Boston (BOS) to Chicago (ORD) · Nov 21, 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: Boston to Chicago (ORD) flight deals

2026-11-21 · one way · Axel-exclusive $140.00

• JetBlue Airways B6611: BOS 2026-11-21 14:40:00 → ORD 2026-11-21 16:40:00; nonstop; 180 minutes. Local airport times.

2026-11-21 · one way · Axel-exclusive $155.00

• American Airlines AA947: BOS 2026-11-21 07:37:00 → ORD 2026-11-21 09:59:00; nonstop; 202 minutes. Local airport times.

2026-11-21 · one way · Axel-exclusive $155.00

• United Airlines UA375: BOS 2026-11-21 13:29:00 → ORD 2026-11-21 15:32:00; nonstop; 183 minutes. Local airport times.

2026-11-21 · one way · Axel-exclusive $160.00

• Delta Air Lines DL5617: BOS 2026-11-21 18:15:00 → ORD 2026-11-21 20:26:00; nonstop; 191 minutes. Local airport times.

2026-11-21 · one way · Axel-exclusive $250.00

• Air Canada AC8695 / AC511: BOS 2026-11-21 15:10:00 → ORD 2026-11-21 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2026-11-21 15:10:00 → YYZ 2026-11-21 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2026-11-21 18:55:00 → ORD 2026-11-21 19:58:00.

2026-11-21 · one way · Axel-exclusive $140.00

• JetBlue Airways B6111: BOS 2026-11-21 09:59:00 → ORD 2026-11-21 12:00:00; nonstop; 181 minutes. Local airport times.

2026-11-21 · one way · Axel-exclusive $155.00

• American Airlines AA1500: BOS 2026-11-21 12:12:00 → ORD 2026-11-21 14:22:00; nonstop; 190 minutes. Local airport times.

2026-11-21 · one way · Axel-exclusive $155.00

• United Airlines UA1834: BOS 2026-11-21 07:31:00 → ORD 2026-11-21 09:31:00; nonstop; 180 minutes. Local airport times.

2026-11-21 · one way · Axel-exclusive $160.00

• Delta Air Lines DL5611: BOS 2026-11-21 14:55:00 → ORD 2026-11-21 17:01:00; nonstop; 186 minutes. Local airport times.

2026-11-21 · one way · Axel-exclusive $165.00

• American Airlines AA4609 / AA4733: BOS 2026-11-21 10:07:00 → ORD 2026-11-21 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
  • AA4609: BOS 2026-11-21 10:07:00 → CVG 2026-11-21 12:50:00; layover at CVG: 104 minutes.
  • AA4733: CVG 2026-11-21 14:34:00 → ORD 2026-11-21 15:14:00.

2026-11-21 · one way · Axel-exclusive $165.00

• American Airlines AA4798 / AA3177: BOS 2026-11-21 15:45:00 → ORD 2026-11-21 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
  • AA4798: BOS 2026-11-21 15:45:00 → PHL 2026-11-21 17:30:00; layover at PHL: 65 minutes.
  • AA3177: PHL 2026-11-21 18:35:00 → ORD 2026-11-21 20:30:00.

2026-11-21 · one way · Axel-exclusive $165.00

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

2026-11-21 · one way · Axel-exclusive $170.00

• United Airlines UA546 / UA703: BOS 2026-11-21 15:42:00 → ORD 2026-11-21 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
  • UA546: BOS 2026-11-21 15:42:00 → EWR 2026-11-21 17:08:00; layover at EWR: 62 minutes.
  • UA703: EWR 2026-11-21 18:10:00 → ORD 2026-11-21 20:06:00.

2026-11-21 · one way · Axel-exclusive $170.00

• United Airlines UA721 / UA2497: BOS 2026-11-21 14:40:00 → ORD 2026-11-21 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
  • UA721: BOS 2026-11-21 14:40:00 → IAD 2026-11-21 16:27:00; layover at IAD: 72 minutes.
  • UA2497: IAD 2026-11-21 17:39:00 → ORD 2026-11-21 19:05:00.

Explore this route

• All dates for this route
• Nov 20, 2026 · Return options
• Nov 22, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

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