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Dallas → Chicago

Jan 2, 2027 · return Jan 7, 2027

DAL → MDW1 adulteconomyRound trip

8 flight options · 1 airline

Nonstop flights

Sat, Jan 2 – Thu, Jan 7

Southwest Airlines
6:40 amDAL
2h 10m
Nonstop
8:50 amMDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 pmDAL

Round-trip total · 1 adult · Taxes included

Sat, Jan 2 – Thu, Jan 7

Southwest Airlines
10:30 pmDAL
2h 15m
Nonstop
12:45 am+1MDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 pmDAL

Round-trip total · 1 adult · Taxes included

One-stop flights

Sat, Jan 2 – Thu, Jan 7

Southwest Airlines
8:45 amDAL
2h 15m
Nonstop
11:00 amMDW
Southwest Airlines
10:05 amMDW
4h 5m
MCI · 1h
2:10 pmDAL

Round-trip total · 1 adult · Taxes included

Sat, Jan 2 – Thu, Jan 7

Southwest Airlines
7:35 amDAL
4h 55m
MSY · 1h 15m
12:30 pmMDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 pmDAL

Round-trip total · 1 adult · Taxes included

Sat, Jan 2 – Thu, Jan 7

Southwest Airlines
12:10 pmDAL
4h 55m
BHM · 1h 35m
5:05 pmMDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 pmDAL

Round-trip total · 1 adult · Taxes included

Sat, Jan 2 – Thu, Jan 7

Southwest Airlines
7:30 amDAL
4h 50m
AUS · 1h 20m
12:20 pmMDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 pmDAL

Round-trip total · 1 adult · Taxes included

Sat, Jan 2 – Thu, Jan 7

Southwest Airlines
12:55 pmDAL
4h 15m
MCI · 1h 20m
5:10 pmMDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 pmDAL

Round-trip total · 1 adult · Taxes included

Sat, Jan 2 – Thu, Jan 7

Southwest Airlines
2:25 pmDAL
5h 10m
CLE · 1h 20m
7:35 pmMDW
Southwest Airlines
8:45 pmMDW
2h 30m
Nonstop
11:15 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)
2027-01-02 → 2027-01-07Southwest AirlinesWN1432 / WN3937$371.252026-10-29T01:01:45Z
2027-01-02 → 2027-01-07Southwest AirlinesWN1769 / WN3937$371.252026-10-29T01:01:45Z
2027-01-02 → 2027-01-07Southwest AirlinesWN1432 / WN946 + WN212$376.252026-10-29T01:01:45Z
2027-01-02 → 2027-01-07Southwest AirlinesWN978 + WN3175 / WN3937$377.502026-10-29T01:01:45Z
2027-01-02 → 2027-01-07Southwest AirlinesWN1246 + WN1030 / WN3937$377.502026-10-29T01:01:45Z
2027-01-02 → 2027-01-07Southwest AirlinesWN733 + WN379 / WN3937$377.502026-10-29T01:01:45Z
2027-01-02 → 2027-01-07Southwest AirlinesWN102 + WN2694 / WN3937$377.502026-10-29T01:01:45Z
2027-01-02 → 2027-01-07Southwest AirlinesWN4819 + WN1220 / WN3937$377.502026-10-29T01:01:45Z

2027-01-02 → 2027-01-07 · $371.25

  • Southwest Airlines WN1432: DAL 2027-01-02 06:40:00 → MDW 2027-01-02 08:50:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN3937: MDW 2027-01-07 20:45:00 → DAL 2027-01-07 23:15:00; nonstop; 150 minutes. Local airport times.

2027-01-02 → 2027-01-07 · $371.25

  • Southwest Airlines WN1769: DAL 2027-01-02 22:30:00 → MDW 2027-01-03 00:45:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN3937: MDW 2027-01-07 20:45:00 → DAL 2027-01-07 23:15:00; nonstop; 150 minutes. Local airport times.

