TPA - MDW

$43 Find Cheap Flights from Tampa to Chicago Midway Airport

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Tampa to Midway departing on 6/26. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago Midway Airport

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Tampa to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Tampa to Chicago, as well as popular online travel agencies
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Flights Deals

Cheap Flights from Tampa to Midway

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Tampa to Midway that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Recent round-trip flight deals from Tampa to Midway

KAYAK's recommended round-trip deals from the most popular airlines that fly from Tampa to Midway.
Discover the best prices for you by selecting your travel dates on KAYAK.
Frontier Logo
8:49 pm - 10:41 pmTPA-MDW
2h 52mnonstop
Frontier Logo
4:06 pm - 7:49 pmMDW-TPA
2h 43mnonstop
$86Frontier
Find Deal
Thu, May 29 - Sun, Jun 1
Frontier Logo
8:44 pm - 10:36 pmTPA-MDW
2h 52mnonstop
Frontier Logo
4:06 pm - 7:50 pmMDW-TPA
2h 44mnonstop
$88Frontier
Find Deal
Thu, Jul 10 - Sun, Jul 13
Frontier Logo
8:49 pm - 10:41 pmTPA-MDW
2h 52mnonstop
Frontier Logo
4:06 pm - 7:49 pmMDW-TPA
2h 43mnonstop
$90Frontier
Find Deal
Thu, May 29 - Sun, Jun 1
Frontier Logo
8:49 pm - 10:41 pmTPA-MDW
2h 52mnonstop
Frontier Logo
4:06 pm - 7:49 pmMDW-TPA
2h 43mnonstop
$91Frontier
Find Deal
Thu, May 29 - Sun, Jun 1
Frontier Logo
8:44 pm - 10:32 pmTPA-MDW
2h 48mnonstop
Frontier Logo
4:06 pm - 7:49 pmMDW-TPA
2h 43mnonstop
$100Frontier
Find Deal
Thu, Jun 26 - Sun, Jun 29
Southwest Logo
7:25 pm - 9:10 pmTPA-MDW
2h 45mnonstop
Southwest Logo
9:00 pm - 12:35 amMDW-TPA
2h 35mnonstop
$169Southwest
Find Deal
Wed, May 28 - Sun, Jun 1
Southwest Logo
8:40 pm - 10:20 pmTPA-MDW
2h 40mnonstop
Southwest Logo
5:15 pm - 8:50 pmMDW-TPA
2h 35mnonstop
$178Southwest
Find Deal
Wed, Jun 11 - Sat, Jun 14
Delta Logo
5:53 pm - 9:27 pmTPA-MDW
4h 34m1 stop
Delta Logo
9:16 am - 4:58 pmMDW-TPA
6h 42m1 stop
$197Delta
Find Deal
Fri, May 30 - Mon, Jun 2
Delta Logo
6:20 am - 9:40 amTPA-MDW
4h 20m1 stop
Delta Logo
4:15 pm - 11:20 pmMDW-TPA
6h 05m1 stop
$198Delta
Find Deal
Wed, May 28 - Wed, Jun 4
 Logo
5:20 am - 7:14 pmTPA-MDW
14h 54m2 stops
 Logo
8:04 pm - 8:17 pmMDW-TPA
23h 13m2 stops
Fri, May 30 - Mon, Jun 2
Expert advice

Expert advice for your flight from Tampa to Midway

 
Snippets provided in this section are AI-generated based on a summarization of KAYAK-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airlines
Frontier

Frontier's Economy Bundle includes a carry-on and seat choice, ideal for budget travelers.


Consider Premium Bundle for priority boarding and extra legroom, just $20 more than Economy.

Read more about Frontierby Stefanie Waldek
Southwest

Southwest offers two free checked bags, saving costs for travelers with luggage.


Use EarlyBird Check-In for a better boarding position, avoiding middle seats.

Read more about Southwestby Blane Bachelor
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on Frontier

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Blane Bachelor

Blane Bachelor

Expert on Southwest

Blane Bachelor

Blane Bachelor

Blane Bachelor is a journalist and editor specializing in travel and aviation who writes regularly for top global outlets. Born and raised in Florida, Blane has worked and lived in four countries, including the Netherlands, where she’s currently based with her family. Her favorite way to get to know a new destination is by running or riding a bike around town – or hearing a spooky ghost story about local history. She will always choose the window seat.

