Boston (BOS) to Chicago (ORD) · Jun 29, 2027 · 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

2027-06-29 · one way · Axel-exclusive $165.00

• JetBlue Airways B6811: BOS 2027-06-29 14:40:00 → ORD 2027-06-29 16:42:00; nonstop; 182 minutes. Local airport times.

2027-06-29 · one way · Axel-exclusive $180.00

• United Airlines UA2040: BOS 2027-06-29 16:54:00 → ORD 2027-06-29 19:00:00; nonstop; 186 minutes. Local airport times.

2027-06-29 · one way · Axel-exclusive $180.00

• American Airlines AA4572: BOS 2027-06-29 21:13:00 → ORD 2027-06-29 23:30:00; nonstop; 197 minutes. Local airport times.

2027-06-29 · one way · Axel-exclusive $185.00

• Delta Air Lines DL2570: BOS 2027-06-29 07:30:00 → ORD 2027-06-29 09:38:00; nonstop; 188 minutes. Local airport times.

2027-06-29 · one way · Axel-exclusive $280.00

• Air Canada AC8695 / AC511: BOS 2027-06-29 15:10:00 → ORD 2027-06-29 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2027-06-29 15:10:00 → YYZ 2027-06-29 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2027-06-29 18:55:00 → ORD 2027-06-29 19:58:00.

2027-06-29 · one way · Axel-exclusive $165.00

• JetBlue Airways B6111: BOS 2027-06-29 09:59:00 → ORD 2027-06-29 12:00:00; nonstop; 181 minutes. Local airport times.

2027-06-29 · one way · Axel-exclusive $180.00

• American Airlines AA2146: BOS 2027-06-29 07:15:00 → ORD 2027-06-29 09:30:00; nonstop; 195 minutes. Local airport times.

2027-06-29 · one way · Axel-exclusive $180.00

• United Airlines UA1414: BOS 2027-06-29 06:00:00 → ORD 2027-06-29 08:00:00; nonstop; 180 minutes. Local airport times.

2027-06-29 · one way · Axel-exclusive $185.00

• Delta Air Lines DL2646: BOS 2027-06-29 16:35:00 → ORD 2027-06-29 18:45:00; nonstop; 190 minutes. Local airport times.

2027-06-29 · one way · Axel-exclusive $190.00

• American Airlines AA4609 / AA4733: BOS 2027-06-29 10:07:00 → ORD 2027-06-29 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
  • AA4609: BOS 2027-06-29 10:07:00 → CVG 2027-06-29 12:50:00; layover at CVG: 104 minutes.
  • AA4733: CVG 2027-06-29 14:34:00 → ORD 2027-06-29 15:14:00.

2027-06-29 · one way · Axel-exclusive $190.00

• American Airlines AA4798 / AA3177: BOS 2027-06-29 15:45:00 → ORD 2027-06-29 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
  • AA4798: BOS 2027-06-29 15:45:00 → PHL 2027-06-29 17:30:00; layover at PHL: 65 minutes.
  • AA3177: PHL 2027-06-29 18:35:00 → ORD 2027-06-29 20:30:00.

2027-06-29 · one way · Axel-exclusive $190.00

• American Airlines AA4133 / AA4390: BOS 2027-06-29 10:00:00 → ORD 2027-06-29 13:59:00; 1 stop(s) via SYR; 299 minutes. Local airport times.
  • AA4133: BOS 2027-06-29 10:00:00 → SYR 2027-06-29 11:23:00; layover at SYR: 68 minutes.
  • AA4390: SYR 2027-06-29 12:31:00 → ORD 2027-06-29 13:59:00.

2027-06-29 · one way · Axel-exclusive $195.00

• United Airlines UA546 / UA703: BOS 2027-06-29 15:42:00 → ORD 2027-06-29 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
  • UA546: BOS 2027-06-29 15:42:00 → EWR 2027-06-29 17:08:00; layover at EWR: 62 minutes.
  • UA703: EWR 2027-06-29 18:10:00 → ORD 2027-06-29 20:06:00.

2027-06-29 · one way · Axel-exclusive $195.00

• United Airlines UA721 / UA2497: BOS 2027-06-29 14:40:00 → ORD 2027-06-29 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
  • UA721: BOS 2027-06-29 14:40:00 → IAD 2027-06-29 16:27:00; layover at IAD: 72 minutes.
  • UA2497: IAD 2027-06-29 17:39:00 → ORD 2027-06-29 19:05:00.

Explore this route

• All dates for this route
• Jun 28, 2027 · Return options
• Jun 30, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

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