$54 Cheap Flights from Tampa to Chicago

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly from Tampa Intl. to Midway Intl.

Amazing TPA to MDW Flight Deals

The cheapest flights to Midway Intl. found within the past 7 days were $108 round trip and $54 one way. Prices and availability subject to change. Additional terms may apply.

Flight Schedule for TPA to MDW

CarrierFlightDepart TPAArrive MDWSat
F9211503:10 pm04:59 pmCheck FareCheck FareCheck FareCheck FareCheck FareCheck Fare
0 Stops
F9211704:45 pm06:34 pm
Check Fare
0 Stops

Best Midway Intl. Flight and Hotel Packages

Midway Intl. flight + hotel packages - economy flights

Hyatt Rosemont Near O'Hare
DoubleTree by Hilton Chicago O'Hare Airport - Rosemont
Embassy Suites by Hilton Chicago O'Hare Rosemont
avid hotel Chicago O’Hare – Des Plaines, an IHG Hotel
Holiday Inn Chicago - Elk Grove, an IHG Hotel
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Frequently asked questions

Can I catch a flight from TPA to Chicago Airport right now?
Ensure you check out the Covid-19 Travel Advisor to discover if there are any current quarantine requirements and travel advice reports in place in Midway Airport when jet-setting from Tampa Airport.
Are there direct flights from Tampa Airport to MDW?
If you’d rather avoid layovers, you should plan your flight from Tampa Airport to MDW ahead of time. Southwest Airlines is the only airline that operates direct flights to Chicago from Tampa.
If I am not able to travel due to COVID-19, can I change my booking to a later date?
For more info about changing your flight to Midway Intl. Airport (MDW), please visit our Customer Service Portal.
How long is the flight from Tampa Intl. Airport (TPA) to Chicago Airport?
The journey from Tampa to Chicago takes just 2 hours and 37 minutes all up. With such minimal air time, you won’t need to worry if you forget to bring a phone charger in your carry-on luggage.
What is the flight distance from TPA to Chicago Airport?
With a flight distance of 1,000 mi between Tampa Intl. Airport (TPA) and Midway Airport, you’re going to be up in the air for a while. It’s the perfect opportunity to watch a movie or two, catch up on work or just sit back and relax with a novel.
What airlines fly from TPA to Midway Airport?
Eager to fly directly from Tampa to Chicago? It’s your lucky day. Southwest Airlines (WN) offers as many as 143 flights per month and is a popular choice with many well-traveled wanderers.
What airlines have practices regarding COVID-19 in place and use social distancing?
From the moment you enter the departure terminal to when you leave the arrivals terminal, if you’re flying with Southwest Airlines, Delta or Volaris you can be sure that COVID-19 measures and social distancing rules have been adhered to. Many airlines have introduced capped capacity flights and keeping the middle seat empty.
What is the best day to buy a plane ticket?
This just in! Airfares offered on Thursdays tend to be the cheapest, according to flight demand on Travelocity in 2021. Tuesday and Wednesday prices are also good, but you may want to prepare your budget if booking during the weekend, as data shows that is when prices are generally at their highest.
What are the cheapest days to fly?
Frequent travelers may already know this, but earlier in the week can be the cheapest time to fly. In 2021, flights departing on a Monday were generally the cheapest of the week, whereas you may pay a premium for weekend flights when demand is usually high. On average, tickets were most expensive for Saturday departures, so if you need to fly out on a weekend, you might look for deals ahead of time.
How far in advance can you book a flight?
Trying to figure out how early you should book your flight? It’s possible to start comparing international airfares on Travelocity up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 0-2 weeks prior to their travel dates.*According to flight demand on Travelocity.com from January to December 2021. Savings are subject to change based on departure location, date and destination.


Traveling From
Tampa Intl.
Traveling To
Midway Intl.
Shortest Flight Time
0 hours 35 mins
Earliest Departure Time
5:00AM CDT
Latest Departure Time
10:20PM CDT
Lowest Flight Price

Route Info

Flight path for flights from Tampa International Airport to Chicago Midway International Airport.

1,004.00 miles

Discover our best flights from Tampa TPA to Chicago MDW. 

With 20 airlines to choose from on Travelocity, you can easily find the best option for you. Use our filters to sort by price, compare airlines, and find the most convenient flight times. 


Find our best return flights from Tampa TPA to Chicago MDW at the right price  

Airfares to Chicago MDW from Tampa TPA currently cost between $108 and $147. It’s usually cheaper to book a round trip than two separate one-way flights. Prices and availability subject to change. Additional terms may apply. 


Book one-way flights from Tampa TPA to Chicago MDW 

If you want to be flexible about when you return, or keep your travel options open ended, a one-way flight could be just the ticket! You’ll find one-way airfares from Tampa TPA to Chicago MDW on Travelocity starting at $54. Prices and availability subject to change. Additional terms may apply. 


Get to Chicago MDW from Tampa TPA quicker with direct flights. 

Get to Chicago faster, without the hassle of changing planes and moving baggage, by booking a direct flight. Expect your direct flight to MDW from TPA to take around 0 hour(s) 35 min(s).  


Find our cheapest airfares for flights from Tampa TPA to Chicago MDW

Find cheap flight deals by using our search filters to sort results starting with the lowest price airfares to MDW from TPA. Our Price Match Promise means if you find a lower rate on Travelocity.com or on another US-based website within 24 hours of booking, we’ll credit or refund the difference.  


Get our best airfare deals for your flight from Tampa TPA to Chicago MDW today 

If you’re flexible about when you travel, August is usually the cheapest month to fly from Tampa TPA to Chicago MDW. If you need to be more specific, search by date and arrival and departure times.Then, compare prices across different airlines, and sort results by lowest price first. 


Book flexible airline tickets for flights to Chicago MDW from Tampa TPA 

Some airlines let you change your travel dates without charging a fee. Use our ‘no change fee’ filter to see which flights to MDW from TPA have this option.  


Travel with confidence when you book flights to Chicago MDW from Tampa TPA with Travelocity 

We’ve secured fantastic deals with all the main airline carriers and it’s easy to compare, choose, and book with Travelocity. With 24/7 customer service and our free 'App', we’ll always keep you moving. 

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.