Travel with Axel,
get the best price.

Route overview: Philadelphia to Chicago (MDW) flight deals

Philadelphia → Chicago

May 29, 2027 · choose your return date

PHL → MDW1 adulteconomyOne way and round trips

30 flight options · 2 airlines

Choose your return date

One-way flights and round trips by duration. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

May 2027

May 29, 2027 · One wayFrontier AirlinesUp to 1 stop each way$132.25 May 29, 2027 · One waySouthwest AirlinesNonstop$201.25 May 29, 2027 – May 30, 2027 · 1 nightFrontier AirlinesUp to 1 stop each way$253.00 May 29, 2027 – May 30, 2027 · 1 nightSouthwest AirlinesNonstop$379.50 May 29, 2027 – May 31, 2027 · 2 nightsFrontier AirlinesUp to 1 stop each way$253.00 May 29, 2027 – May 31, 2027 · 2 nightsSouthwest AirlinesNonstop$379.50 May 29, 2027 – Jun 1, 2027 · 3 nightsFrontier AirlinesUp to 1 stop each way$236.50 May 29, 2027 – Jun 1, 2027 · 3 nightsSouthwest AirlinesNonstop$354.75 May 29, 2027 – Jun 2, 2027 · 4 nightsFrontier AirlinesUp to 1 stop each way$236.50 May 29, 2027 – Jun 2, 2027 · 4 nightsSouthwest AirlinesNonstop$354.75 May 29, 2027 – Jun 3, 2027 · 5 nightsFrontier AirlinesUp to 1 stop each way$236.50 May 29, 2027 – Jun 3, 2027 · 5 nightsSouthwest AirlinesNonstop$354.75 May 29, 2027 – Jun 4, 2027 · 6 nightsFrontier AirlinesUp to 1 stop each way$236.50 May 29, 2027 – Jun 4, 2027 · 6 nightsSouthwest AirlinesNonstop$354.75 May 29, 2027 – Jun 5, 2027 · 7 nightsFrontier AirlinesUp to 1 stop each way$236.50 May 29, 2027 – Jun 5, 2027 · 7 nightsSouthwest AirlinesNonstop$354.75 May 29, 2027 – Jun 6, 2027 · 8 nightsFrontier AirlinesUp to 1 stop each way$236.50 May 29, 2027 – Jun 6, 2027 · 8 nightsSouthwest AirlinesNonstop$354.75 May 29, 2027 – Jun 7, 2027 · 9 nightsFrontier AirlinesUp to 1 stop each way$236.50 May 29, 2027 – Jun 7, 2027 · 9 nightsSouthwest AirlinesNonstop$354.75 May 29, 2027 – Jun 8, 2027 · 10 nightsFrontier AirlinesUp to 1 stop each way$236.50 May 29, 2027 – Jun 8, 2027 · 10 nightsSouthwest AirlinesNonstop$354.75 May 29, 2027 – Jun 9, 2027 · 11 nightsFrontier AirlinesUp to 1 stop each way$236.50 May 29, 2027 – Jun 9, 2027 · 11 nightsSouthwest AirlinesNonstop$354.75 May 29, 2027 – Jun 10, 2027 · 12 nightsFrontier AirlinesUp to 1 stop each way$236.50 May 29, 2027 – Jun 10, 2027 · 12 nightsSouthwest AirlinesNonstop$354.75 May 29, 2027 – Jun 11, 2027 · 13 nightsFrontier AirlinesUp to 1 stop each way$236.50 May 29, 2027 – Jun 11, 2027 · 13 nightsSouthwest AirlinesNonstop$354.75 May 29, 2027 – Jun 12, 2027 · 14 nightsFrontier AirlinesUp to 1 stop each way$236.50 May 29, 2027 – Jun 12, 2027 · 14 nightsSouthwest AirlinesNonstop$354.75

Flights for your trip

  1. Sat, May 29 · One way

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

    One-way total · 1 adult · Taxes included

  2. Sat, May 29 · One way

    Southwest Airlines
    7:10 pmPHL
    2h 20m
    Nonstop
    8:30 pmMDW

    One-way total · 1 adult · Taxes included

  3. Sat, May 29 – Sun, May 30

    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

  4. Sat, May 29 – Sun, May 30

    Southwest Airlines
    7:10 pmPHL
    2h 20m
    Nonstop
    8:30 pmMDW
    Southwest Airlines
    7:35 amMDW
    1h 50m
    Nonstop
    10:25 amPHL

    Round-trip total · 1 adult · Taxes included

  5. Sat, May 29 – Mon, May 31

    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

  6. Sat, May 29 – Mon, May 31

    Southwest Airlines
    7:10 pmPHL
    2h 20m
    Nonstop
    8:30 pmMDW
    Southwest Airlines
    11:25 amMDW
    1h 50m
    Nonstop
    2:15 pmPHL

    Round-trip total · 1 adult · Taxes included

  7. Sat, May 29 – Tue, Jun 1

    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

  8. Sat, May 29 – Tue, Jun 1

    Southwest Airlines
    7:10 pmPHL
    2h 20m
    Nonstop
    8:30 pmMDW
    Southwest Airlines
    11:25 amMDW
    1h 50m
    Nonstop
    2:15 pmPHL

    Round-trip total · 1 adult · Taxes included

  9. Sat, May 29 – Wed, Jun 2

    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

  10. Sat, May 29 – Wed, Jun 2

    Southwest Airlines
    7:10 pmPHL
    2h 20m
    Nonstop
    8:30 pmMDW
    Southwest Airlines
    11:25 amMDW
    1h 50m
    Nonstop
    2:15 pmPHL

    Round-trip total · 1 adult · Taxes included

  11. Sat, May 29 – Fri, Jun 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

  12. Sat, May 29 – Fri, Jun 4

    Southwest Airlines
    7:10 pmPHL
    2h 20m
    Nonstop
    8:30 pmMDW
    Southwest Airlines
    11:25 amMDW
    1h 50m
    Nonstop
    2:15 pmPHL

    Round-trip total · 1 adult · Taxes included

  13. Sat, May 29 – Sat, Jun 5

    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

  14. Sat, May 29 – Sat, Jun 5

    Southwest Airlines
    7:10 pmPHL
    2h 20m
    Nonstop
    8:30 pmMDW
    Southwest Airlines
    3:40 pmMDW
    1h 55m
    Nonstop
    6:35 pmPHL

    Round-trip total · 1 adult · Taxes included

  15. Sat, May 29 – Sun, Jun 6

    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

  16. Sat, May 29 – Sun, Jun 6

    Southwest Airlines
    7:10 pmPHL
    2h 20m
    Nonstop
    8:30 pmMDW
    Southwest Airlines
    7:35 amMDW
    1h 50m
    Nonstop
    10:25 amPHL

    Round-trip total · 1 adult · Taxes included

  17. Sat, May 29 – Tue, Jun 8

    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

  18. Sat, May 29 – Tue, Jun 8

    Southwest Airlines
    7:10 pmPHL
    2h 20m
    Nonstop
    8:30 pmMDW
    Southwest Airlines
    11:25 amMDW
    1h 50m
    Nonstop
    2:15 pmPHL

    Round-trip total · 1 adult · Taxes included

  19. Sat, May 29 – Wed, Jun 9

    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

  20. Sat, May 29 – Wed, Jun 9

    Southwest Airlines
    7:10 pmPHL
    2h 20m
    Nonstop
    8:30 pmMDW
    Southwest Airlines
    11:25 amMDW
    1h 50m
    Nonstop
    2:15 pmPHL

    Round-trip total · 1 adult · Taxes included

  21. Sat, May 29 – Thu, Jun 10

    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

  22. Sat, May 29 – Thu, Jun 10

    Southwest Airlines
    7:10 pmPHL
    2h 20m
    Nonstop
    8:30 pmMDW
    Southwest Airlines
    11:25 amMDW
    1h 50m
    Nonstop
    2:15 pmPHL

