Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago Midway Airport to Florida from $43

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 3/30. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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 - 10:13 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
11:13 am - 1:41 pm
MIA
-
MDW
3h 28mnonstop
$86Frontier
Fri, Mar 13 - Thu, Mar 19
Frontier Logo
6:00 am - 10:13 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
5:05 am - 7:47 pm
MIA
-
MDW
15h 42m
1 stop
$91Frontier
Sat, Mar 7 - Mon, Mar 9
Frontier Logo
6:15 am - 10:28 am
MDW
-
MIA
3h 13mnonstop
Frontier Logo
11:28 am - 1:56 pm
MIA
-
MDW
3h 28mnonstop
$93Frontier
Sun, Feb 15 - Thu, Feb 19
Frontier Logo
6:10 am - 5:49 pm
MDW
-
MIA
10h 39m
1 stop
Frontier Logo
11:28 am - 1:56 pm
MIA
-
MDW
3h 28mnonstop
$94Frontier
Tue, Feb 24 - Thu, Feb 26
Multiple Airlines Logo
7:00 am - 5:02 pm
MDW
-
FLL
9h 02m
1 stop
Multiple Airlines Logo
9:05 pm - 11:27 am
FLL
-
MDW
15h 22m
1 stop
$123Multiple Airlines
Wed, Feb 18 - Wed, Feb 18
Multiple Airlines Logo
7:00 am - 5:02 pm
MDW
-
FLL
9h 02m
1 stop
Multiple Airlines Logo
12:09 pm - 7:07 pm
FLL
-
MDW
7h 58m
1 stop
$129Multiple Airlines
Wed, Feb 18 - Wed, Feb 25
Southwest Logo
5:35 pm - 9:30 pm
MDW
-
FLL
2h 55mnonstop
Southwest Logo
6:35 am - 8:50 am
FLL
-
MDW
3h 15mnonstop
$134Southwest
Tue, Mar 3 - Sat, Mar 7
Southwest Logo
8:35 pm - 12:25 am
MDW
-
RSW
2h 50mnonstop
Southwest Logo
6:15 am - 8:15 am
RSW
-
MDW
3h 00mnonstop
$174Southwest
Sat, Mar 7 - Wed, Mar 11
Delta Logo
6:07 pm - 10:04 pm
MDW
-
PNS
3h 57m
1 stop
Delta Logo
3:55 pm - 10:31 pm
PNS
-
MDW
6h 36m
1 stop
$227Delta
Fri, Mar 13 - Tue, Mar 17
Delta Logo
12:45 pm - 6:52 pm
MDW
-
ECP
6h 07m
1 stop
Delta Logo
2:05 pm - 5:45 pm
ECP
-
MDW
3h 40m
1 stop
$227Delta
Tue, Feb 24 - Fri, Feb 27

Frontier flights from Chicago Midway Airport to Florida

Our best Frontier deals on Chicago Midway Airport to Florida flight tickets
Frontier
Mar 13
MDW6:00 amChicago Midway
3h 13m
MIA10:13 amMiami
Mar 19
MIA11:13 amMiami
3h 28m
MDW1:41 pmChicago Midway
$86
Frontier
Mar 13
MDW6:00 amChicago Midway
3h 13m
MIA10:13 amMiami
Mar 19
MIA11:13 amMiami
3h 28m
MDW1:41 pmChicago Midway
$91
Frontier
Feb 15
MDW6:15 amChicago Midway
3h 13m
MIA10:28 amMiami
Feb 19
MIA11:28 amMiami
3h 28m
MDW1:56 pmChicago Midway
$93

Southwest flights from Chicago Midway Airport to Florida

Our best Southwest deals on Chicago Midway Airport to Florida flight tickets
Southwest
Mar 3
MDW5:35 pmChicago Midway
2h 55m
FLL9:30 pmFort Lauderdale
Mar 7
FLL6:35 amFort Lauderdale
3h 15m
MDW8:50 amChicago Midway
$134
Southwest
Mar 3
MDW5:40 pmChicago Midway
2h 35m
TPA9:15 pmTampa
Mar 10
TPA4:00 pmTampa
2h 50m
MDW5:50 pmChicago Midway
$168
Southwest
Mar 7
MDW8:35 pmChicago Midway
2h 50m
RSW12:25 amFort Myers SW Florida Intl
Mar 11
RSW6:15 amFort Myers SW Florida Intl
3h 00m
MDW8:15 amChicago Midway
$174

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 February 3, 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

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Fri 3/13

6:00 am-10:13 am

Nonstop3h 13m

Miami

Thu 3/19

11:13 am-1:41 pm

Nonstop3h 28m

$86

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sat 3/7

6:00 am-10:13 am

Nonstop3h 13m

Miami

Mon 3/9

5:05 am-7:47 pm

1 stop15h 42m

$91

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Sun 2/15

6:15 am-10:28 am

Nonstop3h 13m

Miami

Thu 2/19

11:28 am-1:56 pm

Nonstop3h 28m

$93

ChicagoMiami

MDW - MIA

MDWMIA

Chicago Midway

Tue 2/24

6:10 am-5:49 pm

1 stop10h 39m

Miami

Thu 2/26

11:28 am-1:56 pm

Nonstop3h 28m

$94

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Wed 2/18

7:00 am-5:02 pm

1 stop9h 02m

Fort Lauderdale

Wed 2/18

9:05 pm-11:27 am

1 stop15h 22m

$123

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Wed 2/18

7:00 am-5:02 pm

1 stop9h 02m

Fort Lauderdale

Wed 2/25

12:09 pm-7:07 pm

1 stop7h 58m

$129

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Tue 3/3

5:35 pm-9:30 pm

Nonstop2h 55m

Fort Lauderdale

Sat 3/7

6:35 am-8:50 am

Nonstop3h 15m

$134

ChicagoFort Myers

MDW - RSW

MDWRSW

Chicago Midway

Sat 3/7

8:35 pm-12:25 am

Nonstop2h 50m

Fort Myers SW Florida Intl

Wed 3/11

6:15 am-8:15 am

Nonstop3h 00m

$174

ChicagoPensacola

MDW - PNS

MDWPNS

Chicago Midway

Fri 3/13

6:07 pm-10:04 pm

1 stop3h 57m

Pensacola

Tue 3/17

3:55 pm-10:31 pm

1 stop6h 36m

$227

ChicagoPanama City

MDW - ECP

MDWECP

Chicago Midway

Tue 2/24

12:45 pm-6:52 pm

1 stop6h 07m

Panama City NW Florida Beaches

Fri 2/27

2:05 pm-5:45 pm

1 stop3h 40m

$227

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $145. 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 $161.

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 $196. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Friday as prices are generally higher than usual. According to our data, the average ticket price to Florida on Friday is $337.

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

Flying to Florida from Chicago Midway Airport at noon is the least expensive time of day to depart. momondo users have found prices as low as $187 when looking at flights departing at noon. Flights to Florida are more costly in the afternoon, with an average ticket price of $296. Departure times in the afternoon 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 $307 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 $198 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

$58

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 $58. The best round-trip flight deal from Chicago Midway Airport to Florida found on momondo in the last 72 hours is $154.
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 Panama City NW Florida Beaches (ECP), 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
Spirit AirlinesPriceFrom $35Free CancellationRating
6.3
8,404 reviews
Search Spirit Airlines flights
FrontierPriceFrom $39Free CancellationRating
5.7
3,051 reviews
Search Frontier flights
DeltaPriceFrom $98Free CancellationRating
7.9
8,138 reviews
Search Delta flights
United AirlinesPriceFrom $119Free CancellationRating
7.4
9,236 reviews
Search United Airlines flights
SouthwestPriceFrom $171Free CancellationRating
8.0
4,272 reviews
Search Southwest flights
American AirlinesPriceFrom $203Free CancellationRating
7.2
11,216 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.

An easier way to manage your Florida trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Thu 3/5
Thu 3/12
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Florida

Popular cities in Florida

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $49
Flights to Los Angelesfrom $46
Flights to Miamifrom $27
Flights to Chicagofrom $49
Flights to Orlandofrom $49
Flights to San Franciscofrom $54
Flights to Las Vegasfrom $49
Flights to Washington, D.C.from $51
Flights to Bostonfrom $51
Flights to Atlantafrom $42
Flights to Dallasfrom $51
Flights to Seattlefrom $73