Boston (BOS) to Chicago (MDW) · Jan 5, 2027 · return Jan 19, 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: Boston to Chicago (MDW) flight deals

2027-01-05 → 2027-01-19 · Axel-exclusive $270.00

• Southwest Airlines WN4995: BOS 2027-01-05 07:10:00 → MDW 2027-01-05 08:55:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN2900: MDW 2027-01-19 13:15:00 → BOS 2027-01-19 16:20:00; nonstop; 125 minutes. Local airport times.

2027-01-05 → 2027-01-19 · Axel-exclusive $225.00

• Frontier Airlines F93511 / F92779: BOS 2027-01-05 12:15:00 → MDW 2027-01-05 17:47:00; 1 stop(s) via ATL; 392 minutes. Local airport times.
  • F93511: BOS 2027-01-05 12:15:00 → ATL 2027-01-05 15:36:00; layover at ATL: 69 minutes.
  • F92779: ATL 2027-01-05 16:45:00 → MDW 2027-01-05 17:47:00.
• Southwest Airlines WN2900: MDW 2027-01-19 13:15:00 → BOS 2027-01-19 16:20:00; nonstop; 125 minutes. Local airport times.

2027-01-05 → 2027-01-19 · Axel-exclusive $350.00

• Delta Air Lines DL2222 / DL4677: BOS 2027-01-05 13:04:00 → MDW 2027-01-05 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-05 13:04:00 → DTW 2027-01-05 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-05 17:40:00 → MDW 2027-01-05 18:01:00.
• Delta Air Lines DL5469 / DL2558: MDW 2027-01-19 10:24:00 → BOS 2027-01-19 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-19 10:24:00 → MSP 2027-01-19 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-19 13:09:00 → BOS 2027-01-19 17:01:00.

2027-01-05 → 2027-01-19 · Axel-exclusive $270.00

• Southwest Airlines WN816: BOS 2027-01-05 17:55:00 → MDW 2027-01-05 19:40:00; nonstop; 165 minutes. Local airport times.
• Southwest Airlines WN2900: MDW 2027-01-19 13:15:00 → BOS 2027-01-19 16:20:00; nonstop; 125 minutes. Local airport times.

2027-01-05 → 2027-01-19 · Axel-exclusive $280.00

• Southwest Airlines WN819 / WN287: BOS 2027-01-05 05:35:00 → MDW 2027-01-05 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-05 05:35:00 → STL 2027-01-05 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-05 10:55:00 → MDW 2027-01-05 12:05:00.
• Southwest Airlines WN2900: MDW 2027-01-19 13:15:00 → BOS 2027-01-19 16:20:00; nonstop; 125 minutes. Local airport times.

2027-01-05 → 2027-01-19 · Axel-exclusive $280.00

• Southwest Airlines WN4765 / WN651: BOS 2027-01-05 14:25:00 → MDW 2027-01-05 21:05:00; 1 stop(s) via BNA; 460 minutes. Local airport times.
  • WN4765: BOS 2027-01-05 14:25:00 → BNA 2027-01-05 16:15:00; layover at BNA: 195 minutes.
  • WN651: BNA 2027-01-05 19:30:00 → MDW 2027-01-05 21:05:00.
• Southwest Airlines WN2900: MDW 2027-01-19 13:15:00 → BOS 2027-01-19 16:20:00; nonstop; 125 minutes. Local airport times.

2027-01-05 → 2027-01-19 · Axel-exclusive $280.00

• Southwest Airlines WN1426 / WN1070: BOS 2027-01-05 07:25:00 → MDW 2027-01-05 12:15:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
  • WN1426: BOS 2027-01-05 07:25:00 → BWI 2027-01-05 09:15:00; layover at BWI: 110 minutes.
  • WN1070: BWI 2027-01-05 11:05:00 → MDW 2027-01-05 12:15:00.
• Southwest Airlines WN2900: MDW 2027-01-19 13:15:00 → BOS 2027-01-19 16:20:00; nonstop; 125 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

• This page: Boston (BOS) to Chicago (MDW) · Jan 5, 2027 · return Jan 19, 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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