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

Southwest, Frontier, and Delta are the most popular carriers operating from Tampa to Chicago Midway

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

3 flights are operational daily from Tampa to Chicago Midway Airport as of November 2025. The most popular departure time for this route is 9:00AM, with 42% of flights per day taking off at noon.

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 51% of people opting to fly with this airline when traveling to Chicago Midway Airport. Keep in mind that there are 4 different airlines that fly to Chicago Midway Airport on a routine basis, so you have a few additional options to choose from.

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

As of November 2025, there are 24 flights per week flying from Tampa to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 21% of flights taking off on this day.

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 November 2025.

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 2025/26

1 adult

0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Tampa to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

8:25 am - 12:41 pmTPA-MDW

5h 16m1 stop

2:49 pm - 11:29 pmMDW-TPA

7h 40m1 stop

$110Frontier

Find Deal

Wed, Nov 19 - Tue, Dec 9

5:45 am - 10:12 pmTPA-MDW

17h 27m1 stop

6:12 am - 12:26 amMDW-TPA

17h 14m1 stop

$113Frontier

Find Deal

Wed, Dec 24 - Wed, Dec 31

7:00 am - 11:08 amTPA-MDW

29h 08m1 stop

6:15 am - 6:46 pmMDW-TPA

11h 31m1 stop

$120Frontier

Find Deal

Sat, Dec 13 - Mon, Dec 15

5:40 am - 1:59 pmTPA-MDW

9h 19m1 stop

8:05 am - 4:31 pmMDW-TPA

7h 26m1 stop

$124Frontier

Find Deal

Sat, Dec 6 - Sun, Dec 7

7:15 am - 9:00 amTPA-MDW

2h 45mnonstop

2:15 pm - 9:00 pmMDW-TPA

5h 45m1 stop

$143Southwest

Find Deal

Wed, Dec 10 - Wed, Dec 10

7:25 am - 12:41 pmTPA-MDW

6h 16m1 stop

8:41 pm - 10:14 amMDW-TPA

12h 33m1 stop

$147Multiple Airlines

Find Deal

Wed, Nov 19 - Thu, Nov 20

7:35 am - 11:25 amTPA-MDW

4h 50m1 stop

1:30 pm - 7:55 pmMDW-TPA

5h 25m1 stop

$153Southwest

Find Deal

Wed, Dec 10 - Wed, Dec 10

7:25 am - 12:41 pmTPA-MDW

6h 16m1 stop

8:41 pm - 10:14 amMDW-TPA

12h 33m1 stop

$156Multiple Airlines

Find Deal

Wed, Nov 19 - Thu, Nov 20

7:06 pm - 11:47 pmTPA-MDW

5h 41m1 stop

9:34 am - 5:03 pmMDW-TPA

6h 29m1 stop

$197Delta

Find Deal

Fri, Dec 12 - Mon, Dec 15

6:30 am - 9:54 amTPA-MDW

4h 24m1 stop

12:50 pm - 6:01 pmMDW-TPA

4h 11m1 stop

$198Delta

Find Deal

Fri, Dec 5 - Mon, Dec 8

Frontier flights from Tampa to Chicago Midway Airport

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

Frontier

Nov 19

TPA8:25 amTampa

5h 16m

1 stop

MDW12:41 pmChicago Midway

Dec 9

MDW2:49 pmChicago Midway

7h 40m

1 stop

TPA11:29 pmTampa

$110

Find similar

Frontier

Dec 24

TPA5:45 amTampa

17h 27m

1 stop

MDW10:12 pmChicago Midway

Dec 31

MDW6:12 amChicago Midway

17h 14m

1 stop

TPA12:26 amTampa

$113

Find similar

Frontier

Nov 14

TPA3:11 pmTampa

2h 46m

MDW4:57 pmChicago Midway

Nov 17

MDW6:06 pmChicago Midway

2h 35m

TPA9:41 pmTampa

$118

Find similar

Delta flights from Tampa to Chicago Midway Airport

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

Delta

Dec 12

TPA7:06 pmTampa

5h 41m

1 stop

MDW11:47 pmChicago Midway

Dec 15

MDW9:34 amChicago Midway

6h 29m

1 stop

TPA5:03 pmTampa

$197

Find similar

Delta

Dec 5

TPA6:30 amTampa

4h 24m

1 stop

MDW9:54 amChicago Midway

Dec 8

MDW12:50 pmChicago Midway

4h 11m

1 stop

TPA6:01 pmTampa

$198

Find similar

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 11/19

8:25 am-12:41 pm

1 stop5h 16m

Chicago Midway

Tue 12/9

2:49 pm-11:29 pm

1 stop7h 40m

$110

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 12/24

5:45 am-10:12 pm

1 stop17h 27m

Chicago Midway

Wed 12/31

6:12 am-12:26 am

1 stop17h 14m

$113

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 12/13

7:00 am-11:08 am

1 stop29h 08m

Chicago Midway

Mon 12/15

6:15 am-6:46 pm

1 stop11h 31m

$120

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 12/6

5:40 am-1:59 pm

1 stop9h 19m

Chicago Midway

Sun 12/7

8:05 am-4:31 pm

1 stop7h 26m

$124

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 12/10

7:15 am-9:00 am

Nonstop2h 45m

Chicago Midway

Wed 12/10

2:15 pm-9:00 pm

1 stop5h 45m

$143

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 11/19

7:25 am-12:41 pm

1 stop6h 16m

Chicago Midway

Thu 11/20

8:41 pm-10:14 am

1 stop12h 33m

$147

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 12/10

7:35 am-11:25 am

1 stop4h 50m

Chicago Midway

Wed 12/10

1:30 pm-7:55 pm

1 stop5h 25m

$153

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 11/19

7:25 am-12:41 pm

1 stop6h 16m

Chicago Midway

Thu 11/20

