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Cheap flights from Florida to Chicago from $44

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 2/8. 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

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Multiple Airlines Logo
8:09 am - 10:35 am
MCO
-
ORD
3h 26mnonstop
Multiple Airlines Logo
10:48 am - 2:38 pm
ORD
-
MCO
2h 50mnonstop
$72Multiple Airlines
Fri, Jan 23 - Tue, Jan 27
Multiple Airlines Logo
3:39 pm - 5:46 pm
MCO
-
ORD
3h 07mnonstop
Multiple Airlines Logo
1:17 pm - 5:18 pm
ORD
-
MCO
3h 01mnonstop
$73Multiple Airlines
Sat, Feb 21 - Sun, Feb 22
Frontier Logo
5:49 pm - 7:52 pm
MCO
-
MDW
3h 03mnonstop
Frontier Logo
1:00 pm - 4:49 pm
MDW
-
MCO
2h 49mnonstop
$73Frontier
Fri, Jan 23 - Fri, Jan 30
Frontier Logo
12:20 pm - 2:26 pm
MCO
-
MDW
3h 06mnonstop
Frontier Logo
7:30 am - 11:20 am
MDW
-
MCO
2h 50mnonstop
$74Frontier
Fri, Feb 20 - Sun, Feb 22
Spirit Airlines Logo
3:43 pm - 5:52 pm
MCO
-
ORD
3h 09mnonstop
Spirit Airlines Logo
12:44 pm - 4:31 pm
ORD
-
MCO
2h 47mnonstop
$77Spirit Airlines
Fri, Jan 16 - Mon, Jan 19
Spirit Airlines Logo
11:04 am - 1:13 pm
MCO
-
ORD
3h 09mnonstop
Spirit Airlines Logo
12:44 pm - 4:31 pm
ORD
-
MCO
2h 47mnonstop
$78Spirit Airlines
Wed, Jan 21 - Sat, Jan 24
American Airlines Logo
4:20 pm - 6:50 pm
PBI
-
ORD
3h 30mnonstop
American Airlines Logo
5:40 pm - 9:49 pm
ORD
-
PBI
3h 09mnonstop
$230American Airlines
Fri, Jan 16 - Thu, Jan 22
JetBlue Logo
11:59 am - 7:36 pm
PBI
-
ORD
8h 37m1 stop
JetBlue Logo
10:15 am - 7:58 pm
ORD
-
PBI
8h 43m1 stop
$231JetBlue
Fri, Jan 16 - Mon, Jan 19
JetBlue Logo
6:00 am - 7:36 pm
PBI
-
ORD
14h 36m1 stop
JetBlue Logo
10:15 am - 7:58 pm
ORD
-
PBI
8h 43m1 stop
$238JetBlue
Fri, Jan 16 - Mon, Jan 19
American Airlines Logo
7:03 am - 8:54 am
JAX
-
ORD
2h 51mnonstop
American Airlines Logo
5:30 pm - 8:58 pm
ORD
-
JAX
2h 28mnonstop
$248American Airlines
Sat, Jan 17 - Sun, Jan 18

Spirit Airlines flights from Florida to Chicago

Our best Spirit Airlines deals on Florida to Chicago flight tickets
Spirit Airlines
Jan 23
MCO5:28 pmOrlando
3h 13m
ORD7:41 pmChicago O'Hare Intl
Jan 26
ORD10:48 amChicago O'Hare Intl
2h 50m
MCO2:38 pmOrlando
$78
Find similar
Spirit Airlines
Jan 26
MIA5:54 amMiami
3h 24m
ORD8:18 amChicago O'Hare Intl
Feb 10
ORD9:23 amChicago O'Hare Intl
3h 18m
MIA1:41 pmMiami
$83
Find similar
Spirit Airlines
Jan 21
MCO6:59 pmOrlando
5h 47m
1 stop
ORD11:46 pmChicago O'Hare Intl
Jan 24
ORD12:44 pmChicago O'Hare Intl
2h 47m
MCO4:31 pmOrlando
$84
Find similar

