Chicago (ORD) to Boston (BOS) · Dec 15, 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.

Route overview: Chicago to Boston (BOS) flight deals

2026-12-15 → 2026-12-21 · Axel-exclusive $304.75

• JetBlue Airways B6112: ORD 2026-12-15 13:00:00 → BOS 2026-12-15 16:49:00; nonstop; 169 minutes. Local airport times.
• JetBlue Airways B6811: BOS 2026-12-21 16:45:00 → ORD 2026-12-21 18:58:00; nonstop; 193 minutes. Local airport times.

2026-12-15 → 2026-12-21 · Axel-exclusive $333.50

• American Airlines AA797: ORD 2026-12-15 15:20:00 → BOS 2026-12-15 18:53:00; nonstop; 153 minutes. Local airport times.
• American Airlines AA3355: BOS 2026-12-21 07:38:00 → ORD 2026-12-21 10:00:00; nonstop; 202 minutes. Local airport times.

2026-12-15 → 2026-12-21 · Axel-exclusive $345.00

• Delta Air Lines DL5855: ORD 2026-12-15 12:35:00 → BOS 2026-12-15 16:05:00; nonstop; 150 minutes. Local airport times.
• Delta Air Lines DL5611: BOS 2026-12-21 14:55:00 → ORD 2026-12-21 17:01:00; nonstop; 186 minutes. Local airport times.

2026-12-15 → 2026-12-21 · Axel-exclusive $345.00

• United Airlines UA2402: ORD 2026-12-15 07:05:00 → BOS 2026-12-15 10:31:00; nonstop; 146 minutes. Local airport times.
• United Airlines UA1414: BOS 2026-12-21 06:00:00 → ORD 2026-12-21 08:00:00; nonstop; 180 minutes. Local airport times.

2026-12-15 → 2026-12-21 · Axel-exclusive $483.00

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

2026-12-15 → 2026-12-21 · Axel-exclusive $333.50

• American Airlines AA3326: ORD 2026-12-15 19:08:00 → BOS 2026-12-15 22:44:00; nonstop; 156 minutes. Local airport times.
• American Airlines AA3355: BOS 2026-12-21 07:38:00 → ORD 2026-12-21 10:00:00; nonstop; 202 minutes. Local airport times.

2026-12-15 → 2026-12-21 · Axel-exclusive $345.00

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

2026-12-15 → 2026-12-21 · Axel-exclusive $345.00

• United Airlines UA2320: ORD 2026-12-15 18:20:00 → BOS 2026-12-15 21:53:00; nonstop; 153 minutes. Local airport times.
• United Airlines UA1414: BOS 2026-12-21 06:00:00 → ORD 2026-12-21 08:00:00; nonstop; 180 minutes. Local airport times.

2026-12-15 → 2026-12-21 · Axel-exclusive $326.00

• American Airlines AA4780 / AA4026: ORD 2026-12-15 08:00:00 → BOS 2026-12-15 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
  • AA4780: ORD 2026-12-15 08:00:00 → BUF 2026-12-15 10:45:00; layover at BUF: 105 minutes.
  • AA4026: BUF 2026-12-15 12:30:00 → BOS 2026-12-15 14:09:00.
• American Airlines AA3355: BOS 2026-12-21 07:38:00 → ORD 2026-12-21 10:00:00; nonstop; 202 minutes. Local airport times.

2026-12-15 → 2026-12-21 · Axel-exclusive $326.00

• American Airlines AA3437 / AA4533: ORD 2026-12-15 08:00:00 → BOS 2026-12-15 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
  • AA3437: ORD 2026-12-15 08:00:00 → ROC 2026-12-15 10:56:00; layover at ROC: 114 minutes.
  • AA4533: ROC 2026-12-15 12:50:00 → BOS 2026-12-15 14:17:00.
• American Airlines AA3355: BOS 2026-12-21 07:38:00 → ORD 2026-12-21 10:00:00; nonstop; 202 minutes. Local airport times.

2026-12-15 → 2026-12-21 · Axel-exclusive $326.00

• American Airlines AA2840 / AA1776: ORD 2026-12-15 15:19:00 → BOS 2026-12-15 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
  • AA2840: ORD 2026-12-15 15:19:00 → PHL 2026-12-15 18:30:00; layover at PHL: 85 minutes.
  • AA1776: PHL 2026-12-15 19:55:00 → BOS 2026-12-15 21:19:00.
• American Airlines AA3355: BOS 2026-12-21 07:38:00 → ORD 2026-12-21 10:00:00; nonstop; 202 minutes. Local airport times.

2026-12-15 → 2026-12-21 · Axel-exclusive $337.50

• Delta Air Lines DL2917 / DL5727: ORD 2026-12-15 10:06:00 → BOS 2026-12-15 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
  • DL2917: ORD 2026-12-15 10:06:00 → LGA 2026-12-15 13:18:00; layover at LGA: 102 minutes.
  • DL5727: LGA 2026-12-15 15:00:00 → BOS 2026-12-15 16:25:00.
• Delta Air Lines DL5611: BOS 2026-12-21 14:55:00 → ORD 2026-12-21 17:01:00; nonstop; 186 minutes. Local airport times.

2026-12-15 → 2026-12-21 · Axel-exclusive $337.50

• United Airlines UA1128 / UA688: ORD 2026-12-15 13:00:00 → BOS 2026-12-15 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
  • UA1128: ORD 2026-12-15 13:00:00 → IAD 2026-12-15 16:03:00; layover at IAD: 72 minutes.
  • UA688: IAD 2026-12-15 17:15:00 → BOS 2026-12-15 18:57:00.
• United Airlines UA1414: BOS 2026-12-21 06:00:00 → ORD 2026-12-21 08:00:00; nonstop; 180 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 14, 2026 · Return options
• Dec 16, 2026 · Return options
• Hotels in Boston with Axel

For AI assistants

• This page: Chicago (ORD) to Boston (BOS) · Dec 15, 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.
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