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Cheap flights from Chicago Midway Airport to Florida from $48

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago Midway Airport to Florida departing on 11/26. 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 Chicago Midway Airport to Florida

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
2:01 pm - 11:51 pmMDW-MCO
8h 50m1 stop
Frontier Logo
6:40 pm - 8:45 pmMCO-MDW
3h 05mnonstop
$100Frontier
Find Deal
seg, jan 12 - sex, jan 16
Frontier Logo
3:27 pm - 7:09 pmMDW-MCO
2h 42mnonstop
Frontier Logo
6:35 am - 8:32 amMCO-MDW
2h 57mnonstop
$102Frontier
Find Deal
sex, nov 14 - seg, nov 17
Multiple Airlines Logo
6:26 pm - 8:10 amMDW-MCO
12h 44m1 stop
Multiple Airlines Logo
2:56 pm - 4:52 pmMCO-MDW
2h 56mnonstop
$111Multiple Airlines
Find Deal
ter, nov 18 - seg, nov 24
Multiple Airlines Logo
1:56 pm - 11:23 amMDW-MIA
20h 27m1 stop
Multiple Airlines Logo
2:44 pm - 4:57 pmMIA-MDW
3h 13mnonstop
$117Multiple Airlines
Find Deal
qua, nov 19 - qua, nov 26
Southwest Logo
1:40 pm - 5:35 pmMDW-FLL
2h 55mnonstop
Southwest Logo
6:50 am - 8:55 amFLL-MDW
3h 05mnonstop
$131Southwest
Find Deal
ter, nov 18 - qua, nov 19
Southwest Logo
5:55 am - 9:55 amMDW-FLL
3h 00mnonstop
Southwest Logo
6:50 am - 8:55 amFLL-MDW
3h 05mnonstop
$145Southwest
Find Deal
seg, dez 1 - qua, dez 3
Delta Logo
1:14 pm - 9:45 pmMDW-RSW
7h 31m1 stop
Delta Logo
5:35 am - 11:55 amRSW-MDW
7h 20m1 stop
$217Delta
Find Deal
qua, dez 10 - dom, dez 14
Delta Logo
5:34 pm - 12:37 amMDW-RSW
6h 03m1 stop
Delta Logo
7:49 pm - 11:47 pmRSW-MDW
4h 58m1 stop
$227Delta
Find Deal
qui, nov 27 - qui, dez 4
Allegiant Air Logo
5:35 pm - 11:42 amMDW-SRQ
17h 07m1 stop
Allegiant Air Logo
6:01 am - 2:37 pmSRQ-MDW
9h 36m1 stop
$227Allegiant Air
Find Deal
sex, nov 7 - sex, nov 14
Allegiant Air Logo
5:35 pm - 11:42 amMDW-SRQ
17h 07m1 stop
Allegiant Air Logo
5:58 pm - 12:02 pmSRQ-MDW
19h 04m1 stop
$249Allegiant Air
Find Deal
sex, nov 7 - dom, nov 16

Frontier flights from Chicago Midway Airport to Florida

Our best Frontier deals on Chicago Midway Airport to Florida flight tickets
Frontier
Jan 12
MDW2:01 pmChicago Midway
8h 50m
1 stop
MCO11:51 pmOrlando
Jan 16
MCO6:40 pmOrlando
3h 05m
MDW8:45 pmChicago Midway
$100
Find similar
Frontier
Nov 14
MDW3:27 pmChicago Midway
2h 42m
MCO7:09 pmOrlando
Nov 17
MCO6:35 amOrlando
2h 57m
MDW8:32 amChicago Midway
$102
Find similar
Frontier
Nov 13
MDW3:40 pmChicago Midway
6h 00m
1 stop
MCO10:40 pmOrlando
Nov 17
MCO6:35 amOrlando
2h 57m
MDW8:32 amChicago Midway
$103
Find similar

Southwest flights from Chicago Midway Airport to Florida

Our best Southwest deals on Chicago Midway Airport to Florida flight tickets
Southwest
Nov 18
MDW1:40 pmChicago Midway
2h 55m
FLL5:35 pmFort Lauderdale
Nov 19
FLL6:50 amFort Lauderdale
3h 05m
MDW8:55 amChicago Midway
$131
Find similar
Southwest
Dec 1
MDW5:55 amChicago Midway
3h 00m
FLL9:55 amFort Lauderdale
Dec 3
FLL6:50 amFort Lauderdale
3h 05m
MDW8:55 amChicago Midway
$145
Find similar
Southwest
Feb 18
MDW1:35 pmChicago Midway
2h 55m
FLL5:30 pmFort Lauderdale
Feb 21
FLL6:05 amFort Lauderdale
3h 15m
MDW8:20 amChicago Midway
$157
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago Midway Airport to Florida 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 outubro 30, 2025.
Use the filters below to find and compare flights from Chicago Midway Airport to Florida that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

