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Cheap flights from Florida to Chicago from $64

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 7/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Florida to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
8:10 am - 10:02 pm
MIA
-
MDW
14h 52m
1 stop
Frontier Logo
6:00 am - 4:31 pm
MDW
-
MIA
9h 31m
1 stop
$131Frontier
Wed, Jun 3 - Tue, Jun 9
Frontier Logo
8:10 am - 10:02 pm
MIA
-
MDW
14h 52m
1 stop
Frontier Logo
6:00 am - 11:03 pm
MDW
-
MIA
16h 03m
1 stop
$134Frontier
Wed, Jun 3 - Wed, Jun 10
Frontier Logo
9:15 pm - 11:09 am
FLL
-
MDW
14h 54m
1 stop
Frontier Logo
6:00 am - 5:02 pm
MDW
-
FLL
10h 02m
1 stop
$134Frontier
Tue, Jun 2 - Tue, Jun 9
Frontier Logo
5:25 am - 11:09 am
MCO
-
MDW
6h 44m
1 stop
Frontier Logo
6:00 am - 6:44 am
MDW
-
MCO
23h 44m
1 stop
$134Frontier
Wed, Jul 1 - Tue, Jul 7
Southwest Logo
9:55 pm - 11:35 pm
TPA
-
MDW
2h 40mnonstop
Southwest Logo
8:15 pm - 11:50 pm
MDW
-
TPA
2h 35mnonstop
$169Southwest
Wed, Jul 8 - Tue, Jul 14
Southwest Logo
7:00 am - 9:05 am
FLL
-
MDW
3h 05mnonstop
Southwest Logo
7:40 am - 11:40 am
MDW
-
FLL
3h 00mnonstop
$169Southwest
Tue, Jul 21 - Tue, Jul 28
Multiple Airlines Logo
9:15 pm - 11:09 am
FLL
-
MDW
14h 54m
1 stop
Multiple Airlines Logo
3:38 pm - 6:10 pm
MDW
-
FLL
25h 32m
1 stop
$174Multiple Airlines
Tue, Jun 2 - Fri, Jun 5
Multiple Airlines Logo
5:10 pm - 10:11 pm
MCO
-
MDW
6h 01m
1 stop
Multiple Airlines Logo
8:20 pm - 10:03 am
MDW
-
MCO
12h 43m
1 stop
$174Multiple Airlines
Tue, Jun 9 - Fri, Jun 12
Delta Logo
11:29 am - 3:27 pm
JAX
-
MDW
4h 58m
1 stop
Delta Logo
1:05 pm - 6:58 pm
MDW
-
JAX
4h 53m
1 stop
$237Delta
Tue, Sep 8 - Tue, Sep 15
Delta Logo
6:00 am - 12:05 pm
SRQ
-
MDW
7h 05m
1 stop
Delta Logo
4:25 pm - 10:29 pm
MDW
-
SRQ
5h 04m
1 stop
$257Delta
Wed, Jun 17 - Tue, Jun 30

Southwest flights from Florida to Chicago Midway Airport

Our best Southwest deals on Florida to Chicago Midway Airport flight tickets
Southwest
Jul 8
TPA9:55 pmTampa
2h 40m
MDW11:35 pmChicago Midway
Jul 14
MDW8:15 pmChicago Midway
2h 35m
TPA11:50 pmTampa
$169
Southwest
Jul 8
TPA6:30 pmTampa
2h 45m
MDW8:15 pmChicago Midway
Jul 14
MDW7:25 amChicago Midway
4h 55m
1 stop
TPA1:20 pmTampa
$175
Southwest
Jul 8
TPA9:05 amTampa
6h 15m
1 stop
MDW2:20 pmChicago Midway
Jul 14
MDW8:15 pmChicago Midway
2h 35m
TPA11:50 pmTampa
$179

Allegiant Air flights from Florida to Chicago Midway Airport

Our best Allegiant Air deals on Florida to Chicago Midway Airport flight tickets
Allegiant Air
May 21
FLL10:07 amFort Lauderdale
4h 50m
1 stop
MDW1:57 pmChicago Midway
May 29
MDW3:42 pmChicago Midway
19h 15m
1 stop
FLL11:57 amFort Lauderdale
$260
Allegiant Air
May 24
SRQ8:32 pmSarasota Bradenton Intl
19h 20m
1 stop
MDW2:52 pmChicago Midway
May 31
MDW2:47 pmChicago Midway
25h 14m
1 stop
SRQ5:01 pmSarasota Bradenton Intl
$299
Allegiant Air
May 24
SRQ8:32 pmSarasota Bradenton Intl
19h 20m
1 stop
MDW2:52 pmChicago Midway
May 28
MDW2:47 pmChicago Midway
25h 14m
1 stop
SRQ5:01 pmSarasota Bradenton Intl
$315

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 May 12, 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

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 6/3

8:10 am-10:02 pm

1 stop14h 52m

Chicago Midway

Tue 6/9

6:00 am-4:31 pm

1 stop9h 31m

$131

MiamiChicago

MIA - MDW

MIAMDW

Miami

Wed 6/3

8:10 am-10:02 pm

1 stop14h 52m

Chicago Midway

Wed 6/10

6:00 am-11:03 pm

1 stop16h 03m

$134

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Tue 6/2

9:15 pm-11:09 am

1 stop14h 54m

Chicago Midway

Tue 6/9

6:00 am-5:02 pm

1 stop10h 02m

$134

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 7/1

5:25 am-11:09 am

1 stop6h 44m

Chicago Midway

Tue 7/7

6:00 am-6:44 am

1 stop23h 44m

$134
Quickest round-trip

TampaChicago

TPA - MDW

TPAMDW

Tampa

Wed 7/8

9:55 pm-11:35 pm

Nonstop2h 40m

Chicago Midway

Tue 7/14

8:15 pm-11:50 pm

Nonstop2h 35m

$169

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Tue 7/21

7:00 am-9:05 am

Nonstop3h 05m

Chicago Midway

Tue 7/28

7:40 am-11:40 am

Nonstop3h 00m

$169

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Tue 6/2

9:15 pm-11:09 am

1 stop14h 54m

Chicago Midway

Fri 6/5

3:38 pm-6:10 pm

1 stop25h 32m

$174

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 6/9

5:10 pm-10:11 pm

1 stop6h 01m

Chicago Midway

Fri 6/12

8:20 pm-10:03 am

1 stop12h 43m

$174

JacksonvilleChicago

JAX - MDW

JAXMDW

Jacksonville

Tue 9/8

11:29 am-3:27 pm

1 stop4h 58m

Chicago Midway

Tue 9/15

1:05 pm-6:58 pm

1 stop4h 53m

$237

SarasotaChicago

SRQ - MDW

SRQMDW

Sarasota Bradenton Intl

Wed 6/17

6:00 am-12:05 pm

1 stop7h 05m

Chicago Midway

Tue 6/30

4:25 pm-10:29 pm

1 stop5h 04m

$257

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 $175. 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 $285.

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 $172 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $237. 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 $220 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 $146 on momondo.

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

$68

Fastest flight time

2h 15m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Florida in the past 72 hours is $68. 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 15m
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
2,952 reviews
Search Frontier flights
DeltaPriceFrom $98Free CancellationRating
7.9
8,446 reviews
Search Delta flights
SouthwestPriceFrom $149Free CancellationRating
8.0
4,295 reviews
Search Southwest flights
JetBluePriceFrom $202Free CancellationRating
7.2
2,975 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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