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Cheap flights from Chicago Midway Airport to Florida from $64

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 6/3. 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
6:00 am - 1:20 pm
MDW
-
MIA
6h 20m
1 stop
Frontier Logo
5:26 pm - 10:11 pm
MIA
-
MDW
5h 45m
1 stop
$132Frontier
mar., jun. 2 - mié., jun. 10
Frontier Logo
6:00 am - 1:20 pm
MDW
-
MIA
6h 20m
1 stop
Frontier Logo
5:26 pm - 10:11 pm
MIA
-
MDW
5h 45m
1 stop
$133Frontier
mar., jun. 2 - mié., jun. 10
Multiple Airlines Logo
3:42 pm - 10:04 am
MDW
-
MCO
17h 22m
1 stop
Multiple Airlines Logo
7:53 am - 10:11 pm
MCO
-
MDW
15h 18m
1 stop
$164Multiple Airlines
vie., may. 29 - mié., jun. 10
Multiple Airlines Logo
12:27 pm - 9:47 pm
MDW
-
MCO
8h 20m
1 stop
Multiple Airlines Logo
11:03 am - 2:48 pm
MCO
-
MDW
4h 45m
1 stop
$165Multiple Airlines
mar., jun. 2 - lun., jun. 8
Southwest Logo
8:35 am - 12:40 pm
MDW
-
FLL
3h 05mnonstop
Southwest Logo
4:55 pm - 7:00 pm
FLL
-
MDW
3h 05mnonstop
$169Southwest
mié., ago. 26 - mié., sep. 2
Southwest Logo
8:15 pm - 11:50 pm
MDW
-
TPA
2h 35mnonstop
Southwest Logo
9:55 pm - 11:35 pm
TPA
-
MDW
2h 40mnonstop
$169Southwest
mar., jun. 30 - mié., jul. 8
Delta Logo
4:25 pm - 10:29 pm
MDW
-
SRQ
5h 04m
1 stop
Delta Logo
6:00 am - 10:05 am
SRQ
-
MDW
5h 05m
1 stop
$257Delta
mar., jun. 30 - mié., jul. 8
Allegiant Air Logo
2:47 pm - 5:01 pm
MDW
-
SRQ
25h 14m
1 stop
Allegiant Air Logo
5:26 pm - 2:48 pm
SRQ
-
MDW
22h 22m
1 stop
$265Allegiant Air
jue., may. 28 - jue., jun. 4
Delta Logo
6:00 am - 11:45 am
MDW
-
PBI
4h 45m
1 stop
Delta Logo
6:27 pm - 10:15 pm
PBI
-
MDW
4h 48m
1 stop
$309Delta
vie., jul. 10 - sáb., jul. 18
Allegiant Air Logo
3:28 pm - 10:48 am
MDW
-
PBI
18h 20m
1 stop
Allegiant Air Logo
4:29 pm - 2:38 pm
PBI
-
MDW
23h 09m
1 stop
$313Allegiant Air
lun., jul. 13 - jue., jul. 23

Frontier flights from Chicago Midway Airport to Florida

Our best Frontier deals on Chicago Midway Airport to Florida flight tickets
Frontier
Jun 2
MDW6:00 amChicago Midway
6h 20m
1 stop
MIA1:20 pmMiami
Jun 10
MIA5:26 pmMiami
5h 45m
1 stop
MDW10:11 pmChicago Midway
$132
Frontier
Jun 2
MDW6:00 amChicago Midway
6h 20m
1 stop
MIA1:20 pmMiami
Jun 10
MIA5:26 pmMiami
5h 45m
1 stop
MDW10:11 pmChicago Midway
$133
Frontier
Jun 2
MDW6:00 amChicago Midway
6h 20m
1 stop
MIA1:20 pmMiami
Jun 10
MIA5:26 pmMiami
5h 45m
1 stop
MDW10:11 pmChicago Midway
$134

