Boston (BOS) to Chicago (ORD), Nov 27–29, 2026: from $371 round trip

Boston (BOS) to Chicago (ORD), Nov 27–29, 2026: from $371 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $371 round trip, Axel-exclusive, JetBlue Airways, nonstop, Nov 27–29, 2026, 1 adult, economy, checked Oct 29, 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 Chicago for these trips

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

• Hotels in Chicago for these nights (Nov 27–29, 2026 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

All hotels in Chicago

Route overview: Boston to Chicago (ORD) flight deals

2026-11-27 → 2026-11-29 · Axel-exclusive $371.00

• JetBlue Airways B6611: BOS 2026-11-27 14:40:00 → ORD 2026-11-27 16:40:00; nonstop; 180 minutes. Local airport times.
• JetBlue Airways B6112: ORD 2026-11-29 13:00:00 → BOS 2026-11-29 16:49:00; nonstop; 169 minutes. Local airport times.

2026-11-27 → 2026-11-29 · Axel-exclusive $406.00

• United Airlines UA2342: BOS 2026-11-27 11:35:00 → ORD 2026-11-27 13:39:00; nonstop; 184 minutes. Local airport times.
• United Airlines UA1186: ORD 2026-11-29 06:15:00 → BOS 2026-11-29 09:34:00; nonstop; 139 minutes. Local airport times.

2026-11-27 → 2026-11-29 · Axel-exclusive $406.00

• American Airlines AA2015: BOS 2026-11-27 10:24:00 → ORD 2026-11-27 12:35:00; nonstop; 191 minutes. Local airport times.
• American Airlines AA981: ORD 2026-11-29 06:59:00 → BOS 2026-11-29 10:22:00; nonstop; 143 minutes. Local airport times.

2026-11-27 → 2026-11-29 · Axel-exclusive $420.00

• Delta Air Lines DL2804: BOS 2026-11-27 20:59:00 → ORD 2026-11-27 22:57:00; nonstop; 178 minutes. Local airport times.
• Delta Air Lines DL2816: ORD 2026-11-29 15:05:00 → BOS 2026-11-29 18:36:00; nonstop; 151 minutes. Local airport times.

2026-11-27 → 2026-11-29 · Axel-exclusive $616.00

• Air Canada AC8695 / AC511: BOS 2026-11-27 15:10:00 → ORD 2026-11-27 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2026-11-27 15:10:00 → YYZ 2026-11-27 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2026-11-27 18:55:00 → ORD 2026-11-27 19:58:00.
• Air Canada AC508 / AC772: ORD 2026-11-29 16:30:00 → BOS 2026-11-29 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2026-11-29 16:30:00 → YYZ 2026-11-29 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2026-11-29 20:55:00 → BOS 2026-11-29 22:37:00.

2026-11-27 → 2026-11-29 · Axel-exclusive $371.00

• JetBlue Airways B6111: BOS 2026-11-27 09:59:00 → ORD 2026-11-27 12:00:00; nonstop; 181 minutes. Local airport times.
• JetBlue Airways B6112: ORD 2026-11-29 13:00:00 → BOS 2026-11-29 16:49:00; nonstop; 169 minutes. Local airport times.

2026-11-27 → 2026-11-29 · Axel-exclusive $406.00

• United Airlines UA2433: BOS 2026-11-27 20:25:00 → ORD 2026-11-27 22:29:00; nonstop; 184 minutes. Local airport times.
• United Airlines UA1186: ORD 2026-11-29 06:15:00 → BOS 2026-11-29 09:34:00; nonstop; 139 minutes. Local airport times.

2026-11-27 → 2026-11-29 · Axel-exclusive $406.00

• American Airlines AA581: BOS 2026-11-27 12:16:00 → ORD 2026-11-27 14:28:00; nonstop; 192 minutes. Local airport times.
• American Airlines AA981: ORD 2026-11-29 06:59:00 → BOS 2026-11-29 10:22:00; nonstop; 143 minutes. Local airport times.

2026-11-27 → 2026-11-29 · Axel-exclusive $420.00

• Delta Air Lines DL2646: BOS 2026-11-27 16:35:00 → ORD 2026-11-27 18:45:00; nonstop; 190 minutes. Local airport times.
• Delta Air Lines DL2816: ORD 2026-11-29 15:05:00 → BOS 2026-11-29 18:36:00; nonstop; 151 minutes. Local airport times.

2026-11-27 → 2026-11-29 · Axel-exclusive $420.00

• American Airlines AA4798 / AA3177: BOS 2026-11-27 15:45:00 → ORD 2026-11-27 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
  • AA4798: BOS 2026-11-27 15:45:00 → PHL 2026-11-27 17:30:00; layover at PHL: 65 minutes.
  • AA3177: PHL 2026-11-27 18:35:00 → ORD 2026-11-27 20:30:00.
• American Airlines AA981: ORD 2026-11-29 06:59:00 → BOS 2026-11-29 10:22:00; nonstop; 143 minutes. Local airport times.

2026-11-27 → 2026-11-29 · Axel-exclusive $420.00

• American Airlines AA4609 / AA4733: BOS 2026-11-27 10:07:00 → ORD 2026-11-27 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
  • AA4609: BOS 2026-11-27 10:07:00 → CVG 2026-11-27 12:50:00; layover at CVG: 104 minutes.
  • AA4733: CVG 2026-11-27 14:34:00 → ORD 2026-11-27 15:14:00.
• American Airlines AA981: ORD 2026-11-29 06:59:00 → BOS 2026-11-29 10:22:00; nonstop; 143 minutes. Local airport times.

2026-11-27 → 2026-11-29 · Axel-exclusive $420.00

• American Airlines AA4133 / AA4390: BOS 2026-11-27 10:00:00 → ORD 2026-11-27 13:59:00; 1 stop(s) via SYR; 299 minutes. Local airport times.
  • AA4133: BOS 2026-11-27 10:00:00 → SYR 2026-11-27 11:23:00; layover at SYR: 68 minutes.
  • AA4390: SYR 2026-11-27 12:31:00 → ORD 2026-11-27 13:59:00.
• American Airlines AA981: ORD 2026-11-29 06:59:00 → BOS 2026-11-29 10:22:00; nonstop; 143 minutes. Local airport times.

2026-11-27 → 2026-11-29 · Axel-exclusive $423.50

• United Airlines UA721 / UA2497: BOS 2026-11-27 14:40:00 → ORD 2026-11-27 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
  • UA721: BOS 2026-11-27 14:40:00 → IAD 2026-11-27 16:27:00; layover at IAD: 72 minutes.
  • UA2497: IAD 2026-11-27 17:39:00 → ORD 2026-11-27 19:05:00.
• United Airlines UA1186: ORD 2026-11-29 06:15:00 → BOS 2026-11-29 09:34:00; nonstop; 139 minutes. Local airport times.

2026-11-27 → 2026-11-29 · Axel-exclusive $423.50

• United Airlines UA546 / UA703: BOS 2026-11-27 15:42:00 → ORD 2026-11-27 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
  • UA546: BOS 2026-11-27 15:42:00 → EWR 2026-11-27 17:08:00; layover at EWR: 62 minutes.
  • UA703: EWR 2026-11-27 18:10:00 → ORD 2026-11-27 20:06:00.
• United Airlines UA1186: ORD 2026-11-29 06:15:00 → BOS 2026-11-29 09:34:00; nonstop; 139 minutes. Local airport times.

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
• Nov 26, 2026 · Return options
• Nov 28, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Boston (BOS) to Chicago (ORD) · Nov 27, 2026 · return Nov 29, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
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