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Cheap flights from Florida to Chicago from £82

MIA — CHI
18 Oct — 25 Oct1
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

Fri 16/1017:01 -
1 stop7h 29m
Mon 19/1007:00 -
1 stop8h 11m
Deal found 17/9£158
Wed 21/1006:00 -
2 stops14h 07m
Wed 28/1014:11 -
2 stops15h 50m
Deal found 16/9£158
Tue 6/1013:50 -
1 stop5h 51m
Wed 7/1007:20 -
Nonstop2h 52m
Deal found 17/9£159
Tue 27/1018:54 -
1 stop6h 03m
Tue 3/1114:42 -
1 stop6h 42m
Deal found 17/9£159
Sat 10/1018:25 -
1 stop6h 05m
Tue 20/1006:10 -
1 stop8h 31m
Deal found 17/9£159
Fri 9/1017:01 -
1 stop7h 29m
Sat 10/1007:00 -
1 stop8h 11m
Deal found 16/9£161
Sat 10/1018:25 -
1 stop6h 05m
Tue 13/1014:55 -
1 stop6h 19m
Deal found 17/9£161
Tue 27/1018:35 -
Nonstop3h 05m
Fri 30/1017:45 -
Nonstop2h 58m
Deal found 16/9£162
Fri 16/1012:19 -
Nonstop3h 03m
Mon 19/1013:55 -
Nonstop2h 48m
Deal found 16/9£163
Tue 6/1009:09 -
1 stop5h 38m
Wed 7/1015:00 -
1 stop5h 35m
Deal found 16/9£164
Thu 15/1017:01 -
1 stop7h 29m
Mon 19/1007:00 -
1 stop8h 11m
Deal found 14/9£165
Fri 23/1019:33 -
Nonstop3h 05m
Mon 26/1006:59 -
1 stop6h 13m
Deal found 14/9£168

Find flight deals from Florida to Chicago

Round-trip from

£158

One-way from

£82

Popular in

June

Cheapest in

February

Average price

£162

Good round-trip deal

£168 or less

Good one-way deal

£51 or less
JetBlue
  • JetBlue
  • 16/10-19/10
  • 2 total stops
  • 15h 40m total
  • Florida to Chicago
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JetBlue
  • JetBlue
  • 24/11-31/12
  • 1 total stop
  • 7h 02m total
  • Florida to Chicago
Search Deals
Highest demand for flights based on searches. 24% potential increase in price (£39 potential increase over avg. return price).
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Cheapest flight prices on average. 5% potential price decrease (£6 potential savings vs. average return price).
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Average for round-trip flights in September 2026
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Price to beat on a round-trip flight from Florida to Chicago (CHI).
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Price to beat on a one-way flight from Florida to Chicago (CHI).
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Cheapflights Fare Finder

 
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 Orlando - ORD Chicago O'Hare Intl

MCOORD

Orlando

Sat 10/10

18:25-23:30

1 stop6h 05m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£82

TampaChicago

TPA Tampa - ORD Chicago O'Hare Intl

TPAORD

Tampa

Mon 25/1

07:11-09:20

Nonstop3h 09m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£85

OrlandoChicago

MCO Orlando - ORD Chicago O'Hare Intl

MCOORD

Orlando

Tue 6/10

19:45-23:57

1 stop5h 12m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£90

OrlandoChicago

MCO Orlando - ORD Chicago O'Hare Intl

MCOORD

Orlando

Wed 17/2

09:15-13:20

1 stop5h 05m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£90

OrlandoChicago

MCO Orlando - ORD Chicago O'Hare Intl

MCOORD

Orlando

Sat 13/2

14:45-18:32

1 stop4h 47m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£90
Fastest return journey

JacksonvilleChicago

JAX Jacksonville - ORD Chicago O'Hare Intl

JAXORD

Jacksonville

Tue 20/10

09:40-11:26

Nonstop2h 46m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£92

JacksonvilleChicago

JAX Jacksonville - ORD Chicago O'Hare Intl

JAXORD

Jacksonville

Tue 27/10

07:30-09:19

Nonstop2h 49m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£92

JacksonvilleChicago

JAX Jacksonville - ORD Chicago O'Hare Intl

JAXORD

Jacksonville

Sat 24/10

07:00-13:50

1 stop7h 50m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£93

TampaChicago

TPA Tampa - ORD Chicago O'Hare Intl

TPAORD

Tampa

Sat 14/11

07:19-09:23

Nonstop3h 04m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£101

OrlandoChicago

MCO Orlando - ORD Chicago O'Hare Intl

MCOORD

Orlando

Mon 9/11

18:54-23:55

1 stop6h 01m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£105

Flights are sorted by cheapest return flights first.

Deals found on 16/9

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

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, February is the cheapest month in which you can book a flight from Florida to Chicago (average of £147). Flying from Florida to Chicago in June is currently the most expensive (average of £270). 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?

A simple way to save on the total cost of your ticket is to fly from Florida to Chicago in the evening. If you’re flexible enough to do this you can expect to save up to 58% on your trip compared to booking a flight in the afternoon.

Weekly flight availability from Florida to Chicago

The most flights from USFL to CHI are scheduled on a Tuesday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (43 on average).

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

The best time to book flights from Florida to Chicago is 47 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.

Related info for your journey

  • How long is the flight from Florida to Chicago?

    Airlines like United Airlines and JetBlue fly from Florida to Chicago in about 3h 05m. The time it takes to get you to your destination can typically vary by up to 2h 58m. The distance from Florida to Chicago is about 1013 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 Orlando - Chicago O'Hare Intl, Jacksonville - 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 (88%), Japan Airlines (86%), Austrian Airlines( 70%).

  • 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, February is the cheapest month in which you can book a flight from Florida to Chicago (average of £147). Flying from Florida to Chicago in June is currently the most expensive (average of £270). 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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Cheapflights makes it easy to find Florida to Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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.

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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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