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Jacksonville → Chicago

Jan 21, 2027 · return Feb 4, 2027

JAX → MDW1 adulteconomyRound trip

8 flight options · 3 airlines

Nonstop flights

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
6:55 pmJAX
2h 25m
Nonstop
8:20 pmMDW
Southwest Airlines
12:50 pmMDW
2h 15m
Nonstop
4:05 pmJAX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
1:30 pmJAX
2h 25m
Nonstop
2:55 pmMDW
Southwest Airlines
12:50 pmMDW
2h 15m
Nonstop
4:05 pmJAX

Round-trip total · 1 adult · Taxes included

One-stop flights

Thu, Jan 21 – Thu, Feb 4

Frontier Airlines
7:03 pmJAX
5h 44m
ATL · 2h 17m
11:47 pmMDW
Frontier Airlines
1:11 pmMDW
5h 14m
ATL · 1h 51m
7:25 pmJAX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Delta Air Lines
6:59 pmJAX
4h 18m
ATL · 1h 1m
10:17 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
8:00 amJAX
5h 15m
BWI · 1h 15m
12:15 pmMDW
Southwest Airlines
12:50 pmMDW
2h 15m
Nonstop
4:05 pmJAX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
11:20 amJAX
5h 55m
BNA · 2h 40m
4:15 pmMDW
Southwest Airlines
12:50 pmMDW
2h 15m
Nonstop
4:05 pmJAX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Southwest Airlines
6:00 amJAX
7h 5m
STL · 3h 35m
12:05 pmMDW
Southwest Airlines
12:50 pmMDW
2h 15m
Nonstop
4:05 pmJAX

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 4

Delta Air Lines
12:00 pmJAX
7h 1m
DTW · 3h 20m
6:01 pmMDW
Delta Air Lines
1:02 pmMDW
6h 41m
ATL · 3h 32m
8:43 pmJAX

Round-trip total · 1 adult · Taxes included

Make this trip yours

JAX ⇄ MDW

Economy

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

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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)
2027-01-21 → 2027-02-04Southwest AirlinesWN2264 / WN2041$282.752026-10-29T01:16:41Z
2027-01-21 → 2027-02-04Frontier AirlinesF91549 + F92291 / F92144 + F91550$180.382026-10-29T01:16:41Z
2027-01-21 → 2027-02-04Delta Air LinesDL2627 + DL1076 / DL2417 + DL2265$321.752026-10-29T01:16:41Z
2027-01-21 → 2027-02-04Southwest AirlinesWN1979 / WN2041$282.752026-10-29T01:16:41Z
2027-01-21 → 2027-02-04Southwest AirlinesWN2256 + WN1070 / WN2041$275.632026-10-29T01:16:41Z
2027-01-21 → 2027-02-04Southwest AirlinesWN2253 + WN2062 / WN2041$275.632026-10-29T01:16:41Z
2027-01-21 → 2027-02-04Southwest AirlinesWN2265 + WN287 / WN2041$275.632026-10-29T01:16:41Z
2027-01-21 → 2027-02-04Delta Air LinesDL2333 + DL4677 / DL2417 + DL2265$321.752026-10-29T01:16:41Z

2027-01-21 → 2027-02-04 · $282.75

  • Southwest Airlines WN2264: JAX 2027-01-21 18:55:00 → MDW 2027-01-21 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2041: MDW 2027-02-04 12:50:00 → JAX 2027-02-04 16:05:00; nonstop; 135 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $180.38

  • Frontier Airlines F91549 / F92291: JAX 2027-01-21 19:03:00 → MDW 2027-01-21 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2027-01-21 19:03:00 → ATL 2027-01-21 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2027-01-21 22:48:00 → MDW 2027-01-21 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2027-02-04 13:11:00 → JAX 2027-02-04 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2027-02-04 13:11:00 → ATL 2027-02-04 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2027-02-04 18:09:00 → JAX 2027-02-04 19:25:00.

2027-01-21 → 2027-02-04 · $321.75

  • Delta Air Lines DL2627 / DL1076: JAX 2027-01-21 18:59:00 → MDW 2027-01-21 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2027-01-21 18:59:00 → ATL 2027-01-21 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2027-01-21 21:20:00 → MDW 2027-01-21 22:17:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2027-02-04 13:02:00 → JAX 2027-02-04 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2027-02-04 13:02:00 → ATL 2027-02-04 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2027-02-04 19:33:00 → JAX 2027-02-04 20:43:00.

2027-01-21 → 2027-02-04 · $282.75

  • Southwest Airlines WN1979: JAX 2027-01-21 13:30:00 → MDW 2027-01-21 14:55:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2041: MDW 2027-02-04 12:50:00 → JAX 2027-02-04 16:05:00; nonstop; 135 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $275.63

  • Southwest Airlines WN2256 / WN1070: JAX 2027-01-21 08:00:00 → MDW 2027-01-21 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2027-01-21 08:00:00 → BWI 2027-01-21 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2027-01-21 11:05:00 → MDW 2027-01-21 12:15:00.
  • Southwest Airlines WN2041: MDW 2027-02-04 12:50:00 → JAX 2027-02-04 16:05:00; nonstop; 135 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $275.63

  • Southwest Airlines WN2253 / WN2062: JAX 2027-01-21 11:20:00 → MDW 2027-01-21 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
    • WN2253: JAX 2027-01-21 11:20:00 → BNA 2027-01-21 12:05:00; layover at BNA: 160 minutes.
    • WN2062: BNA 2027-01-21 14:45:00 → MDW 2027-01-21 16:15:00.
  • Southwest Airlines WN2041: MDW 2027-02-04 12:50:00 → JAX 2027-02-04 16:05:00; nonstop; 135 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $275.63

  • Southwest Airlines WN2265 / WN287: JAX 2027-01-21 06:00:00 → MDW 2027-01-21 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN2265: JAX 2027-01-21 06:00:00 → STL 2027-01-21 07:20:00; layover at STL: 215 minutes.
    • WN287: STL 2027-01-21 10:55:00 → MDW 2027-01-21 12:05:00.
  • Southwest Airlines WN2041: MDW 2027-02-04 12:50:00 → JAX 2027-02-04 16:05:00; nonstop; 135 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $321.75

  • Delta Air Lines DL2333 / DL4677: JAX 2027-01-21 12:00:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
    • DL2333: JAX 2027-01-21 12:00:00 → DTW 2027-01-21 14:20:00; layover at DTW: 200 minutes.
    • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2027-02-04 13:02:00 → JAX 2027-02-04 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2027-02-04 13:02:00 → ATL 2027-02-04 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2027-02-04 19:33:00 → JAX 2027-02-04 20:43:00.

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