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Cheap flights from Florida to Chicago from £49

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 4/3. 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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Cheap return flights

Enter your travel dates to find the best prices.
Spirit Airlines Logo
21:00 - 23:06MCO-ORD
3h 06mdirect
Spirit Airlines Logo
06:48 - 10:30ORD-MCO
2h 42mdirect
£104Spirit Airlines
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Thu, 20 Nov - Fri, 21 Nov
Spirit Airlines Logo
21:00 - 23:06MCO-ORD
3h 06mdirect
Spirit Airlines Logo
21:22 - 10:14ORD-MCO
11h 52m1 stop
£110Spirit Airlines
Find Deal
Thu, 27 Nov - Sun, 30 Nov
Southwest Logo
09:05 - 11:10MCO-ORD
3h 05mdirect
Southwest Logo
13:45 - 21:25ORD-MCO
6h 40m1 stop
£112Southwest
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Fri, 23 Jan - Mon, 26 Jan
United Airlines Logo
10:30 - 12:33MCO-ORD
3h 03mdirect
United Airlines Logo
14:10 - 18:01ORD-MCO
2h 51mdirect
£115United Airlines
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Tue, 9 Dec - Tue, 9 Dec
Southwest Logo
07:30 - 12:15MCO-ORD
5h 45m1 stop
Southwest Logo
14:15 - 22:00ORD-MCO
6h 45m1 stop
£119Southwest
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Tue, 6 Jan - Thu, 8 Jan
United Airlines Logo
09:50 - 11:49TPA-ORD
2h 59mdirect
United Airlines Logo
18:05 - 21:57ORD-TPA
2h 52mdirect
£119United Airlines
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Thu, 4 Dec - Thu, 11 Dec
Delta Logo
19:06 - 00:01TPA-ORD
5h 55m1 stop
Delta Logo
09:52 - 16:50ORD-TPA
5h 58m1 stop
£150Delta
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Thu, 11 Dec - Mon, 26 Jan
Delta Logo
14:31 - 21:04TPA-ORD
7h 33m1 stop
Delta Logo
10:35 - 18:35ORD-TPA
7h 00m1 stop
£150Delta
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Fri, 16 Jan - Mon, 19 Jan
JetBlue Logo
11:00 - 17:31MCO-ORD
7h 31m1 stop
JetBlue Logo
11:30 - 23:07ORD-MCO
10h 37m1 stop
£172JetBlue
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Wed, 8 Apr - Mon, 13 Apr
JetBlue Logo
11:15 - 10:35JAX-ORD
24h 20m1 stop
JetBlue Logo
11:25 - 10:07ORD-JAX
21h 42m1 stop
£192JetBlue
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Sat, 6 Dec - Sat, 13 Dec

Spirit Airlines flights from Florida to Chicago

Our best Spirit Airlines deals on Florida to Chicago flight tickets
Spirit Airlines
20 Nov
MCO21:00Orlando
3h 06m
ORD23:06Chicago O'Hare Intl
21 Nov
ORD06:48Chicago O'Hare Intl
2h 42m
MCO10:30Orlando
£104
Find similar
Spirit Airlines
27 Nov
MCO21:00Orlando
3h 06m
ORD23:06Chicago O'Hare Intl
30 Nov
ORD21:22Chicago O'Hare Intl
11h 52m
1 stop
MCO10:14Orlando
£110
Find similar
Spirit Airlines
28 Feb
TPA14:35Tampa
10h 07m
1 stop
ORD23:42Chicago O'Hare Intl
3 Mar
ORD08:41Chicago O'Hare Intl
12h 37m
1 stop
TPA22:18Tampa
£151
Find similar

