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Cheap flights from Florida to Chicago from $52

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Florida to Chicago departing on 8/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Florida to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Allegiant Air Logo
6:10 pm - 8:30 pm
VPS
-
MDW
2h 20mnonstop
Allegiant Air Logo
9:25 pm - 11:39 pm
MDW
-
VPS
2h 14mnonstop
$87Allegiant Air
Mon, Aug 3 - Mon, Aug 17
Allegiant Air Logo
6:14 pm - 8:35 pm
VPS
-
MDW
2h 21mnonstop
Allegiant Air Logo
9:25 pm - 11:39 pm
MDW
-
VPS
2h 14mnonstop
$130Allegiant Air
Fri, Aug 7 - Mon, Aug 10
Allegiant Air Logo
6:11 pm - 8:31 pm
VPS
-
MDW
2h 20mnonstop
Allegiant Air Logo
9:25 pm - 11:39 pm
MDW
-
VPS
2h 14mnonstop
$146Allegiant Air
Fri, Jul 17 - Fri, Aug 14
Southwest Logo
6:40 am - 8:40 am
FLL
-
MDW
3h 00mnonstop
Southwest Logo
6:10 pm - 10:05 pm
MDW
-
FLL
2h 55mnonstop
$171Southwest
Sat, Sep 5 - Wed, Sep 9
Southwest Logo
7:00 am - 9:05 am
FLL
-
MDW
3h 05mnonstop
Southwest Logo
11:15 am - 5:15 pm
MDW
-
FLL
5h 00m
1 stop
$177Southwest
Tue, Jul 28 - Wed, Jul 29
Frontier Logo
5:15 am - 9:51 am
MCO
-
MDW
5h 36m
1 stop
Frontier Logo
11:50 am - 6:33 pm
MDW
-
MCO
5h 43m
1 stop
$202Frontier
Tue, Aug 11 - Tue, Aug 25
Frontier Logo
5:15 am - 9:51 am
MCO
-
MDW
5h 36m
1 stop
Frontier Logo
11:50 am - 6:33 pm
MDW
-
MCO
5h 43m
1 stop
$203Frontier
Tue, Aug 11 - Tue, Aug 18
Delta Logo
6:00 am - 10:37 am
PNS
-
MDW
4h 37m
1 stop
Delta Logo
1:00 pm - 5:12 pm
MDW
-
PNS
4h 12m
1 stop
$297Delta
Sat, Sep 26 - Tue, Sep 29
Delta Logo
11:51 am - 4:15 pm
PNS
-
MDW
4h 24m
1 stop
Delta Logo
6:05 am - 10:43 am
MDW
-
PNS
4h 38m
1 stop
$300Delta
Wed, Aug 26 - Mon, Aug 31
Multiple Airlines Logo
9:01 pm - 2:38 pm
PBI
-
MDW
18h 37m
1 stop
Multiple Airlines Logo
12:11 pm - 7:04 pm
MDW
-
PBI
29h 53m
2 stops
$308Multiple Airlines
Sun, Jul 19 - Sat, Jul 25

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Delta flights from Florida to Chicago Midway Airport

Our best Delta deals on Florida to Chicago Midway Airport flight tickets
Delta
Aug 12
FLL12:10 pmFort Lauderdale
5h 05m
1 stop
MDW4:15 pmChicago Midway
Aug 17
MDW5:10 pmChicago Midway
6h 34m
1 stop
FLL12:44 amFort Lauderdale
$220
Delta
Sep 2
FLL11:26 amFort Lauderdale
6h 33m
1 stop
MDW4:59 pmChicago Midway
Sep 9
MDW9:29 amChicago Midway
5h 04m
1 stop
FLL3:33 pmFort Lauderdale
$221
Delta
Aug 21
FLL6:30 pmFort Lauderdale
5h 06m
1 stop
MDW10:36 pmChicago Midway
Aug 25
MDW9:24 amChicago Midway
5h 14m
1 stop
FLL3:38 pmFort Lauderdale
$222

Frontier flights from Florida to Chicago Midway Airport

Our best Frontier deals on Florida to Chicago Midway Airport flight tickets
Frontier
Aug 11
MCO5:15 amOrlando
5h 36m
1 stop
MDW9:51 amChicago Midway
Aug 25
MDW11:50 amChicago Midway
5h 43m
1 stop
MCO6:33 pmOrlando
$202
Frontier
Aug 11
MCO5:15 amOrlando
5h 36m
1 stop
MDW9:51 amChicago Midway
Aug 18
MDW11:50 amChicago Midway
5h 43m
1 stop
MCO6:33 pmOrlando
$203
Frontier
Aug 11
MCO5:15 amOrlando
5h 36m
1 stop
MDW9:51 amChicago Midway
Aug 18
MDW11:50 amChicago Midway
5h 43m
1 stop
MCO6:33 pmOrlando
$206

momondo Fare Finder

 
Customize your flight search to find flights from Florida to Chicago Midway Airport 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 June 28, 2026.
Use the filters below to find and compare flights from Florida to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 8/3

6:10 pm-8:30 pm

Nonstop2h 20m

Chicago Midway

Mon 8/17

9:25 pm-11:39 pm

Nonstop2h 14m

$87

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 8/7

6:14 pm-8:35 pm

Nonstop2h 21m

Chicago Midway

Mon 8/10

9:25 pm-11:39 pm

Nonstop2h 14m

$130

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 7/17

6:11 pm-8:31 pm

Nonstop2h 20m

Chicago Midway

Fri 8/14

9:25 pm-11:39 pm

Nonstop2h 14m

$146

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Sat 9/5

6:40 am-8:40 am

Nonstop3h 00m

Chicago Midway

Wed 9/9

6:10 pm-10:05 pm

Nonstop2h 55m

$171

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Tue 7/28

7:00 am-9:05 am

Nonstop3h 05m

Chicago Midway

Wed 7/29

11:15 am-5:15 pm

1 stop5h 00m

$177

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 8/11

5:15 am-9:51 am

1 stop5h 36m

Chicago Midway

Tue 8/25

11:50 am-6:33 pm

1 stop5h 43m

$202

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 8/11

5:15 am-9:51 am

1 stop5h 36m

Chicago Midway

Tue 8/18

11:50 am-6:33 pm

1 stop5h 43m

$203

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Sat 9/26

6:00 am-10:37 am

1 stop4h 37m

Chicago Midway

Tue 9/29

1:00 pm-5:12 pm

1 stop4h 12m

$297

PensacolaChicago

PNS - MDW

PNSMDW

Pensacola

Wed 8/26

11:51 am-4:15 pm

1 stop4h 24m

Chicago Midway

Mon 8/31

6:05 am-10:43 am

1 stop4h 38m

$300

West Palm BeachChicago

PBI - MDW

PBIMDW

Palm Beach Intl

Sun 7/19

9:01 pm-2:38 pm

1 stop18h 37m

Chicago Midway

Sat 7/25

12:11 pm-7:04 pm

2 stops29h 53m

$308

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 Chicago from

How to get the cheapest flight ticket from Florida to Chicago Midway Airport

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 Chicago Midway Airport?

The month of October is, on average, the cheapest month to fly to Chicago Midway Airport from Florida, with most prices found around $37. If you are unable to visit Chicago Midway Airport during the month of October, then departing from Florida during the month December is also very affordable. Most momondo users find prices during this month for around $40.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Friday is the cheapest day to fly to Chicago Midway Airport from Florida. The lowest ticket price found for a Friday departure recently was $179. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Tuesday is the most expensive day to depart from Florida because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $312.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Florida 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. Try not to purchase tickets in the morning because they tend to be around $257. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Florida to Chicago Midway flight route?

Fly from Orlando to Chicago Midway for the best Florida - Chicago Midway flight prices

How far in advance should I book a flight from Florida to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Florida when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $242 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Florida for as low as $159 on momondo.

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

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

No. A direct flight is the cheapest option for a flight between Florida to Chicago Midway Airport.

Cheap Florida to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Florida to Chicago Midway Airport

Best Price Found

$57

Fastest flight time

2h 10m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Florida in the past 72 hours is $57. The best round-trip flight deal from Florida to Chicago Midway Airport found on momondo in the last 72 hours is $203.
The fastest flight from Florida to Chicago Midway Airport takes 2h 10m
Direct flights go from Florida to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Florida to Chicago Midway Airport

  • When did momondo last update prices for flights from Florida to Chicago Midway Airport?

    Prices for flights from Florida to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Florida to Chicago Midway Airport?

  • How old do you have to be to fly from Florida to Chicago Midway Airport?

    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 Florida to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport 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 Chicago Midway Airport. 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 Florida to Chicago Midway Airport?

Best airlines flying from Florida to Chicago Midway Airport

Compare and see reviews for airlines that fly from Florida to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $46Free CancellationRating
5.6
2,856 reviews
Search Frontier flights
DeltaPriceFrom $129Free CancellationRating
7.8
8,456 reviews
Search Delta flights
SouthwestPriceFrom $149Free CancellationRating
7.9
4,246 reviews
Search Southwest flights
JetBluePriceFrom $202Free CancellationRating
7.1
3,014 reviews
Search JetBlue flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Florida to Chicago?

Finding the right flight to Chicago from Florida is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Florida to Chicago with flexible booking policies on momondo?

Flights from Florida to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Florida to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Florida.

I’m not ready to book a flight from Florida to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Florida. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago Midway Airport trip

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