United Airlines flights from Florida to Chicago

Our best United Airlines deals on Florida to Chicago flight tickets
United Airlines
Jan 10
RSW12:30 pmFort Myers SW Florida Intl
3h 24m
ORD2:54 pmChicago O'Hare Intl
Jan 18
ORD4:10 pmChicago O'Hare Intl
3h 02m
RSW8:12 pmFort Myers SW Florida Intl
$207
Find similar
United Airlines
Jan 9
RSW4:27 pmFort Myers SW Florida Intl
3h 23m
ORD6:50 pmChicago O'Hare Intl
Jan 18
ORD7:13 amChicago O'Hare Intl
3h 05m
RSW11:18 amFort Myers SW Florida Intl
$213
Find similar
United Airlines
Feb 26
PBI9:10 amPalm Beach Intl
3h 26m
ORD11:36 amChicago O'Hare Intl
Mar 1
ORD10:40 amChicago O'Hare Intl
3h 18m
PBI2:58 pmPalm Beach Intl
$229
Find similar

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 December 28, 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

Fri 1/23

8:09 am-10:35 am

Nonstop3h 26m

Chicago O'Hare Intl

Tue 1/27

10:48 am-2:38 pm

Nonstop2h 50m

$72

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 2/21

3:39 pm-5:46 pm

Nonstop3h 07m

Chicago O'Hare Intl

Sun 2/22

1:17 pm-5:18 pm

Nonstop3h 01m

$73

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 1/23

5:49 pm-7:52 pm

Nonstop3h 03m

Chicago Midway

Fri 1/30

1:00 pm-4:49 pm

Nonstop2h 49m

$73

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 2/20

12:20 pm-2:26 pm

Nonstop3h 06m

Chicago Midway

Sun 2/22

7:30 am-11:20 am

Nonstop2h 50m

$74

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 1/16

3:43 pm-5:52 pm

Nonstop3h 09m

Chicago O'Hare Intl

Mon 1/19

12:44 pm-4:31 pm

Nonstop2h 47m

$77

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 1/21

11:04 am-1:13 pm

Nonstop3h 09m

Chicago O'Hare Intl

Sat 1/24

12:44 pm-4:31 pm

Nonstop2h 47m

$78

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Fri 1/16

4:20 pm-6:50 pm

Nonstop3h 30m

Chicago O'Hare Intl

Thu 1/22

5:40 pm-9:49 pm

Nonstop3h 09m

$230

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Fri 1/16

11:59 am-7:36 pm

1 stop8h 37m

Chicago O'Hare Intl

Mon 1/19

10:15 am-7:58 pm

1 stop8h 43m

$231

West Palm BeachChicago

PBI - ORD

PBIORD

Palm Beach Intl

Fri 1/16

6:00 am-7:36 pm

1 stop14h 36m

Chicago O'Hare Intl

Mon 1/19

10:15 am-7:58 pm

1 stop8h 43m

$238

JacksonvilleChicago

JAX - ORD

JAXORD

Jacksonville

Sat 1/17

7:03 am-8:54 am

Nonstop2h 51m

Chicago O'Hare Intl

Sun 1/18

5:30 pm-8:58 pm

Nonstop2h 28m

$248

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 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 $177.

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 $291. 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 $462.

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 $282. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $406.

What is the cheapest Florida to Chicago flight route?

Fly from Orlando Sanford Intl to Chicago Greater Rockford 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 $248 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 $178 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

$89

Fastest flight time

2h 15m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Florida in the past 72 hours is $89. The best round-trip flight deal from Florida to Chicago found on momondo in the last 72 hours is $104.
The fastest flight from Florida to Chicago takes 2h 15m
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

  • 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
FrontierPriceFrom $37Free CancellationRating
5.7
3,065 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $62Free CancellationRating
6.3
8,211 reviews
Search Spirit Airlines flights
Allegiant AirPriceFrom $76Free CancellationRating
7.2
703 reviews
Search Allegiant Air flights
DeltaPriceFrom $98Free CancellationRating
7.9
8,019 reviews
Search Delta flights
United AirlinesPriceFrom $131Free CancellationRating
7.4
9,113 reviews
Search United Airlines flights
SouthwestPriceFrom $148Free CancellationRating
8.0
4,256 reviews
Search Southwest flights
American AirlinesPriceFrom $157Free CancellationRating
7.2
11,073 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
Benton Harbor
Saint Joseph
Portage
Lansing
Valparaiso
Schererville
Munster
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