Chicago (MDW) to Boston (BOS), Nov 22, 2026: round trips from $283, one way from $155

Chicago (MDW) to Boston (BOS), Nov 22, 2026: 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, Nov 22, 2026 – Dec 2, 2026; $155 one way, Axel-exclusive, Southwest Airlines, nonstop, Nov 22, 2026; 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 (Nov 22–23, 2026 · 1 night · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $111 a night · 4★ Harborside Inn Of Boston, $124 a night · 5★ Omni Boston Hotel at the Seaport, $184 a night
• Hotels in Boston for these nights (Nov 22–24, 2026 · 2 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $111 a night, $221 for 2 nights · 4★ Harborside Inn Of Boston, $128 a night, $256 for 2 nights · 5★ Omni Boston Hotel at the Seaport, $184 a night, $368 for 2 nights
• Hotels in Boston for these nights (Nov 22–25, 2026 · 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, $127 a night, $381 for 3 nights · 5★ Omni Boston Hotel at the Seaport, $184 a night, $552 for 3 nights
• Hotels in Boston for these nights (Nov 22–26, 2026 · 4 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $112 a night, $446 for 4 nights · 4★ Harborside Inn Of Boston, $129 a night, $516 for 4 nights · 5★ Omni Boston Hotel at the Seaport, $184 a night, $736 for 4 nights
• Hotels in Boston for these nights (Nov 22–27, 2026 · 5 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $116 a night, $580 for 5 nights · 4★ Harborside Inn Of Boston, $128 a night, $639 for 5 nights · 5★ Omni Boston Hotel at the Seaport, $184 a night, $920 for 5 nights
• Hotels in Boston for these nights (Nov 22–28, 2026 · 6 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $116 a night, $695 for 6 nights · 4★ Harborside Inn Of Boston, $138 a night, $828 for 6 nights · 5★ Omni Boston Hotel at the Seaport, $183 a night, $1,100 for 6 nights
• Hotels in Boston for these nights (Nov 22–29, 2026 · 7 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $114 a night, $801 for 7 nights · 4★ Harborside Inn Of Boston, $144 a night, $1,010 for 7 nights · 5★ Omni Boston Hotel at the Seaport, $183 a night, $1,280 for 7 nights
• Hotels in Boston for these nights (Nov 22–30, 2026 · 8 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $113 a night, $906 for 8 nights · 4★ Harborside Inn Of Boston, $144 a night, $1,152 for 8 nights · 5★ Omni Boston Hotel at the Seaport, $183 a night, $1,460 for 8 nights
• Hotels in Boston for these nights (Nov 22 – Dec 1, 2026 · 9 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $113 a night, $1,018 for 9 nights · 4★ Harborside Inn Of Boston, $144 a night, $1,297 for 9 nights · 5★ Omni Boston Hotel at the Seaport, $191 a night, $1,718 for 9 nights
• Hotels in Boston for these nights (Nov 22 – Dec 2, 2026 · 10 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $115 a night, $1,151 for 10 nights · 4★ Harborside Inn Of Boston, $148 a night, $1,480 for 10 nights · 5★ Omni Boston Hotel at the Seaport, $206 a night, $2,064 for 10 nights
• Hotels in Boston for these nights (Nov 22 – Dec 3, 2026 · 11 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $117 a night, $1,284 for 11 nights · 4★ Harborside Inn Of Boston, $154 a night, $1,690 for 11 nights · 5★ Omni Boston Hotel at the Seaport, $223 a night, $2,454 for 11 nights
• Hotels in Boston for these nights (Nov 22 – Dec 4, 2026 · 12 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $117 a night, $1,407 for 12 nights · 4★ Harborside Inn Of Boston, $159 a night, $1,908 for 12 nights · 5★ Omni Boston Hotel at the Seaport, $237 a night, $2,844 for 12 nights
• Hotels in Boston for these nights (Nov 22 – Dec 5, 2026 · 13 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $120 a night, $1,558 for 13 nights · 4★ Harborside Inn Of Boston, $165 a night, $2,149 for 13 nights · 5★ Omni Boston Hotel at the Seaport, $239 a night, $3,110 for 13 nights
• Hotels in Boston for these nights (Nov 22 – Dec 6, 2026 · 14 nights · 2 adults, 1 room): 3★ Holiday Inn Boston - Cambridge Area by IHG, $122 a night, $1,701 for 14 nights · 4★ Harborside Inn Of Boston, $170 a night, $2,381 for 14 nights · 5★ Omni Boston Hotel at the Seaport, $240 a night, $3,364 for 14 nights

All hotels in Boston

Route overview: Chicago to Boston (BOS) flight deals

2026-11-22 · one way · Axel-exclusive $155

• Southwest Airlines WN4113: MDW 2026-11-22 07:45:00 → BOS 2026-11-22 11:00:00; nonstop; 135 minutes. Local airport times.

2026-11-22 · one way · Axel-exclusive $205

• Delta Air Lines DL4688 / DL1707: MDW 2026-11-22 13:31:00 → BOS 2026-11-22 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-11-22 18:52:00 → BOS 2026-11-22 20:51:00.

2026-11-22 → 2026-11-23 · Axel-exclusive $290

• Southwest Airlines WN4113: MDW 2026-11-22 07:45:00 → BOS 2026-11-22 11:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN2185: BOS 2026-11-23 07:05:00 → MDW 2026-11-23 08:50:00; nonstop; 165 minutes. Local airport times.

2026-11-22 → 2026-11-23 · Axel-exclusive $390

• Delta Air Lines DL4688 / DL1707: MDW 2026-11-22 13:31:00 → BOS 2026-11-22 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-11-22 18:52:00 → BOS 2026-11-22 20:51:00.
• Delta Air Lines DL2222 / DL4677: BOS 2026-11-23 13:04:00 → MDW 2026-11-23 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-11-23 13:04:00 → DTW 2026-11-23 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-11-23 17:40:00 → MDW 2026-11-23 18:01:00.

2026-11-22 → 2026-11-24 · Axel-exclusive $341

• Southwest Airlines WN4113: MDW 2026-11-22 07:45:00 → BOS 2026-11-22 11:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN4995: BOS 2026-11-24 07:10:00 → MDW 2026-11-24 08:55:00; nonstop; 165 minutes. Local airport times.

2026-11-22 → 2026-11-24 · Axel-exclusive $458

• Delta Air Lines DL4688 / DL1707: MDW 2026-11-22 13:31:00 → BOS 2026-11-22 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-11-22 18:52:00 → BOS 2026-11-22 20:51:00.
• Delta Air Lines DL2222 / DL4677: BOS 2026-11-24 13:04:00 → MDW 2026-11-24 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-11-24 13:04:00 → DTW 2026-11-24 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-11-24 17:40:00 → MDW 2026-11-24 18:01:00.

2026-11-22 → 2026-11-25 · Axel-exclusive $331

• Southwest Airlines WN4113: MDW 2026-11-22 07:45:00 → BOS 2026-11-22 11:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN819 / WN287: BOS 2026-11-25 05:35:00 → MDW 2026-11-25 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2026-11-25 05:35:00 → STL 2026-11-25 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2026-11-25 10:55:00 → MDW 2026-11-25 12:05:00.

2026-11-22 → 2026-11-25 · Axel-exclusive $458

• Delta Air Lines DL4688 / DL1707: MDW 2026-11-22 13:31:00 → BOS 2026-11-22 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-11-22 18:52:00 → BOS 2026-11-22 20:51:00.
• Delta Air Lines DL2222 / DL4677: BOS 2026-11-25 13:04:00 → MDW 2026-11-25 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-11-25 13:04:00 → DTW 2026-11-25 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-11-25 17:40:00 → MDW 2026-11-25 18:01:00.

2026-11-22 → 2026-11-26 · Axel-exclusive $341

• Southwest Airlines WN4113: MDW 2026-11-22 07:45:00 → BOS 2026-11-22 11:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN2939: BOS 2026-11-26 12:20:00 → MDW 2026-11-26 14:05:00; nonstop; 165 minutes. Local airport times.

2026-11-22 → 2026-11-26 · Axel-exclusive $458

• Delta Air Lines DL4688 / DL1707: MDW 2026-11-22 13:31:00 → BOS 2026-11-22 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-11-22 18:52:00 → BOS 2026-11-22 20:51:00.
• Delta Air Lines DL2222 / DL4677: BOS 2026-11-26 13:04:00 → MDW 2026-11-26 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-11-26 13:04:00 → DTW 2026-11-26 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-11-26 17:40:00 → MDW 2026-11-26 18:01:00.

2026-11-22 → 2026-11-28 · Axel-exclusive $341

• Southwest Airlines WN4113: MDW 2026-11-22 07:45:00 → BOS 2026-11-22 11:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN2939: BOS 2026-11-28 12:20:00 → MDW 2026-11-28 14:05:00; nonstop; 165 minutes. Local airport times.

2026-11-22 → 2026-11-28 · Axel-exclusive $458

• Delta Air Lines DL4688 / DL1707: MDW 2026-11-22 13:31:00 → BOS 2026-11-22 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-11-22 18:52:00 → BOS 2026-11-22 20:51:00.
• Delta Air Lines DL2222 / DL4677: BOS 2026-11-28 13:04:00 → MDW 2026-11-28 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-11-28 13:04:00 → DTW 2026-11-28 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-11-28 17:40:00 → MDW 2026-11-28 18:01:00.

2026-11-22 → 2026-11-29 · Axel-exclusive $341

• Southwest Airlines WN4113: MDW 2026-11-22 07:45:00 → BOS 2026-11-22 11:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN2972: BOS 2026-11-29 06:45:00 → MDW 2026-11-29 08:30:00; nonstop; 165 minutes. Local airport times.

2026-11-22 → 2026-11-29 · Axel-exclusive $458

• Delta Air Lines DL4688 / DL1707: MDW 2026-11-22 13:31:00 → BOS 2026-11-22 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-11-22 18:52:00 → BOS 2026-11-22 20:51:00.
• Delta Air Lines DL2222 / DL4677: BOS 2026-11-29 13:04:00 → MDW 2026-11-29 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-11-29 13:04:00 → DTW 2026-11-29 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-11-29 17:40:00 → MDW 2026-11-29 18:01:00.

2026-11-22 → 2026-11-30 · Axel-exclusive $341

• Southwest Airlines WN4113: MDW 2026-11-22 07:45:00 → BOS 2026-11-22 11:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2026-11-30 18:30:00 → MDW 2026-11-30 20:15:00; nonstop; 165 minutes. Local airport times.

2026-11-22 → 2026-11-30 · Axel-exclusive $458

• Delta Air Lines DL4688 / DL1707: MDW 2026-11-22 13:31:00 → BOS 2026-11-22 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-11-22 18:52:00 → BOS 2026-11-22 20:51:00.
• Delta Air Lines DL2222 / DL4677: BOS 2026-11-30 13:04:00 → MDW 2026-11-30 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-11-30 13:04:00 → DTW 2026-11-30 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-11-30 17:40:00 → MDW 2026-11-30 18:01:00.

2026-11-22 → 2026-12-02 · Axel-exclusive $283

• Southwest Airlines WN4113: MDW 2026-11-22 07:45:00 → BOS 2026-11-22 11:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN819 / WN287: BOS 2026-12-02 05:35:00 → MDW 2026-12-02 12:05:00; 1 stop(s) via STL; 450 minutes. Local airport times.
  • WN819: BOS 2026-12-02 05:35:00 → STL 2026-12-02 07:40:00; layover at STL: 195 minutes.
  • WN287: STL 2026-12-02 10:55:00 → MDW 2026-12-02 12:05:00.

