Cheap Flights From Southwest Florida Intl. (RSW) To O'Hare Intl. (ORD)

Wander Wisely with exceptional service, 24/7 supportOpens in a new window

Feel at ease with free flight cancellations within 24 hours of booking

Change your flight without a fee on select flights

Find The Best Dates To Fly

Cheapest Flights from Fort Myers (RSW) to Chicago (ORD)

The cheapest flights to O'Hare Intl. found within the past 7 days were CA $364 round trip and CA $80 one way. Prices and availability subject to change. Additional terms may apply.

Wed, Oct 29 - Fri, Oct 31
RSW
Fort Myers
ORD
Chicago
CA $364 Roundtrip, found 6 days ago
CA $364
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Oct 29 from Fort Myers to Chicago, returning Fri, Oct 31, priced at CA $364 found 6 days ago
Wed, Oct 29 - Fri, Oct 31
RSW
Fort Myers
ORD
Chicago
CA $396 Roundtrip, found 6 days ago
CA $396
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Oct 29 from Fort Myers to Chicago, returning Fri, Oct 31, priced at CA $396 found 6 days ago
Wed, Oct 29 - Fri, Oct 31
RSW
Fort Myers
ORD
Chicago
CA $406 Roundtrip, found 6 days ago
CA $406
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Oct 29 from Fort Myers to Chicago, returning Fri, Oct 31, priced at CA $406 found 6 days ago
Wed, Oct 29 - Fri, Oct 31
RSW
Fort Myers
ORD
Chicago
CA $408 Roundtrip, found 6 days ago
CA $408
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Oct 29 from Fort Myers to Chicago, returning Fri, Oct 31, priced at CA $408 found 6 days ago
Wed, Oct 29 - Fri, Oct 31
RSW
Fort Myers
ORD
Chicago
CA $416 Roundtrip, found 6 days ago
CA $416
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Oct 29 from Fort Myers to Chicago, returning Fri, Oct 31, priced at CA $416 found 6 days ago
Wed, Oct 29 - Fri, Oct 31
RSW
Fort Myers
ORD
Chicago
CA $421 Roundtrip, found 6 days ago
CA $421
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Oct 29 from Fort Myers to Chicago, returning Fri, Oct 31, priced at CA $421 found 6 days ago
Wed, Oct 29 - Fri, Oct 31
RSW
Fort Myers
ORD
Chicago
CA $423 Roundtrip, found 6 days ago
CA $423
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Oct 29 from Fort Myers to Chicago, returning Fri, Oct 31, priced at CA $423 found 6 days ago
Wed, Oct 29 - Fri, Oct 31
RSW
Fort Myers
ORD
Chicago
CA $430 Roundtrip, found 6 days ago
CA $430
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Oct 29 from Fort Myers to Chicago, returning Fri, Oct 31, priced at CA $430 found 6 days ago
Wed, Oct 29 - Fri, Oct 31
RSW
Fort Myers
ORD
Chicago
CA $433 Roundtrip, found 6 days ago
CA $433
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Oct 29 from Fort Myers to Chicago, returning Fri, Oct 31, priced at CA $433 found 6 days ago
Wed, Oct 29 - Fri, Oct 31
RSW
Fort Myers
ORD
Chicago
CA $446 Roundtrip, found 6 days ago
CA $446
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Oct 29 from Fort Myers to Chicago, returning Fri, Oct 31, priced at CA $446 found 6 days ago

Frequently asked questions

Are there direct flights from Southwest Florida Intl. Airport (RSW) to O'Hare Airport?
If you're eager to travel from Southwest Florida Intl. Airport (RSW) to ORD in the shortest possible time, you'll be glad to know multiple airlines offer direct flights. Choose your favorite seat with United Airlines or American Airlines.
What airlines fly from RSW to O'Hare Airport?
With a number of airlines operating direct flights from RSW to ORD, you'll easily find one that ticks all your boxes. Below are some of the most reputable air carriers:

  • United Airlines - (UA) with 117 flights every month
  • American Airlines - (AA) with 47 flights every month
  • Spirit Airlines - (NK) with 30 flights every month
  • Southwest Airlines - (WN) with 8 flights every month

What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

Popular Flight Routes from Fort Myers (RSW)

Travelers at RSW love to visit these top cities. Roam to the top destinations from Fort Myers (RSW) today with the cheap prices from Travelocity!

Popular Flight Routes from Chicago (ORD)

Travelers at ORD love to visit these top cities. Roam to the top destinations from Chicago(ORD) today with the cheap prices from Travelocity!

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.