Chicago (MDW) to Boston (BOS), Dec 4–6, 2026: from $145 one way

Chicago (MDW) to Boston (BOS), Dec 4–6, 2026: from $145 one way on Axel, checked Oct 29, 2026. Lowest published fare: $145 one way, Axel-exclusive, Southwest Airlines, 1 stop, Dec 4, 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: Chicago to Boston (BOS) flight deals

2026-12-05 · one way · Axel-exclusive $155.00

• Southwest Airlines WN4113: MDW 2026-12-05 07:40:00 → BOS 2026-12-05 10:55:00; nonstop; 135 minutes. Local airport times.

2026-12-05 · one way · Axel-exclusive $205.00

• Delta Air Lines DL4688 / DL1707: MDW 2026-12-05 13:31:00 → BOS 2026-12-05 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-12-05 13:31:00 → DTW 2026-12-05 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-12-05 18:52:00 → BOS 2026-12-05 20:51:00.

2026-12-06 · one way · Axel-exclusive $155.00

• Southwest Airlines WN249: MDW 2026-12-06 20:40:00 → BOS 2026-12-06 23:55:00; nonstop; 135 minutes. Local airport times.

2026-12-04 · one way · Axel-exclusive $155.00

• Southwest Airlines WN2900: MDW 2026-12-04 13:00:00 → BOS 2026-12-04 16:10:00; nonstop; 130 minutes. Local airport times.

2026-12-06 · one way · Axel-exclusive $155.00

• Southwest Airlines WN4113: MDW 2026-12-06 07:45:00 → BOS 2026-12-06 11:00:00; nonstop; 135 minutes. Local airport times.

2026-12-04 · one way · Axel-exclusive $155.00

• Southwest Airlines WN4113: MDW 2026-12-04 07:50:00 → BOS 2026-12-04 11:10:00; nonstop; 140 minutes. Local airport times.

2026-12-05 · one way · Axel-exclusive $155.00

• Southwest Airlines WN2902: MDW 2026-12-05 18:55:00 → BOS 2026-12-05 22:15:00; nonstop; 140 minutes. Local airport times.

2026-12-06 · one way · Axel-exclusive $145.00

• Southwest Airlines WN3092 / WN4431: MDW 2026-12-06 13:40:00 → BOS 2026-12-06 21:45:00; 1 stop(s) via STL; 425 minutes. Local airport times.
  • WN3092: MDW 2026-12-06 13:40:00 → STL 2026-12-06 14:55:00; layover at STL: 195 minutes.
  • WN4431: STL 2026-12-06 18:10:00 → BOS 2026-12-06 21:45:00.

2026-12-04 · one way · Axel-exclusive $145.00

• Southwest Airlines WN14 / WN4024: MDW 2026-12-04 14:30:00 → BOS 2026-12-04 21:20:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
  • WN14: MDW 2026-12-04 14:30:00 → BWI 2026-12-04 17:15:00; layover at BWI: 150 minutes.
  • WN4024: BWI 2026-12-04 19:45:00 → BOS 2026-12-04 21:20:00.

2026-12-04 · one way · Axel-exclusive $145.00

• Southwest Airlines WN2897 / WN497: MDW 2026-12-04 17:25:00 → BOS 2026-12-05 00:40:00; 1 stop(s) via BNA; 375 minutes. Local airport times.
  • WN2897: MDW 2026-12-04 17:25:00 → BNA 2026-12-04 18:50:00; layover at BNA: 140 minutes.
  • WN497: BNA 2026-12-04 21:10:00 → BOS 2026-12-05 00:40:00.

2026-12-06 · one way · Axel-exclusive $145.00

• Southwest Airlines WN14 / WN4024: MDW 2026-12-06 14:30:00 → BOS 2026-12-06 21:20:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
  • WN14: MDW 2026-12-06 14:30:00 → BWI 2026-12-06 17:15:00; layover at BWI: 150 minutes.
  • WN4024: BWI 2026-12-06 19:45:00 → BOS 2026-12-06 21:20:00.

