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Cheap flights from Southwest Florida Intl to Chicago (RSW - CHI)

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The best prices from Southwest Florida Intl to Chicago are usually found in August or January, booked 15 days in advance, depart on a Friday or Thursday and return on a Tuesday

How to find the cheapest flight from
Southwest Florida Intl (RSW) to Chicago (CHI)

RSW - CHI
Price
$70 - $184
CHI
Temperature
33.8 - 84.2 °F
CHI
Rainfall
0.7 - 4.3 inches

Popular in

June

High demand for flights, 28% potential price rise

Cheapest in

August

Best time to find cheap flights, 47% potential price drop

Round-trip from

$70

From Southwest Florida Intl to Chicago

One-way from

$42

One-way flight from Southwest Florida Intl to Chicago

Flight route prices based on searches on Cheapflights within the last 3 days, monthly prices based on aggregated historical data.
What is the cheapest day to fly round-trip from Southwest Florida Intl to Chicago?

Flying to your destination on a Sunday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Chicago. Check prices with Cheapflights to find a great deal for your trip.

How far in advance should I book a flight from Southwest Florida Intl to Chicago?

To save on the cost of your flight from Southwest Florida Intl to Chicago, book at least 20 days before your planned departure. Booking around this time can save you about 10% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $137 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $157.

What is the cheapest month to fly from Southwest Florida Intl to Chicago?

Our data shows that April tends to be the cheapest month to fly to Chicago from Southwest Florida Intl. Users have commonly found prices around $135 for the month, but tickets can be as low as $33. Due to multiple factors, prepare for potentially higher prices in December.

When is the cheapest time to fly from Southwest Florida Intl to Chicago (RSW - CHI)?

It’s optimal to fly from Southwest Florida Intl to Chicago in the evening. By choosing this option you can save up to 33% on the cost of your flight, compared to a flight in the morning.

Cheap flights from Southwest Florida Intl to Chicago in January, February 2021

The best prices found for RSW to CHI flights for January, February
18 Feb - 3 Mar
$46pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl
2 Feb - 14 Feb
$47pp
RSW
Fort Myers SW Florida Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
RSW
Fort Myers SW Florida Intl
5 Feb - 7 Feb
$54pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl

Southwest Florida Intl to Chicago 2021 flight deals

Cheap flights to Chicago from Southwest Florida Intl found for this year
18 Feb - 3 Mar
$46pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl
2 Feb - 14 Feb
$47pp
RSW
Fort Myers SW Florida Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
RSW
Fort Myers SW Florida Intl
3 Mar - 8 Mar
$49pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl

Non-stop flights to Chicago from Southwest Florida Intl

Save time with Southwest Florida Intl to Chicago direct flight deals
18 Feb - 3 Mar
$46pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl
2 Feb - 14 Feb
$47pp
RSW
Fort Myers SW Florida Intl
Multiple Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
RSW
Fort Myers SW Florida Intl
3 Mar - 8 Mar
$49pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl

Last minute flights from Southwest Florida Intl to Chicago

Late deals on round-trip flights to Chicago from Southwest Florida Intl, departing today and this week
27 Jan - 31 Jan
$46pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl
28 Jan - 31 Jan
$54pp
RSW
Fort Myers SW Florida Intl
Spirit Airlines
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Spirit Airlines
Non-Stop
RSW
Fort Myers SW Florida Intl
28 Jan - 31 Jan
$55pp
RSW
Fort Myers SW Florida Intl
Frontier
Non-Stop
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Frontier
Non-Stop
RSW
Fort Myers SW Florida Intl

One-way flights to Chicago from Southwest Florida Intl

The cheapest one-way flights from Southwest Florida Intl to Chicago
4:24 am - 6:24 am
United Airlines
Nonstop
3h 00m
RSW - ORD
United Airlines
$42
United
6:58 am - 9:18 am
American Airlines
Nonstop
3h 20m
RSW - ORD
American Airlines
1:00 am - 2:57 am
Spirit Airlines
Nonstop
2h 57m
RSW - ORD
Spirit Airlines
$71
FareScan

Related info for your journey

Useful info, stats and facts about Southwest Florida Intl to Chicago flights.

Flight FAQs

From Southwest Florida Intl to Chicago

Are flight prices decreasing from Southwest Florida Intl to Chicago due to COVID-19 (coronavirus)?

