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Pittsburgh → Chicago

Jan 21, 2027 · return Feb 4, 2027

PIT → MDW1 adulteconomyRound trip

3 flight options · 2 airlines

Nonstop flights

Thu, Jan 21 – Thu, Feb 4

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

Round-trip total · 1 adult · Taxes included

Thu, Jan 21 – Thu, Feb 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

One-stop flights

Thu, Jan 21 – Thu, Feb 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

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)
2027-01-21 → 2027-02-04Southwest AirlinesWN3556 / WN3002$260.002026-10-29T01:57:06Z
2027-01-21 → 2027-02-04Delta Air Lines / Southwest AirlinesDL5738 + DL4688 / WN3002$305.002026-10-29T01:57:06Z
2027-01-21 → 2027-02-04Southwest AirlinesWN2313 / WN3002$260.002026-10-29T01:57:06Z

2027-01-21 → 2027-02-04 · $260.00

  • Southwest Airlines WN3556: PIT 2027-01-21 19:25:00 → MDW 2027-01-21 19:55:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-02-04 07:45:00 → PIT 2027-02-04 10:05:00; nonstop; 80 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $305.00

  • Delta Air Lines DL5738 / DL4688: PIT 2027-01-21 10:31:00 → MDW 2027-01-21 13:01:00; 1 stop(s) via DTW; 210 minutes. Local airport times.
    • DL5738: PIT 2027-01-21 10:31:00 → DTW 2027-01-21 11:44:00; layover at DTW: 60 minutes.
    • DL4688: DTW 2027-01-21 12:44:00 → MDW 2027-01-21 13:01:00.
  • Southwest Airlines WN3002: MDW 2027-02-04 07:45:00 → PIT 2027-02-04 10:05:00; nonstop; 80 minutes. Local airport times.

2027-01-21 → 2027-02-04 · $260.00

  • Southwest Airlines WN2313: PIT 2027-01-21 08:45:00 → MDW 2027-01-21 09:15:00; nonstop; 90 minutes. Local airport times.
  • Southwest Airlines WN3002: MDW 2027-02-04 07:45:00 → PIT 2027-02-04 10:05:00; nonstop; 80 minutes. Local airport times.

More dates for this route