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$61+ Cheap flights from Fort Myers (RSW) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/2. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — CHI
Dec 24 — Dec 311
Tue 12/24
Tue 12/31
1 adult, Economy
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The best prices from Fort Myers SW Florida Intl to Chicago are usually found in January or May, booked 39 days in advance, depart on a Saturday or Thursday and return on a Tuesday

Cheap flight deals from Fort Myers to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Fort Myers (RSW) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated December 19, 2024.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$107
(Cheapflightsfares)

One-way from

$61
(FlightHub)

Popular in

October

Cheapest in

January

Average price

$262
Provider with most accurate pricing for Fort Myers SW Florida Intl-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Fort Myers SW Florida Intl-Chicago (CHI) flights.
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From Fort Myers SW Florida Intl to Chicago (CHI)
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One-way flight from Fort Myers SW Florida Intl to Chicago (CHI)
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High demand for flights, 9% potential price rise
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Best time to find cheap flights, 3% potential price drop
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Average for round-trip flights in December 2024
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Find flight deals from Fort Myers to Chicago

Cheapest flights from Fort Myers to Chicago
Explore the most affordable flight options available from Fort Myers to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on December 19, 2024.

This Frontier deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/299:57 amRSW - ORD
Nonstop3h 15mFrontier
Thu 1/210:15 pmORD - RSW
1 stop8h 55mFrontier
Deal found 12/18$151
This Kiwi.com deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/3010:45 pmRSW - ORD
Nonstop3h 02mMultiple Airlines
Thu 1/210:15 pmORD - RSW
1 stop8h 55mMultiple Airlines
Deal found 12/18$152
This Cheapflightsfares deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2610:45 pmRSW - ORD
Nonstop3h 02mSpirit Airlines
Wed 1/16:05 amORD - RSW
Nonstop2h 59mSpirit Airlines
Deal found 12/18$177
This Trip.com deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/2810:21 pmRSW - MDW
1 stop9h 18mFrontier
Mon 12/309:59 pmMDW - RSW
1 stop9h 21mFrontier
Deal found 12/17$308
This Delta deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/312:51 pmRSW - ORD
1 stop5h 01mDelta
Tue 1/71:40 pmORD - RSW
1 stop6h 38mDelta
Deal found 12/18$332
This Delta deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/314:52 pmRSW - MDW
1 stop6h 14mDelta
Tue 1/710:57 amMDW - RSW
1 stop5h 08mDelta
Deal found 12/18$332
This Cheapflightsfares deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/235:49 pmRSW - ORD
1 stop16h 14mSun Country Air
Mon 12/307:30 pmORD - RSW
1 stop14h 26mSun Country Air
Deal found 12/18$382
This Mytrip deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2910:22 amRSW - RFD
2 stops25h 35mMultiple Airlines
Thu 1/25:05 pmRFD - RSW
2 stops25h 31mMultiple Airlines
Deal found 12/18$586
This Mytrip deal was found by Cheapflights users on 12/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/236:56 pmRSW - MDW
1 stop14h 53mMultiple Airlines
Sun 12/296:51 pmMDW - RSW
1 stop15h 04mMultiple Airlines
Deal found 12/17$637
This Southwest deal was found by Cheapflights users on 12/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2912:45 pmRSW - MDW
Nonstop2h 55mSouthwest
Thu 1/28:00 pmMDW - RSW
Nonstop2h 50mSouthwest
Deal found 12/18$646

Find flights from Fort Myers to Chicago within your budget

Customize your flight search to find flights from Fort Myers 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, Cheapflights users made 2,558,603 searches. Data last updated December 19, 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 2/6

