Cheap flights from Florida to Chicago from £37

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Florida to Chicago departing on 24/1. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags
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Cheap return flights

Spirit Airlines Logo
15:53 - 17:53MCO-ORD
3h 00mdirect
Spirit Airlines Logo
06:00 - 09:44ORD-MCO
2h 44mdirect
£73Spirit Airlines
Find Deal
Tue, 14 Oct - Tue, 21 Oct
United Airlines Logo
09:30 - 11:29TPA-ORD
2h 59mdirect
United Airlines Logo
07:30 - 11:20ORD-TPA
2h 50mdirect
£108United Airlines
Find Deal
Sat, 8 Nov - Tue, 11 Nov
Southwest Logo
10:20 - 12:15TPA-ORD
2h 55mdirect
Southwest Logo
13:45 - 21:30ORD-TPA
6h 45m1 stop
£115Southwest
Find Deal
Thu, 27 Nov - Tue, 2 Dec
Southwest Logo
06:30 - 15:20TPA-ORD
9h 50m2 stops
Southwest Logo
12:40 - 22:25ORD-TPA
8h 45m1 stop
£119Southwest
Find Deal
Wed, 15 Oct - Wed, 22 Oct
Delta Logo
07:00 - 12:04TPA-ORD
6h 04m1 stop
Delta Logo
11:15 - 17:00ORD-TPA
4h 45m1 stop
£144Delta
Find Deal
Thu, 27 Nov - Wed, 3 Dec
Delta Logo
09:00 - 12:16MCO-ORD
4h 16m1 stop
Delta Logo
10:30 - 18:40ORD-MCO
7h 10m1 stop
£144Delta
Find Deal
Wed, 22 Oct - Mon, 27 Oct
JetBlue Logo
12:47 - 18:55JAX-ORD
7h 08m1 stop
JetBlue Logo
10:08 - 17:59ORD-JAX
6h 51m1 stop
£164JetBlue
Find Deal
Wed, 1 Oct - Tue, 7 Oct
JetBlue Logo
06:35 - 12:10JAX-ORD
6h 35m1 stop
JetBlue Logo
10:08 - 17:59ORD-JAX
6h 51m1 stop
£178JetBlue
Find Deal
Tue, 30 Sep - Tue, 7 Oct
Sun Country Air Logo
11:43 - 10:03TPA-ORD
23h 20m1 stop
Sun Country Air Logo
20:22 - 10:56ORD-TPA
13h 34m1 stop
£192Sun Country Air
Find Deal
Thu, 27 Nov - Mon, 1 Dec
Sun Country Air Logo
13:54 - 08:20MCO-ORD
19h 26m1 stop
Sun Country Air Logo
20:22 - 15:54ORD-MCO
18h 32m1 stop
£212Sun Country Air
Find Deal
Wed, 26 Nov - Mon, 1 Dec

United Airlines flights from Florida to Chicago

Our best United Airlines deals on Florida to Chicago flight tickets
United Airlines
8 Nov
TPA09:30Tampa
2h 59m
ORD11:29Chicago O'Hare Intl
11 Nov
ORD07:30Chicago O'Hare Intl
2h 50m
TPA11:20Tampa
United Airlines
7 Nov
TPA16:20Tampa
3h 00m
ORD18:20Chicago O'Hare Intl
11 Nov
ORD07:30Chicago O'Hare Intl
2h 50m
TPA11:20Tampa
United Airlines
8 Nov
TPA09:30Tampa
2h 59m
ORD11:29Chicago O'Hare Intl
11 Nov
ORD09:15Chicago O'Hare Intl
8h 17m
1 stop
TPA18:32Tampa

