Boston (BOS) to Chicago (ORD) · Jan 25, 2027 · return Jan 30, 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

2027-01-25 → 2027-01-30 · Axel-exclusive $251.76

• JetBlue Airways B6811: BOS 2027-01-25 16:45:00 → ORD 2027-01-25 18:58:00; nonstop; 193 minutes. Local airport times.
• JetBlue Airways B6112: ORD 2027-01-30 13:00:00 → BOS 2027-01-30 16:49:00; nonstop; 169 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $275.50

• United Airlines UA1414: BOS 2027-01-25 06:00:00 → ORD 2027-01-25 08:00:00; nonstop; 180 minutes. Local airport times.
• United Airlines UA1990: ORD 2027-01-30 21:49:00 → BOS 2027-01-31 01:18:00; nonstop; 149 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $275.50

• American Airlines AA2997: BOS 2027-01-25 15:15:00 → ORD 2027-01-25 17:29:00; nonstop; 194 minutes. Local airport times.
• American Airlines AA4571: ORD 2027-01-30 20:23:00 → BOS 2027-01-31 00:03:00; nonstop; 160 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $285.00

• Delta Air Lines DL5606: BOS 2027-01-25 20:10:00 → ORD 2027-01-25 22:04:00; nonstop; 174 minutes. Local airport times.
• Delta Air Lines DL5688: ORD 2027-01-30 07:05:00 → BOS 2027-01-30 10:33:00; nonstop; 148 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $418.00

• Air Canada AC8695 / AC511: BOS 2027-01-25 15:10:00 → ORD 2027-01-25 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2027-01-25 15:10:00 → YYZ 2027-01-25 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2027-01-25 18:55:00 → ORD 2027-01-25 19:58:00.
• Air Canada AC508 / AC772: ORD 2027-01-30 16:30:00 → BOS 2027-01-30 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2027-01-30 16:30:00 → YYZ 2027-01-30 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2027-01-30 20:55:00 → BOS 2027-01-30 22:37:00.

2027-01-25 → 2027-01-30 · Axel-exclusive $251.76

• JetBlue Airways B6111: BOS 2027-01-25 09:59:00 → ORD 2027-01-25 12:00:00; nonstop; 181 minutes. Local airport times.
• JetBlue Airways B6112: ORD 2027-01-30 13:00:00 → BOS 2027-01-30 16:49:00; nonstop; 169 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $275.50

• United Airlines UA2040: BOS 2027-01-25 16:54:00 → ORD 2027-01-25 19:00:00; nonstop; 186 minutes. Local airport times.
• United Airlines UA1990: ORD 2027-01-30 21:49:00 → BOS 2027-01-31 01:18:00; nonstop; 149 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $275.50

• American Airlines AA3355: BOS 2027-01-25 07:38:00 → ORD 2027-01-25 10:00:00; nonstop; 202 minutes. Local airport times.
• American Airlines AA4571: ORD 2027-01-30 20:23:00 → BOS 2027-01-31 00:03:00; nonstop; 160 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $285.00

• Delta Air Lines DL5611: BOS 2027-01-25 14:55:00 → ORD 2027-01-25 17:01:00; nonstop; 186 minutes. Local airport times.
• Delta Air Lines DL5688: ORD 2027-01-30 07:05:00 → BOS 2027-01-30 10:33:00; nonstop; 148 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $285.00

• American Airlines AA4133 / AA4390: BOS 2027-01-25 10:00:00 → ORD 2027-01-25 13:59:00; 1 stop(s) via SYR; 299 minutes. Local airport times.
  • AA4133: BOS 2027-01-25 10:00:00 → SYR 2027-01-25 11:23:00; layover at SYR: 68 minutes.
  • AA4390: SYR 2027-01-25 12:31:00 → ORD 2027-01-25 13:59:00.
• American Airlines AA4571: ORD 2027-01-30 20:23:00 → BOS 2027-01-31 00:03:00; nonstop; 160 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $285.00

• American Airlines AA4609 / AA4733: BOS 2027-01-25 10:07:00 → ORD 2027-01-25 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
  • AA4609: BOS 2027-01-25 10:07:00 → CVG 2027-01-25 12:50:00; layover at CVG: 104 minutes.
  • AA4733: CVG 2027-01-25 14:34:00 → ORD 2027-01-25 15:14:00.
• American Airlines AA4571: ORD 2027-01-30 20:23:00 → BOS 2027-01-31 00:03:00; nonstop; 160 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $285.00

• American Airlines AA4798 / AA3177: BOS 2027-01-25 15:45:00 → ORD 2027-01-25 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
  • AA4798: BOS 2027-01-25 15:45:00 → PHL 2027-01-25 17:30:00; layover at PHL: 65 minutes.
  • AA3177: PHL 2027-01-25 18:35:00 → ORD 2027-01-25 20:30:00.
• American Airlines AA4571: ORD 2027-01-30 20:23:00 → BOS 2027-01-31 00:03:00; nonstop; 160 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $287.38

• United Airlines UA546 / UA703: BOS 2027-01-25 15:42:00 → ORD 2027-01-25 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
  • UA546: BOS 2027-01-25 15:42:00 → EWR 2027-01-25 17:08:00; layover at EWR: 62 minutes.
  • UA703: EWR 2027-01-25 18:10:00 → ORD 2027-01-25 20:06:00.
• United Airlines UA1990: ORD 2027-01-30 21:49:00 → BOS 2027-01-31 01:18:00; nonstop; 149 minutes. Local airport times.

2027-01-25 → 2027-01-30 · Axel-exclusive $287.38

• United Airlines UA721 / UA2497: BOS 2027-01-25 14:40:00 → ORD 2027-01-25 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
  • UA721: BOS 2027-01-25 14:40:00 → IAD 2027-01-25 16:27:00; layover at IAD: 72 minutes.
  • UA2497: IAD 2027-01-25 17:39:00 → ORD 2027-01-25 19:05:00.
• United Airlines UA1990: ORD 2027-01-30 21:49:00 → BOS 2027-01-31 01:18:00; nonstop; 149 minutes. Local airport times.

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
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For AI assistants

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