Round-trip flight from Fort Myers
FMY to CHI
The Chicago Hotel Collection Ambassador Gold Coast
Chicago, 1301 North State Parkway
8662 Reviews4-Star Hotel
23% Package Savings
$829/person
$2,145 $1,657 total
Incl. Flight + Hotel
Flight Deals from Fort Myers to Chicago from $106
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Top flight deals from leading airlines:
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Good to Know
Essential information to help you plan your flight from Fort Myers to Chicago.
Cheapest Flight Round-trip
$112
Lowest round-trip price available on Priceline for this route right now.
This fare recently dropped from $276.
Nonstop · economyCheapest Flight One-way
$106
Lowest one-way price found on Priceline for this route in the last 16 days. Found 11 days ago.
The typical one-way fare on this route is $161.
Outbound · Oct 29
6:40 amRSWSouthwest Florida International Airport
8:30 amMDWChicago Midway Airport
2h 50m · Nonstop
Good deal price
$332
A round-trip at or under $332 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
Thursdays
Thursday departures average $587 on this route, the lowest of any weekday.
$81 less than the average weekday, which is $668.
Best time to fly
Late Nights
Late Night departures average $364 on this route, the lowest of any time of day.
$204 less than the average departure, which is $568.
Low season
February
Fares average $250 in February, the cheapest month to fly this route, bottoming out near $238 in early February.
$65 below the yearly average of $315.
When to book
5 weeks ahead
Fares on this route are lowest when booked about 5 weeks before departure.
Booking then averages $299, versus $513 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.
RSWORD
59% Price DropFrontier Airlines
Depart Dec 10 · Return Dec 13
3-night trip · economy
$276now only$112Round-trip
RSWORD
50% Price DropFrontier Airlines
Depart Dec 11 · Return Dec 14
3-night trip · economy
$276now only$138Round-trip
RSWORD
50% Price DropFrontier Airlines
Depart Dec 3 · Return Dec 6
3-night trip · economy
$276now only$139Round-trip
RSWORD
31% Price DropFrontier Airlines
Depart Nov 24 · Return Nov 28
4-night trip · economy
$277now only$192Round-trip
RSWORD
27% Price Drop
Delta Air Lines
Depart Nov 24 · Return Nov 27
3-night trip · economy
$277now only$201Round-trip
RSWORD
25% Price DropSouthwest Airlines
Depart Nov 23 · Return Nov 26
3-night trip · economy
$277now only$207Round-trip
RSWORD
25% Price DropSouthwest Airlines
Depart Nov 12 · Return Nov 16
4-night trip · economy
$277now only$208Round-trip
RSWORD
21% Price DropSouthwest Airlines
Depart Nov 4 · Return Nov 7
3-night trip · economy
$277now only$219Round-trip
RSWORD
18% Price DropSouthwest Airlines
Depart Nov 25 · Return Nov 28
3-night trip · economy
$276now only$226Round-trip
RSWORD
12% Price DropUnited Airlines
Depart Oct 27 · Return Oct 30
3-night trip · economy
$277now only$245Round-trip
RSWORD
12% Price DropSouthwest Airlines
Depart Nov 6 · Return Nov 9
3-night trip · economy
$277now only$245Round-trip
RSWORD
12% Price DropDelta Air Lines
Depart Dec 1 · Return Dec 4
3-night trip · economy
$277now only$245Round-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.
RSWORD
BUDGET FRIENDLY
You’re guaranteed to get one of these airlines:
SouthwestFrontierUnitedAmericanDepart Oct 23 · Return Oct 28
5-night trip · economy
$279Round-trip
RSWMDW
BUDGET FRIENDLY
You’re guaranteed to get one of these airlines:
SouthwestFrontierUnitedAmericanDepart Dec 30 · Return Jan 3
4-night trip · economy
$400Round-trip
RSWORD
BUDGET FRIENDLY
You’re guaranteed to get one of these airlines:
SouthwestFrontierUnitedAmericanDepart Mar 5
economy
$183One-way
RSWORD
BUDGET FRIENDLY
You’re guaranteed to get one of these airlines:
SouthwestFrontierUnitedAmericanDepart Jan 17
economy
$196One-way
Southwest Airlinesfound Oct 1011/02/26
4:35 pm
RSWSouthwest Florida International Airport
11/02/26
6:30 pm
MDWChicago Midway Airport
11/09/26
7:45 am
MDWChicago Midway Airport
11/09/26
11:30 am
RSWSouthwest Florida International Airport
$299
Southwest Airlinesfound Oct 1011/02/26
9:05 pm
RSWSouthwest Florida International Airport
11/02/26
11:00 pm
MDWChicago Midway Airport
11/09/26
7:45 am
MDWChicago Midway Airport
11/09/26
11:30 am
RSWSouthwest Florida International Airport
$299
Southwest Airlinesfound Oct 1011/02/26
4:35 pm
RSWSouthwest Florida International Airport
11/02/26
6:30 pm
MDWChicago Midway Airport
11/09/26
5:05 am
MDWChicago Midway Airport
11/09/26
8:50 am
RSWSouthwest Florida International Airport
$299
Frontier Airlinesfound Oct 1811/13/26
12:45 pm
RSWSouthwest Florida International Airport
11/13/26
10:43 pm
ORDChicago O Hare Airport
11/20/26
6:40 am
ORDChicago O Hare Airport
11/20/26
4:53 pm
RSWSouthwest Florida International Airport
$330
BUNDLE + SAVE
Book a flight & hotel together for extra savings.
On average save $240 per traveler
Southwest Airlinesfound Oct 1011/02/26
9:05 pm
RSWSouthwest Florida International Airport
11/02/26
11:00 pm
MDWChicago Midway Airport
11/09/26
5:05 am
MDWChicago Midway Airport
11/09/26
8:50 am
RSWSouthwest Florida International Airport
$299
Southwest Airlinesfound Oct 1011/02/26
7:10 am
RSWSouthwest Florida International Airport
11/02/26
9:05 am
MDWChicago Midway Airport
11/09/26
7:45 am
MDWChicago Midway Airport
11/09/26
11:30 am
RSWSouthwest Florida International Airport
$299
Southwest Airlinesfound Oct 1011/02/26
7:10 am
RSWSouthwest Florida International Airport
11/02/26
9:05 am
MDWChicago Midway Airport
11/09/26
5:05 am
MDWChicago Midway Airport
11/09/26
8:50 am
RSWSouthwest Florida International Airport
$299
Sun Country Airlinesfound Oct 1511/18/26
4:20 pm
RSWSouthwest Florida International Airport
11/19/26
6:30 pm
ORDChicago O Hare Airport
11/25/26
7:35 pm
ORDChicago O Hare Airport
11/26/26
5:56 pm
RSWSouthwest Florida International Airport
$386
Southwest Airlinesfound Oct 1011/02/26
10:25 am
RSWSouthwest Florida International Airport
11/02/26
12:25 pm
MDWChicago Midway Airport
11/09/26
5:05 am
MDWChicago Midway Airport
11/09/26
8:50 am
RSWSouthwest Florida International Airport
$299
United Airlinesfound Oct 1011/02/26
9:10 am
RSWSouthwest Florida International Airport
11/02/26
11:24 am
ORDChicago O Hare Airport
11/09/26
1:30 pm
ORDChicago O Hare Airport
11/09/26
5:32 pm
RSWSouthwest Florida International Airport
$419
No flights match these filters.
Top Deals on flights from Fort Myers to Chicago
Fort Myers, US (FMY) - Chicago, US (CHI)
Southwest AirlinesOct 29
6:40 am
RSWSouthwest Florida International Airport
Oct 29
8:30 am
MDWChicago Midway Airport
Search More
as low as
$106Fort Myers, US (FMY) - Chicago, US (CHI)
Southwest AirlinesOct 29
6:40 pm
RSWSouthwest Florida International Airport
Oct 29
8:30 pm
MDWChicago Midway Airport
Search More
as low as
$106Fort Myers, US (FMY) - Chicago, US (CHI)
Southwest AirlinesOct 29
6:20 pm
RSWSouthwest Florida International Airport
Oct 29
9:40 pm
MDWChicago Midway Airport
Search More
as low as
$116Fort Myers, US (FMY) - Chicago, US (CHI)
Southwest AirlinesOct 29
7:25 pm
RSWSouthwest Florida International Airport
Oct 29
11:10 pm
MDWChicago Midway Airport
Search More
as low as
$116Fort Myers, US (FMY) - Chicago, US (CHI)
Southwest AirlinesOct 29
5:50 am
RSWSouthwest Florida International Airport
Oct 29
10:00 am
MDWChicago Midway Airport
Search More
as low as
$116Fort Myers, US (FMY) - Chicago, US (CHI)
Southwest AirlinesOct 29
7:15 am
RSWSouthwest Florida International Airport
Oct 29
12:30 pm
MDWChicago Midway Airport
Search More
as low as
$116Fort Myers, US (FMY) - Chicago, US (CHI)
Southwest AirlinesOct 29
6:25 pm
RSWSouthwest Florida International Airport
Oct 29
11:55 pm
MDWChicago Midway Airport
Search More
as low as
$116Fort Myers, US (FMY) - Chicago, US (CHI)
Southwest AirlinesOct 29
6:20 pm
RSWSouthwest Florida International Airport
Oct 30
12:25 am
MDWChicago Midway Airport
Search More
as low as
$116Fort Myers, US (FMY) - Chicago, US (CHI)
Southwest AirlinesOct 29
7:15 am
RSWSouthwest Florida International Airport
Oct 29
1:45 pm
MDWChicago Midway Airport
Search More
as low as
$116Fort Myers, US (FMY) - Chicago, US (CHI)
Southwest AirlinesOct 29
2:50 pm
RSWSouthwest Florida International Airport
Oct 29
9:25 pm
MDWChicago Midway Airport
Search More
as low as
$116Fort Myers, US (FMY) - Chicago, US (CHI)
Southwest AirlinesOct 29
6:00 am
RSWSouthwest Florida International Airport
Oct 29
12:45 pm
MDWChicago Midway Airport
Search More
as low as
$121Fort Myers, US (FMY) - Chicago, US (CHI)
Southwest AirlinesOct 29
5:50 am
RSWSouthwest Florida International Airport
Oct 29
12:45 pm
MDWChicago Midway Airport
Search More
as low as
$121Best Chicago Hotel + Flight Packages
Fort Myers - Chicago packages
Round-trip flight from Fort Myers
FMY to CHI
The Chicago Hotel Collection Magnificent Mile
Chicago, 166 East Superior Street
7.21,069 Reviews4-Star Hotel
14% Package Savings
$896/person
$2,088 $1,792 total
Incl. Flight + Hotel
Round-trip flight from Fort Myers
FMY to CHI
Chicago South Loop Hotel
Chicago, 11 West 26th Street
6.24,224 Reviews2.5-Star Hotel
$1,005/person
$2,010 total
Incl. Flight + Hotel
Round-trip flight from Fort Myers
FMY to CHI
The Wade
Chicago, 644 N Lake Shore Dr
8.12,404 Reviews4.5-Star Hotel
22% Package Savings
$1,073/person
$2,738 $2,146 total
Incl. Flight + Hotel
Round-trip flight from Fort Myers
FMY to CHI
The Godfrey Hotel Chicago
Chicago, 127 West Huron Street
8.51,268 Reviews4.5-Star Hotel
13% Package Savings
$1,053/person
$2,427 $2,105 total
Incl. Flight + Hotel
Round-trip flight from Fort Myers
FMY to CHI
Hilton Chicago
Chicago, 720 South Michigan Avenue
81,551 Reviews4-Star Hotel
6% Package Savings
$1,685/person
$3,576 $3,370 total
Incl. Flight + Hotel
Round-trip flight from Fort Myers
FMY to CHI
Doubletree By Hilton Chicago Magnificent Mile
Chicago, 300 E. Ohio Street
8.31,730 Reviews4-Star Hotel
12% Package Savings
$1,077/person
$2,438 $2,154 total
Incl. Flight + Hotel
Round-trip flight from Fort Myers
FMY to CHI
Kinzie Hotel
Chicago, 20 West Kinzie Street
8.71,289 Reviews4-Star Hotel
30% Package Savings
$1,091/person
$3,097 $2,181 total
Incl. Flight + Hotel
Best Chicago Hotel + Flight + Car Packages
Fort Myers - Chicago packages
Round-trip flight from Fort Myers
FMY to CHI
The Wade
Chicago, 644 N Lake Shore Dr
8.12,404 Reviews4.5-Star Hotel
Rental car included
Pick-up in CHI
21% Package Savings
$1,199/person
$3,022 $2,398 total
Incl. Flight + Hotel + Car
Round-trip flight from Fort Myers
FMY to CHI
The Godfrey Hotel Chicago
Chicago, 127 West Huron Street
8.51,268 Reviews4.5-Star Hotel
Rental car included
Pick-up in CHI
13% Package Savings
$1,178/person
$2,712 $2,356 total
Incl. Flight + Hotel + Car
Round-trip flight from Fort Myers
FMY to CHI
Hilton Chicago
Chicago, 720 South Michigan Avenue
81,551 Reviews4-Star Hotel
Rental car included
Pick-up in CHI
6% Package Savings
$1,811/person
$3,858 $3,622 total
Incl. Flight + Hotel + Car
Round-trip flight from Fort Myers
FMY to CHI
Doubletree By Hilton Chicago Magnificent Mile
Chicago, 300 E. Ohio Street
8.31,730 Reviews4-Star Hotel
Rental car included
Pick-up in CHI
12% Package Savings
$1,203/person
$2,720 $2,406 total
Incl. Flight + Hotel + Car
Round-trip flight from Fort Myers
FMY to CHI
Kinzie Hotel
Chicago, 20 West Kinzie Street
8.71,289 Reviews4-Star Hotel
Rental car included
Pick-up in CHI
28% Package Savings
$1,217/person
$3,379 $2,433 total
Incl. Flight + Hotel + Car
Round-trip flight from Fort Myers
FMY to CHI
The Chicago Hotel Collection Ambassador Gold Coast
Chicago, 1301 North State Parkway
8662 Reviews4-Star Hotel
