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JAX → MDW1 adulteconomy

24 flight options · 3 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
1:30 pmJAX
2h 25m
Nonstop
2:55 pmMDW
Southwest Airlines
7:00 pmMDW
2h 15m
Nonstop
10:15 pmJAX

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 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

Fri, Nov 27 – Fri, Dec 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

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
6:55 pmJAX
2h 25m
Nonstop
8:20 pmMDW
Southwest Airlines
7:00 pmMDW
2h 15m
Nonstop
10:15 pmJAX

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
6:55 pmJAX
2h 25m
Nonstop
8:20 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
1:30 pmJAX
2h 25m
Nonstop
2:55 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
11:20 amJAX
5h 55m
BNA · 2h 40m
4:15 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Show 8 more flights

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
8:00 amJAX
5h 15m
BWI · 1h 15m
12:15 pmMDW
Southwest Airlines
8:00 amMDW
2h 25m
Nonstop
11:25 amJAX

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
11:20 amJAX
5h 55m
BNA · 2h 40m
4:15 pmMDW
Southwest Airlines
7:00 pmMDW
2h 15m
Nonstop
10:15 pmJAX

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
6:00 amJAX
7h 5m
STL · 3h 35m
12:05 pmMDW
Southwest Airlines
7:00 pmMDW
2h 15m
Nonstop
10:15 pmJAX

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
6:50 pmJAX
2h 30m
Nonstop
8:20 pmMDW
Southwest Airlines
5:25 pmMDW
5h 20m
BNA · 2h 20m
11:45 pmJAX

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
8:00 amJAX
5h 15m
BWI · 1h 15m
12:15 pmMDW
Southwest Airlines
7:00 pmMDW
2h 15m
Nonstop
10:15 pmJAX

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 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

Fri, Nov 20 – Mon, Nov 23

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

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
6:55 pmJAX
2h 25m
Nonstop
8:20 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

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

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
12:00 pmJAX
7h 1m
DTW · 3h 20m
6:01 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
1:30 pmJAX
2h 25m
Nonstop
2:55 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
6:00 amJAX
7h 5m
STL · 3h 35m
12:05 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
8:00 amJAX
5h 15m
BWI · 1h 15m
12:15 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
11:20 amJAX
5h 55m
BNA · 2h 40m
4:15 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
6:59 pmJAX
4h 18m
ATL · 1h 1m
10:17 pmMDW

One-way 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

Nov 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)
2026-11-20 · one waySouthwest AirlinesWN2264$155.002026-10-29T01:16:41Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1979 / WN2946$340.752026-10-29T01:16:41Z
2026-11-20 · one wayFrontier AirlinesF91549 + F92291$100.002026-10-29T01:16:41Z
2026-11-20 · one wayDelta Air LinesDL2333 + DL4677$175.002026-10-29T01:16:41Z
2026-11-27 → 2026-12-04Frontier AirlinesF91549 + F92291 / F92144 + F91550$217.382026-10-29T01:16:41Z
2026-11-27 → 2026-12-04Delta Air LinesDL2333 + DL4677 / DL2417 + DL2265$387.752026-10-29T01:16:41Z
2026-11-20 · one waySouthwest AirlinesWN1979$155.002026-10-29T01:16:41Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2264 / WN2946$340.752026-10-29T01:16:41Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2264 / WN2262$340.752026-10-29T01:16:41Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1979 / WN2262$340.752026-10-29T01:16:41Z
2026-11-20 · one waySouthwest AirlinesWN2265 + WN287$145.002026-10-29T01:16:41Z
2026-11-20 · one waySouthwest AirlinesWN2256 + WN1070$145.002026-10-29T01:16:41Z
2026-11-20 · one waySouthwest AirlinesWN2253 + WN2062$145.002026-10-29T01:16:41Z
2026-11-20 · one wayDelta Air LinesDL2627 + DL1076$175.002026-10-29T01:16:41Z
2026-11-20 → 2026-11-23Frontier AirlinesF91549 + F92291 / F92144 + F91550$217.382026-10-29T01:16:41Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2253 + WN2062 / WN2262$330.632026-10-29T01:16:41Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2256 + WN1070 / WN2262$330.632026-10-29T01:16:41Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2253 + WN2062 / WN2946$333.252026-10-29T01:16:41Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2265 + WN287 / WN2946$333.252026-10-29T01:16:41Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2264 / WN2897 + WN1516$333.252026-10-29T01:16:41Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2256 + WN1070 / WN2946$333.252026-10-29T01:16:41Z
2026-11-20 → 2026-11-23Delta Air LinesDL2333 + DL4677 / DL2417 + DL2265$387.752026-10-29T01:16:41Z
2026-11-27 → 2026-12-04Delta Air LinesDL2627 + DL1076 / DL2417 + DL2265$387.752026-10-29T01:16:41Z
2026-11-20 → 2026-11-23Delta Air LinesDL2627 + DL1076 / DL2417 + DL2265$387.752026-10-29T01:16:41Z