2027-01-02 → 2027-01-07 · $376.25

  • Southwest Airlines WN1432: DAL 2027-01-02 08:45:00 → MDW 2027-01-02 11:00:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN946 / WN212: MDW 2027-01-07 10:05:00 → DAL 2027-01-07 14:10:00; 1 stop(s) via MCI; 245 minutes. Local airport times.
    • WN946: MDW 2027-01-07 10:05:00 → MCI 2027-01-07 11:35:00; layover at MCI: 60 minutes.
    • WN212: MCI 2027-01-07 12:35:00 → DAL 2027-01-07 14:10:00.

2027-01-02 → 2027-01-07 · $377.50

  • Southwest Airlines WN978 / WN3175: DAL 2027-01-02 07:35:00 → MDW 2027-01-02 12:30:00; 1 stop(s) via MSY; 295 minutes. Local airport times.
    • WN978: DAL 2027-01-02 07:35:00 → MSY 2027-01-02 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2027-01-02 10:10:00 → MDW 2027-01-02 12:30:00.
  • Southwest Airlines WN3937: MDW 2027-01-07 20:45:00 → DAL 2027-01-07 23:15:00; nonstop; 150 minutes. Local airport times.

2027-01-02 → 2027-01-07 · $377.50

  • Southwest Airlines WN1246 / WN1030: DAL 2027-01-02 12:10:00 → MDW 2027-01-02 17:05:00; 1 stop(s) via BHM; 295 minutes. Local airport times.
    • WN1246: DAL 2027-01-02 12:10:00 → BHM 2027-01-02 13:40:00; layover at BHM: 95 minutes.
    • WN1030: BHM 2027-01-02 15:15:00 → MDW 2027-01-02 17:05:00.
  • Southwest Airlines WN3937: MDW 2027-01-07 20:45:00 → DAL 2027-01-07 23:15:00; nonstop; 150 minutes. Local airport times.

2027-01-02 → 2027-01-07 · $377.50

  • Southwest Airlines WN733 / WN379: DAL 2027-01-02 07:30:00 → MDW 2027-01-02 12:20:00; 1 stop(s) via AUS; 290 minutes. Local airport times.
    • WN733: DAL 2027-01-02 07:30:00 → AUS 2027-01-02 08:30:00; layover at AUS: 80 minutes.
    • WN379: AUS 2027-01-02 09:50:00 → MDW 2027-01-02 12:20:00.
  • Southwest Airlines WN3937: MDW 2027-01-07 20:45:00 → DAL 2027-01-07 23:15:00; nonstop; 150 minutes. Local airport times.

2027-01-02 → 2027-01-07 · $377.50

  • Southwest Airlines WN102 / WN2694: DAL 2027-01-02 12:55:00 → MDW 2027-01-02 17:10:00; 1 stop(s) via MCI; 255 minutes. Local airport times.
    • WN102: DAL 2027-01-02 12:55:00 → MCI 2027-01-02 14:30:00; layover at MCI: 80 minutes.
    • WN2694: MCI 2027-01-02 15:50:00 → MDW 2027-01-02 17:10:00.
  • Southwest Airlines WN3937: MDW 2027-01-07 20:45:00 → DAL 2027-01-07 23:15:00; nonstop; 150 minutes. Local airport times.

2027-01-02 → 2027-01-07 · $377.50

  • Southwest Airlines WN4819 / WN1220: DAL 2027-01-02 14:25:00 → MDW 2027-01-02 19:35:00; 1 stop(s) via CLE; 310 minutes. Local airport times.
    • WN4819: DAL 2027-01-02 14:25:00 → CLE 2027-01-02 17:50:00; layover at CLE: 80 minutes.
    • WN1220: CLE 2027-01-02 19:10:00 → MDW 2027-01-02 19:35:00.
  • Southwest Airlines WN3937: MDW 2027-01-07 20:45:00 → DAL 2027-01-07 23:15:00; nonstop; 150 minutes. Local airport times.

More dates for this route