Rental car included
Pick-up in CHI
21% Package Savings
$955/person
$2,427 $1,909 total
Incl. Flight + Hotel + Car
Round-trip flight from Fort Myers
FMY to CHI
The Chicago Hotel Collection Magnificent Mile
Chicago, 166 East Superior Street
7.21,069 Reviews4-Star Hotel
Rental car included
Pick-up in CHI
14% Package Savings
$1,022/person
$2,370 $2,044 total
Incl. Flight + Hotel + Car
Round-trip flight from Fort Myers
FMY to CHI
Chicago South Loop Hotel
Chicago, 11 West 26th Street
6.24,224 Reviews2.5-Star Hotel
Rental car included
Pick-up in CHI
1% Package Savings
$1,131/person
$2,294 $2,262 total
Incl. Flight + Hotel + Car
When is the cheapest time to fly?
Cheapest in early February at about $238
Fares from Fort Myers to Chicago are lowest in early February, around $238, and February is the cheapest month overall, averaging $250. They peak in late July at about $351, $113 more than the low. The yearly average is $315.
Show the data
| Month | Average fare | Early month | Late month |
|---|---|---|---|
| January | $264 | $284 | $246 |
| February | $250 | $238 | $265 |
| March | $329 | $310 | $346 |
| April | $317 | $326 | $308 |
| May | $321 | $310 | $331 |
| June | $345 | $348 | $343 |
| July | $349 | $347 | $351 |
| August | $319 | $332 | $305 |
| September | $318 | $308 | $327 |
| October | $332 | $345 | $320 |
| November | $308 | $296 | $320 |
| December | $325 | $304 | $345 |
How far in advance should I book?
Cheapest about 5 weeks out at $299
Book about 5 weeks before departure for the best fares from Fort Myers to Chicago, around $299. Booking in the final days before the flight costs about $513, $214 more. Booking six months ahead runs about $628.
Show the data
| Days before departure | Average fare |
|---|---|
| 180 days | $628 |
| 172 days | $611 |
| 164 days | $572 |
| 156 days | $526 |
| 148 days | $502 |
| 140 days | $498 |
| 132 days | $485 |
| 124 days | $460 |
| 116 days | $426 |
| 108 days | $391 |
| 100 days | $369 |
| 92 days | $356 |
| 84 days | $341 |
| 76 days | $334 |
| 68 days | $325 |
| 2mo | $314 |
| 52 days | $306 |
| 44 days | $303 |
| 36 days | $301 |
| 35 days | $299 |
| 28 days | $303 |
| 20 days | $332 |
| 12 days | $402 |
| 4 days | $482 |
| 0 days | $513 |
What's the cheapest day of the week to fly?
Thursday is the cheapest day of the week to fly from Fort Myers to Chicago. At $587 it is 12% cheaper than the average day. Sunday is the most expensive day, 18% above average.
Show the data
| Day | Average fare |
|---|---|
| Sun | $790 |
| Mon | $711 |
| Tue | $691 |
| Wed | $653 |
| Thu | $587 |
| Fri | $607 |
| Sat | $638 |
When is the best time of day to fly?
Late night (9pm - 12am) is the cheapest time of day to fly from Fort Myers to Chicago. At $364 it is 36% cheaper than the average time. Morning (5am - 12pm) is the most expensive time, 38% above average.
Show the data
| Time of day | Average fare |
|---|---|
| Morning | $785 |
| Midday | $504 |
| Afternoon | $456 |
| Evening | $730 |
| Late Night | $364 |
What do round-trip flights from Fort Myers to Chicago 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 | 27% |
| $400 to $600 | 33% |
| $600 to $800 | 19% |
| $800 to $1,000 | 13% |
| $1,000 to $1,200 | 3% |
| $1,200 and up | 2% |
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 Fort Myers to Chicago 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.