JetBlue flights from Florida to Chicago

Our best JetBlue deals on Florida to Chicago flight tickets
JetBlue
1 Oct
JAX12:47Jacksonville
7h 08m
1 stop
ORD18:55Chicago O'Hare Intl
7 Oct
ORD10:08Chicago O'Hare Intl
6h 51m
1 stop
JAX17:59Jacksonville
JetBlue
30 Sept
JAX06:35Jacksonville
6h 35m
1 stop
ORD12:10Chicago O'Hare Intl
7 Oct
ORD10:08Chicago O'Hare Intl
6h 51m
1 stop
JAX17:59Jacksonville
JetBlue
4 Oct
JAX11:25Jacksonville
7h 58m
1 stop
ORD18:23Chicago O'Hare Intl
7 Oct
ORD10:08Chicago O'Hare Intl
6h 51m
1 stop
JAX17:59Jacksonville

momondo 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, momondo users made 279,928 searches. Data last updated 17 September 2025.
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

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

£73

TampaChicago

TPA - ORD

TPAORD

Tampa

Sat 8/11

09:30-11:29

Nonstop2h 59m

Chicago O'Hare Intl

Tue 11/11

07:30-11:20

Nonstop2h 50m

£108

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 27/11

10:20-12:15

Nonstop2h 55m

Chicago O'Hare Intl

Tue 2/12

13:45-21:30

1 stop6h 45m

£115

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 15/10

06:30-15:20

2 stops9h 50m

Chicago O'Hare Intl

Wed 22/10

12:40-22:25

1 stop8h 45m

£119

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 27/11

07:00-12:04

1 stop6h 04m

Chicago O'Hare Intl

Wed 3/12

11:15-17:00

1 stop4h 45m

£144

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 22/10

09:00-12:16

1 stop4h 16m

Chicago O'Hare Intl

Mon 27/10

10:30-18:40

1 stop7h 10m

£144

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Wed 1/10

12:47-18:55

1 stop7h 08m

Chicago O'Hare Intl

Tue 7/10

10:08-17:59

1 stop6h 51m

£164

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 30/9

06:35-12:10

1 stop6h 35m

Chicago O'Hare Intl

Tue 7/10

10:08-17:59

1 stop6h 51m

£178

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 27/11

11:43-10:03

1 stop23h 20m

Chicago O'Hare Intl

Mon 1/12

20:22-10:56

1 stop13h 34m

£192

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 26/11

13:54-08:20

1 stop19h 26m

Chicago O'Hare Intl

Mon 1/12

20:22-15:54

1 stop18h 32m

£212

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Florida to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The cheapest month to fly to Chicago from Florida is in September. Flight prices, which tend to average around £109, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from Florida during August instead. Flights to Chicago in August, while not as cheap as those in September, still average around £117.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Wednesday when prices can be found for as low as £111. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Friday, with ticket prices averaging around £485.

What is the cheapest time of day to depart on your flight to Chicago?

Flying to Chicago from Florida in the evening is the least expensive time of day to depart. momondo users have found prices as low as £279 when looking at flights departing in the evening. Flights at midday are often more expensive, with an average ticket price of £492.

What is the cheapest Florida to Chicago flight route?

Fly from Palm Beach Intl to Chicago O'Hare Intl for the best Florida - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Florida when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around £161 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Florida for as low as £129 on momondo.

What cabin class options are available on Florida to Chicago flights?

There are 4 cabin classes available to choose from on Florida to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Florida to Chicago flights?

No. A direct flight is the cheapest option for a flight between Florida to Chicago.

Cheap Florida to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Florida to Chicago

Fastest flight time

2h 34m

Direct flights

Every day

Airports in Chicago

1 airport
The fastest flight from Florida to Chicago takes 2h 34m
Direct flights go from Florida to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)
  • When did momondo last update prices for flights from Florida to Chicago?

    Prices for flights from Florida to Chicago were last updated today.

  • How old do you have to be to fly from Florida to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Florida to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Florida to Chicago?

Why use momondo?

Why should I use momondo to find a flight deal from Florida to Chicago?

It is quick and easy to find Florida to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Florida to Chicago with flexible booking policies on momondo?

Flights from Florida to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Florida to Chicago?

momondo helps you find the best flight between Florida and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Florida to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Florida are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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1 adult
Fri 17/10
Fri 24/10

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago