Cheap flights from Fort Myers to Chicago (RSW - CHI)

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The best prices from Fort Myers SW Florida Intl to Chicago are usually found in August or January, booked 15 days in advance, depart on a Friday or Thursday and return on a Tuesday

How to find the cheapest flight from
Fort Myers (RSW) to Chicago (CHI)

All the information you need to plan the best RSW to CHI flight in 2021: compare Fort Myers to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
RSW - CHI
Price
$70 - $184
CHI
Temperature
23 - 73.4 °F
CHI
Precipitation
1.7 - 4.9 inches

Popular in

June

High demand for flights, 28% potential price rise

Cheapest in

August

Best time to find cheap flights, 47% potential price drop

Round-trip from

$70

From Fort Myers SW Florida Intl to Chicago (CHI)

One-way from

$49

One-way flight from Fort Myers SW Florida Intl to Chicago (CHI)

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest month to fly from Fort Myers to Chicago?

August is one of the best times of the year to fly to Chicago from Fort Myers. Prices for August average $132 per person but you can even find prices for as low as $34. The most expensive prices can be found in the month of June. Opting for a August flight can save you 39% on your journey compared to booking in August

How far in advance should I book a flight from Fort Myers to Chicago?

Find a great deal and save up to 23% by booking at least 15 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from Fort Myers to Chicago within the next two weeks, with the cheapest ticket starting at $111.

When is the cheapest time to fly from Fort Myers to Chicago (RSW - CHI)?

It’s typically best to fly out from Fort Myers to Chicago in the evening. Doing so could potentially save you 39% on the flight price compared to flying in the morning, which is usually more expensive.

What is the cheapest day to fly round-trip from Fort Myers to Chicago?

Thursday is generally a great day to depart. Flying on this day could help you save up to 40%.

Cheap flights from Fort Myers to Chicago in October, November 2021

The best prices found for RSW to CHI flights for October, November
5 Nov - 14 Nov
$53pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl
9 Nov - 10 Nov
$55pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl
23 Nov - 30 Nov
$56pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl

Fort Myers SW Florida Intl to Chicago 2021 flight deals

Cheap flights to Chicago from Fort Myers found for this year
5 Nov - 14 Nov
$53pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl
9 Nov - 10 Nov
$55pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl
23 Nov - 30 Nov
$56pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl

Non-stop flights to Chicago from Fort Myers

Save time with Fort Myers to Chicago direct flight deals
9 Nov - 10 Nov
$55pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl
9 Nov - 14 Nov
$57pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl
20 Nov - 29 Nov
$58pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl

Last minute flights from Fort Myers to Chicago

Late deals on round-trip flights to Chicago from Fort Myers, departing today and this week
5 Nov - 14 Nov
$53pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl
5 Nov - 8 Nov
$57pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl
3 Nov - 16 Nov
$58pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl

One-way flights to Chicago from Fort Myers

The cheapest one-way flights from Fort Myers to Chicago
2:30 am - 4:35 am
United Airlines
Nonstop
3h 05m
RSW - ORD
United Airlines
$49
United
1:00 am - 1:01 pm
Multiple Airlines
1 Stop
13h 01m
RSW - ORD
Multiple Airlines
$71
FareScan
2:00 am - 4:08 am
Spirit Airlines
Nonstop
3h 08m
RSW - ORD
Spirit Airlines
$72
Spirit

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Fort Myers</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Fort Myers to Chicago

What airport do you fly from for flights from Fort Myers to Chicago?

For a flight from Fort Myers to Chicago, you will be flying from SW Florida Intl. Fort Myers SW Florida Intl (RSW) is just 10.0 mi from the center of the city. SW Florida Intl is the only Fort Myers airport and it handles 16 outbound flights to Chicago per day. 8 airlines have flights to Chicago from Fort Myers SW Florida Intl on a regular basis.

Which airlines flying from Fort Myers SW Florida Intl to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Fort Myers SW Florida Intl to Chicago have new flexible policies in place due to COVID-19. Spirit Airlines, American Airlines, and United Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Spirit Airlines with this kind of flexibility.

Can I find flights from Fort Myers to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Fort Myers to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $55, but on average you can expect to pay $70.

Are there nonstop flights from Fort Myers to Chicago for under $100 on Cheapflights?

Cheapflights has at least 20 direct flights from Fort Myers to Chicago under $100. A good price for a nonstop flight from Fort Myers to Chicago is less than $70.

Are there last-minute flights available from Fort Myers to Chicago for under $100?

There are currently 20+ open flights from Fort Myers to Chicago within the next 7 days for less than $100.

What days are nonstop flights available from Fort Myers to Chicago?

Days when nonstop flights are available for this flight are: Sunday, Monday, Wednesday, Thursday, Friday, Saturday.

How many flights depart from Fort Myers to Chicago on average per day?

Per day, 23 flights depart from Fort Myers to Chicago on average.
Morning (6am - Noon) - 30% of flight departures
Afternoon (Noon - 6pm) - 70% of flight departures

How long is the flight from Fort Myers to Chicago?

Airlines like Spirit Airlines, Frontier, and United Airlines fly from Fort Myers to Chicago in about 3h 04m. The time it takes to get you to your destination is usually consistent. Airlines will cover a distance of 1129 mi. Generally, flights for this route are nonstop.

What are the cheapest airlines flying from Fort Myers to Chicago round-trip?

Our cheapest airline available from Fort Myers to Chicago is Spirit Airlines. Our recent data shows that you can find tickets from as low as $55 on this airline. Additional options worth looking into are Frontier and United Airlines, starting at $75 and $92 round-trip. You may be able to fly from Fort Myers to Chicago for 58% less than the average price by searching for these airlines.

What are the cheapest airlines to fly from Fort Myers to Chicago one-way?

To fly one-way, consider booking your trip with Spirit Airlines, which is currently one of the cheapest options available, starting at $27. Frontier flights start at $35 while deals on United Airlines start at $49 one-way.

What are the most popular routes from Fort Myers to Chicago?

While some choose either Fort Myers SW Florida Intl - Chicago Midway or Fort Myers SW Florida Intl - Chicago Greater Rockford, Fort Myers SW Florida Intl - Chicago O'Hare Intl is the most popular route from Fort Myers to Chicago.

What are the cheapest flights from Fort Myers to Chicago?

On average you can expect to pay $469 for a flight from Fort Myers to Chicago. The cheapest flight overall is $56 while the most popular route, (Fort Myers SW Florida Intl - Chicago O'Hare Intl) is currently priced at $58.

What are the most reliable airlines from Fort Myers to Chicago?

The top 3 most reliable airlines when flying from Fort Myers to Chicago are Republic Airways (100%), Spirit Airlines (91%) and Iberia (85%).

What are the most popular airlines that fly from Fort Myers to Chicago?

Before booking your flight from Fort Myers to Chicago check out the most popular airlines for this route: Major Airline, American Airlines or Delta.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Fort Myers?

Information is based on travel restrictions for travel to Chicago within the United States

Most visitors from Fort Myers SW Florida Intl need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Fort Myers SW Florida Intl must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Chicago.

Quarantine requirements
Visitors from Fort Myers SW Florida Intl are not required to quarantine after entering Chicago.

Do I need a test to fly back to Fort Myers from Chicago?

Returning to Fort Myers SW Florida Intl from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours before departing to Fort Myers SW Florida Intl.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Fort Myers SW Florida Intl.

Hide COVID Travel Restrictions for Chicago, IL

Alternative routes for Fort Myers to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Destination information for Chicago

Things to know before you go - useful duration and weather info for your trip from Fort Myers to Chicago.
Flight duration from RSW to Chicago
3h 04m
Average temperature for October in Chicago
64.4 °F
Avg rainfall for October in Chicago
2.6 ″

Airports servicing Fort Myers

Airports servicing Chicago

Midway (MDW)
Rockford (RFD)

Top 5 airlines flying from Fort Myers SW Florida Intl to Chicago

The chart below displays the airlines Cheapflights users traveling from Fort Myers to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
$37 $116 No cancel fee 62%
Spirit Airlines
$56 $173 No cancel fee 65%
United Airlines
$60 $229 No cancel fee 69%
American Airlines
$63 $197 No cancel fee 71%
Delta
$97 $296 No cancel fee N/A

Hourly flight availability from Fort Myers to Chicago

See what time of day planes typically take off from Fort Myers towards Chicago.
Afternoon Noon to 6 PM 53% of RSW to CHI departures
Morning 6 AM to noon 33% of RSW to CHI departures
Early morning Midnight to 6 AM 10% of RSW to CHI departures
Evening 6 PM to midnight 4% of RSW to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Fort Myers to Chicago
See how many times per day planes take to the skies headed from Fort Myers to Chicago.
Sunday
8 daily flights
Monday
19 daily flights
Tuesday
22 daily flights
Wednesday
25 daily flights
Thursday
16 daily flights
Friday
18 daily flights
Saturday
8 daily flights
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