How long does it take to fly to Chicago?

Average flight duration from Florida to Chicago depends on which airport you fly into and out of. Flying from Tampa to Chicago O'Hare Intl Airport is 2h 55m on average, while flying from Orlando to Chicago O'Hare Intl Airport is 2h 59m on average. Chicago O'Hare Intl Airport is the most popular airport in Chicago.

What airlines fly to Chicago?

American Airlines, Spirit Airlines and United Airlines are the top three most popular airlines that fly to Chicago from Florida according to our data. American Airlines is the first choice among our users, with 34% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Florida to Chicago on average per week?

947 flights are operational weekly from Florida to Chicago as of September 2025. The most popular departure day for this route is Wed, with 19% of flights per week taking off on this day.

What is the cheapest airline that flies from Florida to Chicago?

Frontier and Spirit Airlines are the most popular carriers operating from Florida to Chicago

How many flights depart from Florida to Chicago on average per day?

As of September 2025, 135 flights take off from Florida and land in Chicago each day. The most common flight departure time for this route is 4:00PM, with 58% of daily flights taking off in the afternoon.

When did momondo last update prices for flights from Florida to Chicago?

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

How many operators does momondo search for flights from Florida to Chicago?

As of September 2025, there are 6 operators available to choose from for flights from Florida to Chicago.

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

The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$50 Cheap Flights from Florida to Chicago in 2025

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Find the cheapest flights from Florida to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

7:50 pm - 9:58 pmMCO-ORD

3h 08mnonstop

6:30 am - 10:13 amORD-MCO

2h 43mnonstop

$88Spirit Airlines

Find Deal

Thu, Sep 18 - Mon, Sep 22

5:24 pm - 7:44 pmMCO-ORD

3h 20mnonstop

8:00 am - 11:57 amORD-MCO

2h 57mnonstop

$89Frontier

Find Deal

Thu, Sep 18 - Sat, Sep 20

1:02 pm - 3:17 pmMCO-ORD

3h 15mnonstop

5:17 pm - 9:06 pmORD-MCO

2h 49mnonstop

$97

Find Deal

Sat, Sep 27 - Wed, Oct 1

5:01 am - 7:10 amTPA-ORD

3h 09mnonstop

6:16 pm - 9:54 pmORD-TPA

2h 38mnonstop

$100

Find Deal

Thu, Sep 25 - Tue, Oct 7

6:20 am - 8:35 amMIA-MDW

3h 15mnonstop

9:00 am - 1:05 pmMDW-MIA

3h 05mnonstop

$157Southwest

Find Deal

Fri, Nov 7 - Tue, Nov 11

12:35 pm - 2:45 pmMIA-MDW

3h 10mnonstop

2:10 pm - 6:10 pmMDW-MIA

3h 00mnonstop

$177Southwest

Find Deal

Fri, Sep 26 - Mon, Sep 29

6:55 am - 9:05 amRSW-ORD

3h 10mnonstop

2:44 pm - 6:50 pmORD-RSW

3h 06mnonstop

$177American Airlines

Find Deal

Sat, Oct 4 - Sat, Oct 4

3:48 pm - 6:14 pmRSW-ORD

3h 26mnonstop

7:34 pm - 11:35 pmORD-RSW

3h 01mnonstop

$178American Airlines

Find Deal

Thu, Nov 6 - Sat, Nov 8

9:10 am - 11:22 amRSW-ORD

3h 12mnonstop

4:15 pm - 8:16 pmORD-RSW

3h 01mnonstop

$191United Airlines

Find Deal

Sat, Nov 1 - Sat, Nov 1

7:00 am - 1:08 pmPBI-ORD

7h 08m1 stop

10:58 am - 3:08 pmORD-PBI

3h 10mnonstop

$235United Airlines

Find Deal

Wed, Oct 1 - Wed, Oct 8

American Airlines flights from Florida to Chicago

Our best American Airlines deals on Florida to Chicago flight tickets

American Airlines

Oct 4

RSW6:55 amFort Myers SW Florida Intl

3h 10m

ORD9:05 amChicago O'Hare Intl

Oct 4

ORD2:44 pmChicago O'Hare Intl

3h 06m

RSW6:50 pmFort Myers SW Florida Intl

$177

Find similar

American Airlines

Nov 6

RSW3:48 pmFort Myers SW Florida Intl

3h 26m

ORD6:14 pmChicago O'Hare Intl

Nov 8

ORD7:34 pmChicago O'Hare Intl

3h 01m

RSW11:35 pmFort Myers SW Florida Intl

$178

Find similar

American Airlines

Oct 2

RSW8:00 amFort Myers SW Florida Intl

3h 09m

ORD10:09 amChicago O'Hare Intl

Oct 5

ORD7:05 amChicago O'Hare Intl

2h 51m

RSW10:56 amFort Myers SW Florida Intl

$179

Find similar

Spirit Airlines flights from Florida to Chicago

Our best Spirit Airlines deals on Florida to Chicago flight tickets

Spirit Airlines

Sep 18

MCO7:50 pmOrlando

3h 08m

ORD9:58 pmChicago O'Hare Intl

Sep 22

ORD6:30 amChicago O'Hare Intl

2h 43m

MCO10:13 amOrlando

$88

Find similar

Spirit Airlines

Sep 12

MCO7:50 pmOrlando

3h 08m

ORD9:58 pmChicago O'Hare Intl

Sep 15

ORD5:17 pmChicago O'Hare Intl

2h 49m

MCO9:06 pmOrlando

$89

Find similar

Spirit Airlines

Sep 18

MCO7:50 pmOrlando

3h 08m

ORD9:58 pmChicago O'Hare Intl

Sep 24

ORD5:17 pmChicago O'Hare Intl

2h 49m

MCO9:06 pmOrlando

$90

Find similar

Fly from

Fly to

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 9/18

7:50 pm-9:58 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 9/22

6:30 am-10:13 am

Nonstop2h 43m

$88

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 9/18

5:24 pm-7:44 pm

Nonstop3h 20m

Chicago O'Hare Intl

Sat 9/20

8:00 am-11:57 am

Nonstop2h 57m

$89

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 9/27

1:02 pm-3:17 pm

Nonstop3h 15m

Chicago O'Hare Intl

Wed 10/1

5:17 pm-9:06 pm

Nonstop2h 49m

$97

TampaChicago

TPA - ORD

TPAORD

Tampa

Thu 9/25

5:01 am-7:10 am

Nonstop3h 09m

Chicago O'Hare Intl

Tue 10/7

6:16 pm-9:54 pm

Nonstop2h 38m

$100

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 11/7

6:20 am-8:35 am

Nonstop3h 15m

Chicago Midway

Tue 11/11

9:00 am-1:05 pm

Nonstop3h 05m

$157

MiamiChicago

MIA - MDW

MIAMDW

Miami

Fri 9/26

12:35 pm-2:45 pm

Nonstop3h 10m

Chicago Midway

Mon 9/29

2:10 pm-6:10 pm

Nonstop3h 00m

$177

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 10/4

6:55 am-9:05 am

Nonstop3h 10m

Chicago O'Hare Intl

Sat 10/4

2:44 pm-6:50 pm

Nonstop3h 06m

$177

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 11/6

3:48 pm-6:14 pm

Nonstop3h 26m

Chicago O'Hare Intl

Sat 11/8

7:34 pm-11:35 pm

Nonstop3h 01m

$178

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sat 11/1

9:10 am-11:22 am

Nonstop3h 12m

Chicago O'Hare Intl

Sat 11/1

4:15 pm-8:16 pm

Nonstop3h 01m

$191

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Wed 10/1

7:00 am-1:08 pm

1 stop7h 08m

Chicago O'Hare Intl

Wed 10/8

10:58 am-3:08 pm

Nonstop3h 10m

$235

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Other information

What is the cheapest month to fly to Chicago?

The month of February is, on average, the cheapest month to fly to Chicago from Florida, with most prices found around $160. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Florida to Chicago during September average around $187.

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 Friday when prices can be found for as low as $281. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Florida to Chicago for around $458.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Florida to Chicago during this time can be as low as $285. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $355.

What is the cheapest Florida to Chicago flight route?

Fly from Orlando to Chicago Midway 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 $250 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Florida for as low as $202 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

Best Price Found	$78
Fastest flight time	2h 34m
Direct flights	Every day
Airports in Chicago	2 airports

The best one-way flight to Chicago from Florida in the past 72 hours is $78. The best round-trip flight deal from Florida to Chicago found on momondo in the last 72 hours is $96.

The fastest flight from Florida to Chicago takes 2h 34m

Direct flights go from Florida to Chicago every day.

There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)

Search flight deals

When did momondo last update prices for flights from Florida to Chicago?
Prices for flights from Florida to Chicago were last updated today.
How many operators does momondo search for flights from Florida to Chicago?
As of September 2025, there are 6 operators available to choose from for flights from Florida to Chicago.
How old do you have to be to fly from Florida to Chicago?
The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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 travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Florida to Chicago?
Based on momondo bookings for this flight route, the most popular plane model on flight routes from Florida to Chicago is Boeing 737-800 (20.49% of total bookings). The next most popular plane models are Boeing 737 MAX 8 (11.26%), Airbus A321-100/200 (10.82%), and Airbus A321neo (9.45%).

Best airlines flying from Florida to Chicago

Compare and see reviews for airlines that fly from Florida to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Frontier	PriceFrom $46	Free Cancellation	Rating 5.8 3,196 reviews	Search Frontier flights
Spirit Airlines	PriceFrom $66	Free Cancellation	Rating 6.3 8,012 reviews	Search Spirit Airlines flights
Allegiant Air	PriceFrom $90	Free Cancellation	Rating 7.2 701 reviews	Search Allegiant Air flights
Delta	PriceFrom $114	Free Cancellation	Rating 7.9 7,972 reviews	Search Delta flights
Southwest	PriceFrom $143	Free Cancellation	Rating 8.0 4,238 reviews	Search Southwest flights
American Airlines	PriceFrom $158	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights
United Airlines	PriceFrom $158	Free Cancellation	Rating 7.4 8,937 reviews	Search United Airlines flights

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Hammond

Benton Harbor

Saint Joseph

Lansing

Portage

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Florida.

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

momondo does allow users to show only those flights to Chicago from Florida which offer a flexible booking policy as well as other useful filters and features.

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

Once you have performed a search for Florida to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Florida and alert you when they change.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Chicago Greater Rockford Airport

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Flights to Dallasfrom $63

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Flights to Denverfrom $51

Cheap flights from Florida to Chicago from $50

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 11/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names and deals

Big names and deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Florida to Chicago

Cheap round-trip flights

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Cheap last minute flights

Cheap direct flights

American Airlines flights from Florida to Chicago

Our best American Airlines deals on Florida to Chicago flight tickets

Spirit Airlines flights from Florida to Chicago

Our best Spirit Airlines deals on Florida to Chicago flight tickets

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Use the filters below to find and compare flights from Florida to Chicago that are best for you.

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 month of February is, on average, the cheapest month to fly to Chicago from Florida, with most prices found around $160. If you’re not able to fly to Chicago in February, then September is your next best option. Flight prices from Florida to Chicago during September average around $187.

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

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Florida to Chicago during this time can be as low as $285. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $355.

What is the cheapest Florida to Chicago flight route?

Fly from Orlando to Chicago Midway for the best Florida - Chicago flight prices

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

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.

What is the cheapest airline that flies from Florida to Chicago?

Frontier and Spirit Airlines are the most popular carriers operating from Florida to Chicago

What airlines fly to Chicago?

How many flights depart from Florida to Chicago on average per day?

As of September 2025, 135 flights take off from Florida and land in Chicago each day. The most common flight departure time for this route is 4:00PM, with 58% of daily flights taking off in the afternoon.

How many flights depart from Florida to Chicago on average per week?

947 flights are operational weekly from Florida to Chicago as of September 2025. The most popular departure day for this route is Wed, with 19% of flights per week taking off on this day.

How long does it take to fly 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

Best Price Found

Fastest flight time

Direct flights

Airports in Chicago

When did momondo last update prices for flights from Florida to Chicago?

How many operators does momondo search for flights from Florida to Chicago?

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

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

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

Best airlines flying from Florida to Chicago

Compare and see reviews for airlines that fly from Florida to Chicago with momondo

Traveling to a place near Chicago?

Why use momondo?

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

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

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

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

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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