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Cheap flights from Chicago Midway Airport to Florida from $45

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 9/26. 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

Frontier Logo
10:51 am - 2:34 pmMDW-MCO
2h 43mnonstop
Frontier Logo
8:00 am - 9:51 amMCO-MDW
2h 51mnonstop
$78Frontier
Find Deal
Sat, Aug 30 - Sat, Sep 6
Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
Frontier Logo
7:00 am - 8:53 amMCO-MDW
2h 53mnonstop
$79Frontier
Find Deal
Fri, Sep 19 - Fri, Sep 26
Frontier Logo
10:51 am - 2:33 pmMDW-MCO
2h 42mnonstop
Frontier Logo
8:00 am - 9:51 amMCO-MDW
2h 51mnonstop
$88Frontier
Find Deal
Sat, Sep 13 - Sat, Sep 20
Frontier Logo
9:48 am - 1:28 pmMDW-MCO
2h 40mnonstop
Frontier Logo
5:35 am - 7:23 amMCO-MDW
2h 48mnonstop
$89Frontier
Find Deal
Fri, Sep 5 - Mon, Sep 8
Southwest Logo
2:10 pm - 6:10 pmMDW-MIA
3h 00mnonstop
Southwest Logo
12:35 pm - 2:45 pmMIA-MDW
3h 10mnonstop
$137Southwest
Find Deal
Mon, Sep 15 - Fri, Sep 19
Southwest Logo
5:25 am - 3:15 pmMDW-MIA
8h 50m1 stop
Southwest Logo
7:30 am - 9:35 amMIA-MDW
3h 05mnonstop
$147Southwest
Find Deal
Thu, Sep 4 - Sun, Sep 7
Delta Logo
6:00 am - 1:55 pmMDW-TPA
6h 55m1 stop
Delta Logo
6:00 am - 9:16 amTPA-MDW
4h 16m1 stop
$197Delta
Find Deal
Sat, Aug 30 - Wed, Sep 3
Delta Logo
10:31 am - 3:58 pmMDW-SRQ
4h 27m1 stop
Delta Logo
5:03 pm - 9:26 pmSRQ-MDW
5h 23m1 stop
$197Delta
Find Deal
Sat, Sep 6 - Tue, Sep 9
Allegiant Air Logo
9:32 am - 7:00 pmMDW-FLL
8h 28m1 stop
Allegiant Air Logo
8:07 pm - 8:42 amFLL-MDW
13h 35m1 stop
$198Allegiant Air
Find Deal
Fri, Aug 22 - Sun, Aug 24
Allegiant Air Logo
5:35 pm - 9:01 amMDW-EYW
14h 26m2 stops
Allegiant Air Logo
10:41 am - 3:22 pmEYW-MDW
5h 41m1 stop
$335Allegiant Air
Find Deal
Fri, Nov 14 - Mon, Nov 17

Southwest flights from Chicago Midway Airport to Florida

Our best Southwest deals on Chicago Midway Airport to Florida flight tickets
Southwest
Sep 15
MDW2:10 pmChicago Midway
3h 00m
MIA6:10 pmMiami
Sep 19
MIA12:35 pmMiami
3h 10m
MDW2:45 pmChicago Midway
$137
Find similar
Southwest
Sep 4
MDW5:25 amChicago Midway
8h 50m
1 stop
MIA3:15 pmMiami
Sep 7
MIA7:30 amMiami
3h 05m
MDW9:35 amChicago Midway
$147
Find similar
Southwest
Sep 24
MDW2:05 pmChicago Midway
5h 35m
1 stop
MIA8:40 pmMiami
Oct 1
MIA5:25 pmMiami
5h 15m
1 stop
MDW9:40 pmChicago Midway
$157
Find similar

Delta flights from Chicago Midway Airport to Florida

Our best Delta deals on Chicago Midway Airport to Florida flight tickets
Delta
Aug 30
MDW6:00 amChicago Midway
6h 55m
1 stop
TPA1:55 pmTampa
Sep 3
TPA6:00 amTampa
4h 16m
1 stop
MDW9:16 amChicago Midway
$197
Find similar
Delta
Aug 25
MDW6:00 amChicago Midway
4h 27m
1 stop
TPA11:27 amTampa
Aug 30
TPA6:21 amTampa
7h 07m
1 stop
MDW12:28 pmChicago Midway
$203
Find similar
Delta
Sep 30
MDW10:35 amChicago Midway
6h 58m
1 stop
MIA6:33 pmMiami
Oct 8
MIA12:20 pmMiami
7h 05m
1 stop
MDW6:25 pmChicago Midway
$217
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 July 31, 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

Sat 8/30

10:51 am-2:34 pm

Nonstop2h 43m

Orlando

Sat 9/6

8:00 am-9:51 am

Nonstop2h 51m

$78

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 9/19

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

Fri 9/26

7:00 am-8:53 am

Nonstop2h 53m

$79

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 9/13

10:51 am-2:33 pm

Nonstop2h 42m

Orlando

Sat 9/20

8:00 am-9:51 am

Nonstop2h 51m

$88

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Fri 9/5

9:48 am-1:28 pm

Nonstop2h 40m

Orlando

Mon 9/8

5:35 am-7:23 am

Nonstop2h 48m

$89

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Mon 9/15

2:10 pm-6:10 pm

Nonstop3h 00m

Miami

Fri 9/19

12:35 pm-2:45 pm

Nonstop3h 10m

$137

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Thu 9/4

5:25 am-3:15 pm

1 stop8h 50m

Miami

Sun 9/7

7:30 am-9:35 am

Nonstop3h 05m

$147

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 8/30

6:00 am-1:55 pm

1 stop6h 55m

Tampa

Wed 9/3

6:00 am-9:16 am

1 stop4h 16m

$197

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Sat 9/6

10:31 am-3:58 pm

1 stop4h 27m

Sarasota Bradenton Intl

Tue 9/9

5:03 pm-9:26 pm

1 stop5h 23m

$197

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Fri 8/22

9:32 am-7:00 pm

1 stop8h 28m

Fort Lauderdale

Sun 8/24

8:07 pm-8:42 am

1 stop13h 35m

$198

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Fri 11/14

5:35 pm-9:01 am

2 stops14h 26m

Key West

Mon 11/17

10:41 am-3:22 pm

1 stop5h 41m

$335

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, October 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 $172. If you’re not able to fly to Florida in October, then February is your next best option. Flight prices from Chicago Midway Airport to Florida during February average around $174.

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 $181. 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 $292.

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 $197 when looking at flights departing in the evening. Flights to Florida are more costly at noon, with an average ticket price of $313. 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 Jacksonville 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 $280 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 $170 on momondo.

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

There are 1 cabin classes 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

$45

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Florida

6 airports
The best one-way flight to Florida from Chicago Midway Airport in the past 72 hours is $45. The best round-trip flight deal from Chicago Midway Airport to Florida found on momondo in the last 72 hours is $78.
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 6 airports near Florida: Jacksonville (JAX), Sarasota Bradenton Intl (SRQ), Miami (MIA), Tampa (TPA), Pensacola (PNS), Orlando (MCO)
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  • 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
5.9
3,239 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $85Free CancellationRating
6.3
8,048 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $127Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
DeltaPriceFrom $131Free CancellationRating
8.0
7,981 reviews
Search Delta flights
SouthwestPriceFrom $173Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
American AirlinesPriceFrom $270Free CancellationRating
7.2
10,000 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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