What is the cheapest airline that flies from Tampa to Chicago Midway?

Southwest is the most popular carrier operating from Tampa to Chicago Midway

How many flights depart from Tampa to Chicago Midway Airport on average per week?

As of January 2026, there are 9 flights per week flying from Tampa to Chicago Midway Airport. The most common day of the week flights depart is Fri, with 56% of flights taking off on this day.

How many flights depart from Tampa to Chicago Midway Airport on average per day?

1 flights are operational daily from Tampa to Chicago Midway Airport as of January 2026. The most popular departure time for this route is 5:00PM, with 42% of flights per day taking off in the afternoon.

What airlines fly to Chicago Midway Airport?

Southwest, Frontier and Delta are the top three most popular airlines that fly to Chicago Midway Airport from Tampa according to our data. Southwest is the first choice among our users, with 53% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 3 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

When did momondo last update prices for flights from Tampa Airport to Chicago Midway Airport?

Prices for flights from Tampa Airport to Chicago Midway Airport refresh daily.

How many operators does momondo search for flights from Tampa Airport to Chicago Midway Airport?

There are 3 operators available for flights from Tampa Airport to Chicago Midway Airport as of January 2026.

How old do you have to be to fly from Tampa Airport to Chicago Midway Airport?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Tampa Airport to Chicago Midway Airport.

What documentation or ID do you need to fly to Chicago Midway Airport?

The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$45 Cheap Flights from Tampa to Chicago Midway Airport in 2026

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Cheap round-trip flights

Enter your travel dates to find the best prices.