12:32 pm-2:52 pm

Nonstop3h 20m

Chicago O'Hare Intl

Mon 2/10

6:15 pm-10:16 pm

Nonstop3h 01m

$107

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Tue 1/14

10:52 am-12:57 pm

Nonstop3h 05m

Chicago O'Hare Intl

Thu 1/16

5:35 am-9:29 am

Nonstop2h 54m

$108

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Sun 2/2

10:28 pm-12:48 am

Nonstop3h 20m

Chicago O'Hare Intl

Sun 2/9

5:37 pm-9:38 pm

Nonstop3h 01m

$110

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Fri 2/21

6:45 am-8:45 am

Nonstop3h 00m

Chicago Midway

Sat 2/22

7:20 pm-11:10 pm

Nonstop2h 50m

$164

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 1/31

12:05 pm-6:54 pm

1 stop7h 49m

Chicago O'Hare Intl

Mon 2/3

8:46 am-12:52 pm

Nonstop3h 06m

$174

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 2/5

5:29 pm-7:45 pm

Nonstop3h 16m

Chicago O'Hare Intl

Tue 2/11

7:00 am-1:04 pm

1 stop5h 04m

$183

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 2/6

10:40 am-5:53 pm

1 stop8h 13m

Chicago O'Hare Intl

Mon 2/10

11:00 am-9:43 pm

1 stop9h 43m

$190

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Sat 2/22

5:17 pm-12:17 am

1 stop8h 00m

Chicago Midway

Sat 3/1

6:40 am-4:26 pm

1 stop8h 46m

$198

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 2/5

11:57 am-6:41 pm

1 stop7h 44m

Chicago O'Hare Intl

Thu 2/6

10:05 am-7:36 pm

1 stop8h 31m

$216

Fort MyersChicago

RSW - MDW

RSWMDW

Fort Myers SW Florida Intl

Thu 2/6

6:40 am-12:42 pm

1 stop7h 02m

Chicago Midway

Sun 2/9

3:41 pm-9:13 pm

1 stop4h 32m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/18

Showing 1-10 of 28 results
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Compare providers for flights from Fort Myers to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Fort Myers to Chicago in December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*1 star
PricelinePrice Accuracy1 starTrust Score*3 stars
FareScanPrice Accuracy3 starsTrust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Fort Myers-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Fort Myers-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Fort Myers-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Fort Myers-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Fort Myers-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Fort Myers to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Fort Myers with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Fort Myers to Chicago

Get recent, data-driven insights about flights from Fort Myers to Chicago including ideal travel times, pricing trends, and more.

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

Use this chart to determine the optimal time to book a round-trip flight from Fort Myers to Chicago. Price data was last updated on December 13, 2024.

The price you pay for your flight from Fort Myers to Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 23 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Fort Myers to Chicago?

Currently, September is the cheapest month in which you can book a flight from Fort Myers to Chicago (average of $232). Flying from Fort Myers to Chicago in June is currently the most expensive (average of $308). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from RSW to CHI?

Find hourly flight availability from Fort Myers to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 19, 2024.

It’s typically best to fly out from Fort Myers to Chicago in the evening. Doing so could potentially save you 34% on the flight price compared to flying in the morning, which is usually more expensive.

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

Use this chart to determine the cheapest time to fly round-trip from Fort Myers to Chicago. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Fort Myers to Chicago flight should consider departing on Saturday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Fort Myers to Chicago

Explore weekly flight availability from Fort Myers to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated December 19, 2024.

The most flights from RSW to CHI are scheduled on a Thursday (30 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated December 19, 2024.
Read reviews from past customers who have flown Spirit Airlines, Frontier and United Airlines from Fort Myers to Chicago. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,836 reviews
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,600 reviews
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Avelo Airlines
7.5
Good
74 reviews
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

JetBlue
7.4
Good
3,274 reviews
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

United Airlines
7.4
Good
9,048 reviews
Southwest
8.1
Very good
4,836 reviews

Crew

8.7

Entertainment

7.7

Boarding

8.2

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Related info for your journey

Find useful and relevant information for your journey from Fort Myers to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 15 outbound flights to Chicago per day. 6 airlines have flights to Chicago from Fort Myers SW Florida Intl on a regular basis.

  • 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 $108 on this airline. Additional options worth looking into are Frontier and Southwest, starting at $110 and $164 round-trip. You may be able to fly from Fort Myers to Chicago for 56% 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 $61. Frontier flights start at $62 while deals on United Airlines start at $79 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 most reliable airlines from Fort Myers to Chicago?

    The top 3 most reliable airlines when flying from Fort Myers to Chicago are Qatar Airways (93%), SWISS (93%) and Emirates (93%).

  • What are the cheapest flights from Fort Myers to Chicago?

    On average you can expect to pay $960 for a flight from Fort Myers to Chicago. The cheapest flight overall is $57 while the most popular route, (Fort Myers SW Florida Intl - Chicago O'Hare Intl) is currently priced at $81.

  • Can I find deals for flights from Fort Myers to Chicago that include hotel bookings?

    Yes. In addition to deals on Fort Myers to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Fort Myers to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Fort Myers to Chicago.

  • Can I find deals for business class flights from Fort Myers to Chicago?

    Yes. Cheapflights offers flight deals from Fort Myers to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Fort Myers to Chicago?

    Currently, September is the cheapest month in which you can book a flight from Fort Myers to Chicago (average of $232). Flying from Fort Myers to Chicago in June is currently the most expensive (average of $308). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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Top 6 airlines flying from Fort Myers to Chicago

Discover the top 6 airlines that operate flights from Fort Myers to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated December 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$35Average$117FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$63Average$159FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$158Average$275FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$166Average$327FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$210Average$410FlexibilityNo cancel feeOn-time63%
DeltaCheapest$216Average$391FlexibilityNo cancel feeOn-timeN/A
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