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Cheap flights from Florida to Chicago from $29

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 8/22. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Spirit Airlines Logo
7:00 am - 9:13 amRSW-ORD
3h 13mnonstop
Spirit Airlines Logo
5:31 pm - 9:24 pmORD-RSW
2h 53mnonstop
$58Spirit Airlines
Find Deal
Thu, Sep 25 - Mon, Sep 29
Spirit Airlines Logo
7:00 am - 9:13 amRSW-ORD
3h 13mnonstop
Spirit Airlines Logo
5:31 pm - 9:24 pmORD-RSW
2h 53mnonstop
$59Spirit Airlines
Find Deal
Fri, Oct 10 - Mon, Oct 20
Frontier Logo
2:50 pm - 5:04 pmMCO-ORD
3h 14mnonstop
Frontier Logo
6:10 am - 9:53 amORD-MCO
2h 43mnonstop
$64Frontier
Find Deal
Sun, Oct 12 - Fri, Oct 17
Frontier Logo
4:18 pm - 6:41 pmMCO-ORD
3h 23mnonstop
Frontier Logo
8:49 pm - 12:35 amORD-MCO
2h 46mnonstop
$74Frontier
Find Deal
Fri, Aug 29 - Fri, Sep 5
Logo
2:07 pm - 4:10 pmMCO-ORD
3h 03mnonstop
Logo
7:46 pm - 11:52 pmORD-MCO
3h 06mnonstop
$111
Find Deal
Wed, Aug 20 - Thu, Aug 28
Logo
8:15 am - 10:18 amTPA-ORD
3h 03mnonstop
Logo
8:05 am - 12:05 pmORD-TPA
3h 00mnonstop
$117
Find Deal
Wed, Sep 10 - Sun, Sep 14
American Airlines Logo
6:20 am - 8:40 amMIA-ORD
3h 20mnonstop
American Airlines Logo
6:09 am - 10:14 amORD-MIA
3h 05mnonstop
$137American Airlines
Find Deal
Sat, Sep 6 - Mon, Sep 8
American Airlines Logo
8:00 am - 10:09 amRSW-ORD
3h 09mnonstop
American Airlines Logo
7:05 am - 10:56 amORD-RSW
2h 51mnonstop
$158American Airlines
Find Deal
Tue, Sep 9 - Sun, Sep 14
United Airlines Logo
6:54 pm - 11:15 pmJAX-ORD
5h 21m1 stop
United Airlines Logo
6:26 pm - 9:58 pmORD-JAX
2h 32mnonstop
$191United Airlines
Find Deal
Tue, Sep 9 - Tue, Sep 16
United Airlines Logo
6:55 pm - 11:30 pmJAX-ORD
5h 35m1 stop
United Airlines Logo
6:26 pm - 9:58 pmORD-JAX
2h 32mnonstop
$213United Airlines
Find Deal
Mon, Aug 18 - Wed, Aug 20

American Airlines flights from Florida to Chicago O'Hare Intl Airport

Our best American Airlines deals on Florida to Chicago O'Hare Intl Airport flight tickets
American Airlines
Sep 6
MIA6:20 amMiami
3h 20m
ORD8:40 amChicago O'Hare Intl
Sep 8
ORD6:09 amChicago O'Hare Intl
3h 05m
MIA10:14 amMiami
$137
Find similar
American Airlines
Sep 9
RSW8:00 amFort Myers SW Florida Intl
3h 09m
ORD10:09 amChicago O'Hare Intl
Sep 14
ORD7:05 amChicago O'Hare Intl
2h 51m
RSW10:56 amFort Myers SW Florida Intl
$158
Find similar
American Airlines
Sep 9
JAX2:05 pmJacksonville
2h 43m
ORD3:48 pmChicago O'Hare Intl
Sep 16
ORD9:56 amChicago O'Hare Intl
2h 29m
JAX1:25 pmJacksonville
$181
Find similar

United Airlines flights from Florida to Chicago O'Hare Intl Airport

Our best United Airlines deals on Florida to Chicago O'Hare Intl Airport flight tickets
United Airlines
Sep 9
JAX6:54 pmJacksonville
5h 21m
1 stop
ORD11:15 pmChicago O'Hare Intl
Sep 16
ORD6:26 pmChicago O'Hare Intl
2h 32m
JAX9:58 pmJacksonville
$191
Find similar
United Airlines
Aug 18
JAX6:55 pmJacksonville
5h 35m
1 stop
ORD11:30 pmChicago O'Hare Intl
Aug 20
ORD6:26 pmChicago O'Hare Intl
2h 32m
JAX9:58 pmJacksonville
$213
Find similar
United Airlines
Sep 9
ECP5:11 pmPanama City NW Florida Beaches
2h 39m
ORD7:50 pmChicago O'Hare Intl
Sep 16
ORD10:35 amChicago O'Hare Intl
2h 28m
ECP1:03 pmPanama City NW Florida Beaches
$217
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momondo Fare Finder

 
Customize your flight search to find flights from Florida to Chicago O'Hare Intl Airport 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 832,500 searches. Data last updated July 31, 2025.
Use the filters below to find and compare flights from Florida to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 9/25

