Travel with Axel,
get the best price.

Fort Myers → Chicago

Dec 21, 2026 · one way

RSW → MDW1 adulteconomyOne way

8 flight options · 2 airlines

Nonstop flights

Mon, Dec 21 · One way

Southwest Airlines
7:20 amRSW
2h 55m
Nonstop
9:15 amMDW

One-way total · 1 adult · Taxes included

Mon, Dec 21 · One way

Southwest Airlines
1:05 pmRSW
2h 55m
Nonstop
3:00 pmMDW

One-way total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 · One way

Delta Air Lines
8:00 amRSW
6h 1m
DTW · 1h 50m
1:01 pmMDW

One-way total · 1 adult · Taxes included

Mon, Dec 21 · One way

Southwest Airlines
7:10 amRSW
5h 55m
MCO · 2h 5m
12:05 pmMDW

One-way total · 1 adult · Taxes included

Mon, Dec 21 · One way

Southwest Airlines
10:35 amRSW
6h 40m
BNA · 3h
4:15 pmMDW

One-way total · 1 adult · Taxes included

Mon, Dec 21 · One way

Southwest Airlines
10:05 amRSW
5h 45m
BUF · 1h
2:50 pmMDW

One-way total · 1 adult · Taxes included

Mon, Dec 21 · One way

Southwest Airlines
11:50 amRSW
6h 20m
MCI · 1h 50m
5:10 pmMDW

One-way total · 1 adult · Taxes included

Mon, Dec 21 · One way

Southwest Airlines
11:10 amRSW
4h 50m
CMH · 1h 5m
3:00 pmMDW

One-way total · 1 adult · Taxes included

Make this trip yours

RSW ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

No account needed to see prices.

Already have an account? Log in

Why book with Axel
  • A real airline bookingThe booking is in the airline’s own system under your name. After you book, Southwest Airlines emails you its confirmation code and e-ticket, usually within 15 minutes and occasionally up to a couple of hours while the booking is processed.
  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. Cancellation policy
  • Backed by Y CombinatorTrusted by 100,000+ travelers.

Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

More dates

All dates for this routeNov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-21 · one waySouthwest AirlinesWN1590$243.002026-10-29T01:07:18Z
2026-12-21 · one wayDelta Air LinesDL2277 + DL4688$276.752026-10-29T01:07:18Z
2026-12-21 · one waySouthwest AirlinesWN2106$243.002026-10-29T01:07:18Z
2026-12-21 · one waySouthwest AirlinesWN4492 + WN2803$222.752026-10-29T01:07:18Z
2026-12-21 · one waySouthwest AirlinesWN1388 + WN2062$222.752026-10-29T01:07:18Z
2026-12-21 · one waySouthwest AirlinesWN3207 + WN726$222.752026-10-29T01:07:18Z
2026-12-21 · one waySouthwest AirlinesWN3648 + WN2694$222.752026-10-29T01:07:18Z
2026-12-21 · one waySouthwest AirlinesWN1254 + WN2988$222.752026-10-29T01:07:18Z

2026-12-21 · one way · $243.00

  • Southwest Airlines WN1590: RSW 2026-12-21 07:20:00 → MDW 2026-12-21 09:15:00; nonstop; 175 minutes. Local airport times.

2026-12-21 · one way · $276.75

  • Delta Air Lines DL2277 / DL4688: RSW 2026-12-21 08:00:00 → MDW 2026-12-21 13:01:00; 1 stop(s) via DTW; 361 minutes. Local airport times.
    • DL2277: RSW 2026-12-21 08:00:00 → DTW 2026-12-21 10:54:00; layover at DTW: 110 minutes.
    • DL4688: DTW 2026-12-21 12:44:00 → MDW 2026-12-21 13:01:00.

2026-12-21 · one way · $243.00

  • Southwest Airlines WN2106: RSW 2026-12-21 13:05:00 → MDW 2026-12-21 15:00:00; nonstop; 175 minutes. Local airport times.

2026-12-21 · one way · $222.75

  • Southwest Airlines WN4492 / WN2803: RSW 2026-12-21 07:10:00 → MDW 2026-12-21 12:05:00; 1 stop(s) via MCO; 355 minutes. Local airport times.
    • WN4492: RSW 2026-12-21 07:10:00 → MCO 2026-12-21 08:05:00; layover at MCO: 125 minutes.
    • WN2803: MCO 2026-12-21 10:10:00 → MDW 2026-12-21 12:05:00.

2026-12-21 · one way · $222.75

  • Southwest Airlines WN1388 / WN2062: RSW 2026-12-21 10:35:00 → MDW 2026-12-21 16:15:00; 1 stop(s) via BNA; 400 minutes. Local airport times.
    • WN1388: RSW 2026-12-21 10:35:00 → BNA 2026-12-21 11:45:00; layover at BNA: 180 minutes.
    • WN2062: BNA 2026-12-21 14:45:00 → MDW 2026-12-21 16:15:00.

2026-12-21 · one way · $222.75

  • Southwest Airlines WN3207 / WN726: RSW 2026-12-21 10:05:00 → MDW 2026-12-21 14:50:00; 1 stop(s) via BUF; 345 minutes. Local airport times.
    • WN3207: RSW 2026-12-21 10:05:00 → BUF 2026-12-21 13:00:00; layover at BUF: 60 minutes.
    • WN726: BUF 2026-12-21 14:00:00 → MDW 2026-12-21 14:50:00.

2026-12-21 · one way · $222.75

  • Southwest Airlines WN3648 / WN2694: RSW 2026-12-21 11:50:00 → MDW 2026-12-21 17:10:00; 1 stop(s) via MCI; 380 minutes. Local airport times.
    • WN3648: RSW 2026-12-21 11:50:00 → MCI 2026-12-21 14:00:00; layover at MCI: 110 minutes.
    • WN2694: MCI 2026-12-21 15:50:00 → MDW 2026-12-21 17:10:00.

2026-12-21 · one way · $222.75

  • Southwest Airlines WN1254 / WN2988: RSW 2026-12-21 11:10:00 → MDW 2026-12-21 15:00:00; 1 stop(s) via CMH; 290 minutes. Local airport times.
    • WN1254: RSW 2026-12-21 11:10:00 → CMH 2026-12-21 13:40:00; layover at CMH: 65 minutes.
    • WN2988: CMH 2026-12-21 14:45:00 → MDW 2026-12-21 15:00:00.

More dates for this route