Boston (BOS) to Chicago (MDW) · Nov 27, 2026 · return Dec 4, 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

2026-11-27 → 2026-12-04 · Axel-exclusive $317.25

• Southwest Airlines WN816: BOS 2026-11-27 18:30:00 → MDW 2026-11-27 20:15:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN2900: MDW 2026-12-04 13:00:00 → BOS 2026-12-04 16:10:00; nonstop; 130 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $256.50

• Frontier Airlines F93511 / F92779: BOS 2026-11-27 12:15:00 → MDW 2026-11-27 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2026-11-27 12:15:00 → ATL 2026-11-27 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2026-11-27 16:45:00 → MDW 2026-11-27 17:47:00.
• Southwest Airlines WN2900: MDW 2026-12-04 13:00:00 → BOS 2026-12-04 16:10:00; nonstop; 130 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $411.25

• Delta Air Lines DL2222 / DL4677: BOS 2026-11-27 13:04:00 → MDW 2026-11-27 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-11-27 13:04:00 → DTW 2026-11-27 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-11-27 17:40:00 → MDW 2026-11-27 18:01:00.
• Delta Air Lines DL5469 / DL2558: MDW 2026-12-04 10:24:00 → BOS 2026-12-04 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2026-12-04 10:24:00 → MSP 2026-12-04 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2026-12-04 13:09:00 → BOS 2026-12-04 17:01:00.

2026-11-27 → 2026-12-04 · Axel-exclusive $317.25

• Southwest Airlines WN4995: BOS 2026-11-27 07:10:00 → MDW 2026-11-27 08:55:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN2900: MDW 2026-12-04 13:00:00 → BOS 2026-12-04 16:10:00; nonstop; 130 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $330.75

• Southwest Airlines WN819 / WN287: BOS 2026-11-27 05:35:00 → MDW 2026-11-27 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2026-11-27 05:35:00 → STL 2026-11-27 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2026-11-27 10:55:00 → MDW 2026-11-27 12:05:00.
• Southwest Airlines WN2900: MDW 2026-12-04 13:00:00 → BOS 2026-12-04 16:10:00; nonstop; 130 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $330.75

• Southwest Airlines WN4765 / WN651: BOS 2026-11-27 14:25:00 → MDW 2026-11-27 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
  • WN4765: BOS 2026-11-27 14:25:00 → BNA 2026-11-27 16:15:00; layover at BNA: 195 minutes.
  • WN651: BNA 2026-11-27 19:30:00 → MDW 2026-11-27 21:05:00.
• Southwest Airlines WN2900: MDW 2026-12-04 13:00:00 → BOS 2026-12-04 16:10:00; nonstop; 130 minutes. Local airport times.

2026-11-27 → 2026-12-04 · Axel-exclusive $330.75

• Southwest Airlines WN1426 / WN1070: BOS 2026-11-27 07:25:00 → MDW 2026-11-27 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
  • WN1426: BOS 2026-11-27 07:25:00 → BWI 2026-11-27 09:15:00; layover at BWI: 110 minutes.
  • WN1070: BWI 2026-11-27 11:05:00 → MDW 2026-11-27 12:15:00.
• Southwest Airlines WN2900: MDW 2026-12-04 13:00:00 → BOS 2026-12-04 16:10:00; nonstop; 130 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 26, 2026 · Return options
• Nov 28, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Boston (BOS) to Chicago (MDW) · Nov 27, 2026 · return Dec 4, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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