Find flights
Deals
When to book
FAQs

Cheap flights from Florida to Chicago from £68

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 17/9. Fares are subject to change and may not be available on all flights or dates of travel.
MIA — CHI
20 Jul — 27 Jul1
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 20 June 2026.

Sat 15/807:40
MCO
-
ORD
Nonstop3h 05m
United Airlines
Sat 15/818:03
ORD
-
MCO
Nonstop2h 57m
United Airlines
Deal found 19/6£164
Sat 8/806:00
MCO
-
ORD
1 stop15h 52m
Frontier
Mon 10/817:13
ORD
-
MCO
Nonstop3h 12m
Frontier
Deal found 20/6£168
Sat 8/805:15
TPA
-
ORD
1 stop5h 25m
Delta
Mon 10/806:40
ORD
-
TPA
1 stop4h 49m
Delta
Deal found 19/6£171
Wed 22/720:59
MCO
-
ORD
Nonstop3h 11m
Frontier
Sat 25/717:13
ORD
-
MCO
Nonstop3h 12m
Frontier
Deal found 16/6£172
Tue 14/721:35
TPA
-
ORD
1 stop26h 52m
Frontier
Tue 28/713:50
ORD
-
TPA
1 stop6h 26m
Frontier
Deal found 17/6£174
Sat 5/907:30
TPA
-
ORD
Nonstop3h 03m
United Airlines
Tue 8/917:45
ORD
-
TPA
Nonstop2h 56m
United Airlines
Deal found 20/6£175
Wed 5/807:09
MCO
-
ORD
Nonstop3h 09m
United Airlines
Mon 10/807:20
ORD
-
MCO
Nonstop2h 55m
United Airlines
Deal found 19/6£175
Tue 18/807:30
JAX
-
ORD
Nonstop2h 48m
United Airlines
Tue 25/814:30
ORD
-
JAX
1 stop5h 24m
United Airlines
Deal found 19/6£177
Wed 8/713:45
MCO
-
ORD
1 stop7h 08m
Frontier
Wed 15/713:50
ORD
-
MCO
1 stop7h 25m
Frontier
Deal found 19/6£177
Tue 14/719:42
TPA
-
ORD
Nonstop3h 11m
United Airlines
Tue 21/708:40
ORD
-
TPA
1 stop5h 45m
United Airlines
Deal found 20/6£179
Sat 18/719:55
MCO
-
ORD
1 stop4h 58m
Delta
Sat 25/707:00
ORD
-
MCO
1 stop7h 40m
Delta
Deal found 20/6£179
Tue 14/717:25
TPA
-
ORD
1 stop8h 20m
United Airlines
Wed 22/714:30
ORD
-
TPA
Nonstop2h 54m
United Airlines
Deal found 20/6£183

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 20 June 2026.

Round-trip from

£164

One-way from

£68

Popular in

June

Cheapest in

September

Average price

£240

Good round-trip deal

£338 or less

Good one-way deal

£65 or less
United Airlines
  • United Airlines
  • 15/8-15/8
  • Nonstop
  • 6h 02m total
  • Florida to Chicago
Search Deals
Frontier
  • Frontier
  • 17/9
  • Nonstop
  • 3h 08m total
  • Florida to Chicago
Search Deals
Highest demand for flights based on searches. 24% potential increase in price (£33 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (£7 potential savings vs. average return price).
Search Deals
Average for round-trip flights in June 2026
Search Deals
Price to beat on a round-trip flight from Florida to Chicago (CHI).
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 20 June 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 18/7

19:55-23:53

1 stop4h 58m

Chicago O'Hare Intl

Sat 25/7

07:00-15:40

1 stop7h 40m

£179

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 1/8

19:55-23:53

1 stop4h 58m

Chicago O'Hare Intl

Tue 4/8

06:40-12:00

1 stop4h 20m

£179

TampaChicago

TPA - ORD

TPAORD

Tampa

Tue 14/7

17:25-00:45

1 stop8h 20m

Chicago O'Hare Intl

Wed 22/7

14:30-18:24

Nonstop2h 54m

£183

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 15/7

10:52-13:02

Nonstop3h 10m

Chicago O'Hare Intl

Wed 22/7

18:12-01:01

1 stop5h 49m

£186

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 8/8

05:30-09:40

1 stop5h 10m

Chicago O'Hare Intl

Mon 10/8

18:25-01:04

1 stop5h 39m

£190

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 24/10

06:15-12:06

1 stop6h 51m

Chicago O'Hare Intl

Mon 26/10

09:30-15:09

1 stop4h 39m

£190

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 5/8

15:40-20:55

1 stop6h 15m

Chicago O'Hare Intl

Mon 10/8

18:25-00:04

1 stop4h 39m

£190

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 16/9

08:10-14:47

1 stop7h 37m

Chicago O'Hare Intl

Mon 21/9

17:45-21:41

Nonstop2h 56m

£195

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 8/9

11:59-16:14

1 stop5h 15m

Chicago O'Hare Intl

Thu 10/9

06:40-11:57

1 stop4h 17m

£201

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Thu 6/8

12:02-18:29

1 stop7h 27m

Chicago O'Hare Intl

Tue 11/8

08:48-17:25

1 stop7h 37m

£201

Flights are sorted by cheapest return flights first.

Deals found on 20/6

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
6

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 £138). Flying from Florida to Chicago in June is currently the most expensive (average of £261). 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 20 June 2026.

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 51% 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 20 June 2026.

The most flights from USFL to CHI are scheduled on a Friday (57 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (38 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

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 Delta and United Airlines fly from Florida to Chicago in about 2h 53m. The time it takes to get you to your destination can typically vary by up to 1h 43m. The distance from Florida to Chicago is about 865 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 Tampa - Chicago O'Hare Intl, Jacksonville - 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 (89%), Frontier (88%), Volaris( 88%).

  • What are the cheapest flights from Florida to Chicago?

    The cheapest flight price from Florida to Chicago is £332. On average you can expect to pay £411. The most popular route, (Tampa - Chicago O'Hare Intl), can usually be booked for £161.

  • 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 £138). Flying from Florida to Chicago in June is currently the most expensive (average of £261). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Florida to Chicago?

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.

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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.