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Cheap flights from Florida to Chicago from £63

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 3/6. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — CHI
5 Jun — 12 Jun1
1 adult
1 adult, Economy, 0 bags

Cheap 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 6 May 2026.

Wed 17/619:42
TPA
-
ORD
Nonstop3h 11m
United Airlines
Wed 16/910:45
ORD
-
TPA
Nonstop2h 55m
United Airlines
Deal found 2/5£125
Wed 27/507:35
MCO
-
ORD
Nonstop3h 10m
Southwest
Tue 2/619:35
ORD
-
MCO
Nonstop2h 45m
Southwest
Deal found 1/5£125
Tue 16/607:52
MCO
-
ORD
Nonstop3h 08m
American Airlines
Tue 23/618:45
ORD
-
MCO
Nonstop2h 51m
American Airlines
Deal found 2/5£126
Tue 7/719:42
TPA
-
ORD
Nonstop3h 11m
United Airlines
Tue 14/708:40
ORD
-
TPA
1 stop5h 45m
United Airlines
Deal found 4/5£129
Wed 27/515:05
MCO
-
ORD
1 stop6h 16m
United Airlines
Wed 3/606:02
ORD
-
MCO
Nonstop2h 43m
United Airlines
Deal found 5/5£129
Wed 27/506:20
TPA
-
ORD
1 stop7h 30m
Southwest
Wed 3/614:00
ORD
-
TPA
Nonstop2h 50m
Southwest
Deal found 5/5£132
Wed 27/508:30
MCO
-
ORD
1 stop5h 20m
Southwest
Wed 3/613:35
ORD
-
MCO
Nonstop2h 50m
Southwest
Deal found 5/5£132
Wed 19/809:00
TPA
-
ORD
1 stop6h 36m
United Airlines
Tue 25/808:40
ORD
-
TPA
1 stop5h 30m
United Airlines
Deal found 6/5£133
Tue 2/610:51
MCO
-
ORD
Nonstop3h 09m
United Airlines
Thu 4/606:02
ORD
-
MCO
Nonstop2h 43m
United Airlines
Deal found 5/5£136
Wed 3/609:40
MCO
-
ORD
Nonstop3h 08m
United Airlines
Wed 10/607:25
ORD
-
MCO
1 stop6h 22m
United Airlines
Deal found 2/5£139
Sat 15/809:55
TPA
-
ORD
Nonstop3h 01m
United Airlines
Wed 19/808:40
ORD
-
TPA
1 stop5h 30m
United Airlines
Deal found 5/5£140
Wed 27/515:05
MCO
-
ORD
1 stop6h 16m
United Airlines
Sat 30/507:20
ORD
-
MCO
Nonstop2h 55m
United Airlines
Deal found 6/5£140

Find flight deals from Florida to Chicago

Keep the following information in mind while searching for Florida to Chicago flight deals. Data was last updated 6 May 2026.

Round-trip from

£125

One-way from

£63

Popular in

March

Cheapest in

September

Average price

£120

Good one-way deal

£63 or less
United Airlines
  • United Airlines
  • 17/6-16/9
  • Nonstop
  • 6h 06m total
  • Florida to Chicago
Search Deals
United Airlines
  • United Airlines
  • 24/6
  • Nonstop
  • 3h 13m total
  • Florida to Chicago
Search Deals
Highest demand for flights based on searches. 12% potential increase in price (£14 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease (£4 potential savings vs. average return price).
Search Deals
Average for round-trip flights in May 2026
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 6 May 2026.
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

Cheapest return flight

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 30/5

07:00-09:10

Nonstop3h 10m

Chicago O'Hare Intl

Tue 2/6

14:40-20:30

1 stop4h 50m

£143

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 17/6

06:20-12:36

1 stop7h 16m

Chicago O'Hare Intl

Wed 24/6

15:22-21:30

1 stop5h 08m

£145

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 17/6

05:30-10:13

1 stop5h 43m

Chicago O'Hare Intl

Wed 24/6

09:48-16:37

1 stop5h 49m

£145

TampaChicago

TPA - ORD

TPAORD

Tampa

Mon 25/5

06:33-10:16

1 stop4h 43m

Chicago O'Hare Intl

Wed 27/5

09:49-15:32

1 stop4h 43m

£154

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 23/5

13:45-18:41

1 stop5h 56m

Chicago O'Hare Intl

Wed 27/5

18:06-00:31

1 stop5h 25m

£154

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 11/8

09:05-14:05

1 stop6h 00m

Chicago O'Hare Intl

Sat 15/8

13:48-19:48

1 stop5h 00m

£154

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 3/6

06:15-13:01

1 stop7h 46m

Chicago O'Hare Intl

Thu 4/6

18:06-00:55

1 stop5h 49m

£154

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 30/5

07:15-15:30

2 stops9h 15m

Chicago O'Hare Intl

Tue 2/6

14:40-20:30

1 stop4h 50m

£154

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 29/5

15:05-20:21

1 stop6h 16m

Chicago O'Hare Intl

Sat 30/5

12:50-16:48

Nonstop2h 58m

£158

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 19/8

11:45-18:06

1 stop7h 21m

Chicago O'Hare Intl

Wed 26/8

16:20-20:15

Nonstop2h 55m

£159

Flights are sorted by cheapest return flights first.

Deals found on 4/5

Showing 1-10 of 60 resultsSorted by cheapest first
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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

How far ahead should I book a flight from Florida to Chicago?

The best time to book flights from Florida to Chicago is 23 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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 £135). Flying from Florida to Chicago in March is currently the most expensive (average of £227). 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 6 May 2026.

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 56% on your trip compared to booking a flight at midday.

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 6 May 2026.

The most flights from USFL to CHI are scheduled on a Wednesday (55 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (38 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 Delta fly from Florida to Chicago in about 3h 10m. The time it takes to get you to your destination can typically vary by up to 4h 06m. The distance from Florida to Chicago is about 1006 mi. This flight may include one or multiple stops.

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

    The cheapest airline one-way is American Airlines, with whom users have recently found tickets for as low as £34. However, be on the lookout for offers from Allegiant Air and Spirit Airlines, 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 Tampa - Chicago O'Hare Intl, Orlando - Chicago O'Hare Intl and Jacksonville - 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: Emirates (92%), Cathay Pacific (90%), United Airlines( 82%).

  • What are the cheapest flights from Florida to Chicago?

    The cheapest flight price from Florida to Chicago is £65. On average you can expect to pay £94. The most popular route, (Tampa - Chicago O'Hare Intl), can usually be booked for £224.

  • 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 £135). Flying from Florida to Chicago in March is currently the most expensive (average of £227). 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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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.

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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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