Chicago (MDW) to Boston (BOS), Jan 14, 2027: round trips from $283, one way from $155

Chicago (MDW) to Boston (BOS), Jan 14, 2027: round trips from $283, one way from $155 on Axel, checked Nov 13, 2026. Lowest published fares: $283 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 14–20, 2027; $155 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 14, 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 14–15, 2027 · 1 night · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $104 a night · 4★ Hyatt Regency Boston/Cambridge, $129 a night · 5★ Omni Boston Hotel at the Seaport, $323 a night
• Hotels in Boston for these nights (Jan 14–16, 2027 · 2 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $111 a night, $221 for 2 nights · 4★ Hyatt Regency Boston/Cambridge, $134 a night, $267 for 2 nights · 5★ The Langham, Boston, $353 a night, $705 for 2 nights
• Hotels in Boston for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $113 a night, $338 for 3 nights · 4★ Hyatt Regency Boston/Cambridge, $134 a night, $403 for 3 nights · 5★ The Langham, Boston, $356 a night, $1,068 for 3 nights
• Hotels in Boston for these nights (Jan 14–18, 2027 · 4 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $439 for 4 nights · 4★ Hyatt Regency Boston/Cambridge, $131 a night, $523 for 4 nights · 5★ The Langham, Boston, $353 a night, $1,413 for 4 nights
• Hotels in Boston for these nights (Jan 14–19, 2027 · 5 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $109 a night, $545 for 5 nights · 4★ Hyatt Regency Boston/Cambridge, $131 a night, $653 for 5 nights · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $350 a night, $1,750 for 5 nights
• Hotels in Boston for these nights (Jan 14–20, 2027 · 6 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $660 for 6 nights · 4★ Harborside Inn Of Boston, $135 a night, $812 for 6 nights · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $347 a night, $2,084 for 6 nights
• Hotels in Boston for these nights (Jan 14–21, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $771 for 7 nights · 4★ Harborside Inn Of Boston, $136 a night, $951 for 7 nights · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $345 a night, $2,413 for 7 nights
• Hotels in Boston for these nights (Jan 14–22, 2027 · 8 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $882 for 8 nights · 4★ Harborside Inn Of Boston, $135 a night, $1,083 for 8 nights · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $340 a night, $2,722 for 8 nights
• Hotels in Boston for these nights (Jan 14–23, 2027 · 9 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $111 a night, $995 for 9 nights · 4★ Harborside Inn Of Boston, $136 a night, $1,220 for 9 nights · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $346 a night, $3,113 for 9 nights
• Hotels in Boston for these nights (Jan 14–24, 2027 · 10 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $111 a night, $1,108 for 10 nights · 4★ Harborside Inn Of Boston, $135 a night, $1,352 for 10 nights · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $352 a night, $3,521 for 10 nights
• Hotels in Boston for these nights (Jan 14–25, 2027 · 11 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $1,212 for 11 nights · 4★ Harborside Inn Of Boston, $135 a night, $1,488 for 11 nights · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $346 a night, $3,801 for 11 nights
• Hotels in Boston for these nights (Jan 14–26, 2027 · 12 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $1,318 for 12 nights · 4★ Harborside Inn Of Boston, $136 a night, $1,627 for 12 nights · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $344 a night, $4,133 for 12 nights
• Hotels in Boston for these nights (Jan 14–27, 2027 · 13 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $1,433 for 13 nights · 4★ Harborside Inn Of Boston, $136 a night, $1,764 for 13 nights · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $346 a night, $4,493 for 13 nights
• Hotels in Boston for these nights (Jan 14–28, 2027 · 14 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $1,544 for 14 nights · 4★ Harborside Inn Of Boston, $136 a night, $1,900 for 14 nights · 5★ The Liberty, a Marriott Luxury Collection Hotel, Boston, $344 a night, $4,820 for 14 nights

All hotels in Boston

Route overview: Chicago to Boston (BOS) flight deals

2027-01-14 · one way · Axel-exclusive $155

• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 minutes. Local airport times.

2027-01-14 · one way · Axel-exclusive $205

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-14 10:24:00 → BOS 2027-01-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-14 10:24:00 → MSP 2027-01-14 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-14 13:09:00 → BOS 2027-01-14 17:01:00.

2027-01-14 → 2027-01-15 · Axel-exclusive $290

• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 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.

2027-01-14 → 2027-01-15 · Axel-exclusive $390

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-14 10:24:00 → BOS 2027-01-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-14 10:24:00 → MSP 2027-01-14 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-14 13:09:00 → BOS 2027-01-14 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.

2027-01-14 → 2027-01-16 · Axel-exclusive $290

• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN2939: BOS 2027-01-16 12:20:00 → MDW 2027-01-16 14:05:00; nonstop; 165 minutes. Local airport times.

2027-01-14 → 2027-01-16 · Axel-exclusive $390

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-14 10:24:00 → BOS 2027-01-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-14 10:24:00 → MSP 2027-01-14 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-14 13:09:00 → BOS 2027-01-14 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-16 13:04:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-16 13:04:00 → DTW 2027-01-16 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.

2027-01-14 → 2027-01-17 · Axel-exclusive $290

• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 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.

2027-01-14 → 2027-01-17 · Axel-exclusive $390

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-14 10:24:00 → BOS 2027-01-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-14 10:24:00 → MSP 2027-01-14 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-14 13:09:00 → BOS 2027-01-14 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.

