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Dallas → Chicago

Jan 23, 2027 · return Feb 6, 2027

DAL → MDW1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Sat, Jan 23 – Sat, Feb 6

Southwest Airlines
10:30 pmDAL
2h 15m
Nonstop
12:45 am+1MDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Sat, Jan 23 – Sat, Feb 6

Southwest Airlines
6:40 amDAL
2h 10m
Nonstop
8:50 amMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

One-stop flights

Sat, Jan 23 – Sat, Feb 6

Southwest Airlines
7:35 amDAL
4h 55m
MSY · 1h 15m
12:30 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Sat, Jan 23 – Sat, Feb 6

Southwest Airlines
12:55 pmDAL
4h 15m
MCI · 1h 20m
5:10 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Sat, Jan 23 – Sat, Feb 6

Southwest Airlines
7:30 amDAL
4h 50m
AUS · 1h 20m
12:20 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Sat, Jan 23 – Sat, Feb 6

Southwest Airlines
12:15 pmDAL
5h 10m
SAT · 1h 35m
5:25 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Sat, Jan 23 – Sat, Feb 6

Southwest Airlines
2:25 pmDAL
5h 10m
CLE · 1h 20m
7:35 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Sat, Jan 23 – Sat, Feb 6

Southwest Airlines
12:10 pmDAL
4h 55m
BHM · 1h 35m
5:05 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

Make this trip yours

DAL ⇄ 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 5, 2026 → Nov 8, 2026Nov 14, 2026 → Nov 21, 2026Nov 24, 2026 → Nov 29, 2026Dec 5, 2026 → Dec 12, 2026Dec 17, 2026 → Dec 20, 2026Dec 26, 2026 → Jan 2, 2027Jan 5, 2027 · One wayJan 16, 2027 → Jan 23, 2027Feb 5, 2027 → Feb 8, 2027Apr 3, 2027 → Apr 10, 2027Jun 26, 2027 → Jul 3, 2027Sep 17, 2027 → Sep 20, 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.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-01-23 → 2027-02-06Southwest AirlinesWN1769 / WN2092$330.002026-10-29T01:01:45Z
2027-01-23 → 2027-02-06Southwest AirlinesWN1432 / WN2092$330.002026-10-29T01:01:45Z
2027-01-23 → 2027-02-06Southwest AirlinesWN978 + WN3175 / WN2092$335.002026-10-29T01:01:45Z
2027-01-23 → 2027-02-06Southwest AirlinesWN102 + WN2694 / WN2092$335.002026-10-29T01:01:45Z
2027-01-23 → 2027-02-06Southwest AirlinesWN733 + WN379 / WN2092$335.002026-10-29T01:01:45Z
2027-01-23 → 2027-02-06Southwest AirlinesWN1165 + WN3791 / WN2092$335.002026-10-29T01:01:45Z
2027-01-23 → 2027-02-06Southwest AirlinesWN4819 + WN1220 / WN2092$335.002026-10-29T01:01:45Z
2027-01-23 → 2027-02-06Southwest AirlinesWN1246 + WN1030 / WN2092$335.002026-10-29T01:01:45Z

2027-01-23 → 2027-02-06 · $330.00

  • Southwest Airlines WN1769: DAL 2027-01-23 22:30:00 → MDW 2027-01-24 00:45:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN2092: MDW 2027-02-06 14:30:00 → DAL 2027-02-06 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-23 → 2027-02-06 · $330.00

  • Southwest Airlines WN1432: DAL 2027-01-23 06:40:00 → MDW 2027-01-23 08:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN2092: MDW 2027-02-06 14:30:00 → DAL 2027-02-06 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-23 → 2027-02-06 · $335.00

  • Southwest Airlines WN978 / WN3175: DAL 2027-01-23 07:35:00 → MDW 2027-01-23 12:30:00; 1 stop(s) via MSY; 295 minutes. Local airport times.
    • WN978: DAL 2027-01-23 07:35:00 → MSY 2027-01-23 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2027-01-23 10:10:00 → MDW 2027-01-23 12:30:00.
  • Southwest Airlines WN2092: MDW 2027-02-06 14:30:00 → DAL 2027-02-06 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-23 → 2027-02-06 · $335.00

  • Southwest Airlines WN102 / WN2694: DAL 2027-01-23 12:55:00 → MDW 2027-01-23 17:10:00; 1 stop(s) via MCI; 255 minutes. Local airport times.
    • WN102: DAL 2027-01-23 12:55:00 → MCI 2027-01-23 14:30:00; layover at MCI: 80 minutes.
    • WN2694: MCI 2027-01-23 15:50:00 → MDW 2027-01-23 17:10:00.
  • Southwest Airlines WN2092: MDW 2027-02-06 14:30:00 → DAL 2027-02-06 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-23 → 2027-02-06 · $335.00

  • Southwest Airlines WN733 / WN379: DAL 2027-01-23 07:30:00 → MDW 2027-01-23 12:20:00; 1 stop(s) via AUS; 290 minutes. Local airport times.
    • WN733: DAL 2027-01-23 07:30:00 → AUS 2027-01-23 08:30:00; layover at AUS: 80 minutes.
    • WN379: AUS 2027-01-23 09:50:00 → MDW 2027-01-23 12:20:00.
  • Southwest Airlines WN2092: MDW 2027-02-06 14:30:00 → DAL 2027-02-06 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-23 → 2027-02-06 · $335.00

  • Southwest Airlines WN1165 / WN3791: DAL 2027-01-23 12:15:00 → MDW 2027-01-23 17:25:00; 1 stop(s) via SAT; 310 minutes. Local airport times.
    • WN1165: DAL 2027-01-23 12:15:00 → SAT 2027-01-23 13:15:00; layover at SAT: 95 minutes.
    • WN3791: SAT 2027-01-23 14:50:00 → MDW 2027-01-23 17:25:00.
  • Southwest Airlines WN2092: MDW 2027-02-06 14:30:00 → DAL 2027-02-06 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-23 → 2027-02-06 · $335.00

  • Southwest Airlines WN4819 / WN1220: DAL 2027-01-23 14:25:00 → MDW 2027-01-23 19:35:00; 1 stop(s) via CLE; 310 minutes. Local airport times.
    • WN4819: DAL 2027-01-23 14:25:00 → CLE 2027-01-23 17:50:00; layover at CLE: 80 minutes.
    • WN1220: CLE 2027-01-23 19:10:00 → MDW 2027-01-23 19:35:00.
  • Southwest Airlines WN2092: MDW 2027-02-06 14:30:00 → DAL 2027-02-06 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-23 → 2027-02-06 · $335.00

  • Southwest Airlines WN1246 / WN1030: DAL 2027-01-23 12:10:00 → MDW 2027-01-23 17:05:00; 1 stop(s) via BHM; 295 minutes. Local airport times.
    • WN1246: DAL 2027-01-23 12:10:00 → BHM 2027-01-23 13:40:00; layover at BHM: 95 minutes.
    • WN1030: BHM 2027-01-23 15:15:00 → MDW 2027-01-23 17:05:00.
  • Southwest Airlines WN2092: MDW 2027-02-06 14:30:00 → DAL 2027-02-06 16:55:00; nonstop; 145 minutes. Local airport times.

More dates for this route