At this time, Cheapflights has noticed price decreases for many domestic flights due to COVID-19. Travel is not necessarily recommended at this time, and flights may be prone to cancellation: please check with local authorities in both Southwest Florida Intl and Chicago for travel alerts, and be sure to review the airline's cancellation policy and travel advisories before booking. For more information, please view our post on what to know about COVID-19 (coronavirus) and travel.

What safety measures are being taken by airlines flying from Fort Myers SW Florida Intl to Chicago to control the spread of COVID-19?

New policies can now be found on Delta to help keep travelers safe while flying. New policies for travelers booking flights from Fort Myers SW Florida Intl to Chicago include masks being provided and required on board, daily cleaning and sanitization, use of HEPA filters, pre-flight testing for antibodies and symptoms, and socially distanced seating (for a limited time). Keep in mind that policies will vary by airline.

Which airlines flying from Fort Myers SW Florida Intl to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Fort Myers SW Florida Intl to Chicago have new flexible policies in place due to COVID-19. Spirit Airlines, American Airlines, and United Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Spirit Airlines with this kind of flexibility.

Can I find flights from Southwest Florida Intl to Chicago for under $100 on Cheapflights?

Yes, there are multiple flights from Southwest Florida Intl to Chicago for under $100. The cheapest flight booked recently is on Spirit Airlines for just $46, but on average you can expect to pay $59.

Are there nonstop flights from Southwest Florida Intl to Chicago for under $100 on Cheapflights?

Cheapflights has at least 20 direct flights from Southwest Florida Intl to Chicago under $100. A good price for a nonstop flight from Southwest Florida Intl to Chicago is less than $60.

Are there last-minute flights available from Southwest Florida Intl to Chicago for under $100?

There are currently 20+ open flights from Southwest Florida Intl to Chicago within the next 7 days for less than $100.

How long is the flight from Southwest Florida Intl to Chicago?

Spirit Airlines, Frontier, and American Airlines can get you from Southwest Florida Intl to Chicago in just under 3h. Your travel time will be generally consistent. Generally, flights for this route are nonstop.

What are the cheapest airlines flying from Southwest Florida Intl to Chicago round-trip?

Cheapflights users have booked flights from Southwest Florida Intl to Chicago round-trip from $46. Other airlines that can offer you cheap pricing are Frontier, from $55, and American Airlines, from $83. Spirit Airlines is priced at 65% lower than the current average price of a flight leaving 3 months from now.

What are the cheapest airlines to fly from Southwest Florida Intl 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 $19. Frontier flights start at $28 while deals on United Airlines start at $42 one-way.

Alternative routes for Southwest Florida Intl to Chicago

Destination information for Chicago

Things to know before you go. Useful info for your trip from Southwest Florida Intl to Chicago
Flight duration
3h 02m
Average temperature for January in Chicago
33.8 °F
Avg rainfall for January in Chicago
0.7 ″

Airports servicing Fort Myers

Airports servicing Chicago

Chicago Midway (MDW)
Rockford (RFD)

Top 5 airlines flying from Southwest Florida Intl to Chicago

The chart below displays the airlines Cheapflights users traveling from Southwest Florida Intl to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.

Airline Cheapest Average Flexibility On-time COVID-19 safety
Frontier
$37 $116 No cancel fee 62%
Spirit Airlines
$56 $173 No cancel fee 65%
American Airlines
$63 $197 No cancel fee 71%
United Airlines
$60 $229 No cancel fee 69%
Delta
$97 $296 No cancel fee N/A

Hourly flight availability from Southwest Florida Intl to Chicago

Morning 6 AM to noon 50% of RSW to CHI departures
Afternoon Noon to 6 PM 46% of RSW to CHI departures
Evening 6 PM to midnight 3% of RSW to CHI departures
Early morning Midnight to 6 AM 1% of RSW to CHI departures
Midnight
6 AM
Noon
6 PM
Weekly flight availability
from Southwest Florida Intl to Chicago
Sunday
17 daily flights
Monday
14 daily flights
Tuesday
12 daily flights
Wednesday
12 daily flights
Thursday
16 daily flights
Friday
16 daily flights
Saturday
12 daily flights
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