Delta flights from Chicago Midway Airport to Florida

Our best Delta deals on Chicago Midway Airport to Florida flight tickets
Delta
Sep 15
MDW1:05 pmChicago Midway
6h 34m
1 stop
MCO8:39 pmOrlando
Sep 22
MCO3:10 pmOrlando
7h 36m
1 stop
MDW9:46 pmChicago Midway
$197
Delta
Aug 11
MDW1:27 pmChicago Midway
6h 38m
1 stop
MCO9:05 pmOrlando
Aug 15
MCO5:45 pmOrlando
5h 51m
1 stop
MDW10:36 pmChicago Midway
$208
Delta
May 28
MDW5:10 pmChicago Midway
6h 45m
1 stop
MCO12:55 amOrlando
Jun 3
MCO6:15 amOrlando
7h 27m
1 stop
MDW12:42 pmChicago Midway
$217

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 mayo 15, 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

mar. 6/2

6:00 am-1:20 pm

1 stop6h 20m

Miami

mié. 6/10

5:26 pm-10:11 pm

1 stop5h 45m

$132

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

mar. 6/2

6:00 am-1:20 pm

1 stop6h 20m

Miami

mié. 6/10

5:26 pm-10:11 pm

1 stop5h 45m

$133

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

vie. 5/29

3:42 pm-10:04 am

1 stop17h 22m

Orlando

mié. 6/10

7:53 am-10:11 pm

1 stop15h 18m

$164

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

mar. 6/2

12:27 pm-9:47 pm

1 stop8h 20m

Orlando

lun. 6/8

11:03 am-2:48 pm

1 stop4h 45m

$165

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

mié. 8/26

8:35 am-12:40 pm

Nonstop3h 05m

Fort Lauderdale

mié. 9/2

4:55 pm-7:00 pm

Nonstop3h 05m

$169
Quickest round-trip

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mar. 6/30

8:15 pm-11:50 pm

Nonstop2h 35m

Tampa

mié. 7/8

9:55 pm-11:35 pm

Nonstop2h 40m

$169

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

mar. 6/30

4:25 pm-10:29 pm

1 stop5h 04m

Sarasota Bradenton Intl

mié. 7/8

6:00 am-10:05 am

1 stop5h 05m

$257

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

jue. 5/28

2:47 pm-5:01 pm

1 stop25h 14m

Sarasota Bradenton Intl

jue. 6/4

5:26 pm-2:48 pm

1 stop22h 22m

$265

ChicagoWest Palm Beach

MDW - PBI

MDWPBI

Chicago Midway

vie. 7/10

6:00 am-11:45 am

1 stop4h 45m

Palm Beach Intl

sáb. 7/18

6:27 pm-10:15 pm

1 stop4h 48m

$309

ChicagoWest Palm Beach

MDW - PBI

MDWPBI

Chicago Midway

lun. 7/13

3:28 pm-10:48 am

1 stop18h 20m

Palm Beach Intl

jue. 7/23

4:29 pm-2:38 pm

1 stop23h 09m

$313

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, August 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 $27. If you’re not able to fly to Florida in August, then February is your next best option. Flight prices from Chicago Midway Airport to Florida during February average around $29.

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 $254. 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 $343.

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

Flying to Florida from Chicago Midway Airport in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as $264 when looking at flights departing in the afternoon. Flights to Florida are more costly at noon, with an average ticket price of $305. 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 from Chicago Midway Airport 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 $289 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 $207 on momondo.

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

$28

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 $28. The best round-trip flight deal from Chicago Midway Airport to Florida found on momondo in the last 72 hours is $118.
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).
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
5.6
2,951 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $71Free CancellationRating
6.2
8,626 reviews
Search Spirit Airlines flights
DeltaPriceFrom $98Free CancellationRating
7.9
8,456 reviews
Search Delta flights
United AirlinesPriceFrom $168Free CancellationRating
7.4
9,723 reviews
Search United Airlines flights
SouthwestPriceFrom $169Free CancellationRating
8.0
4,299 reviews
Search Southwest flights
American AirlinesPriceFrom $203Free CancellationRating
7.1
11,665 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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