2026-12-04 · one way · Axel-exclusive $145.00

• Southwest Airlines WN3092 / WN4431: MDW 2026-12-04 13:40:00 → BOS 2026-12-04 21:45:00; 1 stop(s) via STL; 425 minutes. Local airport times.
  • WN3092: MDW 2026-12-04 13:40:00 → STL 2026-12-04 14:55:00; layover at STL: 195 minutes.
  • WN4431: STL 2026-12-04 18:10:00 → BOS 2026-12-04 21:45:00.

2026-12-05 · one way · Axel-exclusive $145.00

• Southwest Airlines WN14 / WN4024: MDW 2026-12-05 14:30:00 → BOS 2026-12-05 21:20:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
  • WN14: MDW 2026-12-05 14:30:00 → BWI 2026-12-05 17:15:00; layover at BWI: 150 minutes.
  • WN4024: BWI 2026-12-05 19:45:00 → BOS 2026-12-05 21:20:00.

2026-12-05 · one way · Axel-exclusive $145.00

• Southwest Airlines WN2897 / WN497: MDW 2026-12-05 17:25:00 → BOS 2026-12-06 00:40:00; 1 stop(s) via BNA; 375 minutes. Local airport times.
  • WN2897: MDW 2026-12-05 17:25:00 → BNA 2026-12-05 18:50:00; layover at BNA: 140 minutes.
  • WN497: BNA 2026-12-05 21:10:00 → BOS 2026-12-06 00:40:00.

2026-12-06 · one way · Axel-exclusive $145.00

• Southwest Airlines WN2897 / WN497: MDW 2026-12-06 17:25:00 → BOS 2026-12-07 00:40:00; 1 stop(s) via BNA; 375 minutes. Local airport times.
  • WN2897: MDW 2026-12-06 17:25:00 → BNA 2026-12-06 18:50:00; layover at BNA: 140 minutes.
  • WN497: BNA 2026-12-06 21:10:00 → BOS 2026-12-07 00:40:00.

2026-12-05 · one way · Axel-exclusive $145.00

• Southwest Airlines WN3092 / WN4431: MDW 2026-12-05 13:40:00 → BOS 2026-12-05 21:45:00; 1 stop(s) via STL; 425 minutes. Local airport times.
  • WN3092: MDW 2026-12-05 13:40:00 → STL 2026-12-05 14:55:00; layover at STL: 195 minutes.
  • WN4431: STL 2026-12-05 18:10:00 → BOS 2026-12-05 21:45:00.

2026-12-04 · one way · Axel-exclusive $205.00

• 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.

2026-12-06 · one way · Axel-exclusive $205.00

• Delta Air Lines DL5469 / DL2558: MDW 2026-12-06 10:24:00 → BOS 2026-12-06 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2026-12-06 10:24:00 → MSP 2026-12-06 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2026-12-06 13:09:00 → BOS 2026-12-06 17:01:00.

2026-12-06 · one way · Axel-exclusive $205.00

• Delta Air Lines DL4688 / DL1707: MDW 2026-12-06 13:31:00 → BOS 2026-12-06 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-12-06 13:31:00 → DTW 2026-12-06 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-12-06 18:52:00 → BOS 2026-12-06 20:51:00.

2026-12-05 · one way · Axel-exclusive $205.00

• Delta Air Lines DL5469 / DL2558: MDW 2026-12-05 10:24:00 → BOS 2026-12-05 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2026-12-05 10:24:00 → MSP 2026-12-05 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2026-12-05 13:09:00 → BOS 2026-12-05 17:01:00.

2026-12-04 · one way · Axel-exclusive $205.00

• Delta Air Lines DL4688 / DL1707: MDW 2026-12-04 13:31:00 → BOS 2026-12-04 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-12-04 13:31:00 → DTW 2026-12-04 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-12-04 18:52:00 → BOS 2026-12-04 20:51:00.

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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