Read more
Useful Info

KAYAK's insights & trends for Tampa to Midway flights

Get data-powered insights and trends into flights from Tampa to Midway to help you find the cheapest flights, the best time to fly and much more.

What’s the cheapest day of the week to fly from Tampa to Chicago Midway Airport?

The average price of all round-trip flights from Tampa to Chicago Midway Airport clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Tampa to Chicago Midway Airport, look for departures on Fridays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from Chicago Midway Airport, Tuesday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly from Tampa to Chicago Midway Airport?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Tampa to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Tampa to Chicago Midway Airport is June, where tickets cost $159 (return) on average. On the other hand, the most expensive months are February and October, where the average cost of round-trip tickets is $257 and $250 respectively.

How far in advance should I book a flight from Tampa to Chicago Midway Airport?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Tampa to Chicago Midway Airport, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Tampa to Chicago Midway Airport, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 13 weeks before departure.

Good to know

Low seasonJanuary
High seasonAugust
Cheapest flight$43
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Tampa to Chicago Midway Airport

When to book flights from Tampa to Midway

Are your dates flexible? Find out the best times to travel from Tampa to Midway based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

Flights from Tampa to Midway: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew the route from Tampa to Midway 
RachelFlew with SouthwestTPA-MDWJan 2025
Tampa Intl was a surprisingly easy airport to navigate!
CindyFlew with SouthwestTPA-MDWMar 2024
Don’t check a bag. Chicago takes forever to get your baggage.

FAQs for booking Tampa to Chicago Midway Airport flights

  • Tampa International Airport (TPA) offers different services and amenities to accommodate passengers with limited mobility. You’ll find wheelchair assistance, service animals, gate access for companions, accessible parking, boarding assistance, elevators, accessible restrooms, telephones, and accessible parking spaces.

    If you’re looking for eco-friendly flights from Tampa to Chicago Midway Airport, you can book Frontier Airlines or Southwest Airlines. These airlines have flights that emit less CO₂ on their direct connections. They have implemented several sustainable practices in their daily operations to reduce carbon emissions.

  • How do I get to downtown Chicago from Chicago Midway Airport (MDW)?

    You can take the Orange Line trains operated by the Chicago Transit Authority (CTA), which connects the airport to downtown Chicago. The journey time is 20 to 25 minutes. If the train isn’t operational, take the N62 Archer bus or the PACE suburban public bus system. Taxis and car rentals are readily available at the airport.

  • Which airline has the best carry-on weight allowance for direct flights from Tampa to Chicago Midway Airport (MDW)?

    Consider booking Southwest Airlines, which has no maximum carry-on weight limit for carry-on luggage. However, your carry-on bag shouldn’t be bigger than 24 x 16 x 10 inches and should fit in the overhead bin easily. Your small personal item should comfortably fit beneath the seat in front of you.

  • What lounges are available at Tampa International Airport (TPA)?

    TPA has multiple lounges to relax in before your flight to Chicago Midway Airport. You can check into American Airlines Admirals Club at Concourse F, which can be accessed by paying at the door with proof of an American Airlines ticket or Delta Sky Club at Concourse E. These lounges offer complimentary drinks and snacks, comfortable sofas, a broad menu, free internet, cable TV, a flight information monitor, magazines, newspapers, and workspaces.

  • What is the cheapest flight from Tampa to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Tampa to Chicago Midway Airport was $43 for a one-way ticket and $86 for a round-trip.

  • Do I need a passport to fly between Tampa and Chicago Midway Airport?

    Even though you are not required to have a passport, keep in mind that an official ID is needed to board the airplane.

  • Which airports will I be using when flying from Tampa to Chicago Midway Airport?

    Tampa and Chicago Midway Airport are both served by 1 main airport. You will leave Tampa from Tampa and will be arriving at Chicago Midway.

  • Which airlines offer Wi-Fi service onboard planes from Tampa to Chicago Midway Airport?

    American Airlines, and Delta offer inflight Wi-Fi service on the Tampa to Chicago Midway Airport flight route.

