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Cheap flights from Florida to Chicago from $27

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 2/15. 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

These are some of the best round-trip flight deals from Florida to Chicago that have been recently found on momondo from popular airlines, departing in the coming months.

Cheap one-way flights

Flying one-way? These are some of the best deals recently discovered on momondo for flights from Florida to Chicago.

Cheap last minute flights

Planning a quick getaway from Florida to Chicago? These are the last-minute flight deals available now.

Cheap direct flights

If you prefer a non-stop journey, check out our latest direct flight deals to Chicago, so you can enjoy a seamless trip without layovers.

Cheap bus & train deals from Florida to Chicago

Find recent round-trip train or bus tickets from Florida to Chicago.

All round-trip flight deals to Chicago

The cheapest plane tickets to Chicago found on KAYAK recently.
10:03 am - 12:10 pmTPA-ORD
3h 07mnonstop
5:05 am - 8:53 amORD-TPA
2h 48mnonstop
$57Frontier
Find Deal
Fri, Feb 21 - Sun, Feb 23
11:49 am - 2:17 pmPBI-ORD
3h 28mnonstop
6:40 am - 10:49 amORD-PBI
3h 09mnonstop
$57Frontier
Find Deal
Fri, Feb 28 - Mon, Mar 3
11:43 am - 1:50 pmTPA-ORD
3h 07mnonstop
7:26 am - 11:11 amORD-TPA
2h 45mnonstop
Thu, Feb 6 - Tue, Feb 11
10:00 am - 12:29 pmMIA-ORD
3h 29mnonstop
2:02 pm - 6:16 pmORD-MIA
3h 14mnonstop
$72Spirit Airlines
Find Deal
Wed, Feb 5 - Tue, Feb 11
12:16 pm - 2:23 pmTPA-ORD
3h 07mnonstop
7:00 am - 10:48 amORD-TPA
2h 48mnonstop
Wed, Feb 5 - Sun, Feb 9
3:13 pm - 5:20 pmTPA-ORD
3h 07mnonstop
7:26 am - 11:11 amORD-TPA
2h 45mnonstop
$75Spirit Airlines
Find Deal
Fri, Jan 24 - Sun, Jan 26
8:27 am - 10:58 amMIA-ORD
3h 31mnonstop
1:59 pm - 6:07 pmORD-MIA
3h 08mnonstop
$157American Airlines
Find Deal
Thu, Feb 13 - Wed, Feb 19
7:20 pm - 9:05 pmTPA-MDW
2h 45mnonstop
1:20 pm - 4:55 pmMDW-TPA
2h 35mnonstop
$163Southwest
Find Deal
Thu, Feb 6 - Tue, Feb 11
1:20 pm - 3:39 pmPBI-ORD
3h 19mnonstop
12:00 pm - 3:55 pmORD-PBI
2h 55mnonstop
$164American Airlines
Find Deal
Fri, Feb 14 - Tue, Feb 18
10:15 am - 12:00 pmTPA-MDW
2h 45mnonstop
1:20 pm - 4:55 pmMDW-TPA
2h 35mnonstop
$173Southwest
Find Deal
Tue, Feb 4 - Tue, Feb 11
11:49 am - 2:17 pmPBI-ORD
3h 28mnonstop
$27Frontier
Find Deal
Sat, Feb 15
11:43 am - 1:50 pmTPA-ORD
3h 07mnonstop
$28Frontier
Find Deal
Thu, Feb 6
10:00 am - 12:29 pmMIA-ORD
3h 29mnonstop
$37Spirit Airlines
Find Deal
Tue, Feb 11
9:12 am - 11:20 amMCO-ORD
3h 08mnonstop
$37Spirit Airlines
Find Deal
Thu, Jan 16
9:00 pm - 8:27 amFLL-ORD
12h 27m1 stop
Mon, Apr 14
11:25 am - 1:10 pmTPA-MDW
2h 45mnonstop
$79Southwest
Find Deal
Sat, Feb 8
8:10 am - 10:20 amMIA-MDW
3h 10mnonstop
$79Southwest
