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Cheap flights from Florida to Chicago from £41

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 17/3. 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

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Multiple Airlines Logo
17:15 - 22:24MCO-ORD
6h 09m1 stop
Multiple Airlines Logo
07:20 - 11:12ORD-MCO
2h 52mdirect
£83Multiple Airlines
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Wed, 31 Dec - Wed, 7 Jan
Spirit Airlines Logo
16:56 - 19:02MCO-ORD
3h 06mdirect
Spirit Airlines Logo
12:09 - 16:01ORD-MCO
2h 52mdirect
£93Spirit Airlines
Find Deal
Wed, 31 Dec - Wed, 7 Jan
Frontier Logo
17:05 - 22:45MCO-ORD
6h 40m1 stop
Frontier Logo
16:49 - 00:21ORD-MCO
6h 32m1 stop
£96Frontier
Find Deal
Wed, 31 Dec - Wed, 7 Jan
United Airlines Logo
15:00 - 17:08MCO-ORD
3h 08mdirect
United Airlines Logo
19:45 - 23:44ORD-MCO
2h 59mdirect
£100United Airlines
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Tue, 13 Jan - Tue, 13 Jan
Southwest Logo
19:40 - 21:50MCO-ORD
3h 10mdirect
Southwest Logo
15:45 - 19:30ORD-MCO
2h 45mdirect
£104Southwest
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Thu, 8 Jan - Sun, 11 Jan
Southwest Logo
06:40 - 12:15MCO-ORD
6h 35m1 stop
Southwest Logo
06:05 - 09:45ORD-MCO
2h 40mdirect
£112Southwest
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Sun, 15 Feb - Mon, 23 Feb
United Airlines Logo
12:25 - 14:28TPA-ORD
3h 03mdirect
United Airlines Logo
13:55 - 17:48ORD-TPA
2h 53mdirect
£119United Airlines
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Sat, 24 Jan - Sat, 31 Jan
Southwest Logo
06:40 - 12:15MCO-ORD
6h 35m1 stop
Southwest Logo
13:45 - 20:50ORD-MCO
6h 05m1 stop
£119Southwest
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Sun, 15 Feb - Mon, 23 Feb
Delta Logo
14:31 - 21:05TPA-ORD
7h 34m1 stop
Delta Logo
08:00 - 14:47ORD-TPA
5h 47m1 stop
£149Delta
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Sat, 10 Jan - Sat, 17 Jan
Delta Logo
13:10 - 16:44MCO-ORD
4h 34m1 stop
Delta Logo
07:05 - 14:08ORD-MCO
6h 03m1 stop
£149Delta
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Tue, 6 Jan - Fri, 9 Jan

Southwest flights from Florida to Chicago

Our best Southwest deals on Florida to Chicago flight tickets
Southwest
8 Jan
MCO19:40Orlando
3h 10m
ORD21:50Chicago O'Hare Intl
11 Jan
ORD15:45Chicago O'Hare Intl
2h 45m
MCO19:30Orlando
£104
Find similar
Southwest
15 Feb
MCO06:40Orlando
6h 35m
1 stop
ORD12:15Chicago O'Hare Intl
23 Feb
ORD06:05Chicago O'Hare Intl
2h 40m
MCO09:45Orlando
£112
Find similar
Southwest
15 Feb
MCO06:40Orlando
6h 35m
1 stop
ORD12:15Chicago O'Hare Intl
23 Feb
ORD13:45Chicago O'Hare Intl
6h 05m
1 stop
MCO20:50Orlando
£119
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Spirit Airlines flights from Florida to Chicago

Our best Spirit Airlines deals on Florida to Chicago flight tickets
Spirit Airlines
31 Dec
MCO16:56Orlando
3h 06m
ORD19:02Chicago O'Hare Intl
7 Jan
ORD12:09Chicago O'Hare Intl
2h 52m
MCO16:01Orlando
£93
Find similar
Spirit Airlines
23 Nov
MCO21:00Orlando
3h 06m
ORD23:06Chicago O'Hare Intl
30 Nov
ORD06:48Chicago O'Hare Intl
2h 42m
MCO10:30Orlando
£122
Find similar
Spirit Airlines
31 Jan
TPA07:00Tampa
16h 37m
2 stops
ORD22:37Chicago O'Hare Intl
7 Feb
ORD10:07Chicago O'Hare Intl
2h 47m
TPA13:54Tampa
£124
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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 17 November 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

Wed 31/12

17:15-22:24

1 stop6h 09m

Chicago O'Hare Intl

Wed 7/1

07:20-11:12

Nonstop2h 52m

£83

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 31/12

16:56-19:02

Nonstop3h 06m

Chicago O'Hare Intl

Wed 7/1

12:09-16:01

Nonstop2h 52m

£93

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 31/12

17:05-22:45

1 stop6h 40m

Chicago O'Hare Intl

Wed 7/1

16:49-00:21

1 stop6h 32m

£96

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 13/1

15:00-17:08

Nonstop3h 08m

Chicago O'Hare Intl

Tue 13/1

19:45-23:44

Nonstop2h 59m

£100

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 8/1

19:40-21:50

Nonstop3h 10m

Chicago O'Hare Intl

Sun 11/1

15:45-19:30

Nonstop2h 45m

£104

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sun 15/2

06:40-12:15

1 stop6h 35m

Chicago O'Hare Intl

Mon 23/2

06:05-09:45

Nonstop2h 40m

£112

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 24/1

12:25-14:28

Nonstop3h 03m

Chicago O'Hare Intl

Sat 31/1

13:55-17:48

Nonstop2h 53m

£119

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sun 15/2

06:40-12:15

1 stop6h 35m

Chicago O'Hare Intl

Mon 23/2

13:45-20:50

1 stop6h 05m

£119

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 10/1

14:31-21:05

1 stop7h 34m

Chicago O'Hare Intl

Sat 17/1

08:00-14:47

1 stop5h 47m

£149

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 6/1

13:10-16:44

1 stop4h 34m

Chicago O'Hare Intl

Fri 9/1

07:05-14:08

1 stop6h 03m

£149

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 £113.

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 £163 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 £134 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 44m

Direct flights

Every day

Airports in Chicago

1 airport
The fastest flight from Florida to Chicago takes 2h 44m
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