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Cheap flights from Florida to Chicago from $51

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 10/27. 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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Cheap round-trip flights

Frontier Logo
8:00 am - 9:51 amMCO-MDW
2h 51mnonstop
Frontier Logo
10:13 am - 1:55 pmMDW-MCO
2h 42mnonstop
$108Frontier
Find Deal
Sa, Sep 13 - So, Sep 21
Frontier Logo
5:50 am - 7:44 amMCO-MDW
2h 54mnonstop
Frontier Logo
8:39 am - 12:20 pmMDW-MCO
2h 41mnonstop
$114Frontier
Find Deal
So, Okt 12 - Fr, Okt 17
Southwest Logo
12:35 pm - 2:45 pmMIA-MDW
3h 10mnonstop
Southwest Logo
2:45 pm - 6:45 pmMDW-MIA
3h 00mnonstop
$137Southwest
Find Deal
Fr, Sep 19 - So, Sep 21
Southwest Logo
6:15 pm - 12:05 amMIA-MDW
6h 50m1 stop
Southwest Logo
2:45 pm - 6:45 pmMDW-MIA
3h 00mnonstop
$147Southwest
Find Deal
Fr, Sep 26 - So, Sep 28
Allegiant Air Logo
6:45 am - 4:43 pmFLL-MDW
10h 58m1 stop
Allegiant Air Logo
12:50 pm - 8:21 pmMDW-FLL
6h 31m1 stop
$187Allegiant Air
Find Deal
Fr, Sep 5 - Mo, Sep 8
Allegiant Air Logo
6:45 am - 4:43 pmFLL-MDW
10h 58m1 stop
Allegiant Air Logo
12:50 pm - 8:21 pmMDW-FLL
6h 31m1 stop
$188Allegiant Air
Find Deal
Fr, Sep 26 - Mo, Sep 29
Delta Logo
6:00 am - 9:40 amTPA-MDW
4h 40m1 stop
Delta Logo
6:00 am - 12:36 pmMDW-TPA
5h 36m1 stop
$197Delta
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Do, Okt 23 - Sa, Okt 25
Delta Logo
5:08 pm - 9:10 pmJAX-MDW
5h 02m1 stop
Delta Logo
6:00 am - 11:40 amMDW-JAX
4h 40m1 stop
$201Delta
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Sa, Sep 20 - Di, Sep 23
Logo
6:45 am - 4:43 pmFLL-MDW
10h 58m1 stop
Logo
7:03 pm - 4:19 pmMDW-FLL
20h 16m2 stops
$236
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Fr, Sep 26 - Mo, Sep 29
Logo
9:45 pm - 6:17 pmFLL-MDW
21h 32m2 stops
Logo
9:32 am - 7:00 pmMDW-FLL
8h 28m1 stop
$241
Find Deal
So, Aug 17 - Fr, Aug 22

Frontier flights from Florida to Chicago Midway Airport

Our best Frontier deals on Florida to Chicago Midway Airport flight tickets
Frontier
Sep 13
MCO8:00 amOrlando
2h 51m
MDW9:51 amChicago Midway
Sep 21
MDW10:13 amChicago Midway
2h 42m
MCO1:55 pmOrlando
$108
Find similar
Frontier
Oct 12
MCO5:50 amOrlando
2h 54m
MDW7:44 amChicago Midway
Oct 17
MDW8:39 amChicago Midway
2h 41m
MCO12:20 pmOrlando
$114
Find similar
Frontier
Sep 12
TPA10:55 amTampa
2h 49m
MDW12:44 pmChicago Midway
Sep 19
MDW6:21 amChicago Midway
2h 36m
TPA9:57 amTampa
$117
Find similar

Southwest flights from Florida to Chicago Midway Airport

Our best Southwest deals on Florida to Chicago Midway Airport flight tickets
Southwest
Sep 19
MIA12:35 pmMiami
3h 10m
MDW2:45 pmChicago Midway
Sep 21
MDW2:45 pmChicago Midway
3h 00m
MIA6:45 pmMiami
$137
Find similar
Southwest
Sep 26
MIA6:15 pmMiami
6h 50m
1 stop
MDW12:05 amChicago Midway
Sep 28
MDW2:45 pmChicago Midway
3h 00m
MIA6:45 pmMiami
$147
Find similar
Southwest
Oct 22
MIA11:45 amMiami
8h 25m
2 stops
MDW7:10 pmChicago Midway
Oct 27
MDW8:10 amChicago Midway
3h 00m
MIA12:10 pmMiami
$152
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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 August 1, 2025.
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

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sa 9/13

8:00 am-9:51 am

Nonstop2h 51m

Chicago Midway

So 9/21

10:13 am-1:55 pm

Nonstop2h 42m

$108

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

So 10/12

5:50 am-7:44 am

Nonstop2h 54m

Chicago Midway

Fr 10/17

8:39 am-12:20 pm

Nonstop2h 41m

$114

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fr 9/19

12:35 pm-2:45 pm

Nonstop3h 10m

Chicago Midway

So 9/21

2:45 pm-6:45 pm

Nonstop3h 00m

$137

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fr 9/26

6:15 pm-12:05 am

1 stop6h 50m

Chicago Midway

So 9/28

2:45 pm-6:45 pm

Nonstop3h 00m

$147

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Fr 9/5

6:45 am-4:43 pm

1 stop10h 58m

Chicago Midway

Mo 9/8

12:50 pm-8:21 pm

1 stop6h 31m

$187

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Fr 9/26

6:45 am-4:43 pm

1 stop10h 58m

Chicago Midway

Mo 9/29

12:50 pm-8:21 pm

1 stop6h 31m

$188

TampaChicago

TPA - MDW

TPAMDW

Tampa

Do 10/23

6:00 am-9:40 am

1 stop4h 40m

Chicago Midway

Sa 10/25

6:00 am-12:36 pm

1 stop5h 36m

$197

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Sa 9/20

5:08 pm-9:10 pm

1 stop5h 02m

Chicago Midway

Di 9/23

6:00 am-11:40 am

1 stop4h 40m

$201

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Fr 9/26

6:45 am-4:43 pm

1 stop10h 58m

Chicago Midway

Mo 9/29

7:03 pm-4:19 pm

2 stops20h 16m

$236

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

So 8/17

9:45 pm-6:17 pm

2 stops21h 32m

Chicago Midway

Fr 8/22

9:32 am-7:00 pm

1 stop8h 28m

$241

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 August is, on average, the cheapest month to fly to Chicago Midway Airport from Florida, with most prices found around $126. If you are unable to visit Chicago Midway Airport during the month of August, then departing from Florida during the month July is also very affordable. Most momondo users find prices during this month for around $143.

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 $178. 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, Sunday 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 $287.

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 $158 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $203. 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 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 $215 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 $144 on momondo.

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

There are 1 cabin classes available to choose from on Florida to Chicago Midway 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

$51

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 $51. The best round-trip flight deal from Florida to Chicago Midway Airport found on momondo in the last 72 hours is $108.
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

  • 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
Spirit AirlinesPriceFrom $76Free CancellationRating
6.3
8,049 reviews
Search Spirit Airlines flights
FrontierPriceFrom $80Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
DeltaPriceFrom $114Free CancellationRating
8.0
7,981 reviews
Search Delta flights
SouthwestPriceFrom $149Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

Traveling to a place near Chicago?

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