Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Chicago to Florida from $49

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Florida departing on 12/9. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Chicago to Florida

Cheap round-trip flights

Frontier Logo
8:00 am - 11:57 amORD-MCO
2h 57mnonstop
Frontier Logo
12:58 pm - 3:08 pmMCO-ORD
3h 10mnonstop
$92Frontier
Find Deal
Sat, Oct 4 - Wed, Oct 8
Spirit Airlines Logo
6:00 am - 9:44 amORD-MCO
2h 44mnonstop
Spirit Airlines Logo
7:30 pm - 9:33 pmMCO-ORD
3h 03mnonstop
$93Spirit Airlines
Find Deal
Wed, Oct 8 - Fri, Oct 10
Spirit Airlines Logo
6:30 am - 10:13 amORD-MCO
2h 43mnonstop
Spirit Airlines Logo
7:50 pm - 9:58 pmMCO-ORD
3h 08mnonstop
$94Spirit Airlines
Find Deal
Mon, Sep 29 - Tue, Sep 30
Frontier Logo
11:21 am - 3:04 pmMDW-MCO
2h 43mnonstop
Frontier Logo
1:16 pm - 3:11 pmMCO-MDW
2h 55mnonstop
$99Frontier
Find Deal
Sat, Oct 4 - Sat, Oct 11
American Airlines Logo
7:05 am - 11:09 amORD-MIA
3h 04mnonstop
American Airlines Logo
6:59 pm - 9:23 pmMIA-ORD
3h 24mnonstop
$133American Airlines
Find Deal
Wed, Oct 1 - Wed, Oct 8
United Airlines Logo
4:10 pm - 8:12 pmORD-RSW
3h 02mnonstop
United Airlines Logo
5:55 pm - 8:18 pmRSW-ORD
3h 23mnonstop
$133United Airlines
Find Deal
Sat, Jan 17 - Wed, Jan 21
American Airlines Logo
2:39 pm - 6:29 pmORD-TPA
2h 50mnonstop
American Airlines Logo
7:20 pm - 9:24 pmTPA-ORD
3h 04mnonstop
$147American Airlines
Find Deal
Tue, Dec 2 - Mon, Dec 8
Southwest Logo
1:45 pm - 8:10 pmORD-RSW
5h 25m1 stop
Southwest Logo
7:10 am - 11:10 amRSW-ORD
5h 00m1 stop
$153Southwest
Find Deal
Tue, Nov 4 - Wed, Nov 12
Southwest Logo
6:10 pm - 10:05 pmMDW-FLL
2h 55mnonstop
Southwest Logo
8:35 pm - 10:45 pmFLL-MDW
3h 10mnonstop
$153Southwest
Find Deal
Tue, Oct 14 - Tue, Oct 21
United Airlines Logo
9:20 am - 1:26 pmORD-RSW
3h 06mnonstop
United Airlines Logo
9:20 am - 11:32 amRSW-ORD
3h 12mnonstop
$157United Airlines
Find Deal
Wed, Dec 10 - Tue, Dec 16

United Airlines flights from Chicago to Florida

Our best United Airlines deals on Chicago to Florida flight tickets
United Airlines
Jan 17
ORD4:10 pmChicago O'Hare Intl
3h 02m
RSW8:12 pmFort Myers SW Florida Intl
Jan 21
RSW5:55 pmFort Myers SW Florida Intl
3h 23m
ORD8:18 pmChicago O'Hare Intl
$133
Find similar
United Airlines
Oct 29
ORD10:35 amChicago O'Hare Intl
3h 15m
MIA2:50 pmMiami
Nov 2
MIA7:00 amMiami
3h 29m
ORD9:29 amChicago O'Hare Intl
$157
Find similar
United Airlines
Oct 21
ORD7:15 amChicago O'Hare Intl
3h 03m
RSW11:18 amFort Myers SW Florida Intl
Oct 25
RSW12:25 pmFort Myers SW Florida Intl
3h 15m
ORD2:40 pmChicago O'Hare Intl
$159
Find similar

Spirit Airlines flights from Chicago to Florida

Our best Spirit Airlines deals on Chicago to Florida flight tickets
Spirit Airlines
Oct 8
ORD6:00 amChicago O'Hare Intl
2h 44m
MCO9:44 amOrlando
Oct 10
MCO7:30 pmOrlando
3h 03m
ORD9:33 pmChicago O'Hare Intl
$93
Find similar
Spirit Airlines
Sep 29
ORD6:30 amChicago O'Hare Intl
2h 43m
MCO10:13 amOrlando
Sep 30
MCO7:50 pmOrlando
3h 08m
ORD9:58 pmChicago O'Hare Intl
$94
Find similar
Spirit Airlines
Nov 7
ORD10:49 amChicago O'Hare Intl
3h 04m
FLL2:53 pmFort Lauderdale
Nov 14
FLL9:25 pmFort Lauderdale
3h 17m
ORD11:42 pmChicago O'Hare Intl
$97
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Florida 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 September 15, 2025.
Use the filters below to find and compare flights from Chicago to Florida that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Sat 10/4

8:00 am-11:57 am

Nonstop2h 57m

Orlando

Wed 10/8

12:58 pm-3:08 pm

Nonstop3h 10m

$92

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Wed 10/8

6:00 am-9:44 am

Nonstop2h 44m

Orlando

Fri 10/10

7:30 pm-9:33 pm

Nonstop3h 03m

$93

ChicagoOrlando

ORD - MCO

ORDMCO

Chicago O'Hare Intl

Mon 9/29

6:30 am-10:13 am

Nonstop2h 43m

Orlando

Tue 9/30

7:50 pm-9:58 pm

Nonstop3h 08m

$94

ChicagoOrlando

MDW - MCO

MDWMCO

Chicago Midway

Sat 10/4

11:21 am-3:04 pm

Nonstop2h 43m

Orlando

Sat 10/11

1:16 pm-3:11 pm

Nonstop2h 55m

$99

ChicagoMiami

ORD - MIA

ORDMIA

Chicago O'Hare Intl

Wed 10/1

7:05 am-11:09 am

Nonstop3h 04m

Miami

Wed 10/8

6:59 pm-9:23 pm

Nonstop3h 24m

$133

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Sat 1/17

4:10 pm-8:12 pm

Nonstop3h 02m

Fort Myers SW Florida Intl

Wed 1/21

5:55 pm-8:18 pm

Nonstop3h 23m

$133

ChicagoTampa

ORD - TPA

ORDTPA

Chicago O'Hare Intl

Tue 12/2

2:39 pm-6:29 pm

Nonstop2h 50m

Tampa

Mon 12/8

7:20 pm-9:24 pm

Nonstop3h 04m

$147

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Tue 11/4

1:45 pm-8:10 pm

1 stop5h 25m

Fort Myers SW Florida Intl

Wed 11/12

7:10 am-11:10 am

1 stop5h 00m

$153

ChicagoFort Lauderdale

MDW - FLL

MDWFLL

Chicago Midway

Tue 10/14

6:10 pm-10:05 pm

Nonstop2h 55m

Fort Lauderdale

Tue 10/21

8:35 pm-10:45 pm

Nonstop3h 10m

$153

ChicagoFort Myers

ORD - RSW

ORDRSW

Chicago O'Hare Intl

Wed 12/10

9:20 am-1:26 pm

Nonstop3h 06m

Fort Myers SW Florida Intl

Tue 12/16

9:20 am-11:32 am

Nonstop3h 12m

$157

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Florida from

How to get the cheapest flight ticket from Chicago to Florida

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 Florida?

In general, September is the cheapest month to fly from Chicago to Florida. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $231. If you’re not able to fly to Florida in September, then January is your next best option. Flight prices from Chicago to Florida during January average around $237.

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

On average, the least expensive day to fly to Florida from Chicago is on a Friday. momondo users have found tickets for Friday departures for as low as $429. However, this price may fluctuate depending on the airline, the season, and holidays. Be sure to avoid booking your departure on a Sunday as prices are generally higher than usual. According to our data, the average ticket price to Florida on Sunday is $448.

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

Flying to Florida from Chicago in the evening is the least expensive time of day to depart. momondo users have found prices as low as $262 when looking at flights departing in the evening. Flights to Florida are more costly in the morning, with an average ticket price of $465. Departure times in the morning fall within the peak daily travel times, which is why tickets can be more expensive.

What is the cheapest Chicago to Florida flight route?

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

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

You are more likely to see cheaper flights to Florida from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Florida for around $273 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Florida from Chicago for as low as $222 on momondo.

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

There are 4 cabin classes available to choose from on Chicago to Florida 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 Chicago to Florida flights?

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

Cheap Chicago to Florida flight deals and tips

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

Best Price Found

$64

Fastest flight time

2h 10m

Direct flights

Every day

Airports in Florida

2 airports
The best one-way flight to Florida from Chicago in the past 72 hours is $64. The best round-trip flight deal from Chicago to Florida found on momondo in the last 72 hours is $91.
The fastest flight from Chicago to Florida takes 2h 10m
Direct flights go from Chicago to Florida every day.
There are 2 airports near Florida: Jacksonville (JAX), Orlando (MCO)
Search flight deals

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

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

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

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

    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 Chicago to Florida.

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

    The travel and health documents required for your trip to Florida 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 Florida. 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 Chicago to Florida?

Best airlines flying from Chicago to Florida

Compare and see reviews for airlines that fly from Chicago to Florida with momondo
Airline
Rating
Free Cancellation
Price
FrontierPriceFrom $37Free CancellationRating
5.8
3,172 reviews
Search Frontier flights
Spirit AirlinesPriceFrom $42Free CancellationRating
6.3
8,015 reviews
Search Spirit Airlines flights
Allegiant AirPriceFrom $89Free CancellationRating
7.2
699 reviews
Search Allegiant Air flights
United AirlinesPriceFrom $127Free CancellationRating
7.4
8,929 reviews
Search United Airlines flights
DeltaPriceFrom $131Free CancellationRating
7.9
7,954 reviews
Search Delta flights
SouthwestPriceFrom $157Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
American AirlinesPriceFrom $160Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
Alaska AirlinesPriceFrom $176Free CancellationRating
8.0
10,000 reviews
Search Alaska Airlines flights
JetBluePriceFrom $233Free CancellationRating
7.2
2,912 reviews
Search JetBlue flights

Why use momondo?

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

It is quick and easy to find Chicago to Florida 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 Florida that suits you.

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

Yes. All flights to Florida from Chicago on momondo can be compared and filtered by various policies on offer, including flexible booking.

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

Once all potential Chicago to Florida flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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

Price alerts on flights to Florida from Chicago 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.

An easier way to manage your Florida 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.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 10/15
Wed 10/22
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Florida

Popular cities in Florida

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $49
Flights to Los Angelesfrom $49
Flights to Miamifrom $49
Flights to Chicagofrom $49
Flights to Orlandofrom $59
Flights to Las Vegasfrom $49
Flights to San Franciscofrom $58
Flights to Washington, D.C.from $54
Flights to Bostonfrom $62
Flights to Atlantafrom $49
Flights to Dallasfrom $68
Flights to Seattlefrom $69