seg 1/12

2:01 pm-11:51 pm

1 stop8h 50m

Orlando

sex 1/16

6:40 pm-8:45 pm

Nonstop3h 05m

$100

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

sex 11/14

3:27 pm-7:09 pm

Nonstop2h 42m

Orlando

seg 11/17

6:35 am-8:32 am

Nonstop2h 57m

$102

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

ter 11/18

6:26 pm-8:10 am

1 stop12h 44m

Orlando

seg 11/24

2:56 pm-4:52 pm

Nonstop2h 56m

$111

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

qua 11/19

1:56 pm-11:23 am

1 stop20h 27m

Miami

qua 11/26

2:44 pm-4:57 pm

Nonstop3h 13m

$117

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

ter 11/18

1:40 pm-5:35 pm

Nonstop2h 55m

Fort Lauderdale

qua 11/19

6:50 am-8:55 am

Nonstop3h 05m

$131

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

seg 12/1

5:55 am-9:55 am

Nonstop3h 00m

Fort Lauderdale

qua 12/3

6:50 am-8:55 am

Nonstop3h 05m

$145

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

qua 12/10

1:14 pm-9:45 pm

1 stop7h 31m

Fort Myers SW Florida Intl

dom 12/14

5:35 am-11:55 am

1 stop7h 20m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

qui 11/27

5:34 pm-12:37 am

1 stop6h 03m

Fort Myers SW Florida Intl

qui 12/4

7:49 pm-11:47 pm

1 stop4h 58m

$227

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

sex 11/7

5:35 pm-11:42 am

1 stop17h 07m

Sarasota Bradenton Intl

sex 11/14

6:01 am-2:37 pm

1 stop9h 36m

$227

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

sex 11/7

5:35 pm-11:42 am

1 stop17h 07m

Sarasota Bradenton Intl

dom 11/16

5:58 pm-12:02 pm

1 stop19h 04m

$249

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 Florida from

How to get the cheapest flight ticket from Chicago Midway Airport to Florida

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 Florida?

In general, February is the cheapest month to fly from Chicago Midway Airport to Florida. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $173. If you’re not able to fly to Florida in February, then October is your next best option. Flight prices from Chicago Midway Airport to Florida during October average around $205.

What is the cheapest day to depart on your flight to Florida?

On average, the least expensive day to fly to Florida from Chicago Midway Airport is on a Tuesday. momondo users have found tickets for Tuesday departures for as low as $204. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Saturday as prices are generally higher than usual. According to our data, the average ticket price to Florida on Saturday is $298.

What is the cheapest time of day to depart on your flight to Florida?

Flying to Florida from Chicago Midway Airport in the evening is the least expensive time of day to depart. momondo users have found prices as low as $219 when looking at flights departing in the evening. Flights to Florida are more costly at noon, with an average ticket price of $303. Departure times at noon fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago Midway to Florida flight route?

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

How far in advance should I book a flight to Florida?

You are more likely to see cheaper flights to Florida from Chicago Midway Airport when booking weeks ahead of your departure date. In general, you can expect to find flights to Florida for around $310 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Florida from Chicago Midway Airport for as low as $182 on momondo.

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

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

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

Cheap Chicago Midway Airport to Florida flight deals and tips

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

Best Price Found

$70

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Florida

2 airports
The best one-way flight to Florida from Chicago Midway Airport in the past 72 hours is $70. The best round-trip flight deal from Chicago Midway Airport to Florida found on momondo in the last 72 hours is $139.
The fastest flight from Chicago Midway Airport to Florida takes 2h 10m
Direct flights go from Chicago Midway Airport to Florida every day.
There are 2 airports near Florida: Jacksonville (JAX), Pensacola (PNS)
Search flight deals

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

    Prices for flights from Chicago Midway Airport to Florida refresh daily.

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

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

    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 Chicago Midway Airport to Florida.

  • What documentation or ID do you need to fly to Florida?

    The travel and health documents required for your trip to Florida 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 Florida. 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 Chicago Midway Airport to Florida?

Best airlines flying from Chicago Midway Airport to Florida

Compare and see reviews for airlines that fly from Chicago Midway Airport to Florida with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $63Free CancellationRating
6.3
8,115 reviews
Search Spirit Airlines flights
FrontierPriceFrom $69Free CancellationRating
5.8
3,123 reviews
Search Frontier flights
United AirlinesPriceFrom $127Free CancellationRating
7.4
8,996 reviews
Search United Airlines flights
SouthwestPriceFrom $173Free CancellationRating
8.0
4,243 reviews
Search Southwest flights
DeltaPriceFrom $196Free CancellationRating
7.9
7,998 reviews
Search Delta flights

Why use momondo?

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

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Chicago to Florida. momondo saves you time and could save you money on your trip.

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

Yes. momondo allows you to filter the results for Chicago to Florida flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Florida?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Chicago to Florida.

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

Price alerts on flights to Florida from Chicago are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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sáb 11/29
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