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

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

The cheapest flights to O'Hare Intl. found within the past 7 days were CA $83 round trip and CA $42 one way. Prices and availability subject to change. Additional terms may apply.

Tue, Jan 13 - Sun, Jan 25
RSW
Fort Myers
ORD
Chicago
CA $83 Roundtrip, found 20 hours ago
CA $83
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Tue, Jan 13 from Fort Myers to Chicago, returning Sun, Jan 25, priced at CA $83 found 20 hours ago
Tue, Jan 13 - Sun, Jan 25
RSW
Fort Myers
ORD
Chicago
CA $167 Roundtrip, found 20 hours ago
CA $167
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Tue, Jan 13 from Fort Myers to Chicago, returning Sun, Jan 25, priced at CA $167 found 20 hours ago
Fri, Jan 9 - Sun, Jan 11
RSW
Fort Myers
ORD
Chicago
CA $168 Roundtrip, found 20 hours ago
CA $168
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Fri, Jan 9 from Fort Myers to Chicago, returning Sun, Jan 11, priced at CA $168 found 20 hours ago
Tue, Jan 13 - Sun, Jan 25
RSW
Fort Myers
ORD
Chicago
CA $170 Roundtrip, found 20 hours ago
CA $170
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Tue, Jan 13 from Fort Myers to Chicago, returning Sun, Jan 25, priced at CA $170 found 20 hours ago
Fri, Jan 9 - Sun, Jan 11
RSW
Fort Myers
ORD
Chicago
CA $176 Roundtrip, found 20 hours ago
CA $176
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Fri, Jan 9 from Fort Myers to Chicago, returning Sun, Jan 11, priced at CA $176 found 20 hours ago
Tue, Jan 13 - Sun, Jan 25
RSW
Fort Myers
ORD
Chicago
CA $178 Roundtrip, found 20 hours ago
CA $178
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Tue, Jan 13 from Fort Myers to Chicago, returning Sun, Jan 25, priced at CA $178 found 20 hours ago
Tue, Jan 13 - Sun, Jan 25
RSW
Fort Myers
ORD
Chicago
CA $250 Roundtrip, found 20 hours ago
CA $250
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Tue, Jan 13 from Fort Myers to Chicago, returning Sun, Jan 25, priced at CA $250 found 20 hours ago
Fri, Jan 9 - Sun, Jan 11
RSW
Fort Myers
ORD
Chicago
CA $254 Roundtrip, found 20 hours ago
CA $254
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Fri, Jan 9 from Fort Myers to Chicago, returning Sun, Jan 11, priced at CA $254 found 20 hours ago
Tue, Jan 13 - Sun, Jan 25
RSW
Fort Myers
ORD
Chicago
CA $256 Roundtrip, found 20 hours ago
CA $256
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Tue, Jan 13 from Fort Myers to Chicago, returning Sun, Jan 25, priced at CA $256 found 20 hours ago
Tue, Jan 13 - Sun, Jan 25
RSW
Fort Myers
ORD
Chicago
CA $335 Roundtrip, found 20 hours ago
CA $335
Roundtrip
found 20 hours ago
Select JetBlue Airways flight, departing Tue, Jan 13 from Fort Myers to Chicago, returning Sun, Jan 25, priced at CA $335 found 20 hours 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.