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£52 Find cheap flights from Florida to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 3/7. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
0 bags
Sat 1/6
Sat 8/6

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Good to know - Cheap tickets from Florida to Chicago

Low season

January

High season

June

Cheapest flight

£52
Best time to beat the crowds (0% less expensive on average)
Most popular time to fly (18% more expensive on average)
Flight from Orlando to Chicago

FAQs for booking flights from Florida to Chicago

  • How does KAYAK find such low prices on flights from Florida to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Florida to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Florida to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Florida is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Florida to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional return ticket. You could then fly to Chicago with an airline and back to Florida with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Florida to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Florida up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Prefer to fly direct from Florida to Chicago?

Find which airlines fly direct from Florida to Chicago, which days they fly and book direct flights.

Direct departures

Florida to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

See more direct flights

Direct returns

Chicago to Florida

Monday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

Wednesday

ANA, Aer Lingus, Aeromexico, +79 more

ANA, Aer Lingus, +80 more

Thursday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

Saturday

ANA, Aer Lingus, Aeromexico, +78 more

ANA, Aer Lingus, +79 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +78 more

ANA, Aer Lingus, +79 more

See more direct flights
See more direct flights

Book cheap flights from Florida to Chicago

Cheapest flights to Chicago from Florida found in 2024

Recent return flight deals

14/5Tue
1 stopSpirit Airlines
15h 40mTPA-ORD
15/5Wed
1 stopSpirit Airlines
13h 40mORD-TPA
£78
14/5Tue
directSpirit Airlines
2h 57mTPA-ORD
15/5Wed
directSpirit Airlines
2h 39mORD-TPA
£113
27/9Fri
directFrontier
3h 00mMCO-ORD
1/10Tue
directFrontier
2h 58mORD-MCO
£120
27/9Fri
directFrontier
3h 00mMCO-ORD
1/10Tue
1 stopFrontier
8h 40mORD-MCO
£135
9/7Tue
1 stopDelta
6h 04mTPA-ORD
10/7Wed
1 stopDelta
5h 28mORD-TPA
£166
6/8Tue
1 stopDelta
5h 17mMCO-ORD
13/8Tue
1 stopDelta
7h 06mORD-MCO
£166
16/7Tue
1 stopSun Country Air
29h 04mMCO-ORD
18/7Thu
2 stopsSun Country Air
29h 48mORD-MCO
£174
3/7Wed
1 stopSun Country Air
23h 25mMCO-ORD
8/7Mon
1 stopSun Country Air
9h 52mORD-MCO
£178
14/5Tue
1 stopSouthwest
12h 30mTPA-ORD
16/5Thu
1 stopSouthwest
11h 40mORD-TPA
£233
15/5Wed
1 stopSouthwest
12h 30mTPA-ORD
17/5Fri
directSouthwest
2h 40mORD-TPA
£236

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Recent one-way flight deals

3/7Wed
directFrontier
3h 09mMCO-ORD
£52
12/5Sun
directFrontier
3h 07mMCO-ORD
£67
3/7Wed
directAmerican Airlines
3h 05mMCO-ORD
£72
9/6Sun
1 stopSun Country Air
24h 46mMCO-ORD
£76
1/6Sat
1 stopDelta
5h 58mTPA-ORD
£82
4/6Tue
1 stopDelta
5h 14mMCO-ORD
£82
9/6Sun
1 stopSun Country Air
24h 46mMCO-ORD
£84
13/6Thu
directSouthwest
2h 55mTPA-ORD
£88
13/6Thu
1 stopSouthwest
6h 40mTPA-ORD
£95
3/7Wed
1 stopAmerican Airlines
6h 09mMCO-ORD
£106

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Search by price

Last minute flights from Florida to Chicago

Last minute flight, train and bus deals

5/5Sun
multi-stop
6h 32mTPA-ORD
7/5Tue
direct
2h 46mORD-TPA
£276
5/5Sun
multi-stopFrontier
6h 32mTPA-ORD
7/5Tue
multi-stopFrontier
9h 37mORD-TPA
£283
6/5Mon
multi-stopDelta
5h 19mTPA-ORD
10/5Fri
multi-stopDelta
7h 01mORD-TPA
£315
5/5Sun
directSpirit Airlines
2h 55mTPA-ORD
7/5Tue
directSpirit Airlines
2h 46mORD-TPA
£331
6/5Mon
multi-stopSouthwest
6h 50mTPA-ORD
10/5Fri
directSouthwest
2h 40mORD-TPA
£332
6/5Mon
directSouthwest
2h 55mTPA-ORD
10/5Fri
directSouthwest
2h 40mORD-TPA
£352
6/5Mon
multi-stopUnited Airlines
5h 31mTPA-ORD
10/5Fri
multi-stopUnited Airlines
15h 47mORD-TPA
£421
6/5Mon
multi-stopAmerican Airlines
8h 57mTPA-ORD
10/5Fri
multi-stopAmerican Airlines
6h 53mORD-TPA
£535
3/5Fri
multi-stopDelta
5h 40mJAX-ORD
6/5Mon
multi-stopDelta
3h 47mORD-JAX
£591
2/5Thu
directUnited Airlines
2h 43mJAX-ORD
7/5Tue
multi-stopUnited Airlines
11h 59mORD-JAX
£749

Search by stops

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Flights to Chicago, Illinois

Return flight deals:

Chicago - Florida

Cabin classes:

£1,078
£1,457
£108

Browse origins:

  • Flights » 
  • Florida

Browse destinations:

  • Flights » 
  • Chicago