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Cheap flights from Tampa to Chicago from $105

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Tampa to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
6:29 pm - 11:47 pmTPA  Tampa-MDW Chicago Midway
6h 18m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:16 am - 5:22 pmMDW  Chicago Midway-TPA Tampa
10h 06m1 stop Atlanta Hartsfield-Jackson
$210Frontier
Sat, Nov 7 - Thu, Nov 12
Frontier Logo
5:57 pm - 11:47 pmTPA  Tampa-MDW Chicago Midway
6h 50m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:16 am - 5:33 pmMDW  Chicago Midway-TPA Tampa
10h 17m1 stop Atlanta Hartsfield-Jackson
$210Frontier
Thu, Oct 29 - Tue, Nov 3
Frontier Logo
5:11 pm - 11:47 pmTPA  Tampa-MDW Chicago Midway
7h 36m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
6:16 am - 5:22 pmMDW  Chicago Midway-TPA Tampa
10h 06m1 stop Atlanta Hartsfield-Jackson
$210Frontier
Tue, Oct 27 - Thu, Oct 29
Multiple Airlines Logo
5:57 pm - 11:43 pmTPA  Tampa-MDW Chicago Midway
6h 46m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
9:53 am - 7:10 amMDW  Chicago Midway-TPA Tampa
20h 17m2 stops Atlanta Hartsfield-Jackson Fort Lauderdale
$241Multiple Airlines
Wed, Oct 21 - Tue, Oct 27
Multiple Airlines Logo
10:49 pm - 5:47 pmTPA  Tampa-MDW Chicago Midway
19h 58m2 stops Fort Lauderdale Atlanta Hartsfield-Jackson
Multiple Airlines Logo
12:28 pm - 8:46 pmMDW  Chicago Midway-TPA Tampa
7h 18m1 stop Atlanta Hartsfield-Jackson
$251Multiple Airlines
Wed, Nov 18 - Wed, Dec 2
Multiple Airlines Logo
9:23 am - 1:33 pmTPA  Tampa-MDW Chicago Midway
5h 10m1 stop Atlanta Hartsfield-Jackson
Multiple Airlines Logo
10:21 am - 7:10 amMDW  Chicago Midway-TPA Tampa
19h 49m2 stops Dallas/Fort Worth Fort Lauderdale
$257Multiple Airlines
Thu, Nov 26 - Wed, Dec 2
Southwest Logo
7:20 pm - 9:10 pmTPA  Tampa-MDW Chicago Midway
2h 50mnonstop
Southwest Logo
9:15 pm - 1:00 amMDW  Chicago Midway-TPA Tampa
2h 45mnonstop
$281Southwest
Sat, Nov 21 - Tue, Nov 24
Southwest Logo
7:20 am - 9:00 amTPA  Tampa-MDW Chicago Midway
2h 40mnonstop
Southwest Logo
7:50 am - 11:25 amMDW  Chicago Midway-TPA Tampa
2h 35mnonstop
$281Southwest
Tue, Oct 27 - Wed, Oct 28
Delta Logo
6:20 am - 10:37 amTPA  Tampa-MDW Chicago Midway
5h 17m1 stop Atlanta Hartsfield-Jackson
Delta Logo
11:27 am - 5:15 pmMDW  Chicago Midway-TPA Tampa
4h 48m1 stop Atlanta Hartsfield-Jackson
$301Delta
Sat, Nov 7 - Sat, Nov 14
Delta Logo
5:10 am - 10:37 amTPA  Tampa-MDW Chicago Midway
6h 27m1 stop Atlanta Hartsfield-Jackson
Delta Logo
4:19 pm - 9:24 pmMDW  Chicago Midway-TPA Tampa
4h 05m1 stop Atlanta Hartsfield-Jackson
$301Delta
Sat, Nov 7 - Sat, Nov 7

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Frontier flights from Tampa to Chicago Midway Airport

Our best Frontier deals on Tampa to Chicago Midway Airport flight tickets
Frontier
Oct 27
TPA5:11 pmTampa
7h 36m
1 stop
MDW11:47 pmChicago Midway
Oct 29
MDW6:16 amChicago Midway
10h 06m
1 stop
TPA5:22 pmTampa
$210
Frontier
Oct 28
TPA5:57 pmTampa
6h 50m
1 stop
MDW11:47 pmChicago Midway
Oct 30
MDW6:16 amChicago Midway
10h 06m
1 stop
TPA5:22 pmTampa
$211
Frontier
Nov 7
TPA1:41 pmTampa
11h 06m
1 stop
MDW11:47 pmChicago Midway
Nov 9
MDW6:16 amChicago Midway
10h 06m
1 stop
TPA5:22 pmTampa
$212