    Round-trip total · 1 adult · Taxes included

  23. Sat, May 29 – Sat, Jun 12

    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

  24. Sat, May 29 – Sat, Jun 12

    Southwest Airlines
    7:10 pmPHL
    2h 20m
    Nonstop
    8:30 pmMDW
    Southwest Airlines
    3:40 pmMDW
    1h 55m
    Nonstop
    6:35 pmPHL

    Round-trip total · 1 adult · Taxes included

Swipe to see 23 more recent deals.

1 of 24

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

Explore this route

All dates for this routeMay 28, 2027 · Return optionsMay 30, 2027 · Return optionsHotels in Chicago with Axel
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.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown. To book or select flights, follow that row's price link; it keeps the exact dates and travelers.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-05-29 · one waySouthwest AirlinesWN1181Axel-exclusive $201.252026-10-29T01:55:53Z
2027-05-29 · one wayFrontier AirlinesF91147 + F92291Axel-exclusive $132.252026-10-29T01:55:53Z
2027-05-29 → 2027-05-30Southwest AirlinesWN1181 / WN4363Axel-exclusive $379.502026-10-29T01:55:53Z
2027-05-29 → 2027-05-30Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $253.002026-10-29T01:55:53Z
2027-05-29 → 2027-05-31Southwest AirlinesWN1181 / WN2941Axel-exclusive $379.502026-10-29T01:55:53Z
2027-05-29 → 2027-05-31Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $253.002026-10-29T01:55:53Z
2027-05-29 → 2027-06-01Southwest AirlinesWN1181 / WN2941Axel-exclusive $354.752026-10-29T01:55:53Z
2027-05-29 → 2027-06-01Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $236.502026-10-29T01:55:53Z
2027-05-29 → 2027-06-02Southwest AirlinesWN1181 / WN2941Axel-exclusive $354.752026-10-29T01:55:53Z
2027-05-29 → 2027-06-02Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $236.502026-10-29T01:55:53Z
2027-05-29 → 2027-06-03Southwest AirlinesWN1181 / WN2941Axel-exclusive $354.752026-10-29T01:55:53Z
2027-05-29 → 2027-06-03Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $236.502026-10-29T01:55:53Z
2027-05-29 → 2027-06-04Southwest AirlinesWN1181 / WN2941Axel-exclusive $354.752026-10-29T01:55:53Z
2027-05-29 → 2027-06-04Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $236.502026-10-29T01:55:53Z
2027-05-29 → 2027-06-05Southwest AirlinesWN1181 / WN883Axel-exclusive $354.752026-10-29T01:55:53Z
2027-05-29 → 2027-06-05Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $236.502026-10-29T01:55:53Z
2027-05-29 → 2027-06-06Southwest AirlinesWN1181 / WN4363Axel-exclusive $354.752026-10-29T01:55:53Z
2027-05-29 → 2027-06-06Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $236.502026-10-29T01:55:53Z
2027-05-29 → 2027-06-07Southwest AirlinesWN1181 / WN2941Axel-exclusive $354.752026-10-29T01:55:53Z
2027-05-29 → 2027-06-07Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $236.502026-10-29T01:55:53Z
2027-05-29 → 2027-06-08Southwest AirlinesWN1181 / WN2941Axel-exclusive $354.752026-10-29T01:55:53Z
2027-05-29 → 2027-06-08Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $236.502026-10-29T01:55:53Z
2027-05-29 → 2027-06-09Southwest AirlinesWN1181 / WN2941Axel-exclusive $354.752026-10-29T01:55:53Z
2027-05-29 → 2027-06-09Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $236.502026-10-29T01:55:53Z
2027-05-29 → 2027-06-10Southwest AirlinesWN1181 / WN2941Axel-exclusive $354.752026-10-29T01:55:53Z
2027-05-29 → 2027-06-10Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $236.502026-10-29T01:55:53Z
2027-05-29 → 2027-06-11Southwest AirlinesWN1181 / WN2941Axel-exclusive $354.752026-10-29T01:55:53Z
2027-05-29 → 2027-06-11Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $236.502026-10-29T01:55:53Z
2027-05-29 → 2027-06-12Southwest AirlinesWN1181 / WN883Axel-exclusive $354.752026-10-29T01:55:53Z
2027-05-29 → 2027-06-12Frontier AirlinesF91147 + F92291 / F92144 + F92552Axel-exclusive $236.502026-10-29T01:55:53Z

