Chicago (MDW) to Boston (BOS) · Jan 3, 2027 · return Jan 13, 2027

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

2027-01-03 → 2027-01-13 · Axel-exclusive $309.38

• Southwest Airlines WN2897 / WN497: MDW 2027-01-03 17:25:00 → BOS 2027-01-04 00:40:00; 1 stop(s) via BNA; 375 minutes. Local airport times.
  • WN2897: MDW 2027-01-03 17:25:00 → BNA 2027-01-03 18:50:00; layover at BNA: 140 minutes.
  • WN497: BNA 2027-01-03 21:10:00 → BOS 2027-01-04 00:40:00.
• Southwest Airlines WN819 / WN287: BOS 2027-01-13 05:35:00 → MDW 2027-01-13 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-13 05:35:00 → STL 2027-01-13 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-13 10:55:00 → MDW 2027-01-13 12:05:00.

2027-01-03 → 2027-01-13 · Axel-exclusive $438.75

• Delta Air Lines DL4688 / DL1707: MDW 2027-01-03 13:31:00 → BOS 2027-01-03 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2027-01-03 13:31:00 → DTW 2027-01-03 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2027-01-03 18:52:00 → BOS 2027-01-03 20:51:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-13 13:04:00 → MDW 2027-01-13 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-13 13:04:00 → DTW 2027-01-13 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-13 17:40:00 → MDW 2027-01-13 18:01:00.

2027-01-03 → 2027-01-13 · Axel-exclusive $309.38

• Southwest Airlines WN14 / WN4024: MDW 2027-01-03 14:30:00 → BOS 2027-01-03 21:20:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
  • WN14: MDW 2027-01-03 14:30:00 → BWI 2027-01-03 17:15:00; layover at BWI: 150 minutes.
  • WN4024: BWI 2027-01-03 19:45:00 → BOS 2027-01-03 21:20:00.
• Southwest Airlines WN819 / WN287: BOS 2027-01-13 05:35:00 → MDW 2027-01-13 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-13 05:35:00 → STL 2027-01-13 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-13 10:55:00 → MDW 2027-01-13 12:05:00.

2027-01-03 → 2027-01-13 · Axel-exclusive $309.38

• Southwest Airlines WN3092 / WN4431: MDW 2027-01-03 13:40:00 → BOS 2027-01-03 21:45:00; 1 stop(s) via STL; 425 minutes. Local airport times.
  • WN3092: MDW 2027-01-03 13:40:00 → STL 2027-01-03 14:55:00; layover at STL: 195 minutes.
  • WN4431: STL 2027-01-03 18:10:00 → BOS 2027-01-03 21:45:00.
• Southwest Airlines WN819 / WN287: BOS 2027-01-13 05:35:00 → MDW 2027-01-13 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-13 05:35:00 → STL 2027-01-13 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-13 10:55:00 → MDW 2027-01-13 12:05:00.

2027-01-03 → 2027-01-13 · Axel-exclusive $318.75

• Southwest Airlines WN249: MDW 2027-01-03 20:40:00 → BOS 2027-01-03 23:55:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN819 / WN287: BOS 2027-01-13 05:35:00 → MDW 2027-01-13 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-13 05:35:00 → STL 2027-01-13 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-13 10:55:00 → MDW 2027-01-13 12:05:00.

2027-01-03 → 2027-01-13 · Axel-exclusive $438.75

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-03 10:24:00 → BOS 2027-01-03 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-03 10:24:00 → MSP 2027-01-03 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-03 13:09:00 → BOS 2027-01-03 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-13 13:04:00 → MDW 2027-01-13 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-13 13:04:00 → DTW 2027-01-13 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-13 17:40:00 → MDW 2027-01-13 18:01:00.

Explore this route

• All dates for this route
• Jan 2, 2027 · Return options
• Jan 4, 2027 · Return options
• Hotels in Boston with Axel

For AI assistants

• This page: Chicago (MDW) to Boston (BOS) · Jan 3, 2027 · return Jan 13, 2027: 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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