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Cheap flights from Chicago Midway Airport to Florida from $86

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 7/29. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago Midway Airport to Florida

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
6:15 am - 10:05 am
MDW
-
FLL
2h 50mnonstop
Southwest Logo
6:40 am - 8:40 am
FLL
-
MDW
3h 00mnonstop
$171Southwest
Sat, Aug 15 - Sat, Aug 22
Southwest Logo
11:15 am - 5:15 pm
MDW
-
FLL
5h 00m
1 stop
Southwest Logo
7:20 am - 9:20 am
FLL
-
MDW
3h 00mnonstop
$177Southwest
Wed, Jul 29 - Wed, Aug 5
Southwest Logo
6:00 pm - 9:55 pm
MDW
-
FLL
2h 55mnonstop
Southwest Logo
6:00 am - 8:05 am
FLL
-
MDW
3h 05mnonstop
$178Southwest
Wed, Oct 14 - Mon, Oct 19
Frontier Logo
6:40 am - 2:37 pm
MDW
-
MCO
6h 57m
1 stop
Frontier Logo
5:29 pm - 9:58 pm
MCO
-
MDW
5h 29m
1 stop
$184Frontier
Wed, Oct 14 - Wed, Oct 21
Frontier Logo
12:03 pm - 10:10 pm
MDW
-
MCO
9h 07m
1 stop
Frontier Logo
5:29 pm - 9:58 pm
MCO
-
MDW
5h 29m
1 stop
$194Frontier
Thu, Oct 1 - Tue, Oct 6
Delta Logo
6:11 am - 12:39 pm
MDW
-
TPA
5h 28m
1 stop
Delta Logo
11:10 am - 3:44 pm
TPA
-
MDW
5h 34m
1 stop
$213Delta
Sat, Aug 29 - Tue, Sep 1
Delta Logo
5:11 pm - 12:35 am
MDW
-
SRQ
6h 24m
1 stop
Delta Logo
4:26 pm - 10:45 pm
SRQ
-
MDW
7h 19m
1 stop
$243Delta
Tue, Sep 15 - Thu, Sep 17
Multiple Airlines Logo
2:49 pm - 9:41 am
MDW
-
EYW
17h 52m
1 stop
Multiple Airlines Logo
11:04 am - 10:47 pm
EYW
-
MDW
12h 43m
2 stops
$285Multiple Airlines
Thu, Aug 13 - Thu, Aug 20
Allegiant Air Logo
3:28 pm - 3:26 pm
MDW
-
PBI
22h 58m
1 stop
Allegiant Air Logo
9:01 pm - 2:38 pm
PBI
-
MDW
18h 37m
1 stop
$298Allegiant Air
Fri, Jul 24 - Sun, Jul 26
Multiple Airlines Logo
2:49 pm - 9:41 am
MDW
-
EYW
17h 52m
1 stop
Multiple Airlines Logo
12:05 pm - 10:47 pm
EYW
-
MDW
11h 42m
2 stops
$306Multiple Airlines
Sun, Aug 16 - Sun, Aug 23

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Frontier flights from Chicago Midway Airport to Florida

Our best Frontier deals on Chicago Midway Airport to Florida flight tickets
Frontier
Sep 12
MDW7:25 amChicago Midway
8h 56m
1 stop
MCO5:21 pmOrlando
Sep 15
MCO5:29 pmOrlando
5h 29m
1 stop
MDW9:58 pmChicago Midway
$208
Frontier
Sep 5
MDW11:45 amChicago Midway
7h 15m
1 stop
MCO8:00 pmOrlando
Sep 8
MCO5:24 amOrlando
6h 31m
1 stop
MDW10:55 amChicago Midway
$209
Frontier
Aug 18
MDW11:50 amChicago Midway
5h 43m
1 stop
MCO6:33 pmOrlando
Aug 25
MCO5:23 pmOrlando
6h 24m
1 stop
MDW10:47 pmChicago Midway
$210

