Travel with Axel,
get the best price.

Route overview: Pittsburgh to Chicago (MDW) flight deals

Pittsburgh → Chicago

May 1, 2027 · return May 8, 2027

PIT → MDW1 adulteconomyRound trip

3 flight options · 2 airlines

Nonstop flights

Sat, May 1 – Sat, May 8

Southwest Airlines
8:45 amPIT
1h 30m
Nonstop
9:15 amMDW
Southwest Airlines
6:55 pmMDW
1h 30m
Nonstop
9:25 pmPIT

Round-trip total · 1 adult · Taxes included

Sat, May 1 – Sat, May 8

Southwest Airlines
8:25 pmPIT
1h 30m
Nonstop
8:55 pmMDW
Southwest Airlines
6:55 pmMDW
1h 30m
Nonstop
9:25 pmPIT

Round-trip total · 1 adult · Taxes included

One-stop flights

Sat, May 1 – Sat, May 8

Delta Air Lines
10:31 amPIT
3h 30m
DTW · 1h
1:01 pmMDW
Southwest Airlines
6:55 pmMDW
1h 30m
Nonstop
9:25 pmPIT

Round-trip total · 1 adult · Taxes included

Make this trip yours

PIT ⇄ 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 routeApr 30, 2027 → May 7, 2027May 2, 2027 → May 9, 2027
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.

Route overview: Pittsburgh to Chicago (MDW) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-05-01 → 2027-05-08Southwest AirlinesWN2313 / WN3004$300.002026-10-29T01:57:06Z
2027-05-01 → 2027-05-08Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3004$345.002026-10-29T01:57:06Z
2027-05-01 → 2027-05-08Southwest AirlinesWN3498 / WN3004$300.002026-10-29T01:57:06Z

2027-05-01 → 2027-05-08 · $300.00

  • Southwest Airlines WN2313: PIT 2027-05-01 08:45:00 → MDW 2027-05-01 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2027-05-08 18:55:00 → PIT 2027-05-08 21:25:00; nonstop; 90 minutes. Local airport times.

2027-05-01 → 2027-05-08 · $345.00

  • Delta Air Lines DL5738 / DL4688: PIT 2027-05-01 10:31:00 → MDW 2027-05-01 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-05-01 10:31:00 → DTW 2027-05-01 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-05-01 12:44:00 → MDW 2027-05-01 13:01:00.
  • Southwest Airlines WN3004: MDW 2027-05-08 18:55:00 → PIT 2027-05-08 21:25:00; nonstop; 90 minutes. Local airport times.

2027-05-01 → 2027-05-08 · $300.00

  • Southwest Airlines WN3498: PIT 2027-05-01 20:25:00 → MDW 2027-05-01 20:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3004: MDW 2027-05-08 18:55:00 → PIT 2027-05-08 21:25:00; nonstop; 90 minutes. Local airport times.

Explore this route