2027-01-14 → 2027-01-18 · Axel-exclusive $290

• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-18 17:55:00 → MDW 2027-01-18 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-14 → 2027-01-18 · Axel-exclusive $390

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-14 10:24:00 → BOS 2027-01-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-14 10:24:00 → MSP 2027-01-14 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-14 13:09:00 → BOS 2027-01-14 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-18 13:04:00 → MDW 2027-01-18 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-18 13:04:00 → DTW 2027-01-18 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-18 17:40:00 → MDW 2027-01-18 18:01:00.

2027-01-14 → 2027-01-20 · Axel-exclusive $283

• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN819 / WN287: BOS 2027-01-20 05:35:00 → MDW 2027-01-20 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-01-20 05:35:00 → STL 2027-01-20 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-01-20 10:55:00 → MDW 2027-01-20 12:05:00.

2027-01-14 → 2027-01-20 · Axel-exclusive $390

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-14 10:24:00 → BOS 2027-01-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-14 10:24:00 → MSP 2027-01-14 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-14 13:09:00 → BOS 2027-01-14 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-20 13:04:00 → MDW 2027-01-20 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-20 13:04:00 → DTW 2027-01-20 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-20 17:40:00 → MDW 2027-01-20 18:01:00.

2027-01-14 → 2027-01-21 · Axel-exclusive $290

• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-21 17:55:00 → MDW 2027-01-21 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-14 → 2027-01-21 · Axel-exclusive $390

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-14 10:24:00 → BOS 2027-01-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-14 10:24:00 → MSP 2027-01-14 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-14 13:09:00 → BOS 2027-01-14 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-21 13:04:00 → MDW 2027-01-21 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-21 13:04:00 → DTW 2027-01-21 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-21 17:40:00 → MDW 2027-01-21 18:01:00.

2027-01-14 → 2027-01-22 · Axel-exclusive $290

• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-22 18:30:00 → MDW 2027-01-22 20:15:00; nonstop; 165 minutes. Local airport times.

2027-01-14 → 2027-01-22 · Axel-exclusive $390

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-14 10:24:00 → BOS 2027-01-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-14 10:24:00 → MSP 2027-01-14 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-14 13:09:00 → BOS 2027-01-14 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-22 13:04:00 → MDW 2027-01-22 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-22 13:04:00 → DTW 2027-01-22 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-22 17:40:00 → MDW 2027-01-22 18:01:00.

2027-01-14 → 2027-01-24 · Axel-exclusive $290

• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-24 18:30:00 → MDW 2027-01-24 20:15:00; nonstop; 165 minutes. Local airport times.

2027-01-14 → 2027-01-24 · Axel-exclusive $390

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-14 10:24:00 → BOS 2027-01-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-14 10:24:00 → MSP 2027-01-14 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-14 13:09:00 → BOS 2027-01-14 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-24 13:04:00 → MDW 2027-01-24 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-24 13:04:00 → DTW 2027-01-24 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-24 17:40:00 → MDW 2027-01-24 18:01:00.

2027-01-14 → 2027-01-25 · Axel-exclusive $290

• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-25 17:55:00 → MDW 2027-01-25 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-14 → 2027-01-25 · Axel-exclusive $390

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-14 10:24:00 → BOS 2027-01-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-14 10:24:00 → MSP 2027-01-14 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-14 13:09:00 → BOS 2027-01-14 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-25 13:04:00 → MDW 2027-01-25 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-25 13:04:00 → DTW 2027-01-25 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-25 17:40:00 → MDW 2027-01-25 18:01:00.

2027-01-14 → 2027-01-26 · Axel-exclusive $290

• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-26 17:55:00 → MDW 2027-01-26 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-14 → 2027-01-26 · Axel-exclusive $390

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-14 10:24:00 → BOS 2027-01-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-14 10:24:00 → MSP 2027-01-14 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-14 13:09:00 → BOS 2027-01-14 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-26 13:04:00 → MDW 2027-01-26 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-26 13:04:00 → DTW 2027-01-26 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-26 17:40:00 → MDW 2027-01-26 18:01:00.

2027-01-14 → 2027-01-28 · Axel-exclusive $290

• Southwest Airlines WN2902: MDW 2027-01-14 19:35:00 → BOS 2027-01-14 22:55:00; nonstop; 140 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2027-01-28 17:55:00 → MDW 2027-01-28 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-14 → 2027-01-28 · Axel-exclusive $390

• Delta Air Lines DL5469 / DL2558: MDW 2027-01-14 10:24:00 → BOS 2027-01-14 17:01:00; 1 stop(s) via MSP; 337 minutes. Local airport times.
  • DL5469: MDW 2027-01-14 10:24:00 → MSP 2027-01-14 12:09:00; layover at MSP: 60 minutes.
  • DL2558: MSP 2027-01-14 13:09:00 → BOS 2027-01-14 17:01:00.
• Delta Air Lines DL2222 / DL4677: BOS 2027-01-28 13:04:00 → MDW 2027-01-28 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-28 13:04:00 → DTW 2027-01-28 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-28 17:40:00 → MDW 2027-01-28 18:01:00.

Explore this route

• All dates for this route
• Jan 13, 2027 · Return options
• Jan 15, 2027 · Return options
• Hotels in Boston with Axel

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• This page: Chicago (MDW) to Boston (BOS) · Jan 14, 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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