Travel with Axel,
get the best price.

Pittsburgh → Chicago

Choose your travel dates

PIT → MDW1 adulteconomy

9 flight options · 2 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
8:45 amPIT
1h 30m
Nonstop
9:15 amMDW
Southwest Airlines
7:45 amMDW
1h 20m
Nonstop
10:05 amPIT

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Delta Air Lines
10:31 amPIT
3h 30m
DTW · 1h
1:01 pmMDW
Southwest Airlines
7:45 amMDW
1h 20m
Nonstop
10:05 amPIT

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:55 pmPIT
1h 30m
Nonstop
8:25 pmMDW
Southwest Airlines
7:45 amMDW
1h 20m
Nonstop
10:05 amPIT

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
7:55 pmPIT
1h 30m
Nonstop
8:25 pmMDW
Southwest Airlines
7:45 amMDW
1h 20m
Nonstop
10:05 amPIT

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
8:45 amPIT
1h 30m
Nonstop
9:15 amMDW
Southwest Airlines
7:45 amMDW
1h 20m
Nonstop
10:05 amPIT

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Delta Air Lines
10:31 amPIT
3h 30m
DTW · 1h
1:01 pmMDW
Southwest Airlines
7:45 amMDW
1h 20m
Nonstop
10:05 amPIT

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
8:45 amPIT
1h 30m
Nonstop
9:15 amMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
10:31 amPIT
3h 30m
DTW · 1h
1:01 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:55 pmPIT
1h 30m
Nonstop
8:25 pmMDW

One-way 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.
  • 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 AirlinesWN2313$135.002026-10-29T01:57:06Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2313 / WN3002$260.002026-10-29T01:57:06Z
2026-11-20 · one wayDelta Air LinesDL5738 + DL4688$185.002026-10-29T01:57:06Z
2026-11-20 → 2026-11-23Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002$305.002026-10-29T01:57:06Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3556 / WN3002$299.002026-10-29T01:57:06Z
2026-11-20 · one waySouthwest AirlinesWN3556$135.002026-10-29T01:57:06Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3556 / WN3002$260.002026-10-29T01:57:06Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2313 / WN3002$299.002026-10-29T01:57:06Z
2026-11-27 → 2026-12-04Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002$357.502026-10-29T01:57:06Z

2026-11-20 · one way · $135.00

  • Southwest Airlines WN2313: PIT 2026-11-20 08:45:00 → MDW 2026-11-20 09:15:00; nonstop; 90 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $260.00

  • Southwest Airlines WN2313: PIT 2026-11-20 08:45:00 → MDW 2026-11-20 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2026-11-23 07:45:00 → PIT 2026-11-23 10:05:00; nonstop; 80 minutes. Local airport times.

2026-11-20 · one way · $185.00

  • Delta Air Lines DL5738 / DL4688: PIT 2026-11-20 10:31:00 → MDW 2026-11-20 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-11-20 10:31:00 → DTW 2026-11-20 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-11-20 12:44:00 → MDW 2026-11-20 13:01:00.

2026-11-20 → 2026-11-23 · $305.00

  • Delta Air Lines DL5738 / DL4688: PIT 2026-11-20 10:31:00 → MDW 2026-11-20 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-11-20 10:31:00 → DTW 2026-11-20 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-11-20 12:44:00 → MDW 2026-11-20 13:01:00.
  • Southwest Airlines WN3002: MDW 2026-11-23 07:45:00 → PIT 2026-11-23 10:05:00; nonstop; 80 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $299.00

  • Southwest Airlines WN3556: PIT 2026-11-27 19:55:00 → MDW 2026-11-27 20:25:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2026-12-04 07:45:00 → PIT 2026-12-04 10:05:00; nonstop; 80 minutes. Local airport times.

2026-11-20 · one way · $135.00

  • Southwest Airlines WN3556: PIT 2026-11-20 19:55:00 → MDW 2026-11-20 20:25:00; nonstop; 90 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $260.00

  • Southwest Airlines WN3556: PIT 2026-11-20 19:55:00 → MDW 2026-11-20 20:25:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2026-11-23 07:45:00 → PIT 2026-11-23 10:05:00; nonstop; 80 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $299.00

  • Southwest Airlines WN2313: PIT 2026-11-27 08:45:00 → MDW 2026-11-27 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2026-12-04 07:45:00 → PIT 2026-12-04 10:05:00; nonstop; 80 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $357.50

  • Delta Air Lines DL5738 / DL4688: PIT 2026-11-27 10:31:00 → MDW 2026-11-27 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2026-11-27 10:31:00 → DTW 2026-11-27 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2026-11-27 12:44:00 → MDW 2026-11-27 13:01:00.
  • Southwest Airlines WN3002: MDW 2026-12-04 07:45:00 → PIT 2026-12-04 10:05:00; nonstop; 80 minutes. Local airport times.

More dates for this route