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Pittsburgh → Chicago

Jan 23, 2027 · return Feb 2, 2027

PIT → MDW1 adulteconomyRound trip

3 flight options · 2 airlines

Nonstop flights

Sat, Jan 23 – Tue, Feb 2

Southwest Airlines
8:45 amPIT
1h 30m
Nonstop
9:15 amMDW
Southwest Airlines
8:15 amMDW
1h 25m
Nonstop
10:40 amPIT

Round-trip total · 1 adult · Taxes included

Sat, Jan 23 – Tue, Feb 2

Southwest Airlines
8:25 pmPIT
1h 30m
Nonstop
8:55 pmMDW
Southwest Airlines
8:15 amMDW
1h 25m
Nonstop
10:40 amPIT

Round-trip total · 1 adult · Taxes included

One-stop flights

Sat, Jan 23 – Tue, Feb 2

Delta Air Lines
10:31 amPIT
3h 30m
DTW · 1h
1:01 pmMDW
Southwest Airlines
8:15 amMDW
1h 25m
Nonstop
10:40 amPIT

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.

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More dates

All dates for this routeNov 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)
2027-01-23 → 2027-02-02Southwest AirlinesWN2313 / WN3643$260.002026-10-29T01:57:06Z
2027-01-23 → 2027-02-02Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3643$305.002026-10-29T01:57:06Z
2027-01-23 → 2027-02-02Southwest AirlinesWN3498 / WN3643$260.002026-10-29T01:57:06Z

2027-01-23 → 2027-02-02 · $260.00

  • Southwest Airlines WN2313: PIT 2027-01-23 08:45:00 → MDW 2027-01-23 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3643: MDW 2027-02-02 08:15:00 → PIT 2027-02-02 10:40:00; nonstop; 85 minutes. Local airport times.

2027-01-23 → 2027-02-02 · $305.00

  • Delta Air Lines DL5738 / DL4688: PIT 2027-01-23 10:31:00 → MDW 2027-01-23 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-01-23 10:31:00 → DTW 2027-01-23 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-01-23 12:44:00 → MDW 2027-01-23 13:01:00.
  • Southwest Airlines WN3643: MDW 2027-02-02 08:15:00 → PIT 2027-02-02 10:40:00; nonstop; 85 minutes. Local airport times.

2027-01-23 → 2027-02-02 · $260.00

  • Southwest Airlines WN3498: PIT 2027-01-23 20:25:00 → MDW 2027-01-23 20:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3643: MDW 2027-02-02 08:15:00 → PIT 2027-02-02 10:40:00; nonstop; 85 minutes. Local airport times.

More dates for this route