to Chicago Midway Airport (MDW)

      • July is the busiest month for flights from Tampa International Airport to Chicago Midway Airport. For a quieter experience, go to Chicago in December.

      • Book your flight from Tampa International Airport to Chicago Midway Airport for July if you'd like to visit Chicago during its warmest month. You can expect temperatures of between 16ºC (61ºF) and 28ºC (82ºF).

      • January sees average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for cheap tickets from TPA to MDW sometime then if you want to travel when it's cooler.

      Explore more of the United States

      • Chicago has plenty to offer, but there are so many other corners of the United States waiting to be discovered. About 451 kilometres south-east of Chicago, a visit to Columbus will fill your itinerary to the brim. Check out popular attractions like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.

      • Around 257 kilometres south-east of Chicago, Indianapolis is another essential stop in the United States. No visit is complete without checking out Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.

      Plan smart, explore more

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      Prices shown on this page are estimated lowest prices only. Found in the last 12 days.