Chicago (MDW) to Boston (BOS), Jan 29, 2027: round trips from $283, one way from $155

Chicago (MDW) to Boston (BOS), Jan 29, 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 29, 2027 – Feb 3, 2027; $155 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 29, 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 29–30, 2027 · 1 night · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $117 a night · 4★ Harborside Inn Of Boston, $136 a night · 5★ InterContinental Boston by IHG, $290 a night
• Hotels in Boston for these nights (Jan 29–31, 2027 · 2 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $114 a night, $227 for 2 nights · 4★ Harborside Inn Of Boston, $136 a night, $272 for 2 nights · 5★ Omni Boston Hotel at the Seaport, $282 a night, $564 for 2 nights
• Hotels in Boston for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $110 a night, $331 for 3 nights · 4★ Harborside Inn Of Boston, $135 a night, $406 for 3 nights · 5★ Omni Boston Hotel at the Seaport, $270 a night, $809 for 3 nights
• Hotels in Boston for these nights (Jan 29 – Feb 2, 2027 · 4 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $113 a night, $450 for 4 nights · 4★ Hyatt Regency Boston/Cambridge, $131 a night, $524 for 4 nights · 5★ Omni Boston Hotel at the Seaport, $274 a night, $1,095 for 4 nights
• Hotels in Boston for these nights (Jan 29 – Feb 3, 2027 · 5 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $114 a night, $568 for 5 nights · 4★ Hyatt Regency Boston/Cambridge, $126 a night, $631 for 5 nights · 5★ Omni Boston Hotel at the Seaport, $273 a night, $1,366 for 5 nights
• 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
• Hotels in Boston for these nights (Jan 29 – Feb 5, 2027 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $114 a night, $798 for 7 nights · 4★ Hyatt Regency Boston/Cambridge, $123 a night, $858 for 7 nights · 5★ Omni Boston Hotel at the Seaport, $299 a night, $2,095 for 7 nights
• Hotels in Boston for these nights (Jan 29 – Feb 6, 2027 · 8 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $116 a night, $924 for 8 nights · 4★ Hyatt Regency Boston/Cambridge, $124 a night, $990 for 8 nights · 5★ Omni Boston Hotel at the Seaport, $305 a night, $2,443 for 8 nights
• Hotels in Boston for these nights (Jan 29 – Feb 7, 2027 · 9 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $120 a night, $1,081 for 9 nights · 4★ Hyatt Regency Boston/Cambridge, $125 a night, $1,122 for 9 nights · 5★ Omni Boston Hotel at the Seaport, $308 a night, $2,771 for 9 nights
• Hotels in Boston for these nights (Jan 29 – Feb 8, 2027 · 10 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $121 a night, $1,214 for 10 nights · 4★ Hyatt Regency Boston/Cambridge, $127 a night, $1,268 for 10 nights · 5★ Omni Boston Hotel at the Seaport, $311 a night, $3,105 for 10 nights
• Hotels in Boston for these nights (Jan 29 – Feb 9, 2027 · 11 nights · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $123 a night, $1,354 for 11 nights · 4★ Hyatt Regency Boston/Cambridge, $128 a night, $1,409 for 11 nights · 5★ Omni Boston Hotel at the Seaport, $312 a night, $3,432 for 11 nights
• Hotels in Boston for these nights (Jan 29 – Feb 10, 2027 · 12 nights · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $123 a night, $1,473 for 12 nights · 4★ Hyatt Regency Boston/Cambridge, $133 a night, $1,595 for 12 nights · 5★ Omni Boston Hotel at the Seaport, $314 a night, $3,766 for 12 nights
• Hotels in Boston for these nights (Jan 29 – Feb 11, 2027 · 13 nights · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $123 a night, $1,604 for 13 nights · 4★ Hyatt Regency Boston/Cambridge, $134 a night, $1,736 for 13 nights · 5★ Omni Boston Hotel at the Seaport, $315 a night, $4,098 for 13 nights
• Hotels in Boston for these nights (Jan 29 – Feb 12, 2027 · 14 nights · 2 adults, 1 room): 3★ Wyndham Boston Beacon Hill, $125 a night, $1,755 for 14 nights · 4★ Hyatt Regency Boston/Cambridge, $134 a night, $1,882 for 14 nights · 5★ Omni Boston Hotel at the Seaport, $312 a night, $4,363 for 14 nights

All hotels in Boston

Route overview: Chicago to Boston (BOS) flight deals

2027-01-29 · one way · Axel-exclusive $155

• Southwest Airlines WN2900: MDW 2027-01-29 13:00:00 → BOS 2027-01-29 16:10:00; nonstop; 130 minutes. Local airport times.