Southwest flights from Florida to Chicago

Our best Southwest deals on Florida to Chicago flight tickets
Southwest
23 Jan
MCO09:05Orlando
3h 05m
ORD11:10Chicago O'Hare Intl
26 Jan
ORD13:45Chicago O'Hare Intl
6h 40m
1 stop
MCO21:25Orlando
£112
Find similar
Southwest
6 Jan
MCO07:30Orlando
5h 45m
1 stop
ORD12:15Chicago O'Hare Intl
8 Jan
ORD14:15Chicago O'Hare Intl
6h 45m
1 stop
MCO22:00Orlando
£119
Find similar
Southwest
12 Dec
TPA12:45Tampa
3h 00m
ORD14:45Chicago O'Hare Intl
14 Dec
ORD11:55Chicago O'Hare Intl
2h 40m
TPA15:35Tampa
£121
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momondo Fare Finder

 
Customise your flight search to find flights from Florida to Chicago 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 279,928 searches. Data last updated 31 October 2025.
Use the filters below to find and compare flights from Florida to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 20/11

21:00-23:06

Nonstop3h 06m

Chicago O'Hare Intl

Fri 21/11

06:48-10:30

Nonstop2h 42m

£104

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 27/11

21:00-23:06

Nonstop3h 06m

Chicago O'Hare Intl

Sun 30/11

21:22-10:14

1 stop11h 52m

£110

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 23/1

09:05-11:10

Nonstop3h 05m

Chicago O'Hare Intl

Mon 26/1

13:45-21:25

1 stop6h 40m

£112

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 9/12

10:30-12:33

Nonstop3h 03m

Chicago O'Hare Intl

Tue 9/12

14:10-18:01

Nonstop2h 51m

£115

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 6/1

07:30-12:15

1 stop5h 45m

Chicago O'Hare Intl

Thu 8/1

14:15-22:00

1 stop6h 45m

£119

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 4/12

09:50-11:49

Nonstop2h 59m

Chicago O'Hare Intl

Thu 11/12

18:05-21:57

Nonstop2h 52m

£119

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 11/12

19:06-00:01

1 stop5h 55m

Chicago O'Hare Intl

Mon 26/1

09:52-16:50

1 stop5h 58m

£150

TampaChicago

TPA - ORD

TPAORD

Tampa

Fri 16/1

14:31-21:04

1 stop7h 33m

Chicago O'Hare Intl

Mon 19/1

10:35-18:35

1 stop7h 00m

£150

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 8/4

11:00-17:31

1 stop7h 31m

Chicago O'Hare Intl

Mon 13/4

11:30-23:07

1 stop10h 37m

£172

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 6/12

11:15-10:35

1 stop24h 20m

Chicago O'Hare Intl

Sat 13/12

11:25-10:07

1 stop21h 42m

£192

Flights are sorted by cheapest return 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

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 cheapest month to fly to Chicago from Florida is in September. Flight prices, which tend to average around £89, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from Florida during January instead. Flights to Chicago in January, while not as cheap as those in September, still average around £117.

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 Wednesday when prices can be found for as low as £115. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Thursday, with ticket prices averaging around £473.

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

Flying to Chicago from Florida in the afternoon is the least expensive time of day to depart. momondo users have found prices as low as £248 when looking at flights departing in the afternoon. Flights at midday are often more expensive, with an average ticket price of £510.

What is the cheapest Florida to Chicago flight route?

Fly from Palm Beach Intl to Chicago O'Hare Intl for the best Florida - Chicago flight prices

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

You are more likely to see cheaper flights to Chicago from Florida when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £166 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Florida for as low as £140 on momondo.

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.

Can stopping save me money on Florida to Chicago flights?

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

Cheap Florida to Chicago flight deals and tips

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

Fastest flight time

2h 34m

Direct flights

Every day

Airports in Chicago

1 airport
The fastest flight from Florida to Chicago takes 2h 34m
Direct flights go from Florida to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
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  • When did momondo last update prices for flights from Florida to Chicago?

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

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

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify 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 necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Florida to Chicago?

Why use momondo?

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

It is quick and easy to find Florida to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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?

momondo helps you find the best flight between Florida and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Price alerts on flights to Chicago from Florida 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.

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport