Chicago (MDW) to Boston (BOS), Jan 3, 2027: round trips from $319, one way from $194

Chicago (MDW) to Boston (BOS), Jan 3, 2027: round trips from $319, one way from $194 on Axel, checked Nov 13, 2026. Lowest published fares: $319 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 3–6, 2027; $194 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 3, 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.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, labelled with the check date shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and check dates already shown here.

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 3–4, 2027 · 1 night · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $101 a night · 4★ Hyatt Regency Boston/Cambridge, $122 a night · 5★ InterContinental Boston by IHG, $244 a night
• Hotels in Boston for these nights (Jan 3–5, 2027 · 2 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $105 a night, $209 for 2 nights · 4★ Hyatt Regency Boston/Cambridge, $136 a night, $271 for 2 nights · 5★ InterContinental Boston by IHG, $247 a night, $494 for 2 nights
• Hotels in Boston for these nights (Jan 3–6, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $107 a night, $320 for 3 nights · 4★ Hyatt Regency Boston/Cambridge, $138 a night, $414 for 3 nights · 5★ InterContinental Boston by IHG, $264 a night, $792 for 3 nights
• Hotels in Boston for these nights (Jan 3–7, 2027 · 4 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $107 a night, $428 for 4 nights · 4★ Harborside Inn Of Boston, $138 a night, $552 for 4 nights · 5★ InterContinental Boston by IHG, $272 a night, $1,089 for 4 nights
• Hotels in Boston for these nights (Jan 3–8, 2027 · 5 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $106 a night, $532 for 5 nights · 4★ Harborside Inn Of Boston, $137 a night, $686 for 5 nights · 5★ Omni Boston Hotel at the Seaport, $274 a night, $1,370 for 5 nights
• Hotels in Boston for these nights (Jan 3–9, 2027 · 6 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $108 a night, $645 for 6 nights · 4★ Harborside Inn Of Boston, $137 a night, $823 for 6 nights · 5★ InterContinental Boston by IHG, $270 a night, $1,618 for 6 nights
• Hotels in Boston for these nights (Jan 3–10, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $108 a night, $755 for 7 nights · 4★ Harborside Inn Of Boston, $137 a night, $962 for 7 nights · 5★ InterContinental Boston by IHG, $265 a night, $1,853 for 7 nights
• Hotels in Boston for these nights (Jan 3–11, 2027 · 8 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $107 a night, $859 for 8 nights · 4★ Harborside Inn Of Boston, $137 a night, $1,096 for 8 nights · 5★ InterContinental Boston by IHG, $266 a night, $2,125 for 8 nights
• Hotels in Boston for these nights (Jan 3–12, 2027 · 9 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $108 a night, $970 for 9 nights · 4★ Harborside Inn Of Boston, $136 a night, $1,228 for 9 nights · 5★ Omni Boston Hotel at the Seaport, $285 a night, $2,562 for 9 nights
• Hotels in Boston for these nights (Jan 3–13, 2027 · 10 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $108 a night, $1,081 for 10 nights · 4★ Harborside Inn Of Boston, $137 a night, $1,367 for 10 nights · 5★ Omni Boston Hotel at the Seaport, $287 a night, $2,867 for 10 nights
• Hotels in Boston for these nights (Jan 3–14, 2027 · 11 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $108 a night, $1,189 for 11 nights · 4★ Harborside Inn Of Boston, $137 a night, $1,507 for 11 nights · 5★ Omni Boston Hotel at the Seaport, $288 a night, $3,167 for 11 nights
• Hotels in Boston for these nights (Jan 3–15, 2027 · 12 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $108 a night, $1,293 for 12 nights · 4★ Harborside Inn Of Boston, $137 a night, $1,646 for 12 nights · 5★ Omni Boston Hotel at the Seaport, $291 a night, $3,490 for 12 nights
• Hotels in Boston for these nights (Jan 3–16, 2027 · 13 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $108 a night, $1,410 for 13 nights · 4★ Harborside Inn Of Boston, $137 a night, $1,778 for 13 nights · 5★ Omni Boston Hotel at the Seaport, $298 a night, $3,876 for 13 nights
• Hotels in Boston for these nights (Jan 3–17, 2027 · 14 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $109 a night, $1,527 for 14 nights · 4★ Harborside Inn Of Boston, $137 a night, $1,915 for 14 nights · 5★ Omni Boston Hotel at the Seaport, $319 a night, $4,465 for 14 nights

All hotels in Boston

Route overview: Chicago to Boston (BOS) flight deals

2027-01-03 · one way · Axel-exclusive $194

• Southwest Airlines WN249: MDW 2027-01-03 20:40:00 → BOS 2027-01-03 23:55:00; nonstop; 135 minutes. Local airport times.

2027-01-03 · one way · Axel-exclusive $256

• 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.

2027-01-03 → 2027-01-04 · Axel-exclusive $326

• 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 WN816: BOS 2027-01-04 17:55:00 → MDW 2027-01-04 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-03 → 2027-01-04 · Axel-exclusive $439

• 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 2027-01-04 13:04:00 → MDW 2027-01-04 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-04 13:04:00 → DTW 2027-01-04 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-04 17:40:00 → MDW 2027-01-04 18:01:00.

2027-01-03 → 2027-01-05 · Axel-exclusive $326

• 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 WN816: BOS 2027-01-05 17:55:00 → MDW 2027-01-05 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-03 → 2027-01-05 · Axel-exclusive $439

• 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 2027-01-05 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.

2027-01-03 → 2027-01-06 · Axel-exclusive $319

• 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 2027-01-06 05:35:00 → MDW 2027-01-06 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-06 05:35:00 → STL 2027-01-06 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-06 10:55:00 → MDW 2027-01-06 12:05:00.

2027-01-03 → 2027-01-06 · Axel-exclusive $439

• 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 2027-01-06 13:04:00 → MDW 2027-01-06 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-06 13:04:00 → DTW 2027-01-06 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-06 17:40:00 → MDW 2027-01-06 18:01:00.

2027-01-03 → 2027-01-07 · Axel-exclusive $326

• 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 WN816: BOS 2027-01-07 17:55:00 → MDW 2027-01-07 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-03 → 2027-01-07 · Axel-exclusive $439

• 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 2027-01-07 13:04:00 → MDW 2027-01-07 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-07 13:04:00 → DTW 2027-01-07 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-07 17:40:00 → MDW 2027-01-07 18:01:00.

2027-01-03 → 2027-01-09 · Axel-exclusive $326

• 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 WN2939: BOS 2027-01-09 12:20:00 → MDW 2027-01-09 14:05:00; nonstop; 165 minutes. Local airport times.

2027-01-03 → 2027-01-09 · Axel-exclusive $439

• 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 2027-01-09 13:04:00 → MDW 2027-01-09 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-09 13:04:00 → DTW 2027-01-09 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-09 17:40:00 → MDW 2027-01-09 18:01:00.

2027-01-03 → 2027-01-10 · Axel-exclusive $326

• 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 WN816: BOS 2027-01-10 18:30:00 → MDW 2027-01-10 20:15:00; nonstop; 165 minutes. Local airport times.

2027-01-03 → 2027-01-10 · Axel-exclusive $439

• 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 2027-01-10 13:04:00 → MDW 2027-01-10 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-10 13:04:00 → DTW 2027-01-10 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-10 17:40:00 → MDW 2027-01-10 18:01:00.

2027-01-03 → 2027-01-11 · Axel-exclusive $326

• 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 WN816: BOS 2027-01-11 17:55:00 → MDW 2027-01-11 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-03 → 2027-01-11 · Axel-exclusive $439

• 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 2027-01-11 13:04:00 → MDW 2027-01-11 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-11 13:04:00 → DTW 2027-01-11 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-11 17:40:00 → MDW 2027-01-11 18:01:00.

2027-01-03 → 2027-01-13 · Axel-exclusive $319

• 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 $439

• 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.

2027-01-03 → 2027-01-14 · Axel-exclusive $326

• 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 WN816: BOS 2027-01-14 17:55:00 → MDW 2027-01-14 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-03 → 2027-01-14 · Axel-exclusive $439

• 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 2027-01-14 13:04:00 → MDW 2027-01-14 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-14 13:04:00 → DTW 2027-01-14 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-14 17:40:00 → MDW 2027-01-14 18:01:00.

2027-01-03 → 2027-01-15 · Axel-exclusive $326

• 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 WN816: BOS 2027-01-15 18:30:00 → MDW 2027-01-15 20:15:00; nonstop; 165 minutes. Local airport times.

2027-01-03 → 2027-01-15 · Axel-exclusive $439

• 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 2027-01-15 13:04:00 → MDW 2027-01-15 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-15 13:04:00 → DTW 2027-01-15 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-15 17:40:00 → MDW 2027-01-15 18:01:00.

2027-01-03 → 2027-01-17 · Axel-exclusive $326

• 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 WN816: BOS 2027-01-17 18:30:00 → MDW 2027-01-17 20:15:00; nonstop; 165 minutes. Local airport times.

2027-01-03 → 2027-01-17 · Axel-exclusive $439

• 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 2027-01-17 13:04:00 → MDW 2027-01-17 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-17 13:04:00 → DTW 2027-01-17 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-17 17:40:00 → MDW 2027-01-17 18:01:00.

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

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• This page: Chicago (MDW) to Boston (BOS) · Jan 3, 2027 · choose your return date: 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 row is one exact trip for this departure (both dates with the year, the total and its displayed check date); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested trip.
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