Travel with Axel,
get the best price.

Dallas → Chicago

Jan 22, 2027 · return Feb 1, 2027

DAL → MDW1 adulteconomyRound trip

7 flight options · 1 airline

Nonstop flights

Fri, Jan 22 – Mon, Feb 1

Southwest Airlines
5:40 pmDAL
2h 15m
Nonstop
7:55 pmMDW
Southwest Airlines
2:30 pmMDW
2h 25m
Nonstop
4:55 pmDAL

Round-trip total · 1 adult · Taxes included

One-stop flights

Fri, Jan 22 – Mon, Feb 1

Southwest Airlines
6:50 pmDAL
2h 10m
Nonstop
9:00 pmMDW
Southwest Airlines
1:20 pmMDW
5h 5m
CMH · 1h 25m
6:25 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Jan 22 – Mon, Feb 1

Southwest Airlines
7:35 amDAL
4h 55m
MSY · 1h 15m
12:30 pmMDW
Southwest Airlines
1:20 pmMDW
5h 5m
CMH · 1h 25m
6:25 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Jan 22 – Mon, Feb 1

Southwest Airlines
7:30 amDAL
4h 50m
AUS · 1h 20m
12:20 pmMDW
Southwest Airlines
1:20 pmMDW
5h 5m
CMH · 1h 25m
6:25 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Jan 22 – Mon, Feb 1

Southwest Airlines
12:55 pmDAL
4h 15m
MCI · 1h 20m
5:10 pmMDW
Southwest Airlines
1:20 pmMDW
5h 5m
CMH · 1h 25m
6:25 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Jan 22 – Mon, Feb 1

Southwest Airlines
12:10 pmDAL
4h 55m
BHM · 1h 35m
5:05 pmMDW
Southwest Airlines
1:20 pmMDW
5h 5m
CMH · 1h 25m
6:25 pmDAL

Round-trip total · 1 adult · Taxes included

Fri, Jan 22 – Mon, Feb 1

Southwest Airlines
12:15 pmDAL
5h 10m
SAT · 1h 35m
5:25 pmMDW
Southwest Airlines
1:20 pmMDW
5h 5m
CMH · 1h 25m
6:25 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.

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.
  • Not satisfied? Full refund.If you are unhappy with the experience for any reason, or simply change your mind, cancel within 24 hours of booking (departure 7+ days away) and we refund you in full. We stand by our product. 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

All dates for this routeNov 24, 2026 → Nov 29, 2026Dec 22, 2026 → Dec 27, 2026Dec 30, 2026 → Jan 2, 2027Jan 15, 2027 → Jan 18, 2027Oct 30, 2026 → Nov 2, 2026Oct 31, 2026 → Nov 7, 2026Nov 27, 2026 → Nov 30, 2026Nov 28, 2026 → Dec 5, 2026Dec 25, 2026 → Dec 28, 2026Dec 26, 2026 → Jan 2, 2027Jan 22, 2027 → Jan 25, 2027Oct 30, 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)
2027-01-22 → 2027-02-01Southwest AirlinesWN1433 / WN2092$330.002026-10-29T01:01:45Z
2027-01-22 → 2027-02-01Southwest AirlinesWN1433 / WN1354 + WN1472$335.002026-10-29T01:01:45Z
2027-01-22 → 2027-02-01Southwest AirlinesWN978 + WN3175 / WN1354 + WN1472$340.002026-10-29T01:01:45Z
2027-01-22 → 2027-02-01Southwest AirlinesWN733 + WN379 / WN1354 + WN1472$340.002026-10-29T01:01:45Z
2027-01-22 → 2027-02-01Southwest AirlinesWN102 + WN2694 / WN1354 + WN1472$340.002026-10-29T01:01:45Z
2027-01-22 → 2027-02-01Southwest AirlinesWN1246 + WN1030 / WN1354 + WN1472$340.002026-10-29T01:01:45Z
2027-01-22 → 2027-02-01Southwest AirlinesWN1165 + WN3791 / WN1354 + WN1472$340.002026-10-29T01:01:45Z

2027-01-22 → 2027-02-01 · $330.00

  • Southwest Airlines WN1433: DAL 2027-01-22 17:40:00 → MDW 2027-01-22 19:55:00; nonstop; 135 minutes. Local airport times.
  • Southwest Airlines WN2092: MDW 2027-02-01 14:30:00 → DAL 2027-02-01 16:55:00; nonstop; 145 minutes. Local airport times.