  • Which aircraft models fly most regularly from Tampa to Chicago Midway Airport?

    The Airbus A320neo is the aircraft model that flies most regularly on the Tampa to Chicago Midway Airport flight route.

  • On which days can I fly direct from Tampa to Chicago Midway Airport?

    There are nonstop flights from Tampa to Chicago Midway Airport on a daily basis.

  • Which is the best airline for flights from Tampa to Chicago, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Tampa to Chicago are Southwest and Delta. With an average price for the route of $307 and an overall rating of 8.0, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $324 and an overall rating of 8.0.

  • How does KAYAK find such low prices on flights from Tampa to Chicago Midway Airport?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Tampa to Chicago Midway Airport.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Tampa to Chicago Midway Airport?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago Midway Airport from Tampa is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Tampa to Chicago Midway Airport?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago Midway Airport with an airline and back to Tampa with another airline. Booking your flights between Tampa and MDW can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Tampa to Chicago Midway Airport?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago Midway Airport from Tampa up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

KAYAK’s top tips for finding a cheap flight from Tampa to Chicago Midway Airport

  • Looking for a cheap flight? 25% of our users found flights on this route for $103 or less one-way and $219 or less round-trip.
  • Which other cities can I fly to from San Francisco?
  • From San Francisco International Airport (SFO), you can extend your trip to domestic destinations like Las Vegas, Dallas, Los Angeles, Seattle, Boston, Miami, Denver, Atlanta, Chicago, and New York City or international destinations like Tokyo, Dubai, London, Vancouver, Beijing, Paris, Seoul, and Sydney.
  • Several connecting and non-stop flights serve the Tampa (TPA) to Chicago Midway Airport (MDW) flight route. You’ll likely have a layover in Atlanta (ATL), Minneapolis (MSP), Detroit (DTW), Philadelphia (PHL), Dallas (DFW), Denver (DEN), or Nashville (BNA) when you opt for a one-stop flight on this route.
  • If you have a minor flying alone, consider booking them with Southwest Airlines, which has a special service for Unaccompanied Minors on its direct flights from Tampa to Chicago Midway Airport (MDW). This service is available and mandatory for children aged 5 to 11. Your child will receive assistance throughout the flight.
  • Delta Air Lines has several Business Class flights from Tampa to Chicago Midway Airport (MDW). This option is available on its one-stop connections. You’ll enjoy access to the Delta Sky Club Lounge, special baggage allowance, premium dining on board, comfortable seats, spacious cabins with more legroom, dedicated services, and in-flight entertainment.

Prefer to fly direct from Tampa to Chicago Midway Airport?

Find which airlines fly direct from Tampa Airport to Chicago Midway Airport, which days they fly and book direct flights.

Direct departures

Tampa to Chicago Midway

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights

Direct returns

Chicago Midway to Tampa

Monday

Southwest

Southwest

Tuesday

Southwest

Southwest

Wednesday

Southwest

Southwest

Thursday

Frontier, Southwest

Frontier, Southwest

Friday

Southwest

Southwest

Saturday

Southwest

Southwest

Sunday

Frontier, Southwest

Frontier, Southwest

See more direct flights
See more direct flights

Top 4 airlines serving from Tampa to Midway

 
See real verified KAYAK customer reviews for airlines flying from Tampa to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Tampa to Midway? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4294 reviews
7.6Entertainment
8.6Crew
8.2Boarding
7.1Food
8.0Comfort
Airline reviews

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

6.0 GoodJennifer, Apr 2025FLL - RDU
Read more Southwest reviews

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

WiFi on the flight was not working. Thus, entertainment options were limited.

Flight was awfully bumpy and landing was a bit jolting. I was in the restroom when snacks and drinks were served and was not asked if i wanted any. I had to ask for water finally.

Crew was great flight was great baggage claim was a failure. It took over 1 hour for bags to arrive. Poor communication poor effort when I spoke to the supervisor about the delay

Planes are aged. The wifi is unreliable and on many fights, no-existent. The flight attendants were very good.

I had a wonderful flight, but the only thing that annoyed me was how crowded TSA was. I still believe airports and all planes work together to bunch everyone together to drive up cost.

Easy to book and to get check in and get on and off.

