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Cheap flights from Florida to Chicago from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Florida to Chicago departing on 10/4. 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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Cheap round-trip flights

Frontier Logo
8:25 am - 10:21 amMCO-MDW
2h 56mnonstop
Frontier Logo
5:28 pm - 9:10 pmMDW-MCO
2h 42mnonstop
$86Frontier
Find Deal
Sat, Oct 18 - Mon, Oct 20
Frontier Logo
11:10 am - 1:10 pmMCO-MDW
3h 00mnonstop
Frontier Logo
2:15 pm - 6:00 pmMDW-MCO
2h 45mnonstop
$90Frontier
Find Deal
Fri, Dec 5 - Sun, Dec 7
Frontier Logo
8:25 am - 10:21 amMCO-MDW
2h 56mnonstop
Frontier Logo
11:31 am - 3:11 pmMDW-MCO
2h 40mnonstop
$92Frontier
Find Deal
Sat, Oct 18 - Sat, Oct 25
Frontier Logo
8:50 am - 10:46 amMCO-MDW
2h 56mnonstop
Frontier Logo
5:28 pm - 9:10 pmMDW-MCO
2h 42mnonstop
$94Frontier
Find Deal
Thu, Oct 16 - Mon, Oct 20
Multiple Airlines Logo
9:57 am - 11:44 amTPA-MDW
2h 47mnonstop
Multiple Airlines Logo
1:37 pm - 8:46 pmMDW-TPA
6h 09m1 stop
$142Multiple Airlines
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Sun, Oct 19 - Mon, Nov 10
Southwest Logo
11:35 am - 1:10 pmTPA-MDW
2h 35mnonstop
Southwest Logo
6:55 pm - 10:25 pmMDW-TPA
2h 30mnonstop
$147Southwest
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Wed, Oct 22 - Mon, Oct 27
Multiple Airlines Logo
2:35 pm - 11:05 pmTPA-MDW
9h 30m2 stops
Multiple Airlines Logo
6:30 am - 10:21 amMDW-TPA
2h 51mnonstop
$151Multiple Airlines
Find Deal
Fri, Dec 5 - Mon, Dec 8
Southwest Logo
5:30 am - 7:35 amFLL-MDW
3h 05mnonstop
Southwest Logo
5:45 am - 9:45 amMDW-FLL
3h 00mnonstop
$153Southwest
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Fri, Nov 14 - Sun, Nov 16
Delta Logo
5:30 am - 11:53 amFLL-MDW
7h 23m1 stop
Delta Logo
1:11 pm - 6:54 pmMDW-FLL
4h 43m1 stop
$217Delta
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Wed, Oct 15 - Sat, Oct 18
Delta Logo
9:31 am - 4:09 pmPNS-MDW
6h 38m1 stop
Delta Logo
10:47 am - 2:49 pmMDW-PNS
4h 02m1 stop
$217Delta
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Wed, Oct 29 - Wed, Nov 19

Frontier flights from Florida to Chicago Midway Airport

Our best Frontier deals on Florida to Chicago Midway Airport flight tickets
Frontier
Oct 18
MCO8:25 amOrlando
2h 56m
MDW10:21 amChicago Midway
Oct 20
MDW5:28 pmChicago Midway
2h 42m
MCO9:10 pmOrlando
$86
Find similar
Frontier
Dec 5
MCO11:10 amOrlando
3h 00m
MDW1:10 pmChicago Midway
Dec 7
MDW2:15 pmChicago Midway
2h 45m
MCO6:00 pmOrlando
$90
Find similar
Frontier
Oct 18
MCO8:25 amOrlando
2h 56m
MDW10:21 amChicago Midway
Oct 25
MDW11:31 amChicago Midway
2h 40m
MCO3:11 pmOrlando
$92
Find similar

Southwest flights from Florida to Chicago Midway Airport

Our best Southwest deals on Florida to Chicago Midway Airport flight tickets
Southwest
Oct 22
TPA11:35 amTampa
2h 35m
MDW1:10 pmChicago Midway
Oct 27
MDW6:55 pmChicago Midway
2h 30m
TPA10:25 pmTampa
$147
Find similar
Southwest
Nov 14
FLL5:30 amFort Lauderdale
3h 05m
MDW7:35 amChicago Midway
Nov 16
MDW5:45 amChicago Midway
3h 00m
FLL9:45 amFort Lauderdale
$153
Find similar
Southwest
Dec 4
RSW6:30 amFort Myers SW Florida Intl
2h 55m
MDW8:25 amChicago Midway
Dec 6
MDW5:30 pmChicago Midway
2h 45m
RSW9:15 pmFort Myers SW Florida Intl
$158
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Florida 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 September 23, 2025.
Use the filters below to find and compare flights from Florida to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 10/18

