Washington (DCA) to Chicago (MDW), Jan 1–3, 2027: from $177 one way

Washington (DCA) to Chicago (MDW), Jan 1–3, 2027: from $177 one way on Axel, checked Oct 29, 2026. Lowest published fare: $177 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 1, 2027, 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

Route overview: Washington, DC to Chicago (MDW) flight deals

2027-01-03 · one way · Axel-exclusive $177.00

• Southwest Airlines WN3718: DCA 2027-01-03 18:40:00 → MDW 2027-01-03 19:50:00; nonstop; 130 minutes. Local airport times.

2027-01-03 · one way · Axel-exclusive $218.30

• Delta Air Lines DL1558 / DL4688: DCA 2027-01-03 09:45:00 → MDW 2027-01-03 13:01:00; 1 stop(s) via DTW; 256 minutes. Local airport times.
  • DL1558: DCA 2027-01-03 09:45:00 → DTW 2027-01-03 11:22:00; layover at DTW: 82 minutes.
  • DL4688: DTW 2027-01-03 12:44:00 → MDW 2027-01-03 13:01:00.

2027-01-01 · one way · Axel-exclusive $177.00

• Southwest Airlines WN3718: DCA 2027-01-01 18:40:00 → MDW 2027-01-01 19:50:00; nonstop; 130 minutes. Local airport times.

2027-01-02 · one way · Axel-exclusive $177.00

• Southwest Airlines WN3718: DCA 2027-01-02 18:40:00 → MDW 2027-01-02 19:50:00; nonstop; 130 minutes. Local airport times.

2027-01-03 · one way · Axel-exclusive $177.00

• Southwest Airlines WN1532: DCA 2027-01-03 06:10:00 → MDW 2027-01-03 07:15:00; nonstop; 125 minutes. Local airport times.

2027-01-02 · one way · Axel-exclusive $177.00

• Southwest Airlines WN1532: DCA 2027-01-02 06:00:00 → MDW 2027-01-02 07:05:00; nonstop; 125 minutes. Local airport times.

2027-01-01 · one way · Axel-exclusive $177.00

• Southwest Airlines WN1532: DCA 2027-01-01 06:00:00 → MDW 2027-01-01 07:05:00; nonstop; 125 minutes. Local airport times.

2027-01-01 · one way · Axel-exclusive $182.90

• Southwest Airlines WN1515 / WN2062: DCA 2027-01-01 12:35:00 → MDW 2027-01-01 16:15:00; 1 stop(s) via BNA; 280 minutes. Local airport times.
  • WN1515: DCA 2027-01-01 12:35:00 → BNA 2027-01-01 13:30:00; layover at BNA: 75 minutes.
  • WN2062: BNA 2027-01-01 14:45:00 → MDW 2027-01-01 16:15:00.

2027-01-02 · one way · Axel-exclusive $182.90

• Southwest Airlines WN1548 / WN4770: DCA 2027-01-02 18:55:00 → MDW 2027-01-02 23:00:00; 1 stop(s) via STL; 305 minutes. Local airport times.
  • WN1548: DCA 2027-01-02 18:55:00 → STL 2027-01-02 20:25:00; layover at STL: 85 minutes.
  • WN4770: STL 2027-01-02 21:50:00 → MDW 2027-01-02 23:00:00.

2027-01-02 · one way · Axel-exclusive $182.90

• Southwest Airlines WN1515 / WN2062: DCA 2027-01-02 12:35:00 → MDW 2027-01-02 16:15:00; 1 stop(s) via BNA; 280 minutes. Local airport times.
  • WN1515: DCA 2027-01-02 12:35:00 → BNA 2027-01-02 13:30:00; layover at BNA: 75 minutes.
  • WN2062: BNA 2027-01-02 14:45:00 → MDW 2027-01-02 16:15:00.

2027-01-01 · one way · Axel-exclusive $182.90

• Southwest Airlines WN1548 / WN4770: DCA 2027-01-01 18:55:00 → MDW 2027-01-01 23:00:00; 1 stop(s) via STL; 305 minutes. Local airport times.
  • WN1548: DCA 2027-01-01 18:55:00 → STL 2027-01-01 20:25:00; layover at STL: 85 minutes.
  • WN4770: STL 2027-01-01 21:50:00 → MDW 2027-01-01 23:00:00.

2027-01-03 · one way · Axel-exclusive $182.90

• Southwest Airlines WN1515 / WN2062: DCA 2027-01-03 12:35:00 → MDW 2027-01-03 16:15:00; 1 stop(s) via BNA; 280 minutes. Local airport times.
  • WN1515: DCA 2027-01-03 12:35:00 → BNA 2027-01-03 13:30:00; layover at BNA: 75 minutes.
  • WN2062: BNA 2027-01-03 14:45:00 → MDW 2027-01-03 16:15:00.

2027-01-03 · one way · Axel-exclusive $182.90

• Southwest Airlines WN1548 / WN4770: DCA 2027-01-03 18:55:00 → MDW 2027-01-03 23:00:00; 1 stop(s) via STL; 305 minutes. Local airport times.
  • WN1548: DCA 2027-01-03 18:55:00 → STL 2027-01-03 20:25:00; layover at STL: 85 minutes.
  • WN4770: STL 2027-01-03 21:50:00 → MDW 2027-01-03 23:00:00.

2027-01-02 · one way · Axel-exclusive $218.30

• Delta Air Lines DL1558 / DL4688: DCA 2027-01-02 09:45:00 → MDW 2027-01-02 13:01:00; 1 stop(s) via DTW; 256 minutes. Local airport times.
  • DL1558: DCA 2027-01-02 09:45:00 → DTW 2027-01-02 11:22:00; layover at DTW: 82 minutes.
  • DL4688: DTW 2027-01-02 12:44:00 → MDW 2027-01-02 13:01:00.

2027-01-01 · one way · Axel-exclusive $218.30

• Delta Air Lines DL1558 / DL4688: DCA 2027-01-01 09:45:00 → MDW 2027-01-01 13:01:00; 1 stop(s) via DTW; 256 minutes. Local airport times.
  • DL1558: DCA 2027-01-01 09:45:00 → DTW 2027-01-01 11:22:00; layover at DTW: 82 minutes.
  • DL4688: DTW 2027-01-01 12:44:00 → MDW 2027-01-01 13:01:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

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