7:00 am-9:13 am

Nonstop3h 13m

Chicago O'Hare Intl

Mon 9/29

5:31 pm-9:24 pm

Nonstop2h 53m

$58

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 10/10

7:00 am-9:13 am

Nonstop3h 13m

Chicago O'Hare Intl

Mon 10/20

5:31 pm-9:24 pm

Nonstop2h 53m

$59

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sun 10/12

2:50 pm-5:04 pm

Nonstop3h 14m

Chicago O'Hare Intl

Fri 10/17

6:10 am-9:53 am

Nonstop2h 43m

$64

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 8/29

4:18 pm-6:41 pm

Nonstop3h 23m

Chicago O'Hare Intl

Fri 9/5

8:49 pm-12:35 am

Nonstop2h 46m

$74

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 8/20

2:07 pm-4:10 pm

Nonstop3h 03m

Chicago O'Hare Intl

Thu 8/28

7:46 pm-11:52 pm

Nonstop3h 06m

$111

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 9/10

8:15 am-10:18 am

Nonstop3h 03m

Chicago O'Hare Intl

Sun 9/14

8:05 am-12:05 pm

Nonstop3h 00m

$117

MiamiChicago

MIA - ORD

MIAORD

Miami

Sat 9/6

6:20 am-8:40 am

Nonstop3h 20m

Chicago O'Hare Intl

Mon 9/8

6:09 am-10:14 am

Nonstop3h 05m

$137

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Tue 9/9

8:00 am-10:09 am

Nonstop3h 09m

Chicago O'Hare Intl

Sun 9/14

7:05 am-10:56 am

Nonstop2h 51m

$158

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 9/9

6:54 pm-11:15 pm

1 stop5h 21m

Chicago O'Hare Intl

Tue 9/16

6:26 pm-9:58 pm

Nonstop2h 32m

$191

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Mon 8/18

6:55 pm-11:30 pm

1 stop5h 35m

Chicago O'Hare Intl

Wed 8/20

6:26 pm-9:58 pm

Nonstop2h 32m

$213

Flights are sorted by cheapest round-trip 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 O'Hare Intl Airport

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 O'Hare Intl Airport?

The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Florida averaging around $217.

What is the cheapest day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $303. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Florida because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $447.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Florida in the evening is the least expensive time of day to depart. momondo users have found prices as low as $278 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $368. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Florida to Chicago O'Hare Intl flight route?

Fly from Fort Myers SW Florida Intl to Chicago O'Hare Intl for the best Florida - Chicago O'Hare Intl flight prices

How far in advance should I book a flight to Chicago O'Hare Intl Airport?

You are more likely to see cheaper flights to Chicago O'Hare Intl Airport from Florida when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago O'Hare Intl Airport for around $247 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago O'Hare Intl Airport from Florida for as low as $211 on momondo.

What cabin class options are available on Florida to Chicago O'Hare Intl flights?

There are 4 cabin classes available to choose from on Florida to Chicago O'Hare Intl 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 O'Hare Intl Airport flights?

No. A direct flight is the cheapest option for a flight between Florida to Chicago O'Hare Intl Airport.

Cheap Florida to Chicago O'Hare Intl Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Florida to Chicago O'Hare Intl Airport

Best Price Found

$29

Fastest flight time

2h 31m

Direct flights

Every day
The best one-way flight to Chicago O'Hare Intl Airport from Florida in the past 72 hours is $29. The best round-trip flight deal from Florida to Chicago O'Hare Intl Airport found on momondo in the last 72 hours is $58.
The fastest flight from Florida to Chicago O'Hare Intl Airport takes 2h 31m
Direct flights go from Florida to Chicago O'Hare Intl Airport every day.
Search flight deals

  • When did momondo last update prices for flights from Florida to Chicago O'Hare Intl Airport?

    Prices for flights from Florida to Chicago O'Hare Intl Airport refresh daily.

  • How many operators does momondo search for flights from Florida to Chicago O'Hare Intl Airport?

  • How old do you have to be to fly from Florida to Chicago O'Hare Intl Airport?

    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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The necessary travel and health documents for your Chicago O'Hare Intl Airport 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 O'Hare Intl Airport?

Best airlines flying from Florida to Chicago O'Hare Intl Airport

Compare and see reviews for airlines that fly from Florida to Chicago O'Hare Intl Airport with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $46Free CancellationRating
5.9
3,239 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $67Free CancellationRating
6.3
8,049 reviews
Search Spirit Airlines flights
DeltaPriceFrom $148Free CancellationRating
8.0
7,981 reviews
Search Delta flights
United AirlinesPriceFrom $157Free CancellationRating
7.4
8,900 reviews
Search United Airlines flights
American AirlinesPriceFrom $158Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
SouthwestPriceFrom $165Free CancellationRating
8.0
4,246 reviews
Search Southwest flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Rockford
Schaumburg
South Haven
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Tinley Park
Elgin
Orland Park
Aurora
Janesville
Benton Harbor

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?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight 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?

Of course. momondo tracks the price of Florida to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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