Find Deal
Sat, Feb 8
9:00 am - 11:34 amMIA-ORD
3h 34mnonstop
$79United Airlines
Find Deal
Wed, Feb 12
7:27 pm - 9:44 pmRSW-ORD
3h 17mnonstop
$79United Airlines
Find Deal
Tue, Feb 18
7:05 am - 10:55 pmMCO-ORD
16h 50m2 stops
Thu, Jan 23
2:57 pm - 5:26 pmRSW-ORD
3h 29mnonstop
5:35 am - 9:29 amORD-RSW
2h 54mnonstop
Sat, Jan 11 - Thu, Jan 23
7:06 pm - 9:16 pmTPA-ORD
3h 10mnonstop
3:25 pm - 7:18 pmORD-TPA
2h 53mnonstop
$99Frontier
Find Deal
Fri, Jan 10 - Mon, Jan 13
12:16 pm - 2:23 pmTPA-ORD
3h 07mnonstop
7:26 am - 11:11 amORD-TPA
2h 45mnonstop
$121Spirit Airlines
Find Deal
Fri, Jan 10 - Mon, Jan 13
3:13 pm - 5:20 pmTPA-ORD
3h 07mnonstop
7:26 am - 11:11 amORD-TPA
2h 45mnonstop
$123Spirit Airlines
Find Deal
Fri, Jan 10 - Sun, Jan 12
12:59 pm - 3:21 pmPBI-ORD
3h 22mnonstop
7:22 am - 5:47 pmORD-PBI
9h 25m1 stop
$336American Airlines
Find Deal
Thu, Jan 9 - Tue, Jan 14
10:52 am - 5:54 pmPBI-ORD
8h 02m1 stop
7:22 am - 5:47 pmORD-PBI
9h 25m1 stop
$346American Airlines
Find Deal
Thu, Jan 9 - Tue, Jan 14
11:51 am - 9:28 pmRSW-ORD
10h 37m1 stop
6:30 pm - 10:56 amORD-RSW
15h 26m1 stop
$383Delta
Find Deal
Sat, Jan 11 - Tue, Jan 14
9:25 am - 8:07 pmJAX-ORD
11h 42m2 stops
2:00 pm - 10:52 amORD-JAX
19h 52m2 stops
$394United Airlines
Find Deal
Sat, Jan 11 - Wed, Jan 15
7:00 am - 8:25 pmPBI-ORD
14h 25m2 stops
7:30 am - 10:30 pmORD-PBI
14h 00m2 stops
$429United Airlines
Find Deal
Mon, Jan 13 - Tue, Jan 14
6:00 am - 9:55 amPBI-ORD
4h 55m1 stop
2:55 pm - 9:45 pmORD-PBI
5h 50m1 stop
$469Delta
Find Deal
Thu, Jan 9 - Sat, Jan 11
10:03 am - 12:10 pmTPA-ORD
3h 07mnonstop
5:05 am - 8:53 amORD-TPA
2h 48mnonstop
$57Frontier
Find Deal
Fri, Feb 21 - Sun, Feb 23
11:43 am - 1:50 pmTPA-ORD
3h 07mnonstop
3:16 pm - 7:04 pmORD-TPA
2h 48mnonstop
$58Frontier
Find Deal
Thu, Jan 30 - Mon, Feb 3
11:43 am - 1:50 pmTPA-ORD
3h 07mnonstop
7:26 am - 11:11 amORD-TPA
2h 45mnonstop
Thu, Feb 6 - Tue, Feb 11
12:16 pm - 2:23 pmTPA-ORD
3h 07mnonstop
7:00 am - 10:48 amORD-TPA
2h 48mnonstop
Wed, Feb 5 - Sun, Feb 9
3:13 pm - 5:20 pmTPA-ORD
3h 07mnonstop
7:26 am - 11:11 amORD-TPA
2h 45mnonstop
$75Spirit Airlines
Find Deal
Fri, Jan 24 - Sun, Jan 26
7:30 am - 9:39 amRSW-ORD
3h 09mnonstop
5:35 am - 9:29 amORD-RSW
2h 54mnonstop
$80Spirit Airlines
Find Deal
Thu, Jan 23 - Wed, Jan 29
9:41 pm - 12:17 amMIA-ORD
3h 36mnonstop
6:24 pm - 10:34 pmORD-MIA
3h 10mnonstop
$157American Airlines
Find Deal
Thu, Feb 20 - Wed, Feb 26
8:10 am - 10:20 amMIA-MDW
3h 10mnonstop
6:10 pm - 10:10 pmMDW-MIA
3h 00mnonstop
$157Southwest
Find Deal
Sat, Feb 8 - Tue, Feb 11
7:20 pm - 9:05 pmTPA-MDW
2h 45mnonstop
1:20 pm - 4:55 pmMDW-TPA
2h 35mnonstop
$163Southwest
Find Deal
Thu, Feb 6 - Tue, Feb 11
5:10 pm - 7:31 pmPBI-ORD
3h 21mnonstop
12:00 pm - 3:55 pmORD-PBI
2h 55mnonstop
$164American Airlines
Find Deal
Fri, Feb 28 - Sun, Mar 2