Everything worked well. Crew was as entertaining as is possible on a plane flight. Southwest still has good legroom:

I like that it was on time and the staff was friendly.

Glad flight made it out. So many delays due to hurricane. everyone did a great job.

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

The worst part was I was NOT allowed in the lounge even though I was holding a first class ticket and have a premium American Express card. I have flown Business or First Class with many airlines. Delta is the ONLY one who does not extend this courtesy to anyone except people who hold the very expensive American Express card. As a result, I won’t fly Delta if I have any other choice.

The Dekta Rep that checked us in was great. She's very personable, pleasant, and can tell she enjoys her job.

Friendly flight attendants, smooth 8-9 hours flight. Economy seats are small and uncomfortable as usual.

The young man who was our flight attendant in first class was lazy and did not do his job well at all. Never offered drinks upon boarding - actually I take that back... said "are you okay with water" as if I do not want to get you anything else, only passed the snacks around once, got my drink order wrong and then never offered a second round of drinks. He was the worst I have ever seen on Delta and we fly a lot.

Flight left early and arrived early. the whole trip was excellent.

Newer plane, relatively easy boarding, not a full flight and was told that we could not be moved up because of weight and balance issues. Otherwise, a very good experience.

Everything was great. Great service, excellent communication, and early arrival

I sat in comfort plus. It was fine. Seats were comfortable. I got drinks and snacks.

Good and consistent Printer in lounge did not work for me :(

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

Not having it be changed after we bought the flight tickets from a direct flight getting in at a reasonable time to a connecting flight red eye of 9 hours, so that we would lose our 35 dollars in nonrefundable insurance would've been great! Our country really does need low-cost carrier options, but this type of "service" ain't it. Fortunately, had a little better success with them flying to and from San Juan PR last month at least.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

If kayak actually provided me this flight and didn’t just send me notifications about it

Terrible-extreme delay with very little communication, plane was overfull, luggage was returned on baggage claim in filthy condition.

Lower cost is the reason to fly Spirit. Should give free baggage with credit card.

Very difficult. Flew out on Dec 24th and it was a mess. They know it is going to be the busiest time of the year and they had no organization. Finally they called for people going on certiam flights so they could get them thru thw line then we had to rush to our gate to get in li e to board.We missed our flight do to being stuck at the border of Mexico. They would not work with us to make an affordable price so we had to wait a day with no where to go and pay 280 more for our flights. I would think that a complimentary drink would be nice. But we had to pay 4.49 for a coke. Not an overall good experience

I’ve now flown Spirit a few times and while the general perception of Spirit I feel is poor, I’ve had a great experience each time. They do charge extra for everything but you should know that going in

Horrible. Take off was delayed by an hour. They were letting people board d the plane right before takeoff. I was delayed an hour when I arrived and late for my meeting. Spirit is NEVER on time.

My other half doesn't have his luggage and I made a mistake by getting 3 check in bags instead of 2 and I'm going through changes to get credit for the one I didn't use. There giving me the run around!

Seats are uncomfortable but price is good. Guess I can put up with misery for four hours.

Cancelled and declined to find alternatives Earlier flight is 2 days later Sent the cancellation notification very late, wish I knew earlier would have stayed to watch the Miami open final game Very disappointing service

They switched my flight to Spirit, Never using Kayak again,

The flight itself was ok and the pilot was very communicative. However, our flight was delayed for almost 3 hours, the gate was changed 3 times and there was no communication as we were waiting. The flight staff was overall a little crabby...I understand as they probably had a long day but we all did.

Asked for a seat change to be w my wife at the gate they were great in sorting it out to make it happen

They cancelled the flight and did nothing. I should be compensated for my uber rides to and from airport. Not a good service by frontier or kayak.

The worst service , the agents from the counter are really bad . Poor customer service . They didnt help me to get in the flight . I was on line when they close the flight without telling and I couldn’t board the plane . I will like to get my money back ey back because it was their fault. Really bad management , bad manners, bad additud

The check in process was a mess for no reason. I spent an hour waiting in line trying to get them to print my boarding pass and as a result I missed my flight.

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

The seats were extremely hard and uncomfortable. It was disappointing even for a budget airline.

Everything you need to know for your flight from Tampa to Midway

Information on your arrival and departure airports

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