2027-01-22 → 2027-02-01 · $335.00

  • Southwest Airlines WN1433: DAL 2027-01-22 18:50:00 → MDW 2027-01-22 21:00:00; nonstop; 130 minutes. Local airport times.
  • Southwest Airlines WN1354 / WN1472: MDW 2027-02-01 13:20:00 → DAL 2027-02-01 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2027-02-01 13:20:00 → CMH 2027-02-01 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2027-02-01 16:50:00 → DAL 2027-02-01 18:25:00.

2027-01-22 → 2027-02-01 · $340.00

  • Southwest Airlines WN978 / WN3175: DAL 2027-01-22 07:35:00 → MDW 2027-01-22 12:30:00; 1 stop(s) via MSY; 295 minutes. Local airport times.
    • WN978: DAL 2027-01-22 07:35:00 → MSY 2027-01-22 08:55:00; layover at MSY: 75 minutes.
    • WN3175: MSY 2027-01-22 10:10:00 → MDW 2027-01-22 12:30:00.
  • Southwest Airlines WN1354 / WN1472: MDW 2027-02-01 13:20:00 → DAL 2027-02-01 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2027-02-01 13:20:00 → CMH 2027-02-01 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2027-02-01 16:50:00 → DAL 2027-02-01 18:25:00.

2027-01-22 → 2027-02-01 · $340.00

  • Southwest Airlines WN733 / WN379: DAL 2027-01-22 07:30:00 → MDW 2027-01-22 12:20:00; 1 stop(s) via AUS; 290 minutes. Local airport times.
    • WN733: DAL 2027-01-22 07:30:00 → AUS 2027-01-22 08:30:00; layover at AUS: 80 minutes.
    • WN379: AUS 2027-01-22 09:50:00 → MDW 2027-01-22 12:20:00.
  • Southwest Airlines WN1354 / WN1472: MDW 2027-02-01 13:20:00 → DAL 2027-02-01 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2027-02-01 13:20:00 → CMH 2027-02-01 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2027-02-01 16:50:00 → DAL 2027-02-01 18:25:00.

2027-01-22 → 2027-02-01 · $340.00

  • Southwest Airlines WN102 / WN2694: DAL 2027-01-22 12:55:00 → MDW 2027-01-22 17:10:00; 1 stop(s) via MCI; 255 minutes. Local airport times.
    • WN102: DAL 2027-01-22 12:55:00 → MCI 2027-01-22 14:30:00; layover at MCI: 80 minutes.
    • WN2694: MCI 2027-01-22 15:50:00 → MDW 2027-01-22 17:10:00.
  • Southwest Airlines WN1354 / WN1472: MDW 2027-02-01 13:20:00 → DAL 2027-02-01 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2027-02-01 13:20:00 → CMH 2027-02-01 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2027-02-01 16:50:00 → DAL 2027-02-01 18:25:00.

2027-01-22 → 2027-02-01 · $340.00

  • Southwest Airlines WN1246 / WN1030: DAL 2027-01-22 12:10:00 → MDW 2027-01-22 17:05:00; 1 stop(s) via BHM; 295 minutes. Local airport times.
    • WN1246: DAL 2027-01-22 12:10:00 → BHM 2027-01-22 13:40:00; layover at BHM: 95 minutes.
    • WN1030: BHM 2027-01-22 15:15:00 → MDW 2027-01-22 17:05:00.
  • Southwest Airlines WN1354 / WN1472: MDW 2027-02-01 13:20:00 → DAL 2027-02-01 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2027-02-01 13:20:00 → CMH 2027-02-01 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2027-02-01 16:50:00 → DAL 2027-02-01 18:25:00.

2027-01-22 → 2027-02-01 · $340.00

  • Southwest Airlines WN1165 / WN3791: DAL 2027-01-22 12:15:00 → MDW 2027-01-22 17:25:00; 1 stop(s) via SAT; 310 minutes. Local airport times.
    • WN1165: DAL 2027-01-22 12:15:00 → SAT 2027-01-22 13:15:00; layover at SAT: 95 minutes.
    • WN3791: SAT 2027-01-22 14:50:00 → MDW 2027-01-22 17:25:00.
  • Southwest Airlines WN1354 / WN1472: MDW 2027-02-01 13:20:00 → DAL 2027-02-01 18:25:00; 1 stop(s) via CMH; 305 minutes. Local airport times.
    • WN1354: MDW 2027-02-01 13:20:00 → CMH 2027-02-01 15:25:00; layover at CMH: 85 minutes.
    • WN1472: CMH 2027-02-01 16:50:00 → DAL 2027-02-01 18:25:00.

More dates for this route