2027-01-29 · one way · Axel-exclusive $205

• 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.

2027-01-29 → 2027-01-30 · 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 WN2939: BOS 2027-01-30 12:20:00 → MDW 2027-01-30 14:05:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-01-30 · 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 2027-01-30 13:04:00 → MDW 2027-01-30 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-30 13:04:00 → DTW 2027-01-30 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-30 17:40:00 → MDW 2027-01-30 18:01:00.

2027-01-29 → 2027-01-31 · 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 2027-01-31 18:30:00 → MDW 2027-01-31 20:15:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-01-31 · 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 2027-01-31 13:04:00 → MDW 2027-01-31 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-01-31 13:04:00 → DTW 2027-01-31 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-01-31 17:40:00 → MDW 2027-01-31 18:01:00.

2027-01-29 → 2027-02-01 · 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 2027-02-01 17:55:00 → MDW 2027-02-01 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-02-01 · 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 2027-02-01 13:04:00 → MDW 2027-02-01 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-02-01 13:04:00 → DTW 2027-02-01 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-02-01 17:40:00 → MDW 2027-02-01 18:01:00.

2027-01-29 → 2027-02-02 · 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 2027-02-02 17:55:00 → MDW 2027-02-02 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-02-02 · 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 2027-02-02 13:04:00 → MDW 2027-02-02 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-02-02 13:04:00 → DTW 2027-02-02 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-02-02 17:40:00 → MDW 2027-02-02 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 $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.

2027-01-29 → 2027-02-05 · 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 2027-02-05 18:30:00 → MDW 2027-02-05 20:15:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-02-05 · 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 2027-02-05 13:04:00 → MDW 2027-02-05 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-02-05 13:04:00 → DTW 2027-02-05 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-02-05 17:40:00 → MDW 2027-02-05 18:01:00.

2027-01-29 → 2027-02-06 · 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 WN2939: BOS 2027-02-06 12:20:00 → MDW 2027-02-06 14:05:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-02-06 · 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 2027-02-06 13:04:00 → MDW 2027-02-06 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-02-06 13:04:00 → DTW 2027-02-06 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-02-06 17:40:00 → MDW 2027-02-06 18:01:00.

2027-01-29 → 2027-02-08 · 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 2027-02-08 17:55:00 → MDW 2027-02-08 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-02-08 · 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 2027-02-08 13:04:00 → MDW 2027-02-08 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-02-08 13:04:00 → DTW 2027-02-08 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-02-08 17:40:00 → MDW 2027-02-08 18:01:00.

2027-01-29 → 2027-02-09 · 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 2027-02-09 17:55:00 → MDW 2027-02-09 19:40:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-02-09 · 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 2027-02-09 13:04:00 → MDW 2027-02-09 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-02-09 13:04:00 → DTW 2027-02-09 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-02-09 17:40:00 → MDW 2027-02-09 18:01:00.

2027-01-29 → 2027-02-10 · Axel-exclusive $283

• 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 WN819 / WN287: BOS 2027-02-10 05:35:00 → MDW 2027-02-10 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2027-02-10 05:35:00 → STL 2027-02-10 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2027-02-10 10:55:00 → MDW 2027-02-10 12:05:00.

2027-01-29 → 2027-02-10 · 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 2027-02-10 13:04:00 → MDW 2027-02-10 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-02-10 13:04:00 → DTW 2027-02-10 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-02-10 17:40:00 → MDW 2027-02-10 18:01:00.

2027-01-29 → 2027-02-12 · 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 2027-02-12 18:30:00 → MDW 2027-02-12 20:15:00; nonstop; 165 minutes. Local airport times.

2027-01-29 → 2027-02-12 · 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 2027-02-12 13:04:00 → MDW 2027-02-12 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2027-02-12 13:04:00 → DTW 2027-02-12 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2027-02-12 17:40:00 → MDW 2027-02-12 18:01:00.

Explore this route

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

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• This page: Chicago (MDW) to Boston (BOS) · Jan 29, 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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