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Cheap flights from Tampa to Chicago from $68

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 3/5. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:05 am - 9:08 pm
TPA
-
MDW
16h 03m
1 stop
Frontier Logo
2:19 pm - 12:35 am
MDW
-
TPA
9h 16m
1 stop
$133Frontier
Sat, Feb 14 - Mon, Feb 16
Frontier Logo
6:15 am - 7:07 pm
TPA
-
MDW
13h 52m
1 stop
Frontier Logo
9:15 am - 10:20 pm
MDW
-
TPA
12h 05m
1 stop
$134Frontier
Tue, Feb 17 - Sat, Feb 21
Frontier Logo
6:05 am - 9:08 pm
TPA
-
MDW
16h 03m
1 stop
Frontier Logo
7:00 am - 10:29 pm
MDW
-
TPA
14h 29m
1 stop
$135Frontier
Sat, Feb 14 - Wed, Feb 18
Frontier Logo
4:13 pm - 7:07 pm
TPA
-
MDW
27h 54m
1 stop
Frontier Logo
6:00 am - 9:00 pm
MDW
-
TPA
14h 00m
1 stop
$138Frontier
Tue, Mar 3 - Tue, Mar 10
Frontier Logo
6:15 am - 7:07 pm
TPA
-
MDW
13h 52m
1 stop
Frontier Logo
6:00 am - 6:30 pm
MDW
-
TPA
11h 30m
1 stop
$139Frontier
Tue, Feb 17 - Sat, Feb 21
Frontier Logo
10:05 pm - 10:24 pm
TPA
-
MDW
25h 19m
1 stop
Frontier Logo
6:05 am - 10:08 am
MDW
-
TPA
27h 03m
1 stop
$143Frontier
Fri, Mar 6 - Fri, Mar 13
Frontier Logo
6:15 am - 7:07 pm
TPA
-
MDW
13h 52m
1 stop
Frontier Logo
12:22 pm - 6:30 pm
MDW
-
TPA
5h 08m
1 stop
$147Frontier
Wed, Feb 18 - Thu, Feb 19
Frontier Logo
1:07 pm - 10:29 pm
TPA
-
MDW
10h 22m
1 stop
Frontier Logo
2:19 pm - 12:25 am
MDW
-
TPA
9h 06m
1 stop
$148Frontier
Thu, Feb 26 - Mon, Mar 2
Frontier Logo
5:30 am - 7:47 pm
TPA
-
MDW
15h 17m
1 stop
Frontier Logo
2:41 pm - 9:00 pm
MDW
-
TPA
5h 19m
1 stop
$150Frontier
Fri, Mar 6 - Mon, Mar 9
Frontier Logo
5:25 am - 11:27 am
TPA
-
MDW
7h 02m
1 stop
Frontier Logo
2:19 pm - 12:25 am
MDW
-
TPA
9h 06m
1 stop
$154Frontier
Thu, Feb 19 - Mon, Feb 23

Frontier flights from Tampa to Chicago Midway Airport

Our best Frontier deals on Tampa to Chicago Midway Airport flight tickets
Frontier
Feb 12
TPA6:00 amTampa
6h 27m
1 stop
MDW11:27 amChicago Midway
Feb 17
MDW6:00 amChicago Midway
15h 29m
1 stop
TPA10:29 pmTampa
$131
Frontier
Feb 14
TPA6:05 amTampa
16h 03m
1 stop
MDW9:08 pmChicago Midway
Feb 16
MDW2:19 pmChicago Midway
9h 16m
1 stop
TPA12:35 amTampa
$133
Frontier
Feb 17
TPA6:15 amTampa
13h 52m
1 stop
MDW7:07 pmChicago Midway
Feb 21
MDW9:15 amChicago Midway
12h 05m
1 stop
TPA10:20 pmTampa
$134

Southwest flights from Tampa to Chicago Midway Airport

Our best Southwest deals on Tampa to Chicago Midway Airport flight tickets
Southwest
Mar 10
TPA10:25 amTampa
2h 50m
MDW12:15 pmChicago Midway
Mar 11
MDW4:30 pmChicago Midway
2h 35m
TPA8:05 pmTampa
$157
Southwest
Mar 7
TPA6:50 pmTampa
2h 50m
MDW8:40 pmChicago Midway
Mar 10
MDW6:10 amChicago Midway
2h 40m
TPA9:50 amTampa
$177
Southwest
Mar 9
TPA8:55 amTampa
4h 10m
1 stop
MDW12:05 pmChicago Midway
Mar 10
MDW4:30 pmChicago Midway
2h 35m
TPA8:05 pmTampa
$183

momondo Fare Finder

 
Customize your flight search to find flights from Tampa to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated February 5, 2026.
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

Sat 2/14

6:05 am-9:08 pm

1 stop16h 03m

Chicago Midway

Mon 2/16

2:19 pm-12:35 am

1 stop9h 16m

$133

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 2/17

6:15 am-7:07 pm

1 stop13h 52m

Chicago Midway

Sat 2/21

9:15 am-10:20 pm

1 stop12h 05m

$134

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 2/14

6:05 am-9:08 pm

1 stop16h 03m

Chicago Midway

Wed 2/18

7:00 am-10:29 pm

1 stop14h 29m

$135

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 3/3

4:13 pm-7:07 pm

1 stop27h 54m

Chicago Midway

Tue 3/10

6:00 am-9:00 pm

1 stop14h 00m

$138

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 2/17

6:15 am-7:07 pm

1 stop13h 52m

Chicago Midway

Sat 2/21

6:00 am-6:30 pm

1 stop11h 30m

$139

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 3/6

10:05 pm-10:24 pm

1 stop25h 19m

Chicago Midway

Fri 3/13

6:05 am-10:08 am

1 stop27h 03m

$143

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 2/18

6:15 am-7:07 pm

1 stop13h 52m

Chicago Midway

Thu 2/19

12:22 pm-6:30 pm

1 stop5h 08m

$147

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 2/26

1:07 pm-10:29 pm

1 stop10h 22m

Chicago Midway

Mon 3/2

2:19 pm-12:25 am

1 stop9h 06m

$148

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 3/6

5:30 am-7:47 pm

1 stop15h 17m

Chicago Midway

Mon 3/9

2:41 pm-9:00 pm

1 stop5h 19m

$150

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 2/19

5:25 am-11:27 am

1 stop7h 02m

Chicago Midway

Mon 2/23

2:19 pm-12:25 am

1 stop9h 06m

$154

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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?

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Tampa, with most prices found around $202. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Tampa during the month March is also very affordable. Most momondo users find prices during this month for around $203.

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 $228. 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, Monday 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 $320.

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 $199 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $293. 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 $248 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 $177 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 50% 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 February 2026, prices for Tampa to Chicago Midway Airport flights are approximately 237% 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

$176

Fastest flight time

2h 35m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Tampa in the past 72 hours is $176. The best round-trip flight deal from Tampa to Chicago Midway Airport found on momondo in the last 72 hours is $246.
The fastest flight from Tampa to Chicago Midway Airport takes 2h 35m
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 35m 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?

  • 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?

  • 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
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $46Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
DeltaPriceFrom $98Free CancellationRating
7.9
8,145 reviews
Search Delta flights
SouthwestPriceFrom $169Free CancellationRating
8.0
4,274 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 $169. Generally, Southwest has 33 flights on this route every week with an average price of $298. Southwest is rated 8.0/10 by our users.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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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