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Cheap flights from Florida to Chicago from $52

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 3/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
$72Frontier
Fri, Mar 6 - Mon, Mar 9
Frontier Logo
3:25 pm - 5:48 pm
MIA
-
MDW
3h 23mnonstop
Frontier Logo
9:42 pm - 1:50 am
MDW
-
MIA
3h 08mnonstop
$74Frontier
Wed, Mar 25 - Mon, Mar 30
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
$80Frontier
Fri, Mar 6 - Mon, Mar 9
Frontier Logo
4:05 pm - 6:13 pm
MCO
-
MDW
3h 08mnonstop
Frontier Logo
11:19 am - 3:04 pm
MDW
-
MCO
2h 45mnonstop
$84Frontier
Tue, Mar 10 - Wed, Mar 11
Multiple Airlines Logo
12:09 pm - 7:07 pm
FLL
-
MDW
7h 58m
1 stop
Multiple Airlines Logo
7:15 am - 5:02 pm
MDW
-
FLL
8h 47m
1 stop
$118Multiple Airlines
Tue, Feb 24 - Wed, Mar 4
Multiple Airlines Logo
7:30 am - 3:19 pm
FLL
-
MDW
8h 49m
1 stop
Multiple Airlines Logo
7:30 am - 5:02 pm
MDW
-
FLL
8h 32m
1 stop
$119Multiple Airlines
Sat, Feb 28 - Tue, Mar 3
Southwest Logo
7:40 pm - 9:40 pm
RSW
-
MDW
3h 00mnonstop
Southwest Logo
7:10 am - 10:55 am
MDW
-
RSW
2h 45mnonstop
$197Southwest
Sat, Mar 7 - Tue, Mar 10
Southwest Logo
5:25 pm - 7:40 pm
PNS
-
MDW
2h 15mnonstop
Southwest Logo
8:00 am - 10:20 am
MDW
-
PNS
2h 20mnonstop
$207Southwest
Thu, Mar 5 - Sun, Mar 8
Delta Logo
6:12 pm - 10:31 pm
PBI
-
MDW
5h 19m
1 stop
Delta Logo
6:00 am - 1:09 pm
MDW
-
PBI
6h 09m
1 stop
$249Delta
Fri, Feb 27 - Sun, Mar 1
Delta Logo
2:50 pm - 9:09 pm
ECP
-
MDW
6h 19m
1 stop
Delta Logo
6:30 am - 12:50 pm
MDW
-
ECP
6h 20m
1 stop
$253Delta
Fri, May 15 - Mon, May 18

Frontier flights from Florida to Chicago Midway Airport

Our best Frontier deals on Florida to Chicago Midway Airport flight tickets
Frontier
Mar 6
MIA11:13 amMiami
3h 28m
MDW1:41 pmChicago Midway
Mar 9
MDW6:00 amChicago Midway
3h 13m
MIA10:13 amMiami
$72
Frontier
Mar 25
MIA3:25 pmMiami
3h 23m
MDW5:48 pmChicago Midway
Mar 30
MDW9:42 pmChicago Midway
3h 08m
MIA1:50 amMiami
$74
Frontier
Mar 6
MIA11:13 amMiami
3h 28m
MDW1:41 pmChicago Midway
Mar 9
MDW6:00 amChicago Midway
3h 13m
MIA10:13 amMiami
$80

Southwest flights from Florida to Chicago Midway Airport

Our best Southwest deals on Florida to Chicago Midway Airport flight tickets
Southwest
Mar 7
TPA6:30 amTampa
2h 50m
MDW8:20 amChicago Midway
Mar 10
MDW9:00 amChicago Midway
2h 35m
TPA12:35 pmTampa
$177
Southwest
Mar 24
FLL6:30 amFort Lauderdale
3h 15m
MDW8:45 amChicago Midway
Apr 7
MDW6:10 pmChicago Midway
2h 55m
FLL10:05 pmFort Lauderdale
$189
Southwest
Mar 10
TPA7:00 amTampa
2h 50m
MDW8:50 amChicago Midway
Mar 14
MDW8:05 pmChicago Midway
2h 30m
TPA11:35 pmTampa
$197

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 February 8, 2026.
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

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 3/6

11:13 am-1:41 pm

Nonstop3h 28m

Chicago Midway

Mon 3/9

6:00 am-10:13 am

Nonstop3h 13m

$72

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 3/25

3:25 pm-5:48 pm

Nonstop3h 23m

Chicago Midway

Mon 3/30

9:42 pm-1:50 am

Nonstop3h 08m

$74

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 3/6

11:13 am-1:41 pm

Nonstop3h 28m

Chicago Midway

Mon 3/9

6:00 am-10:13 am

Nonstop3h 13m

$80

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 3/10

4:05 pm-6:13 pm

Nonstop3h 08m

Chicago Midway

Wed 3/11

11:19 am-3:04 pm

Nonstop2h 45m

$84

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Tue 2/24

12:09 pm-7:07 pm

1 stop7h 58m

Chicago Midway

Wed 3/4

7:15 am-5:02 pm

1 stop8h 47m

$118

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Sat 2/28

7:30 am-3:19 pm

1 stop8h 49m

Chicago Midway

Tue 3/3

7:30 am-5:02 pm

1 stop8h 32m

$119

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 3/7

7:40 pm-9:40 pm

Nonstop3h 00m

Chicago Midway

Tue 3/10

7:10 am-10:55 am

Nonstop2h 45m

$197

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Thu 3/5

5:25 pm-7:40 pm

Nonstop2h 15m

Chicago Midway

Sun 3/8

8:00 am-10:20 am

Nonstop2h 20m

$207

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Fri 2/27

6:12 pm-10:31 pm

1 stop5h 19m

Chicago Midway

Sun 3/1

6:00 am-1:09 pm

1 stop6h 09m

$249

Panama CityChicago

ECP - MDW

ECPMDW

Panama City NW Florida Beaches

Fri 5/15

2:50 pm-9:09 pm

1 stop6h 19m

Chicago Midway

Mon 5/18

6:30 am-12:50 pm

1 stop6h 20m

$253

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 October is, on average, the cheapest month to fly to Chicago Midway Airport from Florida, with most prices found around $89. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Florida during the month January is also very affordable. Most momondo users find prices during this month for around $128.

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

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Florida. The lowest ticket price found for a Thursday departure recently was $196. 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 $383.

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

Flying to Chicago Midway Airport from Florida in the evening is the least expensive time of day to depart. momondo users have found prices as low as $138 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $245. 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 are 2 cabin classes 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

$79

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 $79. The best round-trip flight deal from Florida to Chicago Midway Airport found on momondo in the last 72 hours is $102.
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 $46Free CancellationRating
5.7
3,052 reviews
Search Frontier flights
DeltaPriceFrom $98Free CancellationRating
7.9
8,172 reviews
Search Delta flights
SouthwestPriceFrom $149Free CancellationRating
8.0
4,280 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
Munster
Crown Point
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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