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Cheap flights from Chicago Midway Airport to Florida from $47

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 4/6. 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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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
6:30 am - 10:40 am
MDW
-
MIA
3h 10mnonstop
Frontier Logo
11:10 am - 7:31 pm
MIA
-
MDW
9h 21m
1 stop
$101Frontier
lun, apr 13 - mer, apr 22
Multiple Airlines Logo
6:30 am - 10:40 am
MDW
-
MIA
3h 10mnonstop
Multiple Airlines Logo
3:54 pm - 10:14 pm
MIA
-
MDW
7h 20m
1 stop
$106Multiple Airlines
lun, apr 13 - mer, apr 22
Frontier Logo
6:30 am - 10:40 am
MDW
-
MIA
3h 10mnonstop
Frontier Logo
1:10 pm - 7:31 pm
MIA
-
MDW
7h 21m
1 stop
$117Frontier
lun, apr 13 - mer, apr 15
Frontier Logo
6:30 am - 10:40 am
MDW
-
MIA
3h 10mnonstop
Frontier Logo
12:26 pm - 7:31 pm
MIA
-
MDW
8h 05m
1 stop
$119Frontier
lun, apr 13 - gio, apr 16
Multiple Airlines Logo
6:30 am - 10:40 am
MDW
-
MIA
3h 10mnonstop
Multiple Airlines Logo
3:54 pm - 10:26 pm
MIA
-
MDW
7h 32m
1 stop
$121Multiple Airlines
lun, apr 13 - ven, apr 17
Multiple Airlines Logo
6:30 am - 10:40 am
MDW
-
MIA
3h 10mnonstop
Multiple Airlines Logo
3:54 pm - 10:26 pm
MIA
-
MDW
7h 32m
1 stop
$122Multiple Airlines
lun, apr 13 - ven, apr 17
Southwest Logo
4:05 pm - 7:50 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
6:00 am - 7:55 am
RSW
-
MDW
2h 55mnonstop
$237Southwest
mar, apr 28 - sab, mag 2
Southwest Logo
3:40 pm - 7:25 pm
MDW
-
RSW
2h 45mnonstop
Southwest Logo
8:20 pm - 12:20 am
RSW
-
MDW
5h 00m
1 stop
$247Southwest
sab, mag 2 - dom, mag 3
Delta Logo
2:12 pm - 10:45 pm
MDW
-
RSW
7h 33m
1 stop
Delta Logo
7:50 am - 12:07 pm
RSW
-
MDW
5h 17m
1 stop
$257Delta
sab, mag 2 - mar, mag 5
Delta Logo
1:59 pm - 11:16 pm
MDW
-
RSW
8h 17m
1 stop
Delta Logo
3:41 pm - 9:09 pm
RSW
-
MDW
6h 28m
1 stop
$276Delta
sab, mag 9 - sab, mag 16

Frontier flights from Chicago Midway Airport to Florida

Our best Frontier deals on Chicago Midway Airport to Florida flight tickets
Frontier
Apr 13
MDW6:30 amChicago Midway
3h 10m
MIA10:40 amMiami
Apr 22
MIA11:10 amMiami
9h 21m
1 stop
MDW7:31 pmChicago Midway
$101
Frontier
Apr 6
MDW6:30 amChicago Midway
3h 10m
MIA10:40 amMiami
Apr 10
MIA11:35 amMiami
3h 26m
MDW2:01 pmChicago Midway
$107
Frontier
Apr 6
MDW6:30 amChicago Midway
3h 10m
MIA10:40 amMiami
Apr 11
MIA11:35 amMiami
3h 26m
MDW2:01 pmChicago Midway
$108

Southwest flights from Chicago Midway Airport to Florida

Our best Southwest deals on Chicago Midway Airport to Florida flight tickets
Southwest
May 6
MDW12:50 pmChicago Midway
2h 35m
TPA4:25 pmTampa
May 13
TPA3:55 pmTampa
2h 45m
MDW5:40 pmChicago Midway
$169
Southwest
Apr 22
MDW9:50 amChicago Midway
6h 00m
1 stop
FLL4:50 pmFort Lauderdale
Apr 29
FLL1:35 pmFort Lauderdale
3h 10m
MDW3:45 pmChicago Midway
$179
Southwest
Apr 25
MDW11:40 amChicago Midway
2h 55m
FLL3:35 pmFort Lauderdale
Apr 28
FLL5:30 pmFort Lauderdale
3h 10m
MDW7:40 pmChicago Midway
$184

