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Philadelphia → Chicago

Dec 7, 2026 · return Dec 14, 2026

PHL → MDW1 adulteconomyRound trip

6 flight options · 3 airlines

Nonstop flights

Mon, Dec 7 – Mon, Dec 14

Southwest Airlines
1:25 pmPHL
2h 15m
Nonstop
2:40 pmMDW
Southwest Airlines
11:25 amMDW
1h 50m
Nonstop
2:15 pmPHL

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Mon, Dec 14

Southwest Airlines
6:15 pmPHL
2h 15m
Nonstop
7:30 pmMDW
Southwest Airlines
11:25 amMDW
1h 50m
Nonstop
2:15 pmPHL

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 7 – Mon, Dec 14

Frontier Airlines
5:14 pmPHL
7h 33m
ATL · 2h 54m
11:47 pmMDW
Frontier Airlines
12:28 pmMDW
7h 39m
ATL · 3h 17m
9:07 pmPHL

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Mon, Dec 14

Delta Air Lines
9:43 amPHL
4h 18m
DTW · 1h 9m
1:01 pmMDW
Delta Air Lines
1:31 pmMDW
4h 59m
DTW · 2h 5m
7:30 pmPHL

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Mon, Dec 14

Southwest Airlines
6:00 amPHL
7h 5m
STL · 3h 10m
12:05 pmMDW
Southwest Airlines
11:25 amMDW
1h 50m
Nonstop
2:15 pmPHL

Round-trip total · 1 adult · Taxes included

Mon, Dec 7 – Mon, Dec 14

Southwest Airlines
2:55 pmPHL
7h 10m
BNA · 3h 20m
9:05 pmMDW
Southwest Airlines
11:25 amMDW
1h 50m
Nonstop
2:15 pmPHL

Round-trip total · 1 adult · Taxes included

Make this trip yours

PHL ⇄ 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
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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)
2026-12-07 → 2026-12-14Southwest AirlinesWN2205 / WN2941$280.002026-10-29T01:55:53Z
2026-12-07 → 2026-12-14Frontier AirlinesF91147 + F92291 / F92144 + F92552$180.002026-10-29T01:55:53Z
2026-12-07 → 2026-12-14Delta Air LinesDL2968 + DL4688 / DL4688 + DL1686$330.002026-10-29T01:55:53Z
2026-12-07 → 2026-12-14Southwest AirlinesWN2108 / WN2941$280.002026-10-29T01:55:53Z
2026-12-07 → 2026-12-14Southwest AirlinesWN3375 + WN287 / WN2941$272.502026-10-29T01:55:53Z
2026-12-07 → 2026-12-14Southwest AirlinesWN2080 + WN651 / WN2941$272.502026-10-29T01:55:53Z

2026-12-07 → 2026-12-14 · $280.00

  • Southwest Airlines WN2205: PHL 2026-12-07 13:25:00 → MDW 2026-12-07 14:40:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2026-12-14 11:25:00 → PHL 2026-12-14 14:15:00; nonstop; 110 minutes. Local airport times.

2026-12-07 → 2026-12-14 · $180.00

  • Frontier Airlines F91147 / F92291: PHL 2026-12-07 17:14:00 → MDW 2026-12-07 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2026-12-07 17:14:00 → ATL 2026-12-07 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2026-12-07 22:48:00 → MDW 2026-12-07 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2026-12-14 12:28:00 → PHL 2026-12-14 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2026-12-14 12:28:00 → ATL 2026-12-14 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2026-12-14 18:58:00 → PHL 2026-12-14 21:07:00.

2026-12-07 → 2026-12-14 · $330.00

  • Delta Air Lines DL2968 / DL4688: PHL 2026-12-07 09:43:00 → MDW 2026-12-07 13:01:00; 1 stop(s) via DTW; 258 minutes. Local airport times.
    • DL2968: PHL 2026-12-07 09:43:00 → DTW 2026-12-07 11:35:00; layover at DTW: 69 minutes.
    • DL4688: DTW 2026-12-07 12:44:00 → MDW 2026-12-07 13:01:00.
  • Delta Air Lines DL4688 / DL1686: MDW 2026-12-14 13:31:00 → PHL 2026-12-14 19:30:00; 1 stop(s) via DTW; 299 minutes. Local airport times.
    • DL4688: MDW 2026-12-14 13:31:00 → DTW 2026-12-14 15:44:00; layover at DTW: 125 minutes.
    • DL1686: DTW 2026-12-14 17:49:00 → PHL 2026-12-14 19:30:00.

2026-12-07 → 2026-12-14 · $280.00

  • Southwest Airlines WN2108: PHL 2026-12-07 18:15:00 → MDW 2026-12-07 19:30:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2026-12-14 11:25:00 → PHL 2026-12-14 14:15:00; nonstop; 110 minutes. Local airport times.

2026-12-07 → 2026-12-14 · $272.50

  • Southwest Airlines WN3375 / WN287: PHL 2026-12-07 06:00:00 → MDW 2026-12-07 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN3375: PHL 2026-12-07 06:00:00 → STL 2026-12-07 07:45:00; layover at STL: 190 minutes.
    • WN287: STL 2026-12-07 10:55:00 → MDW 2026-12-07 12:05:00.
  • Southwest Airlines WN2941: MDW 2026-12-14 11:25:00 → PHL 2026-12-14 14:15:00; nonstop; 110 minutes. Local airport times.

2026-12-07 → 2026-12-14 · $272.50

  • Southwest Airlines WN2080 / WN651: PHL 2026-12-07 14:55:00 → MDW 2026-12-07 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
    • WN2080: PHL 2026-12-07 14:55:00 → BNA 2026-12-07 16:10:00; layover at BNA: 200 minutes.
    • WN651: BNA 2026-12-07 19:30:00 → MDW 2026-12-07 21:05:00.
  • Southwest Airlines WN2941: MDW 2026-12-14 11:25:00 → PHL 2026-12-14 14:15:00; nonstop; 110 minutes. Local airport times.

More dates for this route