Boston (BOS) to Chicago (MDW), Nov 26–28, 2026: from $304 round trip

Boston (BOS) to Chicago (MDW), Nov 26–28, 2026: from $304 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $304 round trip, Axel-exclusive, Frontier Airlines / Southwest Airlines, 1 stop, Nov 26–28, 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: Boston to Chicago (MDW) flight deals

2026-11-26 → 2026-11-28 · Axel-exclusive $364.50

• Southwest Airlines WN2939: BOS 2026-11-26 12:20:00 → MDW 2026-11-26 14:05:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN2902: MDW 2026-11-28 18:55:00 → BOS 2026-11-28 22:15:00; nonstop; 140 minutes. Local airport times.

2026-11-26 → 2026-11-28 · Axel-exclusive $303.75

• Frontier Airlines F93511 / F92779: BOS 2026-11-26 12:15:00 → MDW 2026-11-26 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2026-11-26 12:15:00 → ATL 2026-11-26 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2026-11-26 16:45:00 → MDW 2026-11-26 17:47:00.
• Southwest Airlines WN2902: MDW 2026-11-28 18:55:00 → BOS 2026-11-28 22:15:00; nonstop; 140 minutes. Local airport times.

2026-11-26 → 2026-11-28 · Axel-exclusive $472.50

• Delta Air Lines DL2222 / DL4677: BOS 2026-11-26 13:04:00 → MDW 2026-11-26 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-11-26 13:04:00 → DTW 2026-11-26 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-11-26 17:40:00 → MDW 2026-11-26 18:01:00.
• Delta Air Lines DL4688 / DL1707: MDW 2026-11-28 13:31:00 → BOS 2026-11-28 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-11-28 13:31:00 → DTW 2026-11-28 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-11-28 18:52:00 → BOS 2026-11-28 20:51:00.

2026-11-26 → 2026-11-28 · Axel-exclusive $364.50

• Southwest Airlines WN845: BOS 2026-11-26 06:25:00 → MDW 2026-11-26 08:15:00; nonstop; 170 minutes. Local airport times.
• Southwest Airlines WN2902: MDW 2026-11-28 18:55:00 → BOS 2026-11-28 22:15:00; nonstop; 140 minutes. Local airport times.

2026-11-26 → 2026-11-28 · Axel-exclusive $378.00

• Southwest Airlines WN819 / WN287: BOS 2026-11-26 05:35:00 → MDW 2026-11-26 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2026-11-26 05:35:00 → STL 2026-11-26 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2026-11-26 10:55:00 → MDW 2026-11-26 12:05:00.
• Southwest Airlines WN2902: MDW 2026-11-28 18:55:00 → BOS 2026-11-28 22:15:00; nonstop; 140 minutes. Local airport times.

2026-11-26 → 2026-11-28 · Axel-exclusive $378.00

• Southwest Airlines WN4765 / WN651: BOS 2026-11-26 14:25:00 → MDW 2026-11-26 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
  • WN4765: BOS 2026-11-26 14:25:00 → BNA 2026-11-26 16:15:00; layover at BNA: 195 minutes.
  • WN651: BNA 2026-11-26 19:30:00 → MDW 2026-11-26 21:05:00.
• Southwest Airlines WN2902: MDW 2026-11-28 18:55:00 → BOS 2026-11-28 22:15:00; nonstop; 140 minutes. Local airport times.

2026-11-26 → 2026-11-28 · Axel-exclusive $378.00

• Southwest Airlines WN1426 / WN1070: BOS 2026-11-26 07:25:00 → MDW 2026-11-26 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
  • WN1426: BOS 2026-11-26 07:25:00 → BWI 2026-11-26 09:15:00; layover at BWI: 110 minutes.
  • WN1070: BWI 2026-11-26 11:05:00 → MDW 2026-11-26 12:15:00.
• Southwest Airlines WN2902: MDW 2026-11-28 18:55:00 → BOS 2026-11-28 22:15:00; nonstop; 140 minutes. Local airport times.

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.

Explore this route

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For AI assistants

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