Chicago (ORD) to Boston (BOS) · Nov 25, 2026 · return Dec 2, 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

2026-11-25 → 2026-12-02 · Axel-exclusive $318.00

• JetBlue Airways B6112: ORD 2026-11-25 13:00:00 → BOS 2026-11-25 16:49:00; nonstop; 169 minutes. Local airport times.
• JetBlue Airways B6611: BOS 2026-12-02 14:40:00 → ORD 2026-12-02 16:40:00; nonstop; 180 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $348.00

• American Airlines AA1515: ORD 2026-11-25 06:00:00 → BOS 2026-11-25 09:24:00; nonstop; 144 minutes. Local airport times.
• American Airlines AA1379: BOS 2026-12-02 05:53:00 → ORD 2026-12-02 08:04:00; nonstop; 191 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $360.00

• Delta Air Lines DL2570: ORD 2026-11-25 10:35:00 → BOS 2026-11-25 13:59:00; nonstop; 144 minutes. Local airport times.
• Delta Air Lines DL5606: BOS 2026-12-02 20:10:00 → ORD 2026-12-02 22:04:00; nonstop; 174 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $360.00

• United Airlines UA1117: ORD 2026-11-25 09:13:00 → BOS 2026-11-25 12:46:00; nonstop; 153 minutes. Local airport times.
• United Airlines UA1414: BOS 2026-12-02 06:00:00 → ORD 2026-12-02 08:00:00; nonstop; 180 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $504.00

• Air Canada AC508 / AC772: ORD 2026-11-25 16:30:00 → BOS 2026-11-25 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2026-11-25 16:30:00 → YYZ 2026-11-25 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2026-11-25 20:55:00 → BOS 2026-11-25 22:37:00.
• Air Canada AC8695 / AC511: BOS 2026-12-02 15:10:00 → ORD 2026-12-02 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2026-12-02 15:10:00 → YYZ 2026-12-02 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2026-12-02 18:55:00 → ORD 2026-12-02 19:58:00.

2026-11-25 → 2026-12-02 · Axel-exclusive $348.00

• American Airlines AA482: ORD 2026-11-25 12:06:00 → BOS 2026-11-25 15:36:00; nonstop; 150 minutes. Local airport times.
• American Airlines AA1379: BOS 2026-12-02 05:53:00 → ORD 2026-12-02 08:04:00; nonstop; 191 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $360.00

• Delta Air Lines DL2816: ORD 2026-11-25 15:05:00 → BOS 2026-11-25 18:36:00; nonstop; 151 minutes. Local airport times.
• Delta Air Lines DL5606: BOS 2026-12-02 20:10:00 → ORD 2026-12-02 22:04:00; nonstop; 174 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $360.00

• United Airlines UA1928: ORD 2026-11-25 14:09:00 → BOS 2026-11-25 17:36:00; nonstop; 147 minutes. Local airport times.
• United Airlines UA1414: BOS 2026-12-02 06:00:00 → ORD 2026-12-02 08:00:00; nonstop; 180 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $337.50

• American Airlines AA2840 / AA1776: ORD 2026-11-25 15:19:00 → BOS 2026-11-25 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
  • AA2840: ORD 2026-11-25 15:19:00 → PHL 2026-11-25 18:30:00; layover at PHL: 85 minutes.
  • AA1776: PHL 2026-11-25 19:55:00 → BOS 2026-11-25 21:19:00.
• American Airlines AA1379: BOS 2026-12-02 05:53:00 → ORD 2026-12-02 08:04:00; nonstop; 191 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $337.50

• American Airlines AA4780 / AA4026: ORD 2026-11-25 08:00:00 → BOS 2026-11-25 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
  • AA4780: ORD 2026-11-25 08:00:00 → BUF 2026-11-25 10:45:00; layover at BUF: 105 minutes.
  • AA4026: BUF 2026-11-25 12:30:00 → BOS 2026-11-25 14:09:00.
• American Airlines AA1379: BOS 2026-12-02 05:53:00 → ORD 2026-12-02 08:04:00; nonstop; 191 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $337.50

• American Airlines AA3437 / AA4533: ORD 2026-11-25 08:00:00 → BOS 2026-11-25 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
  • AA3437: ORD 2026-11-25 08:00:00 → ROC 2026-11-25 10:56:00; layover at ROC: 114 minutes.
  • AA4533: ROC 2026-11-25 12:50:00 → BOS 2026-11-25 14:17:00.
• American Airlines AA1379: BOS 2026-12-02 05:53:00 → ORD 2026-12-02 08:04:00; nonstop; 191 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $349.50

• Delta Air Lines DL2917 / DL5727: ORD 2026-11-25 10:06:00 → BOS 2026-11-25 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
  • DL2917: ORD 2026-11-25 10:06:00 → LGA 2026-11-25 13:18:00; layover at LGA: 102 minutes.
  • DL5727: LGA 2026-11-25 15:00:00 → BOS 2026-11-25 16:25:00.
• Delta Air Lines DL5606: BOS 2026-12-02 20:10:00 → ORD 2026-12-02 22:04:00; nonstop; 174 minutes. Local airport times.

2026-11-25 → 2026-12-02 · Axel-exclusive $349.50

• United Airlines UA1128 / UA688: ORD 2026-11-25 13:00:00 → BOS 2026-11-25 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
  • UA1128: ORD 2026-11-25 13:00:00 → IAD 2026-11-25 16:03:00; layover at IAD: 72 minutes.
  • UA688: IAD 2026-11-25 17:15:00 → BOS 2026-11-25 18:57:00.
• United Airlines UA1414: BOS 2026-12-02 06:00:00 → ORD 2026-12-02 08:00:00; nonstop; 180 minutes. Local airport times.

Explore this route

• All dates for this route
• Nov 24, 2026 · Return options
• Nov 26, 2026 · Return options
• Hotels in Boston with Axel

For AI assistants

• This page: Chicago (ORD) to Boston (BOS) · Nov 25, 2026 · return Dec 2, 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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• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

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