161 € Cheap Flights from Tampa to Chicago Midway

Compare Tampa to Chicago Midway flight deals

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Flight deals from Tampa to Chicago Midway

Looking for a cheap last-minute deal or the best return flight from Tampa to Chicago Midway Airport? If you want to travel next month, return fares start from 169 €. Find the lowest prices on one-way and return tickets right here.

Find the cheapest month to fly from Tampa to Chicago Midway

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Tampa to Chicago Midway flights are currently cheapest in September.

Direct flights from Tampa to Chicago Midway

Tampa to Chicago Midway: Alternative routes

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

Tampa to Chicago: Flight information

The things to know before you go.
Cheapest flight found161 €
Cheapest month to flySeptember
Average flight time2 hrs, 44 mins
Most popular airlineSouthwest Airlines
Average flights per week34

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

The best price we found for a return flight from Tampa to Chicago Midway is 161 €. 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 44 minutes is the average flight time from Tampa to Chicago Midway.
Southwest Airlines flies direct from Tampa to Chicago Midway.
As of July 2026, there are 32 flights per week flying from Tampa to Chicago Midway.
The cheapest month to fly from Tampa to Chicago Midway is usually September.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Tampa to Chicago Midway Airport on Tuesday, 15 September 2026.
Yes – the average flight time is 2 hours and 44 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.

Flying from Tampa to Chicago Midway International Airport (MDW): What you need to know

  • Start your trip at Tampa International Airport (TPA), the main airport in Tampa. Search for flights from Tampa to Chicago Midway International Airport (MDW) that take off from this terminal.

  • Around 2 hours 45 minutes is the typical travel time on a direct Tampa to Chicago Midway International Airport flight.

  • The timezone in Chicago is UTC-6, which is one hour behind Tampa. Chicago Midway International Airport is located in Chicago.

  • With 23 direct flights a week between the two airports, Tampa International Airport (TPA) to Chicago Midway International Airport (MDW) is the most popular route. Southwest Airlines operates the earliest flight at 5:25am. If you prefer to get more out of your day before flying, the latest departure from TPA to MDW is with Southwest Airlines at 9:55pm.

  • Give yourself enough time to catch your flight from Tampa to MDW. It's generally best to arrive at least two hours before international departures and an hour ahead for domestic flights.

  • Popular months like March or holiday times such as Christmas and New Year will mean bigger queues at check-in and security. Play it safe and get to the terminal even earlier. Arriving two hours before a domestic flight and up four hours ahead of international flights is a wise idea.

Airports in Tampa

Tampa International Airport (TPA)

  • You can hop on a direct flight from Tampa to Chicago Midway International Airport (MDW) out of Tampa International Airport (TPA).

  • Southwest Airlines is a popular airline that operates direct flights from Tampa to Chicago Midway International Airport taking off from TPA.

  • The preferred airline for passengers flying between TPA and MDW is Southwest Airlines.

  • Southwest Airlines is the most punctual carrier operating on this route, with 78.47% of its services landing on schedule.

  • Located around 11 kilometres from central Tampa, TPA can be reached in about 20 minutes by car (depending on traffic). The journey on public transport takes roughly 35 minutes.

  • Booked an early flight from Tampa to Chicago Midway International Airport? Avoid rushing to the terminal (and sneak in some extra snooze time) by staying at one of these hotels close to Tampa International Airport:

  • When it comes to the on-time performance of Tampa International Airport, 78% of flights arrive within the expected time frame.

  • TPA's address is 5507 West Spruce Street.

St. Pete-Clearwater International Airport (PIE)

About Chicago Midway International Airport (MDW)

  • Have a late flight from Tampa to Chicago Midway International Airport? Don't let it end in exhaustion. Stay at one of these hotels near MDW and hit the lights earlier:

  • To get the best deal, reserve your vehicle around four weeks in advance of your Tampa to Chicago Midway International Airport flight.

  • The address for MDW is 5700 South Cicero.

Getting from Chicago Midway International Airport (MDW) to central Chicago

  • Central Chicago is around 16 kilometres from Chicago Midway International Airport and takes about 25 minutes to reach by car. See what your options are for getting into town, whether that's with a taxi, car hire or ride-share.

  • Travelling by public transport will take you around 30 minutes.

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

  • 80 € is the best price for a one-way ticket from Tampa to Chicago Midway International Airport. Return flights start from 161 €. These prices may change based on demand.

  • To find cheap flights from Tampa to MDW, book early. Airlines usually offer their most competitively priced fares when flights are first released.

  • The 'Whole month' tool will show you the cheapest Tampa to Chicago Midway International Airport tickets across each month. It's an easy way to snap up a bargain if your dates are flexible.

  • Locking in a cheap plane ticket from Tampa to MDW is a breeze with Price Alerts. Simply create one of these automatic alerts and we'll notify you when there's a price drop.

  • Find the best deal on a flight from Tampa to Chicago Midway International Airport with the help of the filters. Choose your ideal arrival and departure times, number of stops and airlines. You can also sort your results by 'Fastest,' 'Cheapest' or 'Best.'

The best time to fly from Tampa to Chicago Midway International Airport (MDW)

  • November is the quietest month for flights from Tampa to Chicago Midway International Airport (MDW), while July is the busiest. Work out the ideal time to visit Chicago based on whether you want a lively atmosphere or a more laid-back vibe.

  • When booking your Tampa to MDW plane ticket, consider the kind of weather forecast you're hoping for. July is the warmest month in Chicago, with temperatures ranging from 16ºC (61ºF) to 28ºC (82ºF).

  • January sees temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Search for cheap tickets from Tampa to Chicago Midway International Airport around that time if you want to travel when it's cooler.

More about Chicago

  • When it comes to looking for somewhere to lay your head, you'll find the top stays in Chicago right here. Browse these hotels after you've booked your flight from Tampa to Chicago Midway International Airport:

  • There are so many things to do and see in this city, it can be difficult to know where to begin. Millennium Park, Art Institute of Chicago and Willis Tower are major attractions which should feature on any well-planned Chicago itinerary.

Explore more of the United States

  • You've visited Chicago, now it's time to explore other corners of the United States. Journey about 257 kilometres southeast to Indianapolis to tick off its leading attractions. From Lucas Oil Stadium to Eiteljorg Museum and The Children's Museum of Indianapolis, there's plenty to keep you on the go.

  • If there's time to check out another major stop in the United States, head for Milwaukee, about 137 kilometres north of Chicago. Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo are among the biggest draws.

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