2026-11-20 · one way · $155.00

  • Southwest Airlines WN2264: JAX 2026-11-20 18:55:00 → MDW 2026-11-20 20:20:00; nonstop; 145 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $340.75

  • Southwest Airlines WN1979: JAX 2026-11-20 13:30:00 → MDW 2026-11-20 14:55:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2946: MDW 2026-11-23 19:00:00 → JAX 2026-11-23 22:15:00; nonstop; 135 minutes. Local airport times.

2026-11-20 · one way · $100.00

  • Frontier Airlines F91549 / F92291: JAX 2026-11-20 19:03:00 → MDW 2026-11-20 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-20 19:03:00 → ATL 2026-11-20 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-20 22:48:00 → MDW 2026-11-20 23:47:00.

2026-11-20 · one way · $175.00

  • Delta Air Lines DL2333 / DL4677: JAX 2026-11-20 12:00:00 → MDW 2026-11-20 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
    • DL2333: JAX 2026-11-20 12:00:00 → DTW 2026-11-20 14:20:00; layover at DTW: 200 minutes.
    • DL4677: DTW 2026-11-20 17:40:00 → MDW 2026-11-20 18:01:00.

2026-11-27 → 2026-12-04 · $217.38

  • Frontier Airlines F91549 / F92291: JAX 2026-11-27 19:03:00 → MDW 2026-11-27 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-27 19:03:00 → ATL 2026-11-27 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-27 22:48:00 → MDW 2026-11-27 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-12-04 13:11:00 → JAX 2026-12-04 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-12-04 13:11:00 → ATL 2026-12-04 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-12-04 18:09:00 → JAX 2026-12-04 19:25:00.

2026-11-27 → 2026-12-04 · $387.75

  • Delta Air Lines DL2333 / DL4677: JAX 2026-11-27 12:00:00 → MDW 2026-11-27 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
    • DL2333: JAX 2026-11-27 12:00:00 → DTW 2026-11-27 14:20:00; layover at DTW: 200 minutes.
    • DL4677: DTW 2026-11-27 17:40:00 → MDW 2026-11-27 18:01:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-04 13:02:00 → JAX 2026-12-04 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-04 13:02:00 → ATL 2026-12-04 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-04 19:33:00 → JAX 2026-12-04 20:43:00.

2026-11-20 · one way · $155.00

  • Southwest Airlines WN1979: JAX 2026-11-20 13:30:00 → MDW 2026-11-20 14:55:00; nonstop; 145 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $340.75

  • Southwest Airlines WN2264: JAX 2026-11-20 18:55:00 → MDW 2026-11-20 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2946: MDW 2026-11-23 19:00:00 → JAX 2026-11-23 22:15:00; nonstop; 135 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $340.75

  • Southwest Airlines WN2264: JAX 2026-11-27 18:55:00 → MDW 2026-11-27 20:20:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2262: MDW 2026-12-04 08:00:00 → JAX 2026-12-04 11:25:00; nonstop; 145 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $340.75

  • Southwest Airlines WN1979: JAX 2026-11-27 13:30:00 → MDW 2026-11-27 14:55:00; nonstop; 145 minutes. Local airport times.
  • Southwest Airlines WN2262: MDW 2026-12-04 08:00:00 → JAX 2026-12-04 11:25:00; nonstop; 145 minutes. Local airport times.

