Travel with Axel,
get the best price.

Philadelphia → Chicago

Dec 16, 2026 · return Dec 23, 2026

PHL → MDW1 adulteconomyRound trip

6 flight options · 3 airlines

Nonstop flights

Wed, Dec 16 – Wed, Dec 23

Southwest Airlines
6:20 pmPHL
2h 15m
Nonstop
7:35 pmMDW
Southwest Airlines
11:25 amMDW
1h 50m
Nonstop
2:15 pmPHL

Round-trip total · 1 adult · Taxes included

Wed, Dec 16 – Wed, Dec 23

Southwest Airlines
11:45 amPHL
2h 15m
Nonstop
1:00 pmMDW
Southwest Airlines
11:25 amMDW
1h 50m
Nonstop
2:15 pmPHL

Round-trip total · 1 adult · Taxes included

One-stop flights

Wed, Dec 16 – Wed, Dec 23

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

Wed, Dec 16 – Wed, Dec 23

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

Wed, Dec 16 – Wed, Dec 23

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

Wed, Dec 16 – Wed, Dec 23

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.

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 routeOct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 13, 2026 → Nov 16, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 11, 2026 → Dec 14, 2026Dec 12, 2026 → Dec 19, 2026Dec 22, 2026 → Dec 27, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Dec 30, 2026 → Jan 2, 2027Jan 8, 2027 → Jan 11, 2027Jan 9, 2027 → Jan 16, 2027Jan 15, 2027 → Jan 18, 2027Jan 22, 2027 → Jan 25, 2027Jan 23, 2027 → Jan 30, 2027Feb 5, 2027 → Feb 8, 2027Feb 6, 2027 → Feb 13, 2027Feb 12, 2027 → Feb 15, 2027Mar 5, 2027 → Mar 8, 2027Mar 6, 2027 → Mar 13, 2027Mar 25, 2027 → Mar 29, 2027Apr 2, 2027 → Apr 5, 2027Apr 3, 2027 → Apr 10, 2027Apr 30, 2027 → May 3, 2027May 1, 2027 → May 8, 2027May 28, 2027 → May 31, 2027May 29, 2027 → Jun 5, 2027Jun 25, 2027 → Jun 28, 2027Jun 26, 2027 → Jul 3, 2027Jul 2, 2027 → Jul 6, 2027Jul 23, 2027 → Jul 26, 2027Jul 24, 2027 → Jul 31, 2027Aug 20, 2027 → Aug 23, 2027Aug 21, 2027 → Aug 28, 2027Sep 3, 2027 → Sep 6, 2027Sep 17, 2027 → Sep 20, 2027Oct 30, 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)
2026-12-16 → 2026-12-23Southwest AirlinesWN2108 / WN2941$322.002026-10-29T01:55:53Z
2026-12-16 → 2026-12-23Frontier AirlinesF91147 + F92291 / F92144 + F92552$207.002026-10-29T01:55:53Z
2026-12-16 → 2026-12-23Delta Air LinesDL2968 + DL4688 / DL4688 + DL1686$379.502026-10-29T01:55:53Z
2026-12-16 → 2026-12-23Southwest AirlinesWN2200 / WN2941$322.002026-10-29T01:55:53Z
2026-12-16 → 2026-12-23Southwest AirlinesWN3375 + WN287 / WN2941$314.502026-10-29T01:55:53Z
2026-12-16 → 2026-12-23Southwest AirlinesWN2080 + WN651 / WN2941$314.502026-10-29T01:55:53Z

2026-12-16 → 2026-12-23 · $322.00

  • Southwest Airlines WN2108: PHL 2026-12-16 18:20:00 → MDW 2026-12-16 19:35:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2026-12-23 11:25:00 → PHL 2026-12-23 14:15:00; nonstop; 110 minutes. Local airport times.

2026-12-16 → 2026-12-23 · $207.00

  • Frontier Airlines F91147 / F92291: PHL 2026-12-16 17:14:00 → MDW 2026-12-16 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2026-12-16 17:14:00 → ATL 2026-12-16 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2026-12-16 22:48:00 → MDW 2026-12-16 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2026-12-23 12:28:00 → PHL 2026-12-23 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2026-12-23 12:28:00 → ATL 2026-12-23 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2026-12-23 18:58:00 → PHL 2026-12-23 21:07:00.

2026-12-16 → 2026-12-23 · $379.50

  • Delta Air Lines DL2968 / DL4688: PHL 2026-12-16 09:43:00 → MDW 2026-12-16 13:01:00; 1 stop(s) via DTW; 258 minutes. Local airport times.
    • DL2968: PHL 2026-12-16 09:43:00 → DTW 2026-12-16 11:35:00; layover at DTW: 69 minutes.
    • DL4688: DTW 2026-12-16 12:44:00 → MDW 2026-12-16 13:01:00.
  • Delta Air Lines DL4688 / DL1686: MDW 2026-12-23 13:31:00 → PHL 2026-12-23 19:30:00; 1 stop(s) via DTW; 299 minutes. Local airport times.
    • DL4688: MDW 2026-12-23 13:31:00 → DTW 2026-12-23 15:44:00; layover at DTW: 125 minutes.
    • DL1686: DTW 2026-12-23 17:49:00 → PHL 2026-12-23 19:30:00.

2026-12-16 → 2026-12-23 · $322.00

  • Southwest Airlines WN2200: PHL 2026-12-16 11:45:00 → MDW 2026-12-16 13:00:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2026-12-23 11:25:00 → PHL 2026-12-23 14:15:00; nonstop; 110 minutes. Local airport times.

2026-12-16 → 2026-12-23 · $314.50

  • Southwest Airlines WN3375 / WN287: PHL 2026-12-16 06:00:00 → MDW 2026-12-16 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN3375: PHL 2026-12-16 06:00:00 → STL 2026-12-16 07:45:00; layover at STL: 190 minutes.
    • WN287: STL 2026-12-16 10:55:00 → MDW 2026-12-16 12:05:00.
  • Southwest Airlines WN2941: MDW 2026-12-23 11:25:00 → PHL 2026-12-23 14:15:00; nonstop; 110 minutes. Local airport times.

2026-12-16 → 2026-12-23 · $314.50

  • Southwest Airlines WN2080 / WN651: PHL 2026-12-16 14:55:00 → MDW 2026-12-16 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
    • WN2080: PHL 2026-12-16 14:55:00 → BNA 2026-12-16 16:10:00; layover at BNA: 200 minutes.
    • WN651: BNA 2026-12-16 19:30:00 → MDW 2026-12-16 21:05:00.
  • Southwest Airlines WN2941: MDW 2026-12-23 11:25:00 → PHL 2026-12-23 14:15:00; nonstop; 110 minutes. Local airport times.

More dates for this route