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

Cheapest round-trip

TampaChicago

TPA Tampa - MDW Chicago Midway

TPAMDW

Tampa

Sat 11/7

6:29 pm-11:47 pm

1 stop6h 18m

Chicago Midway

Thu 11/12

6:16 am-5:22 pm

1 stop10h 06m

$210

TampaChicago

TPA Tampa - MDW Chicago Midway

TPAMDW

Tampa

Thu 10/29

5:57 pm-11:47 pm

1 stop6h 50m

Chicago Midway

Tue 11/3

6:16 am-5:33 pm

1 stop10h 17m

$210

TampaChicago

TPA Tampa - MDW Chicago Midway

TPAMDW

Tampa

Tue 10/27

5:11 pm-11:47 pm

1 stop7h 36m

Chicago Midway

Thu 10/29

6:16 am-5:22 pm

1 stop10h 06m

$210

TampaChicago

TPA Tampa - MDW Chicago Midway

TPAMDW

Tampa

Wed 10/21

5:57 pm-11:43 pm

1 stop6h 46m

Chicago Midway

Tue 10/27

9:53 am-7:10 am

2 stops20h 17m

$241

TampaChicago

TPA Tampa - MDW Chicago Midway

TPAMDW

Tampa

Wed 11/18

10:49 pm-5:47 pm

2 stops19h 58m

Chicago Midway

Wed 12/2

12:28 pm-8:46 pm

1 stop7h 18m

$251

TampaChicago

TPA Tampa - MDW Chicago Midway

TPAMDW

Tampa

Thu 11/26

9:23 am-1:33 pm

1 stop5h 10m

Chicago Midway

Wed 12/2

10:21 am-7:10 am

2 stops19h 49m

$257

TampaChicago

TPA Tampa - MDW Chicago Midway

TPAMDW

Tampa

Sat 11/21

7:20 pm-9:10 pm

Nonstop2h 50m

Chicago Midway

Tue 11/24

9:15 pm-1:00 am

Nonstop2h 45m

$281
Quickest round-trip

TampaChicago

TPA Tampa - MDW Chicago Midway

TPAMDW

Tampa

Tue 10/27

7:20 am-9:00 am

Nonstop2h 40m

Chicago Midway

Wed 10/28

7:50 am-11:25 am

Nonstop2h 35m

$281

TampaChicago

TPA Tampa - MDW Chicago Midway

TPAMDW

Tampa

Sat 11/7

6:20 am-10:37 am

1 stop5h 17m

Chicago Midway

Sat 11/14

11:27 am-5:15 pm

1 stop4h 48m

$301

TampaChicago

TPA Tampa - MDW Chicago Midway

TPAMDW

Tampa

Sat 11/7

5:10 am-10:37 am

1 stop6h 27m

Chicago Midway

Sat 11/7

4:19 pm-9:24 pm

1 stop4h 05m

$301

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?

Prices are currently typical for flights on this route.

Typical prices usually range from $192 to $346.
The lowest price recently found on this route was $210.

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

The month of November is, on average, the cheapest month to fly to Chicago Midway Airport from Tampa, with most prices found around $240. If you are unable to visit Chicago Midway Airport during the month of November, then departing from Tampa during the month September is also very affordable. Most momondo users find prices during this month for around $260.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Tampa. The lowest ticket price found for a Wednesday departure recently was $329. 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 $398.

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 $272 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $368. 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 $322 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 $232 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 27% 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 September 2026, prices for Tampa to Chicago Midway Airport flights are approximately 160% 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

$105

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 $105. The best round-trip flight deal from Tampa to Chicago Midway Airport found on momondo in the last 72 hours is $210.
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

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 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?

  • 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 $89Free CancellationRating
5.6
2,579 reviews
Search Frontier flights
DeltaPriceFrom $98Free CancellationRating
7.8
8,591 reviews
Search Delta flights
SouthwestPriceFrom $199Free CancellationRating
8.0
4,196 reviews
Search Southwest flights
JetBluePriceFrom $244Free CancellationRating
7.1
3,037 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 $199. Generally, Southwest has 13 flights on this route every week with an average price of $341. 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
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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

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