2026-11-20 · one way · $145.00

  • Southwest Airlines WN2265 / WN287: JAX 2026-11-20 06:00:00 → MDW 2026-11-20 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN2265: JAX 2026-11-20 06:00:00 → STL 2026-11-20 07:20:00; layover at STL: 215 minutes.
    • WN287: STL 2026-11-20 10:55:00 → MDW 2026-11-20 12:05:00.

2026-11-20 · one way · $145.00

  • Southwest Airlines WN2256 / WN1070: JAX 2026-11-20 08:00:00 → MDW 2026-11-20 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2026-11-20 08:00:00 → BWI 2026-11-20 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2026-11-20 11:05:00 → MDW 2026-11-20 12:15:00.

2026-11-20 · one way · $145.00

  • Southwest Airlines WN2253 / WN2062: JAX 2026-11-20 11:20:00 → MDW 2026-11-20 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
    • WN2253: JAX 2026-11-20 11:20:00 → BNA 2026-11-20 12:05:00; layover at BNA: 160 minutes.
    • WN2062: BNA 2026-11-20 14:45:00 → MDW 2026-11-20 16:15:00.

2026-11-20 · one way · $175.00

  • Delta Air Lines DL2627 / DL1076: JAX 2026-11-20 18:59:00 → MDW 2026-11-20 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-11-20 18:59:00 → ATL 2026-11-20 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-11-20 21:20:00 → MDW 2026-11-20 22:17:00.

2026-11-20 → 2026-11-23 · $217.38

  • Frontier Airlines F91549 / F92291: JAX 2026-11-20 19:03:00 → MDW 2026-11-20 23:47:00; 1 stop(s) via ATL; 344 minutes. Local airport times.
    • F91549: JAX 2026-11-20 19:03:00 → ATL 2026-11-20 20:31:00; layover at ATL: 137 minutes.
    • F92291: ATL 2026-11-20 22:48:00 → MDW 2026-11-20 23:47:00.
  • Frontier Airlines F92144 / F91550: MDW 2026-11-23 13:11:00 → JAX 2026-11-23 19:25:00; 1 stop(s) via ATL; 314 minutes. Local airport times.
    • F92144: MDW 2026-11-23 13:11:00 → ATL 2026-11-23 16:18:00; layover at ATL: 111 minutes.
    • F91550: ATL 2026-11-23 18:09:00 → JAX 2026-11-23 19:25:00.

2026-11-27 → 2026-12-04 · $330.63

  • Southwest Airlines WN2253 / WN2062: JAX 2026-11-27 11:20:00 → MDW 2026-11-27 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
    • WN2253: JAX 2026-11-27 11:20:00 → BNA 2026-11-27 12:05:00; layover at BNA: 160 minutes.
    • WN2062: BNA 2026-11-27 14:45:00 → MDW 2026-11-27 16:15:00.
  • Southwest Airlines WN2262: MDW 2026-12-04 08:00:00 → JAX 2026-12-04 11:25:00; nonstop; 145 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $330.63

  • Southwest Airlines WN2256 / WN1070: JAX 2026-11-27 08:00:00 → MDW 2026-11-27 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2026-11-27 08:00:00 → BWI 2026-11-27 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2026-11-27 11:05:00 → MDW 2026-11-27 12:15:00.
  • Southwest Airlines WN2262: MDW 2026-12-04 08:00:00 → JAX 2026-12-04 11:25:00; nonstop; 145 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $333.25

  • Southwest Airlines WN2253 / WN2062: JAX 2026-11-20 11:20:00 → MDW 2026-11-20 16:15:00; 1 stop(s) via BNA; 355 minutes. Local airport times.
    • WN2253: JAX 2026-11-20 11:20:00 → BNA 2026-11-20 12:05:00; layover at BNA: 160 minutes.
    • WN2062: BNA 2026-11-20 14:45:00 → MDW 2026-11-20 16:15:00.
  • Southwest Airlines WN2946: MDW 2026-11-23 19:00:00 → JAX 2026-11-23 22:15:00; nonstop; 135 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $333.25

