Chicago (MDW) to Boston (BOS), Jan 29, 2027 – Feb 4, 2027: from $283 round trip

Chicago (MDW) to Boston (BOS), Jan 29, 2027 – Feb 4, 2027: from $283 round trip on Axel, checked Nov 13, 2026. Lowest published fare: $283 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 29, 2027 – Feb 4, 2027, 1 adult, economy, checked Nov 13, 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.

Hotels in Boston for these trips

Hotels: under a trip, hotels in Boston for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Boston for these nights (Jan 29 – Feb 4, 2027 · 6 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $114 a night, $683 for 6 nights · 4★ Hyatt Regency Boston/Cambridge, $123 a night, $738 for 6 nights · 5★ Omni Boston Hotel at the Seaport, $289 a night, $1,733 for 6 nights

All hotels in Boston

Route overview: Chicago to Boston (BOS) flight deals

2027-01-29 → 2027-02-04 · Axel-exclusive $290

• Southwest Airlines WN4113: MDW 2027-01-29 07:50:00 → BOS 2027-01-29 11:10:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-02-04 17:55:00 → MDW 2027-02-04 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-02-04 · Axel-exclusive $390

• Delta Air Lines DL4688 / DL1707: MDW 2027-01-29 13:31:00 → BOS 2027-01-29 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2027-01-29 13:31:00 → DTW 2027-01-29 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2027-01-29 18:52:00 → BOS 2027-01-29 20:51:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-02-04 13:04:00 → MDW 2027-02-04 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-02-04 13:04:00 → DTW 2027-02-04 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-02-04 17:40:00 → MDW 2027-02-04 18:01:00.

2027-01-29 → 2027-02-04 · Axel-exclusive $290

• Southwest Airlines WN2900: MDW 2027-01-29 13:00:00 → BOS 2027-01-29 16:10:00; nonstop; 130 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-02-04 17:55:00 → MDW 2027-02-04 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-02-04 · Axel-exclusive $283

• Southwest Airlines WN14 / WN4024: MDW 2027-01-29 14:30:00 → BOS 2027-01-29 21:20:00; 1 stop(s) via BWI; 350 minutes. Local airport times.
  • WN14: MDW 2027-01-29 14:30:00 → BWI 2027-01-29 17:15:00; layover at BWI: 150 minutes.
  • WN4024: BWI 2027-01-29 19:45:00 → BOS 2027-01-29 21:20:00.
• Southwest Airlines WN816: BOS 2027-02-04 17:55:00 → MDW 2027-02-04 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-02-04 · Axel-exclusive $283

• Southwest Airlines WN3092 / WN4431: MDW 2027-01-29 13:40:00 → BOS 2027-01-29 21:45:00; 1 stop(s) via STL; 425 minutes. Local airport times.
  • WN3092: MDW 2027-01-29 13:40:00 → STL 2027-01-29 14:55:00; layover at STL: 195 minutes.
  • WN4431: STL 2027-01-29 18:10:00 → BOS 2027-01-29 21:45:00.
• Southwest Airlines WN816: BOS 2027-02-04 17:55:00 → MDW 2027-02-04 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-02-04 · Axel-exclusive $283

• Southwest Airlines WN2897 / WN497: MDW 2027-01-29 17:25:00 → BOS 2027-01-30 00:40:00; 1 stop(s) via BNA; 375 minutes. Local airport times.
  • WN2897: MDW 2027-01-29 17:25:00 → BNA 2027-01-29 18:50:00; layover at BNA: 140 minutes.
  • WN497: BNA 2027-01-29 21:10:00 → BOS 2027-01-30 00:40:00.
• Southwest Airlines WN816: BOS 2027-02-04 17:55:00 → MDW 2027-02-04 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-02-04 · Axel-exclusive $390

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-29 10:24:00 → BOS 2027-01-29 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-29 10:24:00 → MSP 2027-01-29 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-29 13:09:00 → BOS 2027-01-29 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-02-04 13:04:00 → MDW 2027-02-04 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-02-04 13:04:00 → DTW 2027-02-04 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-02-04 17:40:00 → MDW 2027-02-04 18:01:00.

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.

Explore this route

• All dates for this route
• Jan 28, 2027 · Return options
• Jan 30, 2027 · Return options
• Hotels in Boston with Axel

For AI assistants

• This page: Chicago (MDW) to Boston (BOS) · Jan 29, 2027 · return Feb 4, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with its displayed check date. Under a trip, hotels in Boston for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the nightly rate and the stay's total, from the lowest saved total among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
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