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 aprile 2, 2026.
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

Cheapest round-trip

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

lun 4/13

6:30 am-10:40 am

Nonstop3h 10m

Miami

mer 4/22

11:10 am-7:31 pm

1 stop9h 21m

$101

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

lun 4/13

6:30 am-10:40 am

Nonstop3h 10m

Miami

mer 4/22

3:54 pm-10:14 pm

1 stop7h 20m

$106

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

lun 4/13

6:30 am-10:40 am

Nonstop3h 10m

Miami

mer 4/15

1:10 pm-7:31 pm

1 stop7h 21m

$117

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

lun 4/13

6:30 am-10:40 am

Nonstop3h 10m

Miami

gio 4/16

12:26 pm-7:31 pm

1 stop8h 05m

$119

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

lun 4/13

6:30 am-10:40 am

Nonstop3h 10m

Miami

ven 4/17

3:54 pm-10:26 pm

1 stop7h 32m

$121

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

lun 4/13

6:30 am-10:40 am

Nonstop3h 10m

Miami

ven 4/17

3:54 pm-10:26 pm

1 stop7h 32m

$122
Quickest round-trip

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

mar 4/28

4:05 pm-7:50 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

sab 5/2

6:00 am-7:55 am

Nonstop2h 55m

$237

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

sab 5/2

3:40 pm-7:25 pm

Nonstop2h 45m

Fort Myers SW Florida Intl

dom 5/3

8:20 pm-12:20 am

1 stop5h 00m

$247

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

sab 5/2

2:12 pm-10:45 pm

1 stop7h 33m

Fort Myers SW Florida Intl

mar 5/5

7:50 am-12:07 pm

1 stop5h 17m

$257

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

sab 5/9

1:59 pm-11:16 pm

1 stop8h 17m

Fort Myers SW Florida Intl

sab 5/16

3:41 pm-9:09 pm

1 stop6h 28m

$276

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, September 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 $193. If you’re not able to fly to Florida in September, then April is your next best option. Flight prices from Chicago Midway Airport to Florida during April average around $204.

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 Thursday. momondo users have found tickets for Thursday departures for as low as $250. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Wednesday as prices are generally higher than usual. According to our data, the average ticket price to Florida on Wednesday is $324.

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 $259 when looking at flights departing in the evening. Flights to Florida are more costly in the morning, with an average ticket price of $289. Departure times in the morning 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 $277 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 $215 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

$56

Fastest flight time

2h 05m

Direct flights

Every day

Airports in Florida

256 airports
The best one-way flight to Florida from Chicago Midway Airport in the past 72 hours is $56. The best round-trip flight deal from Chicago Midway Airport to Florida found on momondo in the last 72 hours is $120.
The fastest flight from Chicago Midway Airport to Florida takes 2h 05m
Direct flights go from Chicago Midway Airport to Florida every day.
There are 256 airports in Florida. From Chicago Midway Airport there are direct flights to Jacksonville (JAX), Panama City NW Florida Beaches (ECP), Pensacola (PNS), Tampa (TPA).
Search flight deals

Frequently asked questions about flying from Chicago Midway Airport to Florida

  • 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
FrontierPriceFrom $58Free CancellationRating
5.7
3,004 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $84Free CancellationRating
6.3
8,576 reviews
Search Spirit Airlines flights
DeltaPriceFrom $98Free CancellationRating
7.9
8,371 reviews
Search Delta flights
United AirlinesPriceFrom $119Free CancellationRating
7.4
9,531 reviews
Search United Airlines flights
SouthwestPriceFrom $169Free CancellationRating
8.0
4,337 reviews
Search Southwest flights
American AirlinesPriceFrom $203Free CancellationRating
7.1
11,549 reviews
Search American Airlines 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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1 adult
sab 5/2
sab 5/9
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