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Cheap flights from Florida to Chicago from £37

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 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — CHI
16 Oct — 23 Oct1
1 adult
1 adult, Economy

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 16 September 2025.

Round-trip from

£74

One-way from

£37

Popular in

March

Cheapest in

September

Average price

£109

Good one-way deal

£100 or less
Spirit Airlines
  • Spirit Airlines
  • 14/10-21/10
  • Nonstop
  • 5h 44m total
  • Florida to Chicago
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Spirit Airlines
  • Spirit Airlines
  • 11/2
  • Nonstop
  • 3h 08m total
  • Florida to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (£5 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (£3 potential savings vs. average return price).
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Average for round-trip flights in September 2025
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Price to beat on a one-way flight from Florida to Chicago (CHI).
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Find flight deals from Florida to Chicago

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 16 September 2025.

Tue 14/1015:53MCO - ORD
Nonstop3h 00mSpirit Airlines
Tue 21/1006:00ORD - MCO
Nonstop2h 44mSpirit Airlines
Deal found 14/9£74
Wed 29/1014:26MCO - ORD
Nonstop2h 57mSpirit Airlines
Wed 5/1106:05ORD - MCO
Nonstop2h 43mSpirit Airlines
Deal found 14/9£74
Wed 29/1020:59MCO - ORD
1 stop28h 44mMultiple Airlines
Wed 5/1106:05ORD - MCO
Nonstop2h 43mMultiple Airlines
Deal found 14/9£94
Wed 29/1015:05MCO - ORD
1 stop27h 07mFrontier
Wed 5/1107:20ORD - MCO
1 stop21h 24mFrontier
Deal found 14/9£106
Sat 8/1112:45TPA - ORD
Nonstop3h 00mSouthwest
Tue 11/1111:55ORD - TPA
Nonstop2h 40mSouthwest
Deal found 14/9£108
Wed 12/1112:45TPA - ORD
Nonstop3h 00mSouthwest
Sun 16/1111:55ORD - TPA
Nonstop2h 40mSouthwest
Deal found 13/9£109
Sat 8/1107:40TPA - ORD
Nonstop2h 59mUnited Airlines
Tue 11/1109:15ORD - TPA
1 stop8h 17mUnited Airlines
Deal found 14/9£113
Sat 22/1109:30TPA - ORD
Nonstop2h 55mSouthwest
Mon 24/1111:55ORD - TPA
Nonstop2h 40mSouthwest
Deal found 15/9£116
Tue 14/1018:18MCO - ORD
Nonstop3h 05mUnited Airlines
Tue 21/1014:15ORD - MCO
Nonstop2h 51mUnited Airlines
Deal found 14/9£116
Sat 8/1107:40TPA - ORD
Nonstop2h 59mUnited Airlines
Sun 9/1107:30ORD - TPA
Nonstop2h 50mUnited Airlines
Deal found 15/9£116
Thu 16/1007:15MCO - ORD
Nonstop3h 06mUnited Airlines
Sun 19/1007:13ORD - MCO
Nonstop2h 54mUnited Airlines
Deal found 15/9£117
Tue 14/1008:00TPA - ORD
1 stop5h 45mSouthwest
Tue 21/1013:30ORD - TPA
2 stops7h 50mSouthwest
Deal found 14/9£119

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 16 September 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 14/10

15:53-17:53

Nonstop3h 00m

Chicago O'Hare Intl

Tue 21/10

06:00-09:44

Nonstop2h 44m

£74

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 19/11

12:45-14:45

Nonstop3h 00m

Chicago O'Hare Intl

Sat 22/11

17:15-23:40

1 stop5h 25m

£116

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 16/10

09:45-11:50

Nonstop3h 05m

Chicago O'Hare Intl

Mon 20/10

06:00-09:35

Nonstop2h 35m

£117

TampaChicago

TPA - ORD

TPAORD

Tampa

Mon 13/10

07:54-09:55

Nonstop3h 01m

Chicago O'Hare Intl

Mon 20/10

07:30-11:20

Nonstop2h 50m

£124

TampaChicago

TPA - ORD

TPAORD

Tampa

Mon 24/11

07:30-09:29

Nonstop2h 59m

Chicago O'Hare Intl

Fri 28/11

15:37-19:29

Nonstop2h 52m

£132

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 5/11

12:30-14:29

Nonstop2h 59m

Chicago O'Hare Intl

Sat 8/11

08:50-17:46

1 stop7h 56m

£132

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 9/10

15:50-17:55

Nonstop3h 05m

Chicago O'Hare Intl

Tue 14/10

06:00-09:35

Nonstop2h 35m

£132

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 8/10

11:00-13:05

Nonstop3h 05m

Chicago O'Hare Intl

Sat 11/10

15:10-18:50

Nonstop2h 40m

£132

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 28/2

11:37-13:38

Nonstop3h 01m

Chicago O'Hare Intl

Tue 3/3

07:00-10:42

Nonstop2h 42m

£138

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 10/1

13:36-19:44

1 stop7h 08m

Chicago O'Hare Intl

Sat 17/1

08:00-15:46

1 stop6h 46m

£145

Flights are sorted by cheapest return flights first.

Deals found on 14/9

Showing 1-10 of 59 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 £595). Flying from Florida to Chicago in July is currently the most expensive (average of £843). 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 16 September 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Florida to Chicago as you normally would.

Weekly flight availability from Florida to Chicago

Explore weekly flight availability from Florida to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 16 September 2025.

The most flights from USFL to CHI are scheduled on a Monday (45 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (31 on average).

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 Southwest, United Airlines, and Spirit Airlines fly from Florida to Chicago in about 3h. The time it takes to get you to your destination is usually consistent. The distance from Florida to Chicago is about 1013 mi. All flights are typically direct.

  • What are the cheapest airlines to fly from Florida to Chicago one-way?

    The cheapest airline one-way is Spirit Airlines, with whom users have recently found tickets for as low as £37. However, be on the lookout for offers from United Airlines and Southwest, as they are both options that can get you from Florida to Chicago for a low price.

  • 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, Orlando - Chicago O'Hare Intl and Tampa - 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 (83%), Austrian Airlines (79%), Japan Airlines( 75%).

  • What are the cheapest flights from Florida to Chicago?

    The cheapest flight price from Florida to Chicago is £128. On average you can expect to pay £565. The most popular route, (Jacksonville - Chicago O'Hare Intl), can usually be booked for £213.

  • 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 £595). Flying from Florida to Chicago in July is currently the most expensive (average of £843). 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.

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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.

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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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