Boston (BOS) to Chicago (ORD) · Dec 19, 2026 · return Dec 21, 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: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Chicago for these nights (Dec 19–21, 2026 · 2 nights · 2 adults, 1 room): 3★ The Willows Hotel, $225 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $262 total · 5★ Nobu Hotel Chicago, $672 total

All hotels in Chicago

Route overview: Boston to Chicago (ORD) flight deals

2026-12-19 → 2026-12-21 · Axel-exclusive $344.50

• JetBlue Airways B6111: BOS 2026-12-19 09:59:00 → ORD 2026-12-19 12:00:00; nonstop; 181 minutes. Local airport times.
• JetBlue Airways B61012: ORD 2026-12-21 17:46:00 → BOS 2026-12-21 21:14:00; nonstop; 148 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $377.00

• American Airlines AA947: BOS 2026-12-19 07:37:00 → ORD 2026-12-19 09:59:00; nonstop; 202 minutes. Local airport times.
• American Airlines AA2779: ORD 2026-12-21 10:43:00 → BOS 2026-12-21 14:17:00; nonstop; 154 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $377.00

• United Airlines UA1414: BOS 2026-12-19 06:00:00 → ORD 2026-12-19 08:00:00; nonstop; 180 minutes. Local airport times.
• United Airlines UA1928: ORD 2026-12-21 14:09:00 → BOS 2026-12-21 17:36:00; nonstop; 147 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $390.00

• Delta Air Lines DL5611: BOS 2026-12-19 14:55:00 → ORD 2026-12-19 17:01:00; nonstop; 186 minutes. Local airport times.
• Delta Air Lines DL2570: ORD 2026-12-21 10:38:00 → BOS 2026-12-21 14:15:00; nonstop; 157 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $572.00

• Air Canada AC8695 / AC511: BOS 2026-12-19 15:10:00 → ORD 2026-12-19 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2026-12-19 15:10:00 → YYZ 2026-12-19 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2026-12-19 18:55:00 → ORD 2026-12-19 19:58:00.
• Air Canada AC508 / AC772: ORD 2026-12-21 16:30:00 → BOS 2026-12-21 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2026-12-21 16:30:00 → YYZ 2026-12-21 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2026-12-21 20:55:00 → BOS 2026-12-21 22:37:00.

2026-12-19 → 2026-12-21 · Axel-exclusive $344.50

• JetBlue Airways B6811: BOS 2026-12-19 16:45:00 → ORD 2026-12-19 18:58:00; nonstop; 193 minutes. Local airport times.
• JetBlue Airways B61012: ORD 2026-12-21 17:46:00 → BOS 2026-12-21 21:14:00; nonstop; 148 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $377.00

• United Airlines UA2040: BOS 2026-12-19 16:29:00 → ORD 2026-12-19 18:36:00; nonstop; 187 minutes. Local airport times.
• United Airlines UA1928: ORD 2026-12-21 14:09:00 → BOS 2026-12-21 17:36:00; nonstop; 147 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $377.00

• American Airlines AA581: BOS 2026-12-19 12:16:00 → ORD 2026-12-19 14:28:00; nonstop; 192 minutes. Local airport times.
• American Airlines AA2779: ORD 2026-12-21 10:43:00 → BOS 2026-12-21 14:17:00; nonstop; 154 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $390.00

• Delta Air Lines DL5617: BOS 2026-12-19 18:15:00 → ORD 2026-12-19 20:26:00; nonstop; 191 minutes. Local airport times.
• Delta Air Lines DL2570: ORD 2026-12-21 10:38:00 → BOS 2026-12-21 14:15:00; nonstop; 157 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $390.00

• American Airlines AA4798 / AA3177: BOS 2026-12-19 15:45:00 → ORD 2026-12-19 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
  • AA4798: BOS 2026-12-19 15:45:00 → PHL 2026-12-19 17:30:00; layover at PHL: 65 minutes.
  • AA3177: PHL 2026-12-19 18:35:00 → ORD 2026-12-19 20:30:00.
• American Airlines AA2779: ORD 2026-12-21 10:43:00 → BOS 2026-12-21 14:17:00; nonstop; 154 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $390.00

• American Airlines AA4609 / AA4733: BOS 2026-12-19 10:07:00 → ORD 2026-12-19 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
  • AA4609: BOS 2026-12-19 10:07:00 → CVG 2026-12-19 12:50:00; layover at CVG: 104 minutes.
  • AA4733: CVG 2026-12-19 14:34:00 → ORD 2026-12-19 15:14:00.
• American Airlines AA2779: ORD 2026-12-21 10:43:00 → BOS 2026-12-21 14:17:00; nonstop; 154 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $390.00

• American Airlines AA4133 / AA4390: BOS 2026-12-19 10:00:00 → ORD 2026-12-19 13:59:00; 1 stop(s) via SYR; 299 minutes. Local airport times.
  • AA4133: BOS 2026-12-19 10:00:00 → SYR 2026-12-19 11:23:00; layover at SYR: 68 minutes.
  • AA4390: SYR 2026-12-19 12:31:00 → ORD 2026-12-19 13:59:00.
• American Airlines AA2779: ORD 2026-12-21 10:43:00 → BOS 2026-12-21 14:17:00; nonstop; 154 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $393.25

• United Airlines UA721 / UA2497: BOS 2026-12-19 14:40:00 → ORD 2026-12-19 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
  • UA721: BOS 2026-12-19 14:40:00 → IAD 2026-12-19 16:27:00; layover at IAD: 72 minutes.
  • UA2497: IAD 2026-12-19 17:39:00 → ORD 2026-12-19 19:05:00.
• United Airlines UA1928: ORD 2026-12-21 14:09:00 → BOS 2026-12-21 17:36:00; nonstop; 147 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $393.25

• United Airlines UA546 / UA703: BOS 2026-12-19 15:42:00 → ORD 2026-12-19 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
  • UA546: BOS 2026-12-19 15:42:00 → EWR 2026-12-19 17:08:00; layover at EWR: 62 minutes.
  • UA703: EWR 2026-12-19 18:10:00 → ORD 2026-12-19 20:06:00.
• United Airlines UA1928: ORD 2026-12-21 14:09:00 → BOS 2026-12-21 17:36:00; nonstop; 147 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 18, 2026 · Return options
• Dec 20, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Boston (BOS) to Chicago (ORD) · Dec 19, 2026 · return Dec 21, 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: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
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