6:30 am - 12:05 pm

TPA

MDW

6h 35m1 stop

1:20 pm - 8:01 pm

MDW

TPA

5h 41m1 stop

$128Frontier

Wed, Jan 28 - Wed, Feb 4

6:13 pm - 10:19 pm

TPA

MDW

5h 06m1 stop

1:20 pm - 8:01 pm

MDW

TPA

5h 41m1 stop

$146Frontier

Mon, Feb 2 - Wed, Feb 4

6:13 pm - 10:19 pm

TPA

MDW

5h 06m1 stop

9:38 am - 8:35 pm

MDW

TPA

9h 57m1 stop

$147Frontier

Thu, Feb 5 - Sat, Feb 7

4:50 pm - 6:40 pm

TPA

MDW

2h 50mnonstop

10:10 am - 1:50 pm

MDW

TPA

2h 40mnonstop

$157Southwest

Sat, Jan 17 - Sun, Jan 18

6:13 pm - 10:19 pm

TPA

MDW

5h 06m1 stop

6:20 am - 4:57 pm

MDW

TPA

9h 37m1 stop

$162Frontier

Thu, Jan 29 - Mon, Feb 2

10:44 pm - 7:54 pm

TPA

MDW

22h 10m1 stop

12:25 pm - 6:25 pm

MDW

TPA

5h 00m1 stop

$163Frontier

Thu, Jan 15 - Thu, Feb 12

11:05 am - 12:55 pm

TPA

MDW

2h 50mnonstop

5:40 pm - 9:15 pm

MDW

TPA

2h 35mnonstop

$168Southwest

Fri, Feb 6 - Tue, Feb 10

4:50 pm - 6:40 pm

TPA

MDW

2h 50mnonstop

10:15 am - 5:45 pm

MDW

TPA

6h 30m2 stops

$173Southwest

Sat, Jan 17 - Sun, Jan 18

5:45 am - 11:45 am

TPA

MDW

7h 00m1 stop

6:20 am - 4:57 pm

MDW

TPA

9h 37m1 stop

$174Frontier

Fri, Jan 30 - Sun, Feb 1

7:05 am - 8:55 am

TPA

MDW

2h 50mnonstop

1:25 pm - 5:00 pm

MDW

TPA

2h 35mnonstop

$175Southwest

Sat, Jan 17 - Thu, Jan 22

Frontier flights from Tampa to Chicago Midway Airport

Our best Frontier deals on Tampa to Chicago Midway Airport flight tickets

Frontier

Jan 28

TPA6:30 amTampa

6h 35m

1 stop

MDW12:05 pmChicago Midway

Feb 4

MDW1:20 pmChicago Midway

5h 41m

1 stop

TPA8:01 pmTampa

$128

Find similar

Frontier

Feb 2

TPA6:13 pmTampa

5h 06m

1 stop

MDW10:19 pmChicago Midway

Feb 4

MDW1:20 pmChicago Midway

5h 41m

1 stop

TPA8:01 pmTampa

$146

Find similar

Frontier

Feb 5

TPA6:13 pmTampa

5h 06m

1 stop

MDW10:19 pmChicago Midway

Feb 7

MDW9:38 amChicago Midway

9h 57m

1 stop

TPA8:35 pmTampa

$147

Find similar

Southwest flights from Tampa to Chicago Midway Airport

Our best Southwest deals on Tampa to Chicago Midway Airport flight tickets

Southwest

Jan 17

TPA4:50 pmTampa

2h 50m

MDW6:40 pmChicago Midway

Jan 18

MDW10:10 amChicago Midway

2h 40m

TPA1:50 pmTampa

$157

Find similar

Southwest

Feb 6

TPA11:05 amTampa

2h 50m

MDW12:55 pmChicago Midway

Feb 10

MDW5:40 pmChicago Midway

2h 35m

TPA9:15 pmTampa

$168

Find similar

Southwest

Jan 17

TPA4:50 pmTampa

2h 50m

MDW6:40 pmChicago Midway

Jan 18

MDW10:15 amChicago Midway

6h 30m

2 stops

TPA5:45 pmTampa

$173

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momondo Fare Finder

Use the filters below to find and compare flights from Tampa to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 1/28

6:30 am-12:05 pm

1 stop6h 35m

Chicago Midway

Wed 2/4

1:20 pm-8:01 pm

1 stop5h 41m

$128

TampaChicago

TPA - MDW

TPAMDW

Tampa

Mon 2/2

6:13 pm-10:19 pm

1 stop5h 06m

Chicago Midway

Wed 2/4

1:20 pm-8:01 pm

1 stop5h 41m

$146

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 2/5

6:13 pm-10:19 pm

1 stop5h 06m

Chicago Midway

Sat 2/7

9:38 am-8:35 pm

1 stop9h 57m

$147

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 1/17

4:50 pm-6:40 pm

Nonstop2h 50m

Chicago Midway

Sun 1/18

10:10 am-1:50 pm

Nonstop2h 40m

$157

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 1/29

6:13 pm-10:19 pm

1 stop5h 06m

Chicago Midway

Mon 2/2

6:20 am-4:57 pm

1 stop9h 37m

$162

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 1/15

10:44 pm-7:54 pm

1 stop22h 10m

Chicago Midway

Thu 2/12

12:25 pm-6:25 pm

1 stop5h 00m

$163

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 2/6

11:05 am-12:55 pm

Nonstop2h 50m

Chicago Midway

Tue 2/10

5:40 pm-9:15 pm

Nonstop2h 35m

$168

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 1/17

4:50 pm-6:40 pm

Nonstop2h 50m

Chicago Midway

Sun 1/18

10:15 am-5:45 pm

2 stops6h 30m

$173

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 1/30

5:45 am-11:45 am

1 stop7h 00m

Chicago Midway

Sun 2/1

6:20 am-4:57 pm

1 stop9h 37m

$174

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 1/17

7:05 am-8:55 am

Nonstop2h 50m

Chicago Midway

Thu 1/22

1:25 pm-5:00 pm

Nonstop2h 35m

$175

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How to get the cheapest flight ticket from Tampa to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

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

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Tampa, with most prices found around $179. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Tampa during the month March is also very affordable. Most momondo users find prices during this month for around $188.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Tampa. The lowest ticket price found for a Friday departure recently was $218. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Tampa because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $319.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Tampa in the evening is the least expensive time of day to depart. momondo users have found prices as low as $195 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $289. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Tampa to Chicago Midway flight route?

Fly from Tampa to Chicago Midway for the best Tampa - Chicago Midway flight prices

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

You are more likely to see cheaper flights to Chicago Midway Airport from Tampa when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $239 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Tampa for as low as $161 on momondo.

What cabin class options are available on Tampa to Chicago Midway flights?

There is only 1 cabin class available to choose from on Tampa to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Tampa to Chicago Midway Airport flights?

You could potentially save up to 9% on your flight if you consider stops on a Tampa to Chicago Midway Airport flight.

How have Tampa to Chicago Midway Airport flight prices changed over time?

As of January 2026, prices for Tampa to Chicago Midway Airport flights are approximately 31% cheaper when compared to flights at the same time last year.

When to book flights from Tampa to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Tampa to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Tampa to Chicago Midway Airport (TPA to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Tampa to Chicago Midway Airport

Best Price Found	$163
Fastest flight time	2h 40m
Direct flights	Every day

The best one-way flight to Chicago Midway Airport from Tampa in the past 72 hours is $163. The best round-trip flight deal from Tampa to Chicago Midway Airport found on momondo in the last 72 hours is $233.

The fastest flight from Tampa to Chicago Midway Airport takes 2h 40m

Direct flights go from Tampa to Chicago Midway Airport every day.

Search flight deals

How far is Tampa to Chicago Midway by plane?
There are 1000.5 mi between Tampa and Chicago Midway. Typically, this will take 2h 40m by plane in normal conditions.
When did momondo last update prices for flights from Tampa Airport to Chicago Midway Airport?
Prices for flights from Tampa Airport to Chicago Midway Airport refresh daily.
How many operators does momondo search for flights from Tampa Airport to Chicago Midway Airport?
There are 3 operators available for flights from Tampa Airport to Chicago Midway Airport as of January 2026.
How old do you have to be to fly from Tampa Airport to Chicago Midway Airport?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Tampa Airport to Chicago Midway Airport.
What documentation or ID do you need to fly to Chicago Midway Airport?
The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Tampa to Chicago Midway Airport?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Tampa to Chicago Midway Airport is Boeing 737 MAX 8 (21.89% of total bookings). The next most popular plane models are Boeing 737-800 (16.77%), Airbus A321neo (10.86%), and Boeing 737-700 Passenger/BBJ1 (winglets) (9.38%).
What is the most popular airline from Tampa to Chicago Midway Airport?
Based on momondo bookings for flights between Tampa and Chicago Midway Airport, the leading airline is Southwest, making up 62% of the total bookings. Other popular airlines include Frontier with 35% and Delta with 3%.

Best airlines flying from Tampa to Chicago Midway Airport

Compare and see reviews for airlines that fly from Tampa to Chicago Midway Airport with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $46	Free Cancellation	Rating 5.7 3,066 reviews	Search Frontier flights
Delta	PriceFrom $98	Free Cancellation	Rating 7.9 8,022 reviews	Search Delta flights
Southwest	PriceFrom $170	Free Cancellation	Rating 8.0 4,255 reviews	Search Southwest flights

Southwest Flights From Tampa to Chicago Midway Airport
The lowest priced Southwest flight from Tampa to Chicago Midway Airport from the last 72 hours was $170. Generally, Southwest has 9 flights on this route every week with an average price of $296. Southwest is rated 8.0/10 by our users.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Munster

Crown Point

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Tampa to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Tampa to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Tampa to Chicago with flexible booking policies on momondo?

Flights from Tampa to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Tampa to Chicago?

Once you have performed a search for Tampa to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Tampa to Chicago right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Tampa to Chicago now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Chicago and let you know when they change.

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Cheap flights from Tampa to Chicago from $75

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Tampa to Chicago departing on 2/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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Frontier flights from Tampa to Chicago Midway Airport

Our best Frontier deals on Tampa to Chicago Midway Airport flight tickets

Southwest flights from Tampa to Chicago Midway Airport

Our best Southwest deals on Tampa to Chicago Midway Airport flight tickets

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Use the filters below to find and compare flights from Tampa to Chicago Midway Airport that are best for you.

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How to get the cheapest flight ticket from Tampa to Chicago Midway Airport

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

What is the cheapest day to depart on your flight to Chicago Midway Airport?

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

What is the cheapest Tampa to Chicago Midway flight route?

Fly from Tampa to Chicago Midway for the best Tampa - Chicago Midway flight prices

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

What cabin class options are available on Tampa to Chicago Midway flights?

There is only 1 cabin class available to choose from on Tampa to Chicago Midway flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Tampa to Chicago Midway Airport flights?

You could potentially save up to 9% on your flight if you consider stops on a Tampa to Chicago Midway Airport flight.

How have Tampa to Chicago Midway Airport flight prices changed over time?

As of January 2026, prices for Tampa to Chicago Midway Airport flights are approximately 31% cheaper when compared to flights at the same time last year.

What is the cheapest airline that flies from Tampa to Chicago Midway?

Southwest is the most popular carrier operating from Tampa to Chicago Midway

What airlines fly to Chicago Midway Airport?

How many flights depart from Tampa to Chicago Midway Airport on average per day?

1 flights are operational daily from Tampa to Chicago Midway Airport as of January 2026. The most popular departure time for this route is 5:00PM, with 42% of flights per day taking off in the afternoon.

How many flights depart from Tampa to Chicago Midway Airport on average per week?

As of January 2026, there are 9 flights per week flying from Tampa to Chicago Midway Airport. The most common day of the week flights depart is Fri, with 56% of flights taking off on this day.

When to book flights from Tampa to Chicago Midway Airport

Cheap Tampa to Chicago Midway Airport (TPA to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Tampa to Chicago Midway Airport

Best Price Found

Fastest flight time

Direct flights

How far is Tampa to Chicago Midway by plane?

When did momondo last update prices for flights from Tampa Airport to Chicago Midway Airport?

How many operators does momondo search for flights from Tampa Airport to Chicago Midway Airport?

How old do you have to be to fly from Tampa Airport to Chicago Midway Airport?

What documentation or ID do you need to fly to Chicago Midway Airport?

What is the most popular plane model from Tampa to Chicago Midway Airport?

What is the most popular airline from Tampa to Chicago Midway Airport?

Best airlines flying from Tampa to Chicago Midway Airport

Compare and see reviews for airlines that fly from Tampa to Chicago Midway Airport with momondo

Southwest Flights From Tampa to Chicago Midway Airport

Traveling to a place near Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Tampa to Chicago?

Can I find flights from Tampa to Chicago with flexible booking policies on momondo?

How can momondo help me find flights from Tampa to Chicago?

I’m not ready to book a flight from Tampa to Chicago right now. Can momondo alert me if prices change?

An easier way to manage your Chicago Midway Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to Chicago

Popular cities in the United States

Popular flights according to clicks in the last 7 days on momondo