Cheap Flights from Tampa to Chicago Midway

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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? 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 April.

Direct flights from Tampa to Chicago Midway

Tampa to Chicago: Flight information

The things to know before you go.
Cheapest flight foundRs20,128
Cheapest month to flyApril
Average flight time2 hrs, 45 mins
Most popular airlineSouthwest Airlines
Average flights per week36

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 Rs43,777. 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 45 minutes is the average flight time from Tampa to Chicago Midway.
Southwest Airlines flies direct from Tampa to Chicago Midway.
As of February 2026, there are 36 flights per week flying from Tampa to Chicago Midway.
The cheapest month to fly from Tampa to Chicago Midway is usually May.
After crunching the numbers on our flight calendar, we found that it is currently cheapest to fly from Tampa to Chicago Midway Airport on Saturday, 9 May 2026.
Yes – the average flight time is 2 hours and 45 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.
The cheapest airline that flies to Chicago Midway is Southwest Airlines .

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

  • Begin your journey at one of Tampa's main airports, Tampa International Airport (TPA) or St. Petersburg-Clearwater International Airport (PIE). Check out your options for booking a flight from Tampa to Chicago Midway International Airport (MDW) jetting off from either of these.

  • Expect to be travelling for 2 hours 45 minutes. That's the average time for a direct Tampa to Chicago Midway International Airport flight.

  • Chicago Midway International Airport is located in Chicago. The city operates on the UTC-5 timezone and is one hour behind Tampa.

  • With 18 direct weekly flights 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'd like to make the most of your day before taking off, the last departure from TPA to MDW is with Southwest Airlines at 9:55pm.

  • To ensure you get on your flight from Tampa to MDW, leave plenty of time to check in and find your gate. Turning up two hours before international departures and one hour before domestic flights is the general travel rule.

  • If you're taking off during a bank holiday or other peak period, give yourself extra time. Arrive two hours before domestic flights and up to four hours before international departures. Lines at security and check-in will be longer.

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).

  • Book your direct flight from Tampa to Chicago Midway International Airport with Southwest Airlines. This leading airline operates services from TPA.

  • Southwest Airlines ranks first in bookings for flights from TPA to MDW.

  • Southwest Airlines is the most punctual carrier on this route.

  • The journey from central Tampa to TPA takes around 55 minutes on public transport. If you ride-share, drive or take a cab, you'll cover the 13 kilometres in 15 minutes or so, depending on traffic.

  • Planning to catch an early flight from Tampa to Chicago Midway International Airport? Avoid rushing to the terminal (and get some bonus sleep) by staying at one of these hotels near Tampa International Airport:

  • 78.59% of flights departing from Tampa International Airport reach their destination on schedule.

  • TPA is located at 5507 West Spruce Street.

St. Petersburg-Clearwater International Airport (PIE)

  • You can arrive at PIE from the centre of Tampa in about 25 minutes by car (depending on traffic). The ride on public transport will take roughly 2 hours 10 minutes to travel the 29 kilometres or so.

  • Want to treat yourself to an extra night away before your Tampa to MDW flight? Kick back in a hotel near St. Petersburg-Clearwater International Airport before your holiday officially starts. These stays have a room with your name on it:

  • When it comes to keeping flights on track, St. Petersburg-Clearwater International Airport has an on-time arrival performance of 77.01%.

  • PIE is located at Suite 221 - Terminal Building.

About Chicago Midway International Airport (MDW)

  • The last thing you need is a long journey to your hotel if you're arriving on a late flight from Tampa to Chicago Midway International Airport. Check in to one of these accommodation options near MDW instead:

  • Fast-track your adventure by picking up a Chicago Midway International Airport rental car. Grab your wheels from Dollar, Hertz or Budget and explore beyond Chicago's usual tourist stops.

  • Lock in the lowest price by reserving your vehicle around four weeks before 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

  • Chicago Midway International Airport to central Chicago is around 14 kilometres. If you're taking a cab or renting a car, plan in advance to make your trip as easy as possible. Journey times vary depending on traffic and the time of day.

  • If you're travelling on public transport, expect a journey time of roughly 45 minutes.

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

  • At the moment, Rs20,128 is the lowest price we've found for a one-way ticket from Tampa to Chicago Midway International Airport. The cheapest price for a return flight is Rs43,777. Keep in mind fares can change due to demand at the time of booking.

  • To find cheap flights from Tampa to MDW, book ahead. Airlines typically offer lower prices when flights first go on sale.

  • The 'Whole month' tool shows you the cheapest Tampa to Chicago Midway International Airport tickets across the month. It's a great way to snap up a bargain if your plans are flexible.

  • There's no need to check back in every day to find out if fares have dropped when you set up a Price Alert. We'll let you know as soon as a new deal shows up on flight tickets from Tampa to MDW.

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

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

  • May is the quietest month for flights from Tampa to Chicago Midway International Airport (MDW), while July is the most popular. Pick the best time to visit Chicago based on whether you want a bustling atmosphere or a more laid-back vibe.

  • Before locking in your Tampa to MDW flight ticket, consider what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 15ºC to 29ºC.

  • If you want to travel in cooler conditions, search for a cheap ticket from Tampa to Chicago Midway International Airport in January when temperatures are between -12ºC and 3ºC.

More about Chicago

Explore more of the United States

  • You've seen Chicago, now it's time to discover other parts of the United States. Travel about 257 kilometres south-east to Indianapolis to check off its must-visit sights. From 9-11 Memorial to Lucas Oil Stadium and Eiteljorg Museum, you'll have a full itinerary ahead.

  • If you're ready to explore another well-known destination in the United States, head for Milwaukee, roughly 137 kilometres north of Chicago. Richards Duplex Apartments by Frank Lloyd Wright, Miller Park and Milwaukee County Zoo are the start of reasons to visit.

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.