Chicago (ORD) to Boston (BOS) · Jan 27, 2027 · return Feb 10, 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: Chicago to Boston (BOS) flight deals

2027-01-27 → 2027-02-10 · Axel-exclusive $251.76

• JetBlue Airways B61012: ORD 2027-01-27 17:46:00 → BOS 2027-01-27 21:14:00; nonstop; 148 minutes. Local airport times.
• JetBlue Airways B6811: BOS 2027-02-10 16:45:00 → ORD 2027-02-10 18:58:00; nonstop; 193 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $275.50

• American Airlines AA1457: ORD 2027-01-27 20:00:00 → BOS 2027-01-27 23:32:00; nonstop; 152 minutes. Local airport times.
• American Airlines AA1379: BOS 2027-02-10 05:53:00 → ORD 2027-02-10 08:04:00; nonstop; 191 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $285.00

• United Airlines UA2827: ORD 2027-01-27 18:18:00 → BOS 2027-01-27 21:53:00; nonstop; 155 minutes. Local airport times.
• United Airlines UA1414: BOS 2027-02-10 05:45:00 → ORD 2027-02-10 07:51:00; nonstop; 186 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $285.00

• Delta Air Lines DL5688: ORD 2027-01-27 07:05:00 → BOS 2027-01-27 10:33:00; nonstop; 148 minutes. Local airport times.
• Delta Air Lines DL5606: BOS 2027-02-10 20:10:00 → ORD 2027-02-10 22:04:00; nonstop; 174 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $399.00

• Air Canada AC508 / AC772: ORD 2027-01-27 16:30:00 → BOS 2027-01-27 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2027-01-27 16:30:00 → YYZ 2027-01-27 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2027-01-27 20:55:00 → BOS 2027-01-27 22:37:00.
• Air Canada AC8695 / AC511: BOS 2027-02-10 15:10:00 → ORD 2027-02-10 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2027-02-10 15:10:00 → YYZ 2027-02-10 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2027-02-10 18:55:00 → ORD 2027-02-10 19:58:00.

2027-01-27 → 2027-02-10 · Axel-exclusive $275.50

• American Airlines AA640: ORD 2027-01-27 06:00:00 → BOS 2027-01-27 09:33:00; nonstop; 153 minutes. Local airport times.
• American Airlines AA1379: BOS 2027-02-10 05:53:00 → ORD 2027-02-10 08:04:00; nonstop; 191 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $285.00

• United Airlines UA1606: ORD 2027-01-27 10:30:00 → BOS 2027-01-27 13:55:00; nonstop; 145 minutes. Local airport times.
• United Airlines UA1414: BOS 2027-02-10 05:45:00 → ORD 2