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Cheap flights from Florida to Chicago from $53

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 10/31. 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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0 bags

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Cheap round-trip flights

Enter your travel dates to find the best prices.
Frontier Logo
9:53 am - 12:25 pm
FLL
-
ORD
3h 32mnonstop
Frontier Logo
8:05 am - 12:22 pm
ORD
-
FLL
3h 17mnonstop
$109Frontier
Tue, Jul 7 - Tue, Jul 21
Frontier Logo
9:53 am - 12:25 pm
FLL
-
ORD
3h 32mnonstop
Frontier Logo
8:05 am - 12:22 pm
ORD
-
FLL
3h 17mnonstop
$110Frontier
Thu, Aug 6 - Mon, Aug 10
Multiple Airlines Logo
9:53 am - 12:25 pm
FLL
-
ORD
3h 32mnonstop
Multiple Airlines Logo
7:00 am - 11:14 am
ORD
-
FLL
3h 14mnonstop
$124Multiple Airlines
Tue, Aug 4 - Tue, Aug 11
Southwest Logo
7:35 am - 9:20 am
MCO
-
MDW
2h 45mnonstop
Southwest Logo
3:30 pm - 7:05 pm
MDW
-
MCO
2h 35mnonstop
$171Southwest
Tue, Aug 11 - Tue, Aug 18
Southwest Logo
9:00 am - 12:05 pm
MCO
-
MDW
4h 05m
1 stop
Southwest Logo
12:20 pm - 4:00 pm
MDW
-
MCO
2h 40mnonstop
$177Southwest
Tue, Aug 11 - Tue, Aug 18
Multiple Airlines Logo
10:06 am - 1:56 pm
FLL
-
MDW
4h 50m
1 stop
Multiple Airlines Logo
6:00 am - 12:44 am
MDW
-
FLL
17h 44m
1 stop
$179Multiple Airlines
Thu, Jun 25 - Sat, Jul 4
United Airlines Logo
7:50 am - 10:00 am
TPA
-
ORD
3h 10mnonstop
United Airlines Logo
8:45 am - 3:28 pm
ORD
-
TPA
5h 43m
1 stop
$186United Airlines
Wed, Jul 15 - Tue, Aug 18
United Airlines Logo
7:42 pm - 9:53 pm
TPA
-
ORD
3h 11mnonstop
United Airlines Logo
5:56 pm - 9:49 pm
ORD
-
TPA
2h 53mnonstop
$189United Airlines
Wed, Jul 8 - Tue, Jul 14
Delta Logo
11:40 am - 6:29 pm
JAX
-
ORD
7h 49m
1 stop
Delta Logo
8:52 am - 5:27 pm
ORD
-
JAX
7h 35m
1 stop
$237Delta
Tue, Jun 16 - Tue, Jun 23
Delta Logo
6:34 pm - 11:59 pm
RSW
-
ORD
6h 25m
1 stop
Delta Logo
9:45 am - 4:44 pm
ORD
-
RSW
5h 59m
1 stop
$315Delta
Thu, Jul 2 - Wed, Jul 15

Sun Country Air flights from Florida to Chicago

Our best Sun Country Air deals on Florida to Chicago flight tickets
Sun Country Air
Nov 12
RSW11:30 amFort Myers SW Florida Intl
8h 05m
1 stop
ORD6:35 pmChicago O'Hare Intl
Nov 15
ORD6:08 pmChicago O'Hare Intl
16h 49m
1 stop
RSW11:57 amFort Myers SW Florida Intl
$345
Sun Country Air
Jun 4
RSW9:00 amFort Myers SW Florida Intl
9h 24m
1 stop
ORD5:24 pmChicago O'Hare Intl
Jun 8
ORD7:09 pmChicago O'Hare Intl
14h 31m
1 stop
RSW10:40 amFort Myers SW Florida Intl
$425

United Airlines flights from Florida to Chicago

Our best United Airlines deals on Florida to Chicago flight tickets
United Airlines
Jul 15
TPA7:50 amTampa
3h 10m
ORD10:00 amChicago O'Hare Intl
Aug 18
ORD8:45 amChicago O'Hare Intl
5h 43m
1 stop
TPA3:28 pmTampa
$186
United Airlines
Jul 8
TPA7:42 pmTampa
3h 11m
ORD9:53 pmChicago O'Hare Intl
Jul 14
ORD5:56 pmChicago O'Hare Intl
2h 53m
TPA9:49 pmTampa
$189
United Airlines
Jul 8
TPA7:42 pmTampa
3h 11m
ORD9:53 pmChicago O'Hare Intl
Jul 14
ORD8:40 amChicago O'Hare Intl
5h 45m
1 stop
TPA3:25 pmTampa
$195

momondo Fare Finder

 
Customize 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 832,500 searches. Data last updated May 23, 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 round-trip