8:41 pm-10:14 am

1 stop12h 33m

$156

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 12/12

7:06 pm-11:47 pm

1 stop5h 41m

Chicago Midway

Mon 12/15

9:34 am-5:03 pm

1 stop6h 29m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 12/5

6:30 am-9:54 am

1 stop4h 24m

Chicago Midway

Mon 12/8

12:50 pm-6:01 pm

1 stop4h 11m

$198

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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 December is also very affordable. Most momondo users find prices during this month for around $184.

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 $207. 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 $317.

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 $192 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $276. 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 $238 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 $153 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?

No. A direct flight is the cheapest option for a flight between Tampa to Chicago Midway Airport.

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

As of November 2025, prices for Tampa to Chicago Midway Airport flights are approximately 24% more expensive 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	$91
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 $91. The best round-trip flight deal from Tampa to Chicago Midway Airport found on momondo in the last 72 hours is $104.

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 November 2025.
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 (21.96% of total bookings). The next most popular plane models are Boeing 737-800 (18.48%), Airbus A320neo (12.11%), and Boeing 737-800 Passenger/BBJ2 (winglets) (9.16%).
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 57% of the total bookings. Other popular airlines include Frontier with 40% 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 5.8 3,116 reviews	Search Frontier flights
Delta	PriceFrom $98	Free Cancellation	Rating 7.9 8,000 reviews	Search Delta flights
Southwest	PriceFrom $175	Free Cancellation	Rating 8.0 4,241 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 $175. Generally, Southwest has 24 flights on this route every week with an average price of $300. Southwest is rated 8.0/10 by our users.

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

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.

Start using Trips

Find my bookings

Get notified when prices go down

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

1 adult

Mon 12/8

Mon 12/15

Email me momondo's favorite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago

Popular cities in the United States

Flights to New York John F Kennedy Intl Airportfrom $57

Flights to Newark Airportfrom $44

Flights to Dallas/Fort Worth Airportfrom $58

Flights to New York LaGuardia Airportfrom $58

Flights to Chicago O'Hare Intl Airportfrom $58

Flights to Washington, D.C. Dulles Intl Airportfrom $58

Flights to Orlando Airportfrom $48

Flights to Washington, D.C. Reagan-National Airportfrom $98

Flights to Dallas Love Field Airport

Cheap flights from Tampa to Chicago from $67

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 12/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Tampa to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last minute flights

Cheap direct flights

Frontier flights from Tampa to Chicago Midway Airport

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

Delta flights from Tampa to Chicago Midway Airport

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

momondo Fare Finder

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

See travel insights to Chicago from

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

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?

No. A direct flight is the cheapest option for a flight between Tampa to Chicago Midway Airport.

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

As of November 2025, prices for Tampa to Chicago Midway Airport flights are approximately 24% more expensive when compared to flights at the same time last year.

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

Southwest, Frontier, and Delta are the most popular carriers 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?

3 flights are operational daily from Tampa to Chicago Midway Airport as of November 2025. The most popular departure time for this route is 9:00AM, with 42% of flights per day taking off at noon.

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

As of November 2025, there are 24 flights per week flying from Tampa to Chicago Midway Airport. The most common day of the week flights depart is Mon, with 21% 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