Delta flights from Chicago Midway Airport to Florida

Our best Delta deals on Chicago Midway Airport to Florida flight tickets
Delta
Aug 29
MDW6:11 amChicago Midway
5h 28m
1 stop
TPA12:39 pmTampa
Sep 1
TPA11:10 amTampa
5h 34m
1 stop
MDW3:44 pmChicago Midway
$213
Delta
Aug 5
MDW10:54 amChicago Midway
5h 29m
1 stop
FLL5:23 pmFort Lauderdale
Aug 18
FLL12:10 pmFort Lauderdale
5h 05m
1 stop
MDW4:15 pmChicago Midway
$217
Delta
Aug 14
MDW5:10 pmChicago Midway
5h 13m
1 stop
FLL11:23 pmFort Lauderdale
Aug 16
FLL6:00 amFort Lauderdale
7h 39m
1 stop
MDW12:39 pmChicago Midway
$227

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 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
Quickest round-trip

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Sat 8/15

6:15 am-10:05 am

Nonstop2h 50m

Fort Lauderdale

Sat 8/22

6:40 am-8:40 am

Nonstop3h 00m

$171

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Wed 7/29

11:15 am-5:15 pm

1 stop5h 00m

Fort Lauderdale

Wed 8/5

7:20 am-9:20 am

Nonstop3h 00m

$177

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Wed 10/14

6:00 pm-9:55 pm

Nonstop2h 55m

Fort Lauderdale

Mon 10/19

6:00 am-8:05 am

Nonstop3h 05m

$178

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Wed 10/14

6:40 am-2:37 pm

1 stop6h 57m

Orlando

Wed 10/21

5:29 pm-9:58 pm

1 stop5h 29m

$184

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Thu 10/1

12:03 pm-10:10 pm

1 stop9h 07m

Orlando

Tue 10/6

5:29 pm-9:58 pm

1 stop5h 29m

$194

ChicagoTampa

MDW - TPA

MDWTPA

Chicago Midway

Sat 8/29

6:11 am-12:39 pm

1 stop5h 28m

Tampa

Tue 9/1

11:10 am-3:44 pm

1 stop5h 34m

$213

ChicagoSarasota

MDW - SRQ

MDWSRQ

Chicago Midway

Tue 9/15

5:11 pm-12:35 am

1 stop6h 24m

Sarasota Bradenton Intl

Thu 9/17

4:26 pm-10:45 pm

1 stop7h 19m

$243

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Thu 8/13

2:49 pm-9:41 am

1 stop17h 52m

Key West

Thu 8/20

11:04 am-10:47 pm

2 stops12h 43m

$285

ChicagoWest Palm Beach

MDW - PBI

MDWPBI

Chicago Midway

Fri 7/24

3:28 pm-3:26 pm

1 stop22h 58m

Palm Beach Intl

Sun 7/26

9:01 pm-2:38 pm

1 stop18h 37m

$298

ChicagoKey West

MDW - EYW

MDWEYW

Chicago Midway

Sun 8/16

2:49 pm-9:41 am

1 stop17h 52m

Key West

Sun 8/23

12:05 pm-10:47 pm

2 stops11h 42m

$306

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 $274. 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 $349.

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 $257 when looking at flights departing in the evening. Flights to Florida are more costly at noon, with an average ticket price of $321. 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 $300 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 $229 on momondo.

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

There are 2 cabin classes available to choose from on Chicago Midway Airport 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

$50

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 $50. The best round-trip flight deal from Chicago Midway Airport to Florida found on momondo in the last 72 hours is $149.
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), Pensacola (PNS), Tampa (TPA), Orlando (MCO).
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 $59Free CancellationRating
5.6
2,850 reviews
Search Frontier flights
DeltaPriceFrom $134Free CancellationRating
7.8
8,452 reviews
Search Delta flights
SouthwestPriceFrom $173Free CancellationRating
7.9
4,249 reviews
Search Southwest flights
American AirlinesPriceFrom $203Free CancellationRating
7.1
11,769 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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