Travel with Axel,
get the best price.

Philadelphia → Chicago

Choose your travel dates

PHL → MDW1 adulteconomy

18 flight options · 3 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
11:40 amPHL
2h 10m
Nonstop
12:50 pmMDW
Southwest Airlines
11:25 amMDW
1h 50m
Nonstop
2:15 pmPHL

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 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

Fri, Nov 20 – Mon, Nov 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

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
11:40 amPHL
2h 10m
Nonstop
12:50 pmMDW
Southwest Airlines
11:25 amMDW
1h 50m
Nonstop
2:15 pmPHL

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

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

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 20 – Mon, Nov 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

Show 4 more flights

Fri, Nov 20 – Mon, Nov 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

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

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

Fri, Nov 27 – Fri, Dec 4

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

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
6:15 pmPHL
2h 15m
Nonstop
7:30 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Frontier Airlines
5:14 pmPHL
7h 33m
ATL · 2h 54m
11:47 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
9:43 amPHL
4h 18m
DTW · 1h 9m
1:01 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
11:40 amPHL
2h 10m
Nonstop
12:50 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
2:55 pmPHL
7h 10m
BNA · 3h 20m
9:05 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
6:00 amPHL
7h 5m
STL · 3h 10m
12:05 pmMDW

One-way 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.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. 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

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 AirlinesWN2108$150.002026-10-29T01:55:53Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3374 / WN2941$280.002026-10-29T01:55:53Z
2026-11-20 · one wayFrontier AirlinesF91147 + F92291$95.002026-10-29T01:55:53Z
2026-11-20 · one wayDelta Air LinesDL2968 + DL4688$175.002026-10-29T01:55:53Z
2026-11-20 → 2026-11-23Frontier AirlinesF91147 + F92291 / F92144 + F92552$180.002026-10-29T01:55:53Z
2026-11-20 → 2026-11-23Delta Air LinesDL2968 + DL4688 / DL4688 + DL1686$330.002026-10-29T01:55:53Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3374 / WN2941$329.002026-10-29T01:55:53Z
2026-11-20 · one waySouthwest AirlinesWN3374$150.002026-10-29T01:55:53Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2108 / WN2941$280.002026-10-29T01:55:53Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2108 / WN2941$329.002026-10-29T01:55:53Z
2026-11-20 · one waySouthwest AirlinesWN2080 + WN651$140.002026-10-29T01:55:53Z
2026-11-20 · one waySouthwest AirlinesWN3375 + WN287$140.002026-10-29T01:55:53Z
2026-11-27 → 2026-12-04Frontier AirlinesF91147 + F92291 / F92144 + F92552$211.502026-10-29T01:55:53Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3375 + WN287 / WN2941$272.502026-10-29T01:55:53Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2080 + WN651 / WN2941$272.502026-10-29T01:55:53Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3375 + WN287 / WN2941$318.882026-10-29T01:55:53Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2080 + WN651 / WN2941$318.882026-10-29T01:55:53Z
2026-11-27 → 2026-12-04Delta Air LinesDL2968 + DL4688 / DL4688 + DL1686$387.752026-10-29T01:55:53Z

2026-11-20 · one way · $150.00

  • Southwest Airlines WN2108: PHL 2026-11-20 18:15:00 → MDW 2026-11-20 19:30:00; nonstop; 135 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $280.00

  • Southwest Airlines WN3374: PHL 2026-11-20 11:40:00 → MDW 2026-11-20 12:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2026-11-23 11:25:00 → PHL 2026-11-23 14:15:00; nonstop; 110 minutes. Local airport times.

2026-11-20 · one way · $95.00

  • Frontier Airlines F91147 / F92291: PHL 2026-11-20 17:14:00 → MDW 2026-11-20 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2026-11-20 17:14:00 → ATL 2026-11-20 19:54:00; layover at ATL: 174 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 DL2968 / DL4688: PHL 2026-11-20 09:43:00 → MDW 2026-11-20 13:01:00; 1 stop(s) via DTW; 258 minutes. Local airport times.
    • DL2968: PHL 2026-11-20 09:43:00 → DTW 2026-11-20 11:35:00; layover at DTW: 69 minutes.
    • DL4688: DTW 2026-11-20 12:44:00 → MDW 2026-11-20 13:01:00.

2026-11-20 → 2026-11-23 · $180.00

  • Frontier Airlines F91147 / F92291: PHL 2026-11-20 17:14:00 → MDW 2026-11-20 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2026-11-20 17:14:00 → ATL 2026-11-20 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2026-11-20 22:48:00 → MDW 2026-11-20 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2026-11-23 12:28:00 → PHL 2026-11-23 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2026-11-23 12:28:00 → ATL 2026-11-23 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2026-11-23 18:58:00 → PHL 2026-11-23 21:07:00.

2026-11-20 → 2026-11-23 · $330.00

  • Delta Air Lines DL2968 / DL4688: PHL 2026-11-20 09:43:00 → MDW 2026-11-20 13:01:00; 1 stop(s) via DTW; 258 minutes. Local airport times.
    • DL2968: PHL 2026-11-20 09:43:00 → DTW 2026-11-20 11:35:00; layover at DTW: 69 minutes.
    • DL4688: DTW 2026-11-20 12:44:00 → MDW 2026-11-20 13:01:00.
  • Delta Air Lines DL4688 / DL1686: MDW 2026-11-23 13:31:00 → PHL 2026-11-23 19:30:00; 1 stop(s) via DTW; 299 minutes. Local airport times.
    • DL4688: MDW 2026-11-23 13:31:00 → DTW 2026-11-23 15:44:00; layover at DTW: 125 minutes.
    • DL1686: DTW 2026-11-23 17:49:00 → PHL 2026-11-23 19:30:00.

2026-11-27 → 2026-12-04 · $329.00

  • Southwest Airlines WN3374: PHL 2026-11-27 11:40:00 → MDW 2026-11-27 12:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2026-12-04 11:25:00 → PHL 2026-12-04 14:15:00; nonstop; 110 minutes. Local airport times.

2026-11-20 · one way · $150.00

  • Southwest Airlines WN3374: PHL 2026-11-20 11:40:00 → MDW 2026-11-20 12:50:00; nonstop; 130 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $280.00

  • Southwest Airlines WN2108: PHL 2026-11-20 18:15:00 → MDW 2026-11-20 19:30:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2026-11-23 11:25:00 → PHL 2026-11-23 14:15:00; nonstop; 110 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $329.00

  • Southwest Airlines WN2108: PHL 2026-11-27 18:15:00 → MDW 2026-11-27 19:30:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2026-12-04 11:25:00 → PHL 2026-12-04 14:15:00; nonstop; 110 minutes. Local airport times.

2026-11-20 · one way · $140.00

  • Southwest Airlines WN2080 / WN651: PHL 2026-11-20 14:55:00 → MDW 2026-11-20 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
    • WN2080: PHL 2026-11-20 14:55:00 → BNA 2026-11-20 16:10:00; layover at BNA: 200 minutes.
    • WN651: BNA 2026-11-20 19:30:00 → MDW 2026-11-20 21:05:00.

2026-11-20 · one way · $140.00

  • Southwest Airlines WN3375 / WN287: PHL 2026-11-20 06:00:00 → MDW 2026-11-20 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN3375: PHL 2026-11-20 06:00:00 → STL 2026-11-20 07:45:00; layover at STL: 190 minutes.
    • WN287: STL 2026-11-20 10:55:00 → MDW 2026-11-20 12:05:00.

2026-11-27 → 2026-12-04 · $211.50

  • Frontier Airlines F91147 / F92291: PHL 2026-11-27 17:14:00 → MDW 2026-11-27 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2026-11-27 17:14:00 → ATL 2026-11-27 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2026-11-27 22:48:00 → MDW 2026-11-27 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2026-12-04 12:28:00 → PHL 2026-12-04 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2026-12-04 12:28:00 → ATL 2026-12-04 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2026-12-04 18:58:00 → PHL 2026-12-04 21:07:00.

2026-11-20 → 2026-11-23 · $272.50

  • Southwest Airlines WN3375 / WN287: PHL 2026-11-20 06:00:00 → MDW 2026-11-20 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN3375: PHL 2026-11-20 06:00:00 → STL 2026-11-20 07:45:00; layover at STL: 190 minutes.
    • WN287: STL 2026-11-20 10:55:00 → MDW 2026-11-20 12:05:00.
  • Southwest Airlines WN2941: MDW 2026-11-23 11:25:00 → PHL 2026-11-23 14:15:00; nonstop; 110 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $272.50

  • Southwest Airlines WN2080 / WN651: PHL 2026-11-20 14:55:00 → MDW 2026-11-20 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
    • WN2080: PHL 2026-11-20 14:55:00 → BNA 2026-11-20 16:10:00; layover at BNA: 200 minutes.
    • WN651: BNA 2026-11-20 19:30:00 → MDW 2026-11-20 21:05:00.
  • Southwest Airlines WN2941: MDW 2026-11-23 11:25:00 → PHL 2026-11-23 14:15:00; nonstop; 110 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $318.88

  • Southwest Airlines WN3375 / WN287: PHL 2026-11-27 06:00:00 → MDW 2026-11-27 12:05:00; 1 stop(s) via STL; 425 minutes. Local airport times.
    • WN3375: PHL 2026-11-27 06:00:00 → STL 2026-11-27 07:45:00; layover at STL: 190 minutes.
    • WN287: STL 2026-11-27 10:55:00 → MDW 2026-11-27 12:05:00.
  • Southwest Airlines WN2941: MDW 2026-12-04 11:25:00 → PHL 2026-12-04 14:15:00; nonstop; 110 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $318.88

  • Southwest Airlines WN2080 / WN651: PHL 2026-11-27 14:55:00 → MDW 2026-11-27 21:05:00; 1 stop(s) via BNA; 430 minutes. Local airport times.
    • WN2080: PHL 2026-11-27 14:55:00 → BNA 2026-11-27 16:10:00; layover at BNA: 200 minutes.
    • WN651: BNA 2026-11-27 19:30:00 → MDW 2026-11-27 21:05:00.
  • Southwest Airlines WN2941: MDW 2026-12-04 11:25:00 → PHL 2026-12-04 14:15:00; nonstop; 110 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $387.75

  • Delta Air Lines DL2968 / DL4688: PHL 2026-11-27 09:43:00 → MDW 2026-11-27 13:01:00; 1 stop(s) via DTW; 258 minutes. Local airport times.
    • DL2968: PHL 2026-11-27 09:43:00 → DTW 2026-11-27 11:35:00; layover at DTW: 69 minutes.
    • DL4688: DTW 2026-11-27 12:44:00 → MDW 2026-11-27 13:01:00.
  • Delta Air Lines DL4688 / DL1686: MDW 2026-12-04 13:31:00 → PHL 2026-12-04 19:30:00; 1 stop(s) via DTW; 299 minutes. Local airport times.
    • DL4688: MDW 2026-12-04 13:31:00 → DTW 2026-12-04 15:44:00; layover at DTW: 125 minutes.
    • DL1686: DTW 2026-12-04 17:49:00 → PHL 2026-12-04 19:30:00.

More dates for this route