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Cheap flights from Tampa to Chicago from $86

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 7/8. 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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Find the cheapest flights from Tampa to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
7:00 pm - 10:35 pm
TPA
-
MDW
4h 35m
1 stop
Southwest Logo
5:30 am - 9:00 am
MDW
-
TPA
2h 30mnonstop
$181Southwest
Tue, Jun 23 - Tue, Jun 30
Southwest Logo
12:30 pm - 2:10 pm
TPA
-
MDW
2h 40mnonstop
Southwest Logo
7:50 am - 3:50 pm
MDW
-
TPA
7h 00m
2 stops
$182Southwest
Tue, Oct 6 - Tue, Oct 20
Southwest Logo
8:25 am - 10:05 am
TPA
-
MDW
2h 40mnonstop
Southwest Logo
6:05 pm - 9:40 pm
MDW
-
TPA
2h 35mnonstop
$187Southwest
Thu, Sep 10 - Tue, Sep 15
Southwest Logo
9:55 pm - 11:40 pm
TPA
-
MDW
2h 45mnonstop
Southwest Logo
2:00 pm - 9:55 pm
MDW
-
TPA
6h 55m
1 stop
$190Southwest
Wed, Jul 29 - Tue, Aug 4
Southwest Logo
8:00 am - 12:15 pm
TPA
-
MDW
5h 15m
1 stop
Southwest Logo
5:30 pm - 12:05 am
MDW
-
TPA
5h 35m
1 stop
$191Southwest
Tue, Jun 23 - Tue, Jun 23
Southwest Logo
11:30 am - 2:30 pm
TPA
-
MDW
4h 00m
1 stop
Southwest Logo
6:05 pm - 9:40 pm
MDW
-
TPA
2h 35mnonstop
$193Southwest
Thu, Aug 6 - Tue, Aug 11
Southwest Logo
5:35 pm - 7:10 pm
TPA
-
MDW
2h 35mnonstop
Southwest Logo
3:15 pm - 6:50 pm
MDW
-
TPA
2h 35mnonstop
$195Southwest
Tue, Sep 15 - Thu, Sep 17
Southwest Logo
7:00 pm - 10:40 pm
TPA
-
MDW
4h 40m
1 stop
Southwest Logo
7:40 am - 2:50 pm
MDW
-
TPA
6h 10m
2 stops
$196Southwest
Wed, Jul 29 - Tue, Aug 4
Delta Logo
4:32 pm - 10:36 pm
TPA
-
MDW
7h 04m
1 stop
Delta Logo
6:05 am - 12:29 pm
MDW
-
TPA
5h 24m
1 stop
$197Delta
Wed, Aug 26 - Tue, Sep 1
Southwest Logo
6:15 pm - 8:00 pm
TPA
-
MDW
2h 45mnonstop
Southwest Logo
7:50 am - 3:50 pm
MDW
-
TPA
7h 00m
2 stops
$198Southwest
Sat, Oct 3 - Tue, Oct 6

Frontier flights from Tampa to Chicago Midway Airport

Our best Frontier deals on Tampa to Chicago Midway Airport flight tickets
Frontier
Jul 8
TPA4:46 pmTampa
6h 17m
1 stop
MDW10:03 pmChicago Midway
Jul 14
MDW12:11 pmChicago Midway
5h 41m
1 stop
TPA6:52 pmTampa
$222
Frontier
Jun 23
TPA7:00 amTampa
5h 12m
1 stop
MDW11:12 amChicago Midway
Jul 8
MDW6:05 amChicago Midway
11h 47m
1 stop
TPA6:52 pmTampa
$230
Frontier
Jun 17
TPA4:46 pmTampa
6h 25m
1 stop
MDW10:11 pmChicago Midway
Jun 24
MDW12:04 pmChicago Midway
5h 47m
1 stop
TPA6:51 pmTampa
$237

