Chicago (ORD) to Boston (BOS) · Dec 23, 2026 · one way

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

2026-12-23 · one way · Axel-exclusive $182.00

• JetBlue Airways B61012: ORD 2026-12-23 17:46:00 → BOS 2026-12-23 21:14:00; nonstop; 148 minutes. Local airport times.

2026-12-23 · one way · Axel-exclusive $201.50

• American Airlines AA640: ORD 2026-12-23 06:00:00 → BOS 2026-12-23 09:33:00; nonstop; 153 minutes. Local airport times.

2026-12-23 · one way · Axel-exclusive $208.00

• United Airlines UA1928: ORD 2026-12-23 14:09:00 → BOS 2026-12-23 17:36:00; nonstop; 147 minutes. Local airport times.

2026-12-23 · one way · Axel-exclusive $208.00

• Delta Air Lines DL5855: ORD 2026-12-23 12:35:00 → BOS 2026-12-23 16:05:00; nonstop; 150 minutes. Local airport times.

2026-12-23 · one way · Axel-exclusive $292.50

• Air Canada AC508 / AC772: ORD 2026-12-23 16:30:00 → BOS 2026-12-23 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2026-12-23 16:30:00 → YYZ 2026-12-23 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2026-12-23 20:55:00 → BOS 2026-12-23 22:37:00.

2026-12-23 · one way · Axel-exclusive $201.50

• American Airlines AA1457: ORD 2026-12-23 20:00:00 → BOS 2026-12-23 23:32:00; nonstop; 152 minutes. Local airport times.

2026-12-23 · one way · Axel-exclusive $208.00

• Delta Air Lines DL5688: ORD 2026-12-23 07:05:00 → BOS 2026-12-23 10:33:00; nonstop; 148 minutes. Local airport times.

2026-12-23 · one way · Axel-exclusive $208.00

• United Airlines UA1990: ORD 2026-12-23 21:49:00 → BOS 2026-12-24 01:18:00; nonstop; 149 minutes. Local airport times.

2026-12-23 · one way · Axel-exclusive $188.50

• American Airlines AA4780 / AA4026: ORD 2026-12-23 08:00:00 → BOS 2026-12-23 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
  • AA4780: ORD 2026-12-23 08:00:00 → BUF 2026-12-23 10:45:00; layover at BUF: 105 minutes.
  • AA4026: BUF 2026-12-23 12:30:00 → BOS 2026-12-23 14:09:00.

2026-12-23 · one way · Axel-exclusive $188.50

• American Airlines AA3437 / AA4533: ORD 2026-12-23 08:00:00 → BOS 2026-12-23 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
  • AA3437: ORD 2026-12-23 08:00:00 → ROC 2026-12-23 10:56:00; layover at ROC: 114 minutes.
  • AA4533: ROC 2026-12-23 12:50:00 → BOS 2026-12-23 14:17:00.

2026-12-23 · one way · Axel-exclusive $188.50

• American Airlines AA2840 / AA1776: ORD 2026-12-23 15:19:00 → BOS 2026-12-23 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
  • AA2840: ORD 2026-12-23 15:19:00 → PHL 2026-12-23 18:30:00; layover at PHL: 85 minutes.
  • AA1776: PHL 2026-12-23 19:55:00 → BOS 2026-12-23 21:19:00.

2026-12-23 · one way · Axel-exclusive $195.00

• United Airlines UA1128 / UA688: ORD 2026-12-23 13:00:00 → BOS 2026-12-23 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
  • UA1128: ORD 2026-12-23 13:00:00 → IAD 2026-12-23 16:03:00; layover at IAD: 72 minutes.
  • UA688: IAD 2026-12-23 17:15:00 → BOS 2026-12-23 18:57:00.

2026-12-23 · one way · Axel-exclusive $195.00

• Delta Air Lines DL2917 / DL5727: ORD 2026-12-23 10:06:00 → BOS 2026-12-23 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
  • DL2917: ORD 2026-12-23 10:06:00 → LGA 2026-12-23 13:18:00; layover at LGA: 102 minutes.
  • DL5727: LGA 2026-12-23 15:00:00 → BOS 2026-12-23 16:25:00.

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
• Dec 22, 2026 · Return options
• Dec 24, 2026 · Return options
• Hotels in Boston with Axel

For AI assistants

• This page: Chicago (ORD) to Boston (BOS) · Dec 23, 2026 · one way: 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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