Frontier flights from Florida to Chicago

Our best Frontier deals on Florida to Chicago flight tickets
Frontier
Feb 21
TPA10:03 amTampa
3h 07m
ORD12:10 pmChicago O'Hare Intl
Feb 23
ORD5:05 amChicago O'Hare Intl
2h 48m
TPA8:53 amTampa
Frontier
Jan 30
TPA11:43 amTampa
3h 07m
ORD1:50 pmChicago O'Hare Intl
Feb 3
ORD3:16 pmChicago O'Hare Intl
2h 48m
TPA7:04 pmTampa
Frontier
Feb 6
TPA11:43 amTampa
3h 07m
ORD1:50 pmChicago O'Hare Intl
Feb 9
ORD7:00 amChicago O'Hare Intl
2h 48m
TPA10:48 amTampa

Spirit Airlines flights from Florida to Chicago

Our best Spirit Airlines deals on Florida to Chicago flight tickets
Spirit Airlines
Feb 5
MIA10:00 amMiami
3h 29m
ORD12:29 pmChicago O'Hare Intl
Feb 11
ORD2:02 pmChicago O'Hare Intl
3h 14m
MIA6:16 pmMiami
Spirit Airlines
Jan 24
TPA3:13 pmTampa
3h 07m
ORD5:20 pmChicago O'Hare Intl
Jan 26
ORD7:26 amChicago O'Hare Intl
2h 45m
TPA11:11 amTampa
Spirit Airlines
Jan 17
TPA3:13 pmTampa
3h 07m
ORD5:20 pmChicago O'Hare Intl
Jan 20
ORD7:26 amChicago O'Hare Intl
2h 45m
TPA11:11 amTampa

See travel insights to Chicago from

How to get the cheapest flight ticket from Florida to Chicago

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?

The month of February is, on average, the cheapest month to fly to Chicago from Florida, with most prices found around $138. If you’re not able to fly to Chicago in February, then April is your next best option. Flight prices from Florida to Chicago during April average around $139.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $186. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Florida to Chicago for around $268.

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

Our most recent data shows that the best time of day to fly to Chicago is at noon. Flights from Florida to Chicago during this time can be as low as $177. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $215.

What is the cheapest Florida to Chicago flight route?

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

How far in advance should I book a flight to Chicago?

The best time to book a flight to Chicago from Florida is 31 days out, which is when prices tend to be around $229. Don’t hesitate to check prices now though because momondo users recently found tickets for as low as $114.

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

There are 4 cabin classes available to choose from on Florida to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Cheap Florida to Chicago flight deals and tips

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

Best Price Found

$27

Fastest flight time

2h 40m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Florida in the past 72 hours is $27. The best round-trip flight deal from Florida to Chicago found on momondo in the last 72 hours is $57.
The fastest flight from Florida to Chicago takes 2h 40m
Direct flights go from Florida to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

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

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

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Florida to Chicago.

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

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


Best airlines flying from Florida to Chicago

Compare and see reviews for airlines that fly from Florida to Chicago with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $31Free CancellationRating
6.0
3,428 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $58Free CancellationRating
6.3
8,074 reviews
Search Spirit Airlines flights
Allegiant AirPriceFrom $120Free CancellationRating
7.3
799 reviews
Search Allegiant Air flights
American AirlinesPriceFrom $138Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $149Free CancellationRating
7.4
8,939 reviews
Search United Airlines flights
SouthwestPriceFrom $155Free CancellationRating
8.1
4,648 reviews
Search Southwest flights
DeltaPriceFrom $196Free CancellationRating
8.0
8,499 reviews
Search Delta flights

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Florida.

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

momondo does allow users to show only those flights to Chicago from Florida which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search for Florida to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Florida and alert you when they change.


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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago