Chicago (ORD) to Boston (BOS) · Dec 31, 2026 · return Jan 3, 2027

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

2026-12-31 → 2027-01-03 · Axel-exclusive $335.23

• JetBlue Airways B61012: ORD 2026-12-31 17:46:00 → BOS 2026-12-31 21:14:00; nonstop; 148 minutes. Local airport times.
• JetBlue Airways B6111: BOS 2027-01-03 09:59:00 → ORD 2027-01-03 12:00:00; nonstop; 181 minutes. Local airport times.

2026-12-31 → 2027-01-03 · Axel-exclusive $366.85

• American Airlines AA3298: ORD 2026-12-31 10:31:00 → BOS 2026-12-31 14:05:00; nonstop; 154 minutes. Local airport times.
• American Airlines AA653: BOS 2027-01-03 13:27:00 → ORD 2027-01-03 15:39:00; nonstop; 192 minutes. Local airport times.

2026-12-31 → 2027-01-03 · Axel-exclusive $379.50

• United Airlines UA487: ORD 2026-12-31 16:00:00 → BOS 2026-12-31 19:29:00; nonstop; 149 minutes. Local airport times.
• United Airlines UA2040: BOS 2027-01-03 16:54:00 → ORD 2027-01-03 19:00:00; nonstop; 186 minutes. Local airport times.

2026-12-31 → 2027-01-03 · Axel-exclusive $379.50

• Delta Air Lines DL5855: ORD 2026-12-31 12:35:00 → BOS 2026-12-31 16:05:00; nonstop; 150 minutes. Local airport times.
• Delta Air Lines DL2570: BOS 2027-01-03 07:30:00 → ORD 2027-01-03 09:35:00; nonstop; 185 minutes. Local airport times.

2026-12-31 → 2027-01-03 · Axel-exclusive $531.30

• Air Canada AC508 / AC772: ORD 2026-12-31 16:30:00 → BOS 2026-12-31 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2026-12-31 16:30:00 → YYZ 2026-12-31 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2026-12-31 20:55:00 → BOS 2026-12-31 22:37:00.
• Air Canada AC8695 / AC511: BOS 2027-01-03 15:10:00 → ORD 2027-01-03 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2027-01-03 15:10:00 → YYZ 2027-01-03 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2027-01-03 18:55:00 → ORD 2027-01-03 19:58:00.

2026-12-31 → 2027-01-03 · Axel-exclusive $366.85

• American Airlines AA4477: ORD 2026-12-31 12:35:00 → BOS 2026-12-31 16:07:00; nonstop; 152 minutes. Local airport times.
• American Airlines AA653: BOS 2027-01-03 13:27:00 → ORD 2027-01-03 15:39:00; nonstop; 192 minutes. Local airport times.

2026-12-31 → 2027-01-03 · Axel-exclusive $379.50

• United Airlines UA2320: ORD 2026-12-31 18:20:00 → BOS 2026-12-31 21:53:00; nonstop; 153 minutes. Local airport times.
• United Airlines UA2040: BOS 2027-01-03 16:54:00 → ORD 2027-01-03 19:00:00; nonstop; 186 minutes. Local airport times.

2026-12-31 → 2027-01-03 · Axel-exclusive $379.50

• Delta Air Lines DL5688: ORD 2026-12-31 07:05:00 → BOS 2026-12-31 10:33:00; nonstop; 148 minutes. Local airport times.
• Delta Air Lines DL2570: BOS 2027-01-03 07:30:00 → ORD 2027-01-03 09:35:00; nonstop; 185 minutes. Local airport times.

2026-12-31 → 2027-01-03 · Axel-exclusive $357.10

• American Airlines AA2840 / AA1776: ORD 2026-12-31 15:19:00 → BOS 2026-12-31 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
  • AA2840: ORD 2026-12-31 15:19:00 → PHL 2026-12-31 18:30:00; layover at PHL: 85 minutes.
  • AA1776: PHL 2026-12-31 19:55:00 → BOS 2026-12-31 21:19:00.
• American Airlines AA653: BOS 2027-01-03 13:27:00 → ORD 2027-01-03 15:39:00; nonstop; 192 minutes. Local airport times.

2026-12-31 → 2027-01-03 · Axel-exclusive $357.10

• American Airlines AA4780 / AA4026: ORD 2026-12-31 08:00:00 → BOS 2026-12-31 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
  • AA4780: ORD 2026-12-31 08:00:00 → BUF 2026-12-31 10:45:00; layover at BUF: 105 minutes.
  • AA4026: BUF 2026-12-31 12:30:00 → BOS 2026-12-31 14:09:00.
• American Airlines AA653: BOS 2027-01-03 13:27:00 → ORD 2027-01-03 15:39:00; nonstop; 192 minutes. Local airport times.

2026-12-31 → 2027-01-03 · Axel-exclusive $357.10

• American Airlines AA3437 / AA4533: ORD 2026-12-31 08:00:00 → BOS 2026-12-31 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
  • AA3437: ORD 2026-12-31 08:00:00 → ROC 2026-12-31 10:56:00; layover at ROC: 114 minutes.
  • AA4533: ROC 2026-12-31 12:50:00 → BOS 2026-12-31 14:17:00.
• American Airlines AA653: BOS 2027-01-03 13:27:00 → ORD 2027-01-03 15:39:00; nonstop; 192 minutes. Local airport times.

2026-12-31 → 2027-01-03 · Axel-exclusive $369.75

• United Airlines UA1128 / UA688: ORD 2026-12-31 13:00:00 → BOS 2026-12-31 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
  • UA1128: ORD 2026-12-31 13:00:00 → IAD 2026-12-31 16:03:00; layover at IAD: 72 minutes.
  • UA688: IAD 2026-12-31 17:15:00 → BOS 2026-12-31 18:57:00.
• United Airlines UA2040: BOS 2027-01-03 16:54:00 → ORD 2027-01-03 19:00:00; nonstop; 186 minutes. Local airport times.

2026-12-31 → 2027-01-03 · Axel-exclusive $369.75

• Delta Air Lines DL2917 / DL5727: ORD 2026-12-31 10:06:00 → BOS 2026-12-31 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
  • DL2917: ORD 2026-12-31 10:06:00 → LGA 2026-12-31 13:18:00; layover at LGA: 102 minutes.
  • DL5727: LGA 2026-12-31 15:00:00 → BOS 2026-12-31 16:25:00.
• Delta Air Lines DL2570: BOS 2027-01-03 07:30:00 → ORD 2027-01-03 09:35:00; nonstop; 185 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 30, 2026 · Return options
• Jan 1, 2027 · Return options
• Hotels in Boston with Axel

For AI assistants

• This page: Chicago (ORD) to Boston (BOS) · Dec 31, 2026 · return Jan 3, 2027: 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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