  • Southwest Airlines WN2265 / WN287: JAX 2026-11-20 06:00:00 → MDW 2026-11-20 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN2265: JAX 2026-11-20 06:00:00 → STL 2026-11-20 07:20:00; layover at STL: 215 minutes.
    • WN287: STL 2026-11-20 10:55:00 → MDW 2026-11-20 12:05:00.
  • Southwest Airlines WN2946: MDW 2026-11-23 19:00:00 → JAX 2026-11-23 22:15:00; nonstop; 135 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $333.25

  • Southwest Airlines WN2264: JAX 2026-11-27 18:50:00 → MDW 2026-11-27 20:20:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN2897 / WN1516: MDW 2026-12-04 17:25:00 → JAX 2026-12-04 23:45:00; 1 stop(s) via BNA; 320 minutes. Local airport times.
    • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 140 minutes.
    • WN1516: BNA 2026-12-04 21:10:00 → JAX 2026-12-04 23:45:00.

2026-11-20 → 2026-11-23 · $333.25

  • Southwest Airlines WN2256 / WN1070: JAX 2026-11-20 08:00:00 → MDW 2026-11-20 12:15:00; 1 stop(s) via BWI; 315 minutes. Local airport times.
    • WN2256: JAX 2026-11-20 08:00:00 → BWI 2026-11-20 09:50:00; layover at BWI: 75 minutes.
    • WN1070: BWI 2026-11-20 11:05:00 → MDW 2026-11-20 12:15:00.
  • Southwest Airlines WN2946: MDW 2026-11-23 19:00:00 → JAX 2026-11-23 22:15:00; nonstop; 135 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $387.75

  • Delta Air Lines DL2333 / DL4677: JAX 2026-11-20 12:00:00 → MDW 2026-11-20 18:01:00; 1 stop(s) via DTW; 421 minutes. Local airport times.
    • DL2333: JAX 2026-11-20 12:00:00 → DTW 2026-11-20 14:20:00; layover at DTW: 200 minutes.
    • DL4677: DTW 2026-11-20 17:40:00 → MDW 2026-11-20 18:01:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-11-23 13:02:00 → JAX 2026-11-23 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-11-23 13:02:00 → ATL 2026-11-23 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-11-23 19:33:00 → JAX 2026-11-23 20:43:00.

2026-11-27 → 2026-12-04 · $387.75

  • Delta Air Lines DL2627 / DL1076: JAX 2026-11-27 18:59:00 → MDW 2026-11-27 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-11-27 18:59:00 → ATL 2026-11-27 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-11-27 21:20:00 → MDW 2026-11-27 22:17:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-12-04 13:02:00 → JAX 2026-12-04 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-12-04 13:02:00 → ATL 2026-12-04 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-12-04 19:33:00 → JAX 2026-12-04 20:43:00.

2026-11-20 → 2026-11-23 · $387.75

  • Delta Air Lines DL2627 / DL1076: JAX 2026-11-20 18:59:00 → MDW 2026-11-20 22:17:00; 1 stop(s) via ATL; 258 minutes. Local airport times.
    • DL2627: JAX 2026-11-20 18:59:00 → ATL 2026-11-20 20:19:00; layover at ATL: 61 minutes.
    • DL1076: ATL 2026-11-20 21:20:00 → MDW 2026-11-20 22:17:00.
  • Delta Air Lines DL2417 / DL2265: MDW 2026-11-23 13:02:00 → JAX 2026-11-23 20:43:00; 1 stop(s) via ATL; 401 minutes. Local airport times.
    • DL2417: MDW 2026-11-23 13:02:00 → ATL 2026-11-23 16:01:00; layover at ATL: 212 minutes.
    • DL2265: ATL 2026-11-23 19:33:00 → JAX 2026-11-23 20:43:00.

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