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Cheap flights from Florida to Chicago from £49

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/3. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — CHI
30 Nov — 7 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Florida to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Florida to Chicago
Explore the most affordable flight options available from Florida to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 31 October 2025.

Thu 20/1121:00MCO - ORD
Nonstop3h 06mSpirit Airlines
Fri 21/1106:48ORD - MCO
Nonstop2h 42mSpirit Airlines
Deal found 29/10£104
Thu 27/1121:00MCO - ORD
Nonstop3h 06mSpirit Airlines
Sun 30/1121:22ORD - MCO
1 stop11h 52mSpirit Airlines
Deal found 30/10£110
Tue 9/1210:30MCO - ORD
Nonstop3h 03mUnited Airlines
Tue 9/1214:10ORD - MCO
Nonstop2h 51mUnited Airlines
Deal found 29/10£115
Thu 4/1209:50TPA - ORD
Nonstop2h 59mUnited Airlines
Thu 11/1218:05ORD - TPA
Nonstop2h 52mUnited Airlines
Deal found 29/10£119
Thu 4/1207:30TPA - ORD
Nonstop2h 59mUnited Airlines
Sun 7/1207:30ORD - TPA
Nonstop2h 50mUnited Airlines
Deal found 28/10£120
Fri 12/1212:45TPA - ORD
Nonstop3h 00mSouthwest
Sun 14/1211:55ORD - TPA
Nonstop2h 40mSouthwest
Deal found 30/10£121
Thu 4/1209:25MCO - ORD
Nonstop3h 04mUnited Airlines
Sun 7/1216:05ORD - MCO
Nonstop2h 51mUnited Airlines
Deal found 29/10£121
Tue 9/1207:05TPA - ORD
1 stop6h 55mSouthwest
Tue 16/1211:55ORD - TPA
Nonstop2h 40mSouthwest
Deal found 30/10£127
Wed 19/1109:40MCO - ORD
Nonstop3h 04mUnited Airlines
Wed 19/1116:10ORD - MCO
Nonstop2h 51mUnited Airlines
Deal found 29/10£136
Thu 11/1211:10TPA - ORD
1 stop5h 10mDelta
Mon 19/110:35ORD - TPA
1 stop7h 00mDelta
Deal found 29/10£150
Wed 19/1106:50MCO - ORD
1 stop6h 25mSouthwest
Wed 19/1115:45ORD - MCO
Nonstop2h 40mSouthwest
Deal found 29/10£150
Wed 19/1118:04TPA - ORD
1 stop5h 26mDelta
Thu 27/1113:14ORD - TPA
1 stop7h 09mDelta
Deal found 29/10£158

Cheap flight deals from Florida to Chicago

Keep the following information in mind while searching for Florida to Chicago flight deals. Data was last updated 31 October 2025.

Round-trip from

£104

One-way from

£49

Popular in

June

Cheapest in

September

Average price

£136

Good one-way deal

£28 or less
Spirit Airlines
  • Spirit Airlines
  • 20/11-21/11
  • Nonstop
  • 5h 48m total
  • Florida to Chicago
Search Deals
Frontier
  • Frontier
  • 4/3
  • Nonstop
  • 3h 19m total
  • Florida to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (£8 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease (£3 potential savings vs. average return price).
Search Deals
Average for round-trip flights in October 2025
Search Deals
Price to beat on a one-way flight from Florida to Chicago (CHI).
Search Deals

Cheapflights 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, Cheapflights users made 858,174 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

Florida

Fly to

Chicago

Route

Depart

Return

Price

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 13/1

06:05-13:00

1 stop7h 55m

Chicago O'Hare Intl

Sat 17/1

13:45-20:05

1 stop5h 20m

£119

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

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 19/11

09:40-11:44

Nonstop3h 04m

Chicago O'Hare Intl

Wed 19/11

16:10-20:01

Nonstop2h 51m

£136

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 19/12

06:00-16:00

1 stop11h 00m

Chicago O'Hare Intl

Sun 4/1

12:09-16:01

Nonstop2h 52m

£150

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 19/11

18:04-22:30

1 stop5h 26m

Chicago O'Hare Intl

Thu 27/11

13:14-21:23

1 stop7h 09m

£158

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 28/2

11:37-13:38

Nonstop3h 01m

Chicago O'Hare Intl

Tue 3/3

05:05-13:27

1 stop7h 22m

£168

TampaChicago

TPA - ORD

TPAORD

Tampa

Mon 16/2

14:35-23:10

1 stop9h 35m

Chicago O'Hare Intl

Fri 20/2

06:04-15:11

1 stop8h 07m

£169

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 8/4

07:55-17:31

1 stop10h 36m

Chicago O'Hare Intl

Mon 13/4

11:30-23:07

1 stop10h 37m

£172

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 19/12

13:37-22:04

1 stop9h 27m

Chicago O'Hare Intl

Sun 28/12

06:45-15:03

1 stop7h 18m

£172

Flights are sorted by cheapest return flights first.

Deals found on 30/10

Showing 1-10 of 60 results
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Best time to book a flight from Florida to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Florida with our price prediction graph.
Estimated return price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Florida to Chicago

What is the cheapest month to book a flight from Florida to Chicago?

Currently, January is the cheapest month in which you can book a flight from Florida to Chicago (average of £24). Flying from Florida to Chicago in June is currently the most expensive (average of £81). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from FL to CHI?

Find hourly flight availability from Florida to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 31 October 2025.

A simple way to save on the total cost of your ticket is to fly from Florida to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 55% on your trip compared to booking a flight at midday.

Related info for your journey

Find useful and relevant information for your journey from Florida to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Florida to Chicago?

    Airlines like United Airlines, Southwest, and Delta fly from Florida to Chicago in about 3h 03m. The time it takes to get you to your destination can typically vary by up to 4h 52m. The distance from Florida to Chicago is about 1006 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Florida to Chicago?

    The most popular flight routes from Florida to Chicago are Jacksonville - Chicago O'Hare Intl, Tampa - Chicago O'Hare Intl and Orlando - Chicago O'Hare Intl.

  • What are the most reliable airlines from Florida to Chicago?

    Before booking your flight to Chicago from Florida, check out the most reliable airlines to get you to your destination on time: Cathay Pacific (94%), Austrian Airlines (92%), Spirit Airlines( 91%).

  • What are the cheapest flights from Florida to Chicago?

    The cheapest flight price from Florida to Chicago is £782. On average you can expect to pay £782. The most popular route, (Jacksonville - Chicago O'Hare Intl), can usually be booked for £189.

  • Can I find deals for flights from Florida to Chicago that include hotel bookings?

    Yes. In addition to deals on Florida to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Florida to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Florida to Chicago.

  • Can I find deals for business class flights from Florida to Chicago?

    Yes. Cheapflights offers flight deals from Florida to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Florida to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Florida to Chicago (average of £24). Flying from Florida to Chicago in June is currently the most expensive (average of £81). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Why should you use Cheapflights to find cheap flight tickets from Florida to Chicago?

Millions of users choose and trust Cheapflights to book the best flight deals from Florida to Chicago for free. We help you search and compare prices from hundreds of airlines for the right flight just for you.

Can Cheapflights find flights from Florida to Chicago with no change fees?

Need flexible booking options for your flight to Chicago from Florida? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Florida to Chicago become cheaper?

Not ready to book yet? You can track prices for flights from Florida to Chicago on Cheapflights with our Price Alert feature and get notified when better prices are available.

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