Domestic route
Cheap flights from Fort Myers to Chicago
Southwest Florida International Airport (RSW) to O'Hare International Airport (ORD). 1,122 miles, 2h 45m nonstop.
RSW to ORD at a glance
Computed from airline schedules and the fares we track for this route. Refreshed several times a day.
- Distance
- 1,122 milesgreat-circle
- Typical flight time
- 2h 45mnonstop, gate to gate
- Nonstop airlines
- AAUAWNF94 airlinesAmerican, United, Southwest
- Nonstop flights per day
- 16all airlines combined
- Cheapest month
- January 2027over the next six months
- Best day to fly
- Wednesday20% less than Sunday
- Time difference
- 1h behindChicago vs Fort Myers
Fort Myers to Chicago
Round trips from $76
Per traveler, taxes and fees included. Lowest fare we found departs Tue, Jan 5.
Cheapest month: January 2027
See fares on these datesLock any fare free — pay only when you accept your last-minute deal
Or ask an agent on WhatsAppFort Myers to Chicago fares by month
Lowest round-trip economy fare per traveler in each of the next six months, taxes and fees included. Select a month to search that date.
Airlines flying Fort Myers to Chicago
4 airlines fly nonstop with 16 departures a day combined, plus 5 more with one stop.
- UAUnited AirlinesStar AllianceNonstop · 7 flights a day · first checked bag from $40
- AAAmerican AirlinesoneworldNonstop · 5 flights a day · first checked bag from $40
- F9Frontier AirlinesLow-costNonstop · 2 flights a day · first checked bag from $55
- WNSouthwest AirlinesLow-costNonstop · 2 flights a day · first checked bag from $35
- MXBreeze AirwaysLow-costConnecting via CHS, TPA, RDU, ORF · first checked bag from $45
- DLDelta Air LinesSkyTeamConnecting via ATL, MSP, DTW · first checked bag from $35
- B6JetBlueConnecting via FLL, MCO · first checked bag from $40
- NKSpirit AirlinesLow-costConnecting via FLL, DTW, MCO, ATL, IAH · first checked bag from $55
- SYSun Country AirlinesLow-costConnecting via MSP · first checked bag from $45
Connecting options
Hubs where one airline can carry you on both legs, most choices first.
- Atlanta (ATL)DLNK2 airlines
- Minneapolis (MSP)DLSY2 airlines
- Detroit (DTW)DLNK2 airlines
- Fort Lauderdale (FLL)B6NK2 airlines
- Orlando (MCO)B6NK2 airlines
Which airport should I use?
Fort MyersChicago has 2 airports. Fares can differ by $50 to $150 round trip between them, so check the alternatives before you book.
Other arrival airports near Chicago
Tips for this route
- American, United, Southwest and Frontier all fly RSW to ORD nonstop, so compare the total with bags before picking the lowest base fare: the difference between a basic and a standard economy ticket is often less than one checked bag each way.
- January 2027 is the cheapest month to fly over the next six months, with round trips from $76; September 2026 is the most expensive at $104 and up, a difference of $28 per traveler.
- Departing on a Wednesday averages 20% less than a Sunday on this route. If your dates are flexible, shift the outbound by a day or two and check the calendar view before you book.
- Fares on this route are usually lowest 4 to 8 weeks before departure and rise sharply inside two weeks.
Destination guide
Chicago: Big-shoulders architecture and a lakefront for everyone
Chicago is America's most connected inland hub — O'Hare and Midway between them have nonstops from nearly every US city — so fares are consistently reasonable. The lakefront, the architecture and the food make it a strong long weekend.
Best time to visit: June–September is warm, with festivals almost every weekend (and the highest hotel rates). May and October are cool and cheaper; winter is cold but hotels are a bargain.
Flying the other way? Chicago to Fort MyersFares, airlines and tips for ORD to RSW.Ready to compare live fares?
See every airline on RSW–ORD side by side with bags and seat rules spelled out.
Search Fort Myers to ChicagoFort Myers to Chicago: common questions
How long is the flight from Fort Myers to Chicago?
A nonstop flight from Fort Myers (RSW) to Chicago (ORD) takes about 2h 45m gate to gate, covering 1,122 miles. Connecting itineraries add the layover, typically 1 to 3 hours more in total.
Which airlines fly nonstop from RSW to ORD?
American Airlines, United Airlines, Southwest Airlines and Frontier Airlines operate nonstop flights from Fort Myers (RSW) to Chicago (ORD), with 16 nonstop departures a day between them. One-stop options connect through ATL, MSP and DTW.
What is the cheapest month to fly from Fort Myers to Chicago?
Over the next six months, January 2027 has the lowest round-trip fares from Fort Myers (RSW) to Chicago (ORD), starting at $76 per traveler including taxes and fees. Within any month, Wednesday departures average the lowest prices.
How far in advance should I book Fort Myers to Chicago flights?
Fares on this route are usually lowest 4 to 8 weeks before departure and rise sharply inside two weeks. Air1 Tickets includes free cancellation within 24 hours of booking on every fare, so you can lock in a good price and keep looking.
What is the time difference between Fort Myers and Chicago?
Chicago is 1 hour behind Fort Myers. RSW is on America/New York time and ORD on America/Chicago time. Departure and arrival times in search results are always shown in local time at each airport.
Related routes
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