Richmond (RIC) to Chicago (MDW), Dec 25–27, 2026: from $215 one way

Richmond (RIC) to Chicago (MDW), Dec 25–27, 2026: from $215 one way on Axel, checked Oct 29, 2026. Lowest published fare: $215 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 25, 2026, 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: Richmond to Chicago (MDW) flight deals

2026-12-25 · one way · Axel-exclusive $227.50

• Southwest Airlines WN4353: RIC 2026-12-25 08:10:00 → MDW 2026-12-25 09:15:00; nonstop; 125 minutes. Local airport times.

2026-12-25 · one way · Axel-exclusive $286.00

• Delta Air Lines DL5055 / DL4677: RIC 2026-12-25 12:59:00 → MDW 2026-12-25 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL5055: RIC 2026-12-25 12:59:00 → DTW 2026-12-25 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2026-12-25 17:40:00 → MDW 2026-12-25 18:01:00.

2026-12-27 · one way · Axel-exclusive $227.50

• Southwest Airlines WN2327: RIC 2026-12-27 08:10:00 → MDW 2026-12-27 09:15:00; nonstop; 125 minutes. Local airport times.

2026-12-26 · one way · Axel-exclusive $227.50

• Southwest Airlines WN4353: RIC 2026-12-26 08:10:00 → MDW 2026-12-26 09:15:00; nonstop; 125 minutes. Local airport times.

2026-12-27 · one way · Axel-exclusive $214.50

• Southwest Airlines WN382 / WN2062: RIC 2026-12-27 12:15:00 → MDW 2026-12-27 16:15:00; 1 stop(s) via BNA; 300 minutes. Local airport times.
  • WN382: RIC 2026-12-27 12:15:00 → BNA 2026-12-27 13:05:00; layover at BNA: 100 minutes.
  • WN2062: BNA 2026-12-27 14:45:00 → MDW 2026-12-27 16:15:00.

2026-12-27 · one way · Axel-exclusive $214.50

• Southwest Airlines WN909 / WN1072: RIC 2026-12-27 16:40:00 → MDW 2026-12-27 20:15:00; 1 stop(s) via BWI; 275 minutes. Local airport times.
  • WN909: RIC 2026-12-27 16:40:00 → BWI 2026-12-27 17:35:00; layover at BWI: 95 minutes.
  • WN1072: BWI 2026-12-27 19:10:00 → MDW 2026-12-27 20:15:00.

2026-12-25 · one way · Axel-exclusive $214.50

• Southwest Airlines WN382 / WN2062: RIC 2026-12-25 12:15:00 → MDW 2026-12-25 16:15:00; 1 stop(s) via BNA; 300 minutes. Local airport times.
  • WN382: RIC 2026-12-25 12:15:00 → BNA 2026-12-25 13:05:00; layover at BNA: 100 minutes.
  • WN2062: BNA 2026-12-25 14:45:00 → MDW 2026-12-25 16:15:00.

2026-12-26 · one way · Axel-exclusive $214.50

• Southwest Airlines WN382 / WN2062: RIC 2026-12-26 12:15:00 → MDW 2026-12-26 16:15:00; 1 stop(s) via BNA; 300 minutes. Local airport times.
  • WN382: RIC 2026-12-26 12:15:00 → BNA 2026-12-26 13:05:00; layover at BNA: 100 minutes.
  • WN2062: BNA 2026-12-26 14:45:00 → MDW 2026-12-26 16:15:00.

2026-12-26 · one way · Axel-exclusive $214.50

• Southwest Airlines WN909 / WN1072: RIC 2026-12-26 16:40:00 → MDW 2026-12-26 20:15:00; 1 stop(s) via BWI; 275 minutes. Local airport times.
  • WN909: RIC 2026-12-26 16:40:00 → BWI 2026-12-26 17:35:00; layover at BWI: 95 minutes.
  • WN1072: BWI 2026-12-26 19:10:00 → MDW 2026-12-26 20:15:00.

2026-12-25 · one way · Axel-exclusive $214.50

• Southwest Airlines WN909 / WN1072: RIC 2026-12-25 16:40:00 → MDW 2026-12-25 20:15:00; 1 stop(s) via BWI; 275 minutes. Local airport times.
  • WN909: RIC 2026-12-25 16:40:00 → BWI 2026-12-25 17:35:00; layover at BWI: 95 minutes.
  • WN1072: BWI 2026-12-25 19:10:00 → MDW 2026-12-25 20:15:00.

2026-12-26 · one way · Axel-exclusive $286.00

• Delta Air Lines DL5055 / DL4677: RIC 2026-12-26 12:59:00 → MDW 2026-12-26 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL5055: RIC 2026-12-26 12:59:00 → DTW 2026-12-26 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2026-12-26 17:40:00 → MDW 2026-12-26 18:01:00.

2026-12-27 · one way · Axel-exclusive $286.00

• Delta Air Lines DL1460 / DL1063: RIC 2026-12-27 05:23:00 → MDW 2026-12-27 10:00:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
  • DL1460: RIC 2026-12-27 05:23:00 → ATL 2026-12-27 07:18:00; layover at ATL: 97 minutes.
  • DL1063: ATL 2026-12-27 08:55:00 → MDW 2026-12-27 10:00:00.

2026-12-27 · one way · Axel-exclusive $286.00

• Delta Air Lines DL5055 / DL4677: RIC 2026-12-27 12:59:00 → MDW 2026-12-27 18:01:00; 1 stop(s) via DTW; 362 minutes. Local airport times.
  • DL5055: RIC 2026-12-27 12:59:00 → DTW 2026-12-27 15:00:00; layover at DTW: 160 minutes.
  • DL4677: DTW 2026-12-27 17:40:00 → MDW 2026-12-27 18:01:00.

2026-12-26 · one way · Axel-exclusive $286.00

• Delta Air Lines DL1460 / DL1063: RIC 2026-12-26 05:23:00 → MDW 2026-12-26 10:00:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
  • DL1460: RIC 2026-12-26 05:23:00 → ATL 2026-12-26 07:18:00; layover at ATL: 97 minutes.
  • DL1063: ATL 2026-12-26 08:55:00 → MDW 2026-12-26 10:00:00.

2026-12-25 · one way · Axel-exclusive $286.00

• Delta Air Lines DL1460 / DL1063: RIC 2026-12-25 05:23:00 → MDW 2026-12-25 10:00:00; 1 stop(s) via ATL; 337 minutes. Local airport times.
  • DL1460: RIC 2026-12-25 05:23:00 → ATL 2026-12-25 07:18:00; layover at ATL: 97 minutes.
  • DL1063: ATL 2026-12-25 08:55:00 → MDW 2026-12-25 10:00:00.

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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