2026-11-22 → 2026-12-02 · Axel-exclusive $390

• Delta Air Lines DL4688 / DL1707: MDW 2026-11-22 13:31:00 → BOS 2026-11-22 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-11-22 18:52:00 → BOS 2026-11-22 20:51:00.
• Delta Air Lines DL2222 / DL4677: BOS 2026-12-02 13:04:00 → MDW 2026-12-02 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-12-02 13:04:00 → DTW 2026-12-02 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-12-02 17:40:00 → MDW 2026-12-02 18:01:00.

2026-11-22 → 2026-12-03 · Axel-exclusive $290

• Southwest Airlines WN4113: MDW 2026-11-22 07:45:00 → BOS 2026-11-22 11:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2026-12-03 18:30:00 → MDW 2026-12-03 20:15:00; nonstop; 165 minutes. Local airport times.

2026-11-22 → 2026-12-03 · Axel-exclusive $390

• Delta Air Lines DL4688 / DL1707: MDW 2026-11-22 13:31:00 → BOS 2026-11-22 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-11-22 18:52:00 → BOS 2026-11-22 20:51:00.
• Delta Air Lines DL2222 / DL4677: BOS 2026-12-03 13:04:00 → MDW 2026-12-03 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-12-03 13:04:00 → DTW 2026-12-03 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-12-03 17:40:00 → MDW 2026-12-03 18:01:00.

2026-11-22 → 2026-12-04 · Axel-exclusive $290

• Southwest Airlines WN4113: MDW 2026-11-22 07:45:00 → BOS 2026-11-22 11:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2026-12-04 18:30:00 → MDW 2026-12-04 20:15:00; nonstop; 165 minutes. Local airport times.

2026-11-22 → 2026-12-04 · Axel-exclusive $390

• Delta Air Lines DL4688 / DL1707: MDW 2026-11-22 13:31:00 → BOS 2026-11-22 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-11-22 18:52:00 → BOS 2026-11-22 20:51:00.
• Delta Air Lines DL2222 / DL4677: BOS 2026-12-04 13:04:00 → MDW 2026-12-04 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-12-04 13:04:00 → DTW 2026-12-04 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-12-04 17:40:00 → MDW 2026-12-04 18:01:00.

2026-11-22 → 2026-12-06 · Axel-exclusive $290

• Southwest Airlines WN4113: MDW 2026-11-22 07:45:00 → BOS 2026-11-22 11:00:00; nonstop; 135 minutes. Local airport times.
• Southwest Airlines WN816: BOS 2026-12-06 18:30:00 → MDW 2026-12-06 20:15:00; nonstop; 165 minutes. Local airport times.

2026-11-22 → 2026-12-06 · Axel-exclusive $390

• Delta Air Lines DL4688 / DL1707: MDW 2026-11-22 13:31:00 → BOS 2026-11-22 20:51:00; 1 stop(s) via DTW; 380 minutes. Local airport times.
  • DL4688: MDW 2026-11-22 13:31:00 → DTW 2026-11-22 15:44:00; layover at DTW: 188 minutes.
  • DL1707: DTW 2026-11-22 18:52:00 → BOS 2026-11-22 20:51:00.
• Delta Air Lines DL2222 / DL4677: BOS 2026-12-06 13:04:00 → MDW 2026-12-06 18:01:00; 1 stop(s) via DTW; 357 minutes. Local airport times.
  • DL2222: BOS 2026-12-06 13:04:00 → DTW 2026-12-06 15:19:00; layover at DTW: 141 minutes.
  • DL4677: DTW 2026-12-06 17:40:00 → MDW 2026-12-06 18:01:00.

Explore this route

• All dates for this route
• Nov 21, 2026 · Return options
• Nov 23, 2026 · Return options
• Hotels in Boston with Axel

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• This page: Chicago (MDW) to Boston (BOS) · Nov 22, 2026 · 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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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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