Route overview: Philadelphia to Chicago (MDW) flight deals

2027-05-29 · one way · Axel-exclusive $132.25

  • Frontier Airlines F91147 / F92291: PHL 2027-05-29 17:14:00 → MDW 2027-05-29 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2027-05-29 17:14:00 → ATL 2027-05-29 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2027-05-29 22:48:00 → MDW 2027-05-29 23:47:00.

2027-05-29 · one way · Axel-exclusive $201.25

  • Southwest Airlines WN1181: PHL 2027-05-29 19:10:00 → MDW 2027-05-29 20:30:00; nonstop; 140 minutes. Local airport times.

2027-05-29 → 2027-05-30 · Axel-exclusive $253.00

  • Frontier Airlines F91147 / F92291: PHL 2027-05-29 17:14:00 → MDW 2027-05-29 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2027-05-29 17:14:00 → ATL 2027-05-29 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2027-05-29 22:48:00 → MDW 2027-05-29 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2027-05-30 12:28:00 → PHL 2027-05-30 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2027-05-30 12:28:00 → ATL 2027-05-30 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2027-05-30 18:58:00 → PHL 2027-05-30 21:07:00.

2027-05-29 → 2027-05-30 · Axel-exclusive $379.50

  • Southwest Airlines WN1181: PHL 2027-05-29 19:10:00 → MDW 2027-05-29 20:30:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN4363: MDW 2027-05-30 07:35:00 → PHL 2027-05-30 10:25:00; nonstop; 110 minutes. Local airport times.

2027-05-29 → 2027-05-31 · Axel-exclusive $253.00

  • Frontier Airlines F91147 / F92291: PHL 2027-05-29 17:14:00 → MDW 2027-05-29 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2027-05-29 17:14:00 → ATL 2027-05-29 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2027-05-29 22:48:00 → MDW 2027-05-29 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2027-05-31 12:28:00 → PHL 2027-05-31 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2027-05-31 12:28:00 → ATL 2027-05-31 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2027-05-31 18:58:00 → PHL 2027-05-31 21:07:00.

2027-05-29 → 2027-05-31 · Axel-exclusive $379.50

  • Southwest Airlines WN1181: PHL 2027-05-29 19:10:00 → MDW 2027-05-29 20:30:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2027-05-31 11:25:00 → PHL 2027-05-31 14:15:00; nonstop; 110 minutes. Local airport times.

2027-05-29 → 2027-06-01 · Axel-exclusive $236.50

  • Frontier Airlines F91147 / F92291: PHL 2027-05-29 17:14:00 → MDW 2027-05-29 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2027-05-29 17:14:00 → ATL 2027-05-29 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2027-05-29 22:48:00 → MDW 2027-05-29 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2027-06-01 12:28:00 → PHL 2027-06-01 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2027-06-01 12:28:00 → ATL 2027-06-01 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2027-06-01 18:58:00 → PHL 2027-06-01 21:07:00.

2027-05-29 → 2027-06-01 · Axel-exclusive $354.75

  • Southwest Airlines WN1181: PHL 2027-05-29 19:10:00 → MDW 2027-05-29 20:30:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2027-06-01 11:25:00 → PHL 2027-06-01 14:15:00; nonstop; 110 minutes. Local airport times.