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Tue 7/7

9:53 am-12:25 pm

Nonstop3h 32m

Chicago O'Hare Intl

Tue 7/21

8:05 am-12:22 pm

Nonstop3h 17m

$109

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Thu 8/6

9:53 am-12:25 pm

Nonstop3h 32m

Chicago O'Hare Intl

Mon 8/10

8:05 am-12:22 pm

Nonstop3h 17m

$110

Fort LauderdaleChicago

FLL - ORD

FLLORD

Fort Lauderdale

Tue 8/4

9:53 am-12:25 pm

Nonstop3h 32m

Chicago O'Hare Intl

Tue 8/11

7:00 am-11:14 am

Nonstop3h 14m

$124
Quickest round-trip

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 8/11

7:35 am-9:20 am

Nonstop2h 45m

Chicago Midway

Tue 8/18

3:30 pm-7:05 pm

Nonstop2h 35m

$171

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 8/11

9:00 am-12:05 pm

1 stop4h 05m

Chicago Midway

Tue 8/18

12:20 pm-4:00 pm

Nonstop2h 40m

$177

Fort LauderdaleChicago

FLL - MDW

FLLMDW

Fort Lauderdale

Thu 6/25

10:06 am-1:56 pm

1 stop4h 50m

Chicago Midway

Sat 7/4

6:00 am-12:44 am

1 stop17h 44m

$179

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 7/15

7:50 am-10:00 am

Nonstop3h 10m

Chicago O'Hare Intl

Tue 8/18

8:45 am-3:28 pm

1 stop5h 43m

$186

TampaChicago

TPA - ORD

TPAORD

Tampa

Wed 7/8

7:42 pm-9:53 pm

Nonstop3h 11m

Chicago O'Hare Intl

Tue 7/14

5:56 pm-9:49 pm

Nonstop2h 53m

$189

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Tue 6/16

11:40 am-6:29 pm

1 stop7h 49m

Chicago O'Hare Intl

Tue 6/23

8:52 am-5:27 pm

1 stop7h 35m

$237

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 7/2

6:34 pm-11:59 pm

1 stop6h 25m

Chicago O'Hare Intl

Wed 7/15

9:45 am-4:44 pm

1 stop5h 59m

$315

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

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 January is, on average, the cheapest month to fly to Chicago from Florida, with most prices found around $184. If you’re not able to fly to Chicago in January, then September is your next best option. Flight prices from Florida to Chicago during September average around $189.

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 $244. This is often the case because there is less demand to fly during this day of the week. When flying out on a Monday, the most expensive travel day of the week, you can expect to see flight prices from Florida to Chicago for around $484.

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 $204. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $362.

What is the cheapest Florida to Chicago flight route?

Fly from Fort Lauderdale to Chicago Greater Rockford for the best Florida - Chicago flight prices

How far in advance should I book a flight from Florida 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 $218 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 $166 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

$42

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Florida in the past 72 hours is $42. The best round-trip flight deal from Florida to Chicago found on momondo in the last 72 hours is $93.
The fastest flight from Florida to Chicago takes 2h 10m
Direct flights go from Florida to Chicago every day.
There are 3 airports in Chicago. From Florida there are direct flights to Chicago O'Hare Intl (ORD), Chicago Midway (MDW).
Search flight deals

Frequently asked questions about flying from Florida to Chicago

  • 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?

  • 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?

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
Allegiant AirPriceFrom $41Free CancellationRating
7.3
710 reviews
Search Allegiant Air flights
FrontierPriceFrom $43Free CancellationRating
5.6
2,940 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $58Free CancellationRating
6.2
Search Spirit Airlines flights
JetBluePriceFrom $105Free CancellationRating
7.2
2,981 reviews
Search JetBlue flights
DeltaPriceFrom $121Free CancellationRating
7.9
8,444 reviews
Search Delta flights
United AirlinesPriceFrom $128Free CancellationRating
7.4
9,751 reviews
Search United Airlines flights
SouthwestPriceFrom $149Free CancellationRating
7.9
4,277 reviews
Search Southwest flights
American AirlinesPriceFrom $157Free CancellationRating
7.1
11,642 reviews
Search American Airlines flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
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

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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
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport