Boston (BOS) to Chicago (ORD) · Jun 24, 2027 · return Jul 1, 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: Boston to Chicago (ORD) flight deals

2027-06-24 → 2027-07-01 · Axel-exclusive $341.00

• JetBlue Airways B6811: BOS 2027-06-24 16:45:00 → ORD 2027-06-24 18:58:00; nonstop; 193 minutes. Local airport times.
• JetBlue Airways B61012: ORD 2027-07-01 17:46:00 → BOS 2027-07-01 21:14:00; nonstop; 148 minutes. Local airport times.

2027-06-24 → 2027-07-01 · Axel-exclusive $368.50

• United Airlines UA1414: BOS 2027-06-24 06:00:00 → ORD 2027-06-24 08:00:00; nonstop; 180 minutes. Local airport times.
• United Airlines UA487: ORD 2027-07-01 16:00:00 → BOS 2027-07-01 19:29:00; nonstop; 149 minutes. Local airport times.

2027-06-24 → 2027-07-01 · Axel-exclusive $368.50

• American Airlines AA4572: BOS 2027-06-24 21:13:00 → ORD 2027-06-24 23:30:00; nonstop; 197 minutes. Local airport times.
• American Airlines AA3298: ORD 2027-07-01 10:31:00 → BOS 2027-07-01 14:05:00; nonstop; 154 minutes. Local airport times.

2027-06-24 → 2027-07-01 · Axel-exclusive $379.50

• Delta Air Lines DL5611: BOS 2027-06-24 14:55:00 → ORD 2027-06-24 17:01:00; nonstop; 186 minutes. Local airport times.
• Delta Air Lines DL5688: ORD 2027-07-01 07:05:00 → BOS 2027-07-01 10:33:00; nonstop; 148 minutes. Local airport times.

2027-06-24 → 2027-07-01 · Axel-exclusive $544.50

• Air Canada AC8695 / AC511: BOS 2027-06-24 15:10:00 → ORD 2027-06-24 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2027-06-24 15:10:00 → YYZ 2027-06-24 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2027-06-24 18:55:00 → ORD 2027-06-24 19:58:00.
• Air Canada AC508 / AC772: ORD 2027-07-01 16:30:00 → BOS 2027-07-01 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2027-07-01 16:30:00 → YYZ 2027-07-01 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2027-07-01 20:55:00 → BOS 2027-07-01 22:37:00.

2027-06-24 → 2027-07-01 · Axel-exclusive $341.00

• JetBlue Airways B6111: BOS 2027-06-24 09:59:00 → ORD 2027-06-24 12:00:00; nonstop; 181 minutes. Local airport times.
• JetBlue Airways B61012: ORD 2027-07-01 17:46:00 → BOS 2027-07-01 21:14:00; nonstop; 148 minutes. Local airport times.

2027-06-24 → 2027-07-01 · Axel-exclusive $368.50

• United Airlines UA2433: BOS 2027-06-24 20:25:00 → ORD 2027-06-24 22:29:00; nonstop; 184 minutes. Local airport times.
• United Airlines UA487: ORD 2027-07-01 16:00:00 → BOS 2027-07-01 19:29:00; nonstop; 149 minutes. Local airport times.

2027-06-24 → 2027-07-01 · Axel-exclusive $368.50

• American Airlines AA947: BOS 2027-06-24 05:51:00 → ORD 2027-06-24 08:04:00; nonstop; 193 minutes. Local airport times.
• American Airlines AA3298: ORD 2027-07-01 10:31:00 → BOS 2027-07-01 14:05:00; nonstop; 154 minutes. Local airport times.

2027-06-24 → 2027-07-01 · Axel-exclusive $379.50

• Delta Air Lines DL2804: BOS 2027-06-24 20:40:00 → ORD 2027-06-24 22:36:00; nonstop; 176 minutes. Local airport times.
• Delta Air Lines DL5688: ORD 2027-07-01 07:05:00 → BOS 2027-07-01 10:33:00; nonstop; 148 minutes. Local airport times.

2027-06-24 → 2027-07-01 · Axel-exclusive $378.50

• American Airlines AA4798 / AA3177: BOS 2027-06-24 15:45:00 → ORD 2027-06-24 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
  • AA4798: BOS 2027-06-24 15:45:00 → PHL 2027-06-24 17:30:00; layover at PHL: 65 minutes.
  • AA3177: PHL 2027-06-24 18:35:00 → ORD 2027-06-24 20:30:00.
• American Airlines AA3298: ORD 2027-07-01 10:31:00 → BOS 2027-07-01 14:05:00; nonstop; 154 minutes. Local airport times.

2027-06-24 → 2027-07-01 · Axel-exclusive $378.50

• American Airlines AA4133 / AA4390: BOS 2027-06-24 10:00:00 → ORD 2027-06-24 13:59:00; 1 stop(s) via SYR; 299 minutes. Local airport times.
  • AA4133: BOS 2027-06-24 10:00:00 → SYR 2027-06-24 11:23:00; layover at SYR: 68 minutes.
  • AA4390: SYR 2027-06-24 12:31:00 → ORD 2027-06-24 13:59:00.
• American Airlines AA3298: ORD 2027-07-01 10:31:00 → BOS 2027-07-01 14:05:00; nonstop; 154 minutes. Local airport times.

2027-06-24 → 2027-07-01 · Axel-exclusive $378.50

• American Airlines AA4609 / AA4733: BOS 2027-06-24 10:07:00 → ORD 2027-06-24 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
  • AA4609: BOS 2027-06-24 10:07:00 → CVG 2027-06-24 12:50:00; layover at CVG: 104 minutes.
  • AA4733: CVG 2027-06-24 14:34:00 → ORD 2027-06-24 15:14:00.
• American Airlines AA3298: ORD 2027-07-01 10:31:00 → BOS 2027-07-01 14:05:00; nonstop; 154 minutes. Local airport times.

2027-06-24 → 2027-07-01 · Axel-exclusive $381.00

• United Airlines UA721 / UA2497: BOS 2027-06-24 14:40:00 → ORD 2027-06-24 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
  • UA721: BOS 2027-06-24 14:40:00 → IAD 2027-06-24 16:27:00; layover at IAD: 72 minutes.
  • UA2497: IAD 2027-06-24 17:39:00 → ORD 2027-06-24 19:05:00.
• United Airlines UA487: ORD 2027-07-01 16:00:00 → BOS 2027-07-01 19:29:00; nonstop; 149 minutes. Local airport times.

2027-06-24 → 2027-07-01 · Axel-exclusive $381.00

• United Airlines UA546 / UA703: BOS 2027-06-24 15:42:00 → ORD 2027-06-24 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
  • UA546: BOS 2027-06-24 15:42:00 → EWR 2027-06-24 17:08:00; layover at EWR: 62 minutes.
  • UA703: EWR 2027-06-24 18:10:00 → ORD 2027-06-24 20:06:00.
• United Airlines UA487: ORD 2027-07-01 16:00:00 → BOS 2027-07-01 19:29:00; nonstop; 149 minutes. Local airport times.

Explore this route

• All dates for this route
• Jun 23, 2027 · Return options
• Jun 25, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Boston (BOS) to Chicago (ORD) · Jun 24, 2027 · return Jul 1, 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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