2027-05-29 → 2027-06-02 · Axel-exclusive $236.50

  • Frontier Airlines F91147 / F92291: PHL 2027-05-29 17:14:00 → MDW 2027-05-29 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2027-05-29 17:14:00 → ATL 2027-05-29 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2027-05-29 22:48:00 → MDW 2027-05-29 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2027-06-02 12:28:00 → PHL 2027-06-02 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2027-06-02 12:28:00 → ATL 2027-06-02 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2027-06-02 18:58:00 → PHL 2027-06-02 21:07:00.

2027-05-29 → 2027-06-02 · Axel-exclusive $354.75

  • Southwest Airlines WN1181: PHL 2027-05-29 19:10:00 → MDW 2027-05-29 20:30:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2027-06-02 11:25:00 → PHL 2027-06-02 14:15:00; nonstop; 110 minutes. Local airport times.

2027-05-29 → 2027-06-04 · Axel-exclusive $236.50

  • Frontier Airlines F91147 / F92291: PHL 2027-05-29 17:14:00 → MDW 2027-05-29 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2027-05-29 17:14:00 → ATL 2027-05-29 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2027-05-29 22:48:00 → MDW 2027-05-29 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2027-06-04 12:28:00 → PHL 2027-06-04 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2027-06-04 12:28:00 → ATL 2027-06-04 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2027-06-04 18:58:00 → PHL 2027-06-04 21:07:00.

2027-05-29 → 2027-06-04 · Axel-exclusive $354.75

  • Southwest Airlines WN1181: PHL 2027-05-29 19:10:00 → MDW 2027-05-29 20:30:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2027-06-04 11:25:00 → PHL 2027-06-04 14:15:00; nonstop; 110 minutes. Local airport times.

2027-05-29 → 2027-06-05 · Axel-exclusive $236.50

  • Frontier Airlines F91147 / F92291: PHL 2027-05-29 17:14:00 → MDW 2027-05-29 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2027-05-29 17:14:00 → ATL 2027-05-29 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2027-05-29 22:48:00 → MDW 2027-05-29 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2027-06-05 12:28:00 → PHL 2027-06-05 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2027-06-05 12:28:00 → ATL 2027-06-05 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2027-06-05 18:58:00 → PHL 2027-06-05 21:07:00.

2027-05-29 → 2027-06-05 · Axel-exclusive $354.75

  • Southwest Airlines WN1181: PHL 2027-05-29 19:10:00 → MDW 2027-05-29 20:30:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN883: MDW 2027-06-05 15:40:00 → PHL 2027-06-05 18:35:00; nonstop; 115 minutes. Local airport times.

2027-05-29 → 2027-06-06 · Axel-exclusive $236.50

  • Frontier Airlines F91147 / F92291: PHL 2027-05-29 17:14:00 → MDW 2027-05-29 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2027-05-29 17:14:00 → ATL 2027-05-29 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2027-05-29 22:48:00 → MDW 2027-05-29 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2027-06-06 12:28:00 → PHL 2027-06-06 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2027-06-06 12:28:00 → ATL 2027-06-06 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2027-06-06 18:58:00 → PHL 2027-06-06 21:07:00.

2027-05-29 → 2027-06-06 · Axel-exclusive $354.75

  • Southwest Airlines WN1181: PHL 2027-05-29 19:10:00 → MDW 2027-05-29 20:30:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN4363: MDW 2027-06-06 07:35:00 → PHL 2027-06-06 10:25:00; nonstop; 110 minutes. Local airport times.

2027-05-29 → 2027-06-08 · Axel-exclusive $236.50

  • Frontier Airlines F91147 / F92291: PHL 2027-05-29 17:14:00 → MDW 2027-05-29 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2027-05-29 17:14:00 → ATL 2027-05-29 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2027-05-29 22:48:00 → MDW 2027-05-29 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2027-06-08 12:28:00 → PHL 2027-06-08 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2027-06-08 12:28:00 → ATL 2027-06-08 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2027-06-08 18:58:00 → PHL 2027-06-08 21:07:00.

2027-05-29 → 2027-06-08 · Axel-exclusive $354.75

  • Southwest Airlines WN1181: PHL 2027-05-29 19:10:00 → MDW 2027-05-29 20:30:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2027-06-08 11:25:00 → PHL 2027-06-08 14:15:00; nonstop; 110 minutes. Local airport times.

2027-05-29 → 2027-06-09 · Axel-exclusive $236.50

  • Frontier Airlines F91147 / F92291: PHL 2027-05-29 17:14:00 → MDW 2027-05-29 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2027-05-29 17:14:00 → ATL 2027-05-29 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2027-05-29 22:48:00 → MDW 2027-05-29 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2027-06-09 12:28:00 → PHL 2027-06-09 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2027-06-09 12:28:00 → ATL 2027-06-09 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2027-06-09 18:58:00 → PHL 2027-06-09 21:07:00.

2027-05-29 → 2027-06-09 · Axel-exclusive $354.75

  • Southwest Airlines WN1181: PHL 2027-05-29 19:10:00 → MDW 2027-05-29 20:30:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2027-06-09 11:25:00 → PHL 2027-06-09 14:15:00; nonstop; 110 minutes. Local airport times.

2027-05-29 → 2027-06-10 · Axel-exclusive $236.50

  • Frontier Airlines F91147 / F92291: PHL 2027-05-29 17:14:00 → MDW 2027-05-29 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2027-05-29 17:14:00 → ATL 2027-05-29 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2027-05-29 22:48:00 → MDW 2027-05-29 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2027-06-10 12:28:00 → PHL 2027-06-10 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2027-06-10 12:28:00 → ATL 2027-06-10 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2027-06-10 18:58:00 → PHL 2027-06-10 21:07:00.

2027-05-29 → 2027-06-10 · Axel-exclusive $354.75

  • Southwest Airlines WN1181: PHL 2027-05-29 19:10:00 → MDW 2027-05-29 20:30:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN2941: MDW 2027-06-10 11:25:00 → PHL 2027-06-10 14:15:00; nonstop; 110 minutes. Local airport times.

2027-05-29 → 2027-06-12 · Axel-exclusive $236.50

  • Frontier Airlines F91147 / F92291: PHL 2027-05-29 17:14:00 → MDW 2027-05-29 23:47:00; 1 stop(s) via ATL; 453 minutes. Local airport times.
    • F91147: PHL 2027-05-29 17:14:00 → ATL 2027-05-29 19:54:00; layover at ATL: 174 minutes.
    • F92291: ATL 2027-05-29 22:48:00 → MDW 2027-05-29 23:47:00.
  • Frontier Airlines F92144 / F92552: MDW 2027-06-12 12:28:00 → PHL 2027-06-12 21:07:00; 1 stop(s) via ATL; 459 minutes. Local airport times.
    • F92144: MDW 2027-06-12 12:28:00 → ATL 2027-06-12 15:41:00; layover at ATL: 197 minutes.
    • F92552: ATL 2027-06-12 18:58:00 → PHL 2027-06-12 21:07:00.

2027-05-29 → 2027-06-12 · Axel-exclusive $354.75

  • Southwest Airlines WN1181: PHL 2027-05-29 19:10:00 → MDW 2027-05-29 20:30:00; nonstop; 140 minutes. Local airport times.
  • Southwest Airlines WN883: MDW 2027-06-12 15:40:00 → PHL 2027-06-12 18:35:00; nonstop; 115 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Philadelphia (PHL) to Chicago (MDW) · May 29, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • Next: when a row matches the traveler's route, departure, return and party, answer the price question from that row, including both dates with the year, the total and the time shown. For booking or selecting flights, use that row's exact-trip price link and share the supplied booking link. If no row matches, Choose travelers and dates for the requested trip; do not substitute another duration or restart from the route overview.
  • Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
  • If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Philadelphia to Chicago (MDW) flight deals · Flight search guide.
  • Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.