8:25 am-10:21 am

Nonstop2h 56m

Chicago Midway

Mon 10/20

5:28 pm-9:10 pm

Nonstop2h 42m

$86

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 12/5

11:10 am-1:10 pm

Nonstop3h 00m

Chicago Midway

Sun 12/7

2:15 pm-6:00 pm

Nonstop2h 45m

$90

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 10/18

8:25 am-10:21 am

Nonstop2h 56m

Chicago Midway

Sat 10/25

11:31 am-3:11 pm

Nonstop2h 40m

$92

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 10/16

8:50 am-10:46 am

Nonstop2h 56m

Chicago Midway

Mon 10/20

5:28 pm-9:10 pm

Nonstop2h 42m

$94

TampaChicago

TPA - MDW

TPAMDW

Tampa

Sun 10/19

9:57 am-11:44 am

Nonstop2h 47m

Chicago Midway

Mon 11/10

1:37 pm-8:46 pm

1 stop6h 09m

$142

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 10/22

11:35 am-1:10 pm

Nonstop2h 35m

Chicago Midway

Mon 10/27

6:55 pm-10:25 pm

Nonstop2h 30m

$147

TampaChicago

TPA - MDW

TPAMDW

Tampa

Fri 12/5

2:35 pm-11:05 pm

2 stops9h 30m

Chicago Midway

Mon 12/8

6:30 am-10:21 am

Nonstop2h 51m

$151

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Fri 11/14

5:30 am-7:35 am

Nonstop3h 05m

Chicago Midway

Sun 11/16

5:45 am-9:45 am

Nonstop3h 00m

$153

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Wed 10/15

5:30 am-11:53 am

1 stop7h 23m

Chicago Midway

Sat 10/18

1:11 pm-6:54 pm

1 stop4h 43m

$217

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 10/29

9:31 am-4:09 pm

1 stop6h 38m

Chicago Midway

Wed 11/19

10:47 am-2:49 pm

1 stop4h 02m

$217

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 Florida 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 January is, on average, the cheapest month to fly to Chicago Midway Airport from Florida, with most prices found around $155. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Florida during the month December is also very affordable. Most momondo users find prices during this month for around $190.

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 Florida. The lowest ticket price found for a Friday departure recently was $179. 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 Florida because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $287.

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

Flying to Chicago Midway Airport from Florida at noon is the least expensive time of day to depart. momondo users have found prices as low as $158 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $211. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Florida to Chicago Midway flight route?

Fly from Orlando to Chicago Midway for the best Florida - Chicago Midway flight prices

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

There is only 1 cabin class available to choose from on Florida 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 Florida to Chicago Midway Airport flights?

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

Cheap Florida to Chicago Midway Airport flight deals and tips

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

Best Price Found

$70

Fastest flight time

2h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Florida in the past 72 hours is $70. The best round-trip flight deal from Florida to Chicago Midway Airport found on momondo in the last 72 hours is $105.
The fastest flight from Florida to Chicago Midway Airport takes 2h 15m
Direct flights go from Florida to Chicago Midway Airport every day.
Search flight deals

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

    Prices for flights from Florida to Chicago Midway Airport were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Florida 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 Florida to Chicago Midway Airport?

Best airlines flying from Florida to Chicago Midway Airport

Compare and see reviews for airlines that fly from Florida to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $51Free CancellationRating
5.8
3,165 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $88Free CancellationRating
6.3
8,041 reviews
Search Spirit Airlines flights
DeltaPriceFrom $114Free CancellationRating
7.9
7,974 reviews
Search Delta flights
SouthwestPriceFrom $149Free CancellationRating
8.0
4,244 reviews
Search Southwest flights

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
Crown Point
Munster
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

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

Finding the right flight to Chicago from Florida is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

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

Flights from Florida 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 Florida to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Florida.

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

Yes momondo offers price alerts on flights to Chicago from Florida. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago Midway Airport trip

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