Delta flights from Tampa to Chicago Midway Airport

Our best Delta deals on Tampa to Chicago Midway Airport flight tickets
Delta
Aug 26
TPA4:32 pmTampa
7h 04m
1 stop
MDW10:36 pmChicago Midway
Sep 1
MDW6:05 amChicago Midway
5h 24m
1 stop
TPA12:29 pmTampa
$197
Delta
Aug 11
TPA8:15 amTampa
5h 24m
1 stop
MDW12:39 pmChicago Midway
Aug 15
MDW6:05 amChicago Midway
4h 26m
1 stop
TPA11:31 amTampa
$204
Delta
Aug 8
TPA5:59 pmTampa
5h 37m
1 stop
MDW10:36 pmChicago Midway
Aug 12
MDW6:05 amChicago Midway
4h 24m
1 stop
TPA11:29 amTampa
$210

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 May 31, 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

Cheapest round-trip

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 6/23

7:00 pm-10:35 pm

1 stop4h 35m

Chicago Midway

Tue 6/30

5:30 am-9:00 am

Nonstop2h 30m

$181

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 10/6

12:30 pm-2:10 pm

Nonstop2h 40m

Chicago Midway

Tue 10/20

7:50 am-3:50 pm

2 stops7h 00m

$182

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 9/10

8:25 am-10:05 am

Nonstop2h 40m

Chicago Midway

Tue 9/15

6:05 pm-9:40 pm

Nonstop2h 35m

$187

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 7/29

9:55 pm-11:40 pm

Nonstop2h 45m

Chicago Midway

Tue 8/4

2:00 pm-9:55 pm

1 stop6h 55m

$190

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 6/23

8:00 am-12:15 pm

1 stop5h 15m

Chicago Midway

Tue 6/23

5:30 pm-12:05 am

1 stop5h 35m

$191

TampaChicago

TPA - MDW

TPAMDW

Tampa

Thu 8/6

11:30 am-2:30 pm

1 stop4h 00m

Chicago Midway

Tue 8/11

6:05 pm-9:40 pm

Nonstop2h 35m

$193
Quickest round-trip

TampaChicago

TPA - MDW

TPAMDW

Tampa

Tue 9/15

5:35 pm-7:10 pm

Nonstop2h 35m

Chicago Midway

Thu 9/17

3:15 pm-6:50 pm

Nonstop2h 35m

$195

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 7/29

7:00 pm-10:40 pm

1 stop4h 40m

Chicago Midway

Tue 8/4

7:40 am-2:50 pm

2 stops6h 10m

$196

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 8/26

4:32 pm-10:36 pm

1 stop7h 04m

Chicago Midway

Tue 9/1

6:05 am-12:29 pm

1 stop5h 24m

$197

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sat 10/3

6:15 pm-8:00 pm

Nonstop2h 45m

Chicago Midway

Tue 10/6

7:50 am-3:50 pm

2 stops7h 00m

$198

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 typical price of a round-trip flight between Tampa and Chicago Midway Airport?

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 $196. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Tampa during the month August is also very affordable. Most momondo users find prices during this month for around $233.

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 $240. 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 $348.

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

Flying to Chicago Midway Airport from Tampa at noon is the least expensive time of day to depart. momondo users have found prices as low as $215 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $330. 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 from Tampa 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 $293 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 $229 on momondo.

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

There is only 1 cabin class available to choose from on Tampa to Chicago Midway Airport 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 23% 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 May 2026, prices for Tampa to Chicago Midway Airport flights are approximately 102% 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

$171

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 $171. The best round-trip flight deal from Tampa to Chicago Midway Airport found on momondo in the last 72 hours is $296.
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

Frequently asked questions about flying from Tampa to Chicago Midway Airport

  • 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
5.6
2,925 reviews
Search Frontier flights
SouthwestPriceFrom $169Free CancellationRating
8.0
4,258 reviews
Search Southwest flights
JetBluePriceFrom $202Free CancellationRating
7.1
2,983 reviews
Search JetBlue 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 15 flights on this route every week with an average price of $315. 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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