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O'Hare Intl

$90+ Cheap flights from Fort Myers (RSW) to O'Hare Intl (ORD)

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 7/1. Fares are subject to change and may not be available on all flights or dates of travel.
RSW — ORD
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Fort Myers SW Florida Intl to Chicago O'Hare Intl are usually found in January or August, booked 87 days in advance, depart on a Thursday or Friday and return on a Tuesday

Cheap flight deals from Fort Myers to O'Hare Intl

Discover tips and strategies to find the most affordable flight options for your journey from Fort Myers (RSW) to O'Hare Intl (ORD). 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 June 12, 2025.

Round-trip from

$148
(Cheapflightsfares)

One-way from

$90
(United Airlines)

Popular in

October

Cheapest in

January

Average price

$267
From Fort Myers SW Florida Intl to Chicago O'Hare Intl
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One-way flight from Fort Myers SW Florida Intl to Chicago O'Hare Intl
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Highest demand for flights based on searches. 14% potential increase in price ($43 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in June 2025
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Find flight deals from Fort Myers to O'Hare Intl

Cheapest flights from Fort Myers to O'Hare Intl
Explore the most affordable flight options available from Fort Myers to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/12. 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 7/109:34 pmRSW - ORD
Nonstop3h 10mSpirit Airlines
Thu 7/178:55 amORD - RSW
Nonstop2h 53mSpirit Airlines
Deal found 6/12$148
This United Airlines deal was found by Cheapflights users on 6/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2712:28 pmRSW - ORD
Nonstop3h 15mUnited Airlines
Wed 8/274:20 pmORD - RSW
Nonstop2h 58mUnited Airlines
Deal found 6/10$152
This American Airlines deal was found by Cheapflights users on 6/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/143:38 pmRSW - ORD
Nonstop3h 17mAmerican Airlines
Sun 8/1710:49 amORD - RSW
Nonstop2h 56mAmerican Airlines
Deal found 6/12$159
This FlightHub deal was found by Cheapflights users on 6/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/107:15 pmRSW - ORD
1 stop6h 07mMultiple Airlines
Tue 7/154:34 pmORD - RSW
Nonstop2h 55mMultiple Airlines
Deal found 6/10$195
This JetBlue deal was found by Cheapflights users on 6/11. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/510:35 amRSW - ORD
1 stop7h 52mJetBlue
Wed 12/108:40 amORD - RSW
1 stop10h 01mJetBlue
Deal found 6/11$211
This Delta deal was found by Cheapflights users on 6/11. 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.
Thu 8/216:15 pmRSW - ORD
1 stop6h 41mDelta
Sat 8/237:10 amORD - RSW
1 stop7h 06mDelta
Deal found 6/11$217
This Southwest deal was found by Cheapflights users on 6/10. 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.
Fri 7/116:50 amRSW - ORD
1 stop8h 10mSouthwest
Mon 7/147:00 amORD - RSW
1 stop10h 25mSouthwest
Deal found 6/10$262
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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 8/288:00 amRSW - ORD
1 stop9h 12mSun Country Air
Sun 8/3110:43 amORD - RSW
1 stop9h 47mSun Country Air
Deal found 6/10$270
This FlightHub deal was found by Cheapflights users on 6/12. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/147:15 pmRSW - ORD
1 stop6h 07mFrontier
Sun 8/175:01 amORD - RSW
1 stop12h 20mFrontier
Deal found 6/12$276

Cheapflights Fare Finder

Customize your flight search to find flights from Fort Myers to O'Hare Intl 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 June 12, 2025.
Use the filters below to find and compare flights from Fort Myers to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fort Myers

Fly to

O'Hare Intl

Route

Depart

Return

Price

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 7/10

9:34 pm-11:44 pm

Nonstop3h 10m

Chicago O'Hare Intl

Thu 7/17

8:55 am-12:48 pm

Nonstop2h 53m

$148

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Wed 8/27

12:28 pm-2:43 pm

Nonstop3h 15m

Chicago O'Hare Intl

Wed 8/27

4:20 pm-8:18 pm

Nonstop2h 58m

$152

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 8/14

3:38 pm-5:55 pm

Nonstop3h 17m

Chicago O'Hare Intl

Sun 8/17

10:49 am-2:45 pm

Nonstop2h 56m

$159

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 7/10

7:15 pm-12:22 am

1 stop6h 07m

Chicago O'Hare Intl

Tue 7/15

4:34 pm-8:29 pm

Nonstop2h 55m

$195

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 8/21

6:15 pm-11:56 pm

1 stop6h 41m

Chicago O'Hare Intl

Sat 8/23

7:10 am-3:16 pm

1 stop7h 06m

$217

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Fri 7/11

6:50 am-2:00 pm

1 stop8h 10m

Chicago O'Hare Intl

Mon 7/14

7:00 am-6:25 pm

1 stop10h 25m

$262

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 8/28

8:00 am-4:12 pm

1 stop9h 12m

Chicago O'Hare Intl

Sun 8/31

10:43 am-9:30 pm

1 stop9h 47m

$270

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Thu 8/14

7:15 pm-12:22 am

1 stop6h 07m

Chicago O'Hare Intl

Sun 8/17

5:01 am-6:21 pm

1 stop12h 20m

$276

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Tue 7/1

12:26 pm-2:39 pm

Nonstop3h 13m

$90

Fort MyersChicago

RSW - ORD

RSWORD

Fort Myers SW Florida Intl

Mon 8/11

9:34 pm-11:44 pm

Nonstop3h 10m

$93

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 17 results
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The best insider tips for Fort Myers to Chicago O'Hare Intl Airport flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Fort Myers to Chicago O'Hare Intl Airport trip
Airlines
United Airlines

Basic Economy on United prohibits carry-ons, unless you're a MileagePlus member or have a qualifying card.


United Economy Plus offers extra legroom seats towards the front of the economy cabin.

Read more about United Airlinesby Harriet Baskas
Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom and larger tray tables.


Spirit's self-service bag drop speeds up airport check-in. Print your boarding pass in advance.

Read more about Spirit Airlinesby Daniel Scheffler
Airports
RSW

During peak tourist seasons, plan an extra 20 minutes at RSW for check-in due to smaller airline ticket counters.

Read more about RSWby Matt Meltzer
ORD

For quick city access from ORD, consider taking the 'L' train from the airport to downtown Chicago.

Read more about ORDby Ramsey Qubein
Our travel experts
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Matt Meltzer

Matt Meltzer

Expert on RSW

Matt Meltzer

Matt Meltzer

Matt Meltzer has been a travel writer for over a decade, covering U.S. domestic locations and hotels for Thrillist, Fifty Grande, Matador Network, Conde Nast Traveler, and other top publications. He's won multiple travel journalism awards from the Society of American Travel Writers and North American Travel Journalists Association, and currently resides in South Florida.

Read more

Best time to book a flight from Fort Myers to O'Hare Intl

Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl 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.

Cheapflights Insights

Everything you need to know about your flight from Fort Myers to Chicago O'Hare Intl Airport

How far ahead should I book a flight from Fort Myers to Chicago O'Hare Intl Airport?

Use this chart to determine the optimal time to book a round-trip flight from Fort Myers to O'Hare Intl. Price data was last updated on June 9, 2025.

The best time to book flights from Fort Myers to Chicago O'Hare Intl Airport is 87 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Fort Myers to Chicago O'Hare Intl Airport?

Currently, August is the cheapest month in which you can book a flight from Fort Myers to Chicago O'Hare Intl Airport (average of $245). Flying from Fort Myers to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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 ORD?

Find hourly flight availability from Fort Myers to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated June 12, 2025.

When flying from Fort Myers to Chicago O'Hare Intl Airport, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 47% versus a flight in the morning.

What is the cheapest day to fly from Fort Myers to Chicago O'Hare Intl Airport?

Use this chart to determine the cheapest time to fly round-trip from Fort Myers to O'Hare Intl. Price data was last updated on June 8, 2025.

Travelers seeking maximum savings on their Fort Myers to Chicago O'Hare Intl Airport flight should consider departing on Friday evenings when fares are most often at their lowest. Sunday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Fort Myers to Chicago O'Hare Intl Airport

Explore weekly flight availability from Fort Myers to O'Hare Intl. 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 June 12, 2025.

The most flights from RSW to ORD are scheduled on a Monday (16 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (10 on average).

Rainfall in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago O'Hare Intl Airport 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 O'Hare Intl Airport when rainfall is around 1.7 in.

Temperature in O'Hare Intl by month

Plan your trip to O'Hare Intl by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago O'Hare Intl Airport, 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 O'Hare Intl

Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated June 12, 2025.
Read reviews from past customers who have flown Southwest, Delta 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
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
JetBlue
7.3
Good
2,925 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Boarding

8.2

Food

7.1

Crew

8.6

Comfort

8.0

Overall

8.0

Entertainment

7.6

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Fort Myers to O'Hare Intl. 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 O'Hare Intl?

    Most people fly from Fort Myers SW Florida Intl (RSW) if they book a flight from Fort Myers to Chicago O'Hare Intl. On average, SW Florida Intl has 13 outbound flights to Chicago O'Hare Intl per day from 5 airlines. Fort Myers SW Florida Intl is conveniently located just 10.0 mi from Fort Myers’s city center.

  • What are the cheapest airlines flying from Fort Myers to Chicago O'Hare Intl Airport round-trip?

    Our cheapest airline available from Fort Myers to Chicago O'Hare Intl Airport is Spirit Airlines. Our recent data shows that you can find tickets from as low as $148 on this airline. Additional options worth looking into are United Airlines and American Airlines, starting at $152 and $179 round-trip. These flights start at 41% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Fort Myers to Chicago O'Hare Intl Airport one-way?

    One-way options have recently been found by users for as low as $90 on United Airlines. Other airlines that offer cheap prices include Spirit Airlines from $93 and Delta from $109 one-way.

  • What are the most reliable airlines from Fort Myers to Chicago O'Hare Intl Airport?

    The top 3 most reliable airlines when flying from Fort Myers to Chicago O'Hare Intl Airport are Emirates (97%), SWISS (93%) and Alaska Airlines (86%).

  • What are the cheapest flights from Fort Myers to Chicago O'Hare Intl Airport?

    On average you can expect to pay $1,450 for a flight from Fort Myers to Chicago O'Hare Intl Airport. The cheapest flight overall is $77 while the most popular route, (Fort Myers SW Florida Intl - Chicago O'Hare Intl) is currently priced at $108.

  • Can I find deals for flights from Fort Myers to O'Hare Intl that include hotel bookings?

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

  • How can I find direct flights from Fort Myers to O'Hare Intl?

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

  • Can I find deals for business class flights from Fort Myers to O'Hare Intl?

    Yes. Cheapflights offers flight deals from Fort Myers to O'Hare Intl 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 O'Hare Intl Airport?

    Currently, August is the cheapest month in which you can book a flight from Fort Myers to Chicago O'Hare Intl Airport (average of $245). Flying from Fort Myers to Chicago O'Hare Intl Airport in March is currently the most expensive (average of $321). 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.

See more FAQs

Traveling to a place near Fort Myers?

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Top 5 airlines flying from Fort Myers to O'Hare Intl

Discover the top 5 airlines that operate flights from Fort Myers to O'Hare Intl. 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$46Average$131FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$70Average$164FlexibilityNo cancel feeOn-time65%
American AirlinesCheapest$159Average$270FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$159Average$335FlexibilityNo cancel feeOn-time69%
DeltaCheapest$216Average$313FlexibilityNo cancel feeOn-timeN/A

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