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Cheap flights from Chicago Midway Airport to Florida 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 Chicago Midway Airport to Florida departing on 9/29. 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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Find the cheapest flights from Chicago Midway Airport to Florida

Cheap round-trip flights

Frontier Logo
11:21 am - 3:04 pmMDW-MCO
2h 43mnonstop
Frontier Logo
1:16 pm - 3:11 pmMCO-MDW
2h 55mnonstop
$99Frontier
Find Deal
sáb., oct. 4 - sáb., oct. 11
Frontier Logo
8:19 am - 12:00 pmMDW-MCO
2h 41mnonstop
Frontier Logo
7:25 am - 9:18 amMCO-MDW
2h 53mnonstop
$100Frontier
Find Deal
lun., sep. 29 - dom., oct. 5
Frontier Logo
6:21 am - 9:57 amMDW-TPA
2h 36mnonstop
Frontier Logo
10:55 am - 12:44 pmTPA-MDW
2h 49mnonstop
$102Frontier
Find Deal
vie., sep. 26 - dom., sep. 28
Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
$102Frontier
Find Deal
vie., sep. 26 - vie., oct. 3
Multiple Airlines Logo
2:06 pm - 11:02 amMDW-TPA
19h 56m1 stop
Multiple Airlines Logo
10:41 pm - 12:30 amTPA-MDW
2h 49mnonstop
$134Multiple Airlines
Find Deal
mié., nov. 5 - dom., nov. 9
Southwest Logo
9:05 am - 12:40 pmMDW-TPA
2h 35mnonstop
Southwest Logo
1:05 pm - 5:35 pmTPA-MDW
5h 30m1 stop
$147Southwest
Find Deal
mié., nov. 19 - mar., dic. 2
Southwest Logo
6:00 pm - 9:30 pmMDW-TPA
2h 30mnonstop
Southwest Logo
4:55 pm - 6:35 pmTPA-MDW
2h 40mnonstop
$148Southwest
Find Deal
mié., oct. 15 - vie., oct. 17
Multiple Airlines Logo
6:20 am - 1:40 pmMDW-FLL
6h 20m1 stop
Multiple Airlines Logo
10:38 pm - 4:42 pmFLL-MDW
19h 04m1 stop
$152Multiple Airlines
Find Deal
lun., oct. 6 - mié., oct. 8
Delta Logo
9:30 am - 3:26 pmMDW-FLL
4h 56m1 stop
Delta Logo
8:00 am - 12:01 pmFLL-MDW
5h 01m1 stop
$217Delta
Find Deal
mar., feb. 3 - jue., feb. 5
Delta Logo
5:32 pm - 12:37 amMDW-RSW
6h 05m1 stop
Delta Logo
5:38 pm - 11:32 pmRSW-MDW
6h 54m1 stop
$217Delta
Find Deal
vie., dic. 5 - lun., dic. 15

Southwest flights from Chicago Midway Airport to Florida

Our best Southwest deals on Chicago Midway Airport to Florida flight tickets
Southwest
Nov 19
MDW9:05 amChicago Midway
2h 35m
TPA12:40 pmTampa
Dec 2
TPA1:05 pmTampa
5h 30m
1 stop
MDW5:35 pmChicago Midway
$147
Find similar
Southwest
Oct 15
MDW6:00 pmChicago Midway
2h 30m
TPA9:30 pmTampa
Oct 17
TPA4:55 pmTampa
2h 40m
MDW6:35 pmChicago Midway
$148
Find similar
Southwest
Oct 14
MDW6:10 pmChicago Midway
2h 55m
FLL10:05 pmFort Lauderdale
Oct 21
FLL8:35 pmFort Lauderdale
3h 10m
MDW10:45 pmChicago Midway
$153
Find similar

Frontier flights from Chicago Midway Airport to Florida

Our best Frontier deals on Chicago Midway Airport to Florida flight tickets
Frontier
Oct 4
MDW11:21 amChicago Midway
2h 43m
MCO3:04 pmOrlando
Oct 11
MCO1:16 pmOrlando
2h 55m
MDW3:11 pmChicago Midway
$99
Find similar
Frontier
Sep 29
MDW8:19 amChicago Midway
2h 41m
MCO12:00 pmOrlando
Oct 5
MCO7:25 amOrlando
2h 53m
MDW9:18 amChicago Midway
$100
Find similar
Frontier
Sep 26
MDW9:48 amChicago Midway
2h 40m
MCO1:28 pmOrlando
Sep 28
MCO7:25 amOrlando
2h 53m
MDW9:18 amChicago Midway
$102
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 septiembre 16, 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

sáb. 10/4

11:21 am-3:04 pm

Nonstop2h 43m

Orlando

sáb. 10/11

1:16 pm-3:11 pm

Nonstop2h 55m

$99

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

lun. 9/29

8:19 am-12:00 pm

Nonstop2h 41m

Orlando

dom. 10/5

7:25 am-9:18 am

Nonstop2h 53m

$100

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

vie. 9/26

6:21 am-9:57 am

Nonstop2h 36m

Tampa

dom. 9/28

10:55 am-12:44 pm

Nonstop2h 49m

$102

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

vie. 9/26

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

vie. 10/3

7:00 am-8:53 am

Nonstop2h 53m

$102

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mié. 11/5

2:06 pm-11:02 am

1 stop19h 56m

Tampa

dom. 11/9

10:41 pm-12:30 am

Nonstop2h 49m

$134

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mié. 11/19

9:05 am-12:40 pm

Nonstop2h 35m

Tampa

mar. 12/2

1:05 pm-5:35 pm

1 stop5h 30m

$147

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

mié. 10/15

6:00 pm-9:30 pm

Nonstop2h 30m

Tampa

vie. 10/17

4:55 pm-6:35 pm

Nonstop2h 40m

$148

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

lun. 10/6

6:20 am-1:40 pm

1 stop6h 20m

Fort Lauderdale

mié. 10/8

10:38 pm-4:42 pm

1 stop19h 04m

$152

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

mar. 2/3

9:30 am-3:26 pm

1 stop4h 56m

Fort Lauderdale

jue. 2/5

8:00 am-12:01 pm

1 stop5h 01m

$217

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

vie. 12/5

5:32 pm-12:37 am

1 stop6h 05m

Fort Myers SW Florida Intl

lun. 12/15

5:38 pm-11:32 pm

1 stop6h 54m

$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 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 $206.

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 Wednesday. momondo users have found tickets for Wednesday departures for as low as $215. 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 $297.

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 $214 when looking at flights departing in the evening. Flights to Florida are more costly at noon, with an average ticket price of $317. 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 Orlando 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 $306 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 $169 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

$64

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 $64. The best round-trip flight deal from Chicago Midway Airport to Florida found on momondo in the last 72 hours is $91.
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
FrontierPriceFrom $39Free CancellationRating
5.8
3,174 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $63Free CancellationRating
6.3
8,019 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $127Free CancellationRating
7.4
8,924 reviews
Search United Airlines flights
DeltaPriceFrom $131Free CancellationRating
7.9
7,957 reviews
Search Delta flights
SouthwestPriceFrom $174Free CancellationRating
8.0
4,242 reviews
Search Southwest 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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jue. 10/16
jue. 10/23
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