Round-trip flight from Chicago
CHI to FMY
Hyatt Place Fort Myers Forum
Fort Myers, 2600 Champion Ring Road
8.4795 Reviews3-Star Hotel
28% Package Savings
$558/person
$1,559 $1,115 total
Incl. Flight + Hotel
Flight Deals from Chicago to Fort Myers from $183
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Good to Know
Essential information to help you plan your flight from Chicago to Fort Myers.
Cheapest Flight Round-trip
$207
Lowest round-trip price available on Priceline for this route right now.
This fare recently dropped from $336.
1 stop · economyCheapest Flight One-way
$183
Lowest one-way price found on Priceline for this route in the last 16 days. Found 10 days ago.
The typical one-way fare on this route is $253.
Outbound · Nov 1
6:40 pmMDWChicago Midway Airport
10:25 pmRSWSouthwest Florida International Airport
2h 45m · Nonstop
Cheapest Nonstop
$299
Cheapest nonstop found on Priceline for this route in the last 16 days. Found 8 days ago.
$92 more than the cheapest round-trip.
Outbound · Nov 2
5:05 amMDWChicago Midway Airport
8:50 amRSWSouthwest Florida International Airport
2h 45m · Nonstop
Return · Nov 9
9:05 pmRSWSouthwest Florida International Airport
11:05 pmMDWChicago Midway Airport
3h 0m · Nonstop
Good deal price
$322
A round-trip at or under $322 is a good deal on this route right now.
75% of the fares we found on this route cost more; only a quarter cost less.
Timing Your Trip
The best day, time of day, season and booking window for this route.
Best day to fly
Tuesdays
Tuesday departures average $532 on this route, the lowest of any weekday.
$46 less than the average weekday, which is $578.
Best time to fly
Mornings
Morning departures average $353 on this route, the lowest of any time of day.
$298 less than the average departure, which is $651.
Low season
January
Fares average $262 in January, the cheapest month to fly this route, bottoming out near $255 in late January.
$44 below the yearly average of $306.
When to book
4 weeks ahead
Fares on this route are lowest when booked about 4 weeks before departure.
Booking then averages $299, versus $514 in the final days before the flight.
Price Drop Deals
Priceline is always monitoring flight prices on this route. When we spot an offer on a specific flight that’s significantly lower than what that flight usually sells for, we call it out here as a price drop.
ORDRSW
39% Price DropFrontier Airlines
Depart Dec 13 · Return Dec 17
4-night trip · economy
$336now only$207Round-trip
ORDRSW
35% Price DropFrontier Airlines
Depart Jan 7 · Return Jan 11
4-night trip · economy
$336now only$219Round-trip
ORDRSW
34% Price DropFrontier Airlines
Depart Dec 6 · Return Dec 10
4-night trip · economy
$336now only$223Round-trip
ORDRSW
33% Price DropFrontier Airlines
Depart Nov 20 · Return Nov 24
4-night trip · economy
$336now only$225Round-trip
ORDRSW
28% Price DropFrontier Airlines
Depart Dec 10 · Return Dec 14
4-night trip · economy
$336now only$243Round-trip
ORDRSW
25% Price DropFrontier Airlines
Depart Dec 11 · Return Dec 14
3-night trip · economy
$336now only$252Round-trip
ORDRSW
22% Price DropFrontier Airlines
Depart Jan 10 · Return Jan 14
4-night trip · economy
$336now only$262Round-trip
ORDRSW
22% Price DropFrontier Airlines
Depart Jan 10 · Return Jan 15
5-night trip · economy
$336now only$262Round-trip
ORDRSW
16% Price DropFrontier Airlines
Depart Nov 20 · Return Nov 25
5-night trip · economy
$336now only$282Round-trip
ORDRSW
15% Price DropFrontier Airlines
Depart Dec 3 · Return Dec 6
3-night trip · economy
$336now only$285Round-trip
ORDRSW
14% Price DropFrontier Airlines
Depart Dec 11 · Return Dec 15
4-night trip · economy
$336now only$289Round-trip
ORDRSW
14% Price DropFrontier Airlines
Depart Dec 11 · Return Dec 16
5-night trip · economy
$336now only$289Round-trip
Express Deal
Express Deals® deliver Priceline’s biggest discounts on flights. Pick your route and dates and we’ll match you with a great offer from a trusted airline. These exclusive “mystery deals” reward flexibility with even deeper savings — your airline is revealed after you book.
We don’t use Express Deal prices when calculating this route’s lowest price or price averages, because these offers require extra flexibility from travelers.
ORDRSW
BUDGET FRIENDLY
You’re guaranteed to get one of these airlines:
SouthwestUnitedAmericanSun CountryDepart Nov 14 · Return Nov 18
4-night trip · economy
$398Round-trip
ORDRSW
BUDGET FRIENDLY
You’re guaranteed to get one of these airlines:
SouthwestUnitedAmericanSun CountryDepart Dec 28
economy
$329One-way
Southwest Airlinesfound Oct 1111/02/26
5:05 am
MDWChicago Midway Airport
11/02/26
8:50 am
RSWSouthwest Florida International Airport
11/09/26
9:05 pm
RSWSouthwest Florida International Airport
11/09/26
11:05 pm
MDWChicago Midway Airport
$299
Southwest Airlinesfound Oct 1111/02/26
6:40 pm
MDWChicago Midway Airport
11/02/26
10:25 pm
RSWSouthwest Florida International Airport
11/09/26
9:05 pm
RSWSouthwest Florida International Airport
11/09/26
11:05 pm
MDWChicago Midway Airport
$299
Southwest Airlinesfound Oct 1411/18/26
6:45 am
MDWChicago Midway Airport
11/18/26
10:30 am
RSWSouthwest Florida International Airport
11/25/26
9:45 pm
RSWSouthwest Florida International Airport
11/25/26
11:45 pm
MDWChicago Midway Airport
$299
Southwest Airlinesfound Oct 1111/02/26
6:40 pm
MDWChicago Midway Airport
11/02/26
10:25 pm
RSWSouthwest Florida International Airport
11/09/26
5:40 am
RSWSouthwest Florida International Airport
11/09/26
9:05 am
MDWChicago Midway Airport
$309
BUNDLE + SAVE
Book a flight & hotel together for extra savings.
On average save $240 per traveler
Southwest Airlinesfound Oct 1111/02/26
5:05 am
MDWChicago Midway Airport
11/02/26
8:50 am
RSWSouthwest Florida International Airport
11/09/26
5:40 am
RSWSouthwest Florida International Airport
11/09/26
9:05 am
MDWChicago Midway Airport
$309
Southwest Airlinesfound Oct 1111/02/26
4:00 pm
MDWChicago Midway Airport
11/02/26
9:50 pm
RSWSouthwest Florida International Airport
11/09/26
9:05 pm
RSWSouthwest Florida International Airport
11/09/26
11:05 pm
MDWChicago Midway Airport
$309
Southwest Airlinesfound Oct 1111/02/26
5:05 am
MDWChicago Midway Airport
11/02/26
8:50 am
RSWSouthwest Florida International Airport
11/09/26
8:00 pm
RSWSouthwest Florida International Airport
11/10/26
12:10 am
MDWChicago Midway Airport
$309
United Airlinesfound Oct 1111/02/26
1:30 pm
ORDChicago O Hare Airport
11/02/26
5:32 pm
RSWSouthwest Florida International Airport
11/09/26
9:10 am
RSWSouthwest Florida International Airport
11/09/26
11:24 am
ORDChicago O Hare Airport
$419
American Airlinesfound Oct 1111/02/26
6:50 pm
ORDChicago O Hare Airport
11/02/26
10:43 pm
RSWSouthwest Florida International Airport
11/09/26
7:40 pm
RSWSouthwest Florida International Airport
11/09/26
10:00 pm
ORDChicago O Hare Airport
$420
Southwest Airlinesfound Oct 1111/02/26
6:40 pm
MDWChicago Midway Airport
11/02/26
10:25 pm
RSWSouthwest Florida International Airport
11/09/26
8:00 pm
RSWSouthwest Florida International Airport
11/10/26
12:10 am
MDWChicago Midway Airport
$309
No flights match these filters.
Top Deals on flights from Chicago to Fort Myers
Chicago, US (CHI) - Fort Myers, US (FMY)
Southwest AirlinesNov 1
6:40 pm
MDWChicago Midway Airport
Nov 1
10:25 pm
RSWSouthwest Florida International Airport
Search More
as low as
$183Chicago, US (CHI) - Fort Myers, US (FMY)
Southwest AirlinesNov 1
5:05 am
MDWChicago Midway Airport
Nov 1
8:50 am
RSWSouthwest Florida International Airport
Search More
as low as
$183Chicago, US (CHI) - Fort Myers, US (FMY)
Southwest AirlinesNov 1
8:00 am
MDWChicago Midway Airport
Nov 1
3:55 pm
RSWSouthwest Florida International Airport
Search More
as low as
$193Chicago, US (CHI) - Fort Myers, US (FMY)
Southwest AirlinesNov 1
10:10 am
MDWChicago Midway Airport
Nov 1
7:35 pm
RSWSouthwest Florida International Airport
Search More
as low as
$198Chicago, US (CHI) - Fort Myers, US (FMY)
Southwest AirlinesNov 1
9:15 pm
MDWChicago Midway Airport
Nov 2
7:45 am
RSWSouthwest Florida International Airport
Search More
as low as
$198Chicago, US (CHI) - Fort Myers, US (FMY)
Southwest AirlinesNov 1
8:00 am
MDWChicago Midway Airport
Nov 1
7:25 pm
RSWSouthwest Florida International Airport
Search More
as low as
$198Chicago, US (CHI) - Fort Myers, US (FMY)
Southwest AirlinesNov 1
8:45 am
MDWChicago Midway Airport
Nov 1
8:25 pm
RSWSouthwest Florida International Airport
Search More
as low as
$198Chicago, US (CHI) - Fort Myers, US (FMY)
Southwest AirlinesNov 1
9:20 pm
MDWChicago Midway Airport
Nov 2
9:45 am
RSWSouthwest Florida International Airport
Search More
as low as
$198Chicago, US (CHI) - Fort Myers, US (FMY)
Southwest AirlinesNov 1
6:50 am
MDWChicago Midway Airport
Nov 1
7:20 pm
RSWSouthwest Florida International Airport
Search More
as low as
$198Chicago, US (CHI) - Fort Myers, US (FMY)
Southwest AirlinesNov 1
7:50 am
MDWChicago Midway Airport
Nov 1
8:20 pm
RSWSouthwest Florida International Airport
Search More
as low as
$198Chicago, US (CHI) - Fort Myers, US (FMY)
Southwest AirlinesNov 1
9:15 pm
MDWChicago Midway Airport
Nov 2
10:15 am
RSWSouthwest Florida International Airport
Search More
as low as
$198Chicago, US (CHI) - Fort Myers, US (FMY)
Southwest AirlinesNov 1
7:30 am
MDWChicago Midway Airport
Nov 1
8:35 pm
RSWSouthwest Florida International Airport
Search More
as low as
$198Best Fort Myers Hotel + Flight Packages
Chicago - Fort Myers packages
Round-trip flight from Chicago
CHI to FMY
Quality Inn Fort Myers Cape Coral
Fort Myers, 4760 South Cleveland Avenue
6.7756 Reviews2-Star Hotel
22% Package Savings
$403/person
$1,031 $805 total
Incl. Flight + Hotel
Round-trip flight from Chicago
CHI to FMY
Baymont by Wyndham Fort Myers Central
Fort Myers, 4850 South Cleveland Avenue
5.91,035 Reviews2.5-Star Hotel
16% Package Savings
$448/person
$1,068 $896 total
Incl. Flight + Hotel
Round-trip flight from Chicago
CHI to FMY
HomeTowne Studios by Red Roof Fort Myers
Fort Myers, 4470 Executive Circle
8.426 Reviews2-Star Hotel
4% Package Savings
$461/person
$955 $921 total
Incl. Flight + Hotel
Round-trip flight from Chicago
CHI to FMY
Drury Inn & Suites Fort Myers Airport FGCU
Fort Myers, 9950 University Plaza Dr.
9.2678 Reviews4-Star Hotel
12% Package Savings
$722/person
$1,631 $1,443 total
Incl. Flight + Hotel
Round-trip flight from Chicago
CHI to FMY
Howard Johnson by Wyndham Ft. Myers FL
Fort Myers, 4811 S. Cleveland Ave
6.7557 Reviews2-Star Hotel
6% Package Savings
$430/person
$909 $859 total
Incl. Flight + Hotel
Round-trip flight from Chicago
CHI to FMY
Candlewood Suites Fort Myers/Sanibel Gateway By IHG
Fort Myers, 9740 Commerce Center Ct
7.8341 Reviews2.5-Star Hotel
15% Package Savings
$514/person
$1,208 $1,028 total
Incl. Flight + Hotel
Round-trip flight from Chicago
CHI to FMY
Comfort Inn & Suites Fort Myers Airport
Fort Myers, 10081 Intercom Drive
8.2637 Reviews2.5-Star Hotel
7% Package Savings
$579/person
$1,245 $1,157 total
Incl. Flight + Hotel
Best Fort Myers Hotel + Flight + Car Packages
Chicago - Fort Myers packages
Round-trip flight from Chicago
CHI to FMY
HomeTowne Studios by Red Roof Fort Myers
Fort Myers, 4470 Executive Circle
8.426 Reviews2-Star Hotel
Rental car included
Pick-up in FMY
9% Package Savings
$578/person
$1,272 $1,156 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to FMY
Drury Inn & Suites Fort Myers Airport FGCU
Fort Myers, 9950 University Plaza Dr.
9.2678 Reviews4-Star Hotel
Rental car included
Pick-up in FMY
14% Package Savings
$839/person
$1,950 $1,678 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to FMY
Howard Johnson by Wyndham Ft. Myers FL
Fort Myers, 4811 S. Cleveland Ave
6.7557 Reviews2-Star Hotel
Rental car included
Pick-up in FMY
11% Package Savings
$547/person
$1,228 $1,094 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to FMY
Candlewood Suites Fort Myers/Sanibel Gateway By IHG
Fort Myers, 9740 Commerce Center Ct
7.8341 Reviews2.5-Star Hotel
Rental car included
Pick-up in FMY
17% Package Savings
$632/person
$1,525 $1,263 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to FMY
Comfort Inn & Suites Fort Myers Airport
Fort Myers, 10081 Intercom Drive
8.2637 Reviews2.5-Star Hotel
Rental car included
Pick-up in FMY
11% Package Savings
$697/person
$1,563 $1,393 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to FMY
Hyatt Place Fort Myers Forum
Fort Myers, 2600 Champion Ring Road
8.4795 Reviews3-Star Hotel
Rental car included
Pick-up in FMY
28% Package Savings
$676/person
$1,877 $1,351 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to FMY
Quality Inn Fort Myers Cape Coral
Fort Myers, 4760 South Cleveland Avenue
6.7756 Reviews2-Star Hotel
Rental car included
Pick-up in FMY
23% Package Savings
$521/person
$1,349 $1,041 total
Incl. Flight + Hotel + Car
Round-trip flight from Chicago
CHI to FMY
Baymont by Wyndham Fort Myers Central
Fort Myers, 4850 South Cleveland Avenue
5.91,035 Reviews2.5-Star Hotel
Rental car included
Pick-up in FMY
18% Package Savings
$566/person
$1,386 $1,132 total
Incl. Flight + Hotel + Car
When is the cheapest time to fly?
Cheapest in late January at about $255
Fares from Chicago to Fort Myers are lowest in late January, around $255, and January is the cheapest month overall, averaging $262. They peak in late December at about $365, $110 more than the low. The yearly average is $306.
Show the data
| Month | Average fare | Early month | Late month |
|---|---|---|---|
| January | $262 | $269 | $255 |
| February | $281 | $273 | $289 |
| March | $339 | $312 | $365 |
| April | $328 | $341 | $315 |
| May | $308 | $304 | $312 |
| June | $319 | $319 | $319 |
| July | $303 | $309 | $297 |
| August | $276 | $288 | $263 |
| September | $293 | $283 | $303 |
| October | $322 | $332 | $313 |
| November | $315 | $301 | $329 |
| December | $331 | $295 | $365 |
How far in advance should I book?
Cheapest about 4 weeks out at $299
Book about 4 weeks before departure for the best fares from Chicago to Fort Myers, around $299. Booking in the final days before the flight costs about $514, $215 more. Booking six months ahead runs about $572.
Show the data
| Days before departure | Average fare |
|---|---|
| 180 days | $572 |
| 172 days | $564 |
| 164 days | $545 |
| 156 days | $527 |
| 148 days | $501 |
| 140 days | $470 |
| 132 days | $458 |
| 124 days | $449 |
| 116 days | $419 |
| 108 days | $389 |
| 100 days | $361 |
| 92 days | $340 |
| 84 days | $330 |
| 76 days | $324 |
| 68 days | $320 |
| 2mo | $319 |
| 52 days | $312 |
| 44 days | $307 |
| 36 days | $304 |
| 31 days | $299 |
| 28 days | $301 |
| 20 days | $324 |
| 12 days | $386 |
| 4 days | $475 |
| 0 days | $514 |
What's the cheapest day of the week to fly?
Tuesday is the cheapest day of the week to fly from Chicago to Fort Myers. At $532 it is 8% cheaper than the average day. Friday is the most expensive day, 6% above average.
Show the data
| Day | Average fare |
|---|---|
| Sun | $598 |
| Mon | $587 |
| Tue | $532 |
| Wed | $559 |
| Thu | $585 |
| Fri | $612 |
| Sat | $573 |
When is the best time of day to fly?
Morning (5am - 12pm) is the cheapest time of day to fly from Chicago to Fort Myers. At $353 it is 46% cheaper than the average time. Evening (5pm - 9pm) is the most expensive time, 127% above average.
Show the data
| Time of day | Average fare |
|---|---|
| Morning | $353 |
| Midday | $420 |
| Afternoon | $355 |
| Evening | $1,475 |
What do round-trip flights from Chicago to Fort Myers cost?
Share of fares in each price range, adjusted to current prices.
Show the data
| Price range | Share of fares |
|---|---|
| $0 to $200 | 3% |
| $200 to $400 | 22% |
| $400 to $600 | 41% |
| $600 to $800 | 16% |
| $800 to $1,000 | 9% |
| $1,000 to $1,200 | 5% |
| $1,200 and up | 4% |
Methodology: learn how we calculate these charts
The charts “When is the cheapest time to fly?”, “How far in advance should I book?”, “What's the cheapest day of the week to fly?” and “What do round-trip flights from Chicago to Fort Myers cost?” are built from the prices Priceline customers actually paid for flights on this route over the past 12 months or more.
Where a route has too few bookings to fill every point in a chart, we borrow the shape of the curve from a group of routes with similar price behavior and fit it to the fares booked on this route.
Because past fares don’t reflect today’s market, we then adjust the historical prices for current conditions such as inflation and fuel costs, using the round-trip fares found in recent searches on this route.
The chart “When is the best time of day to fly?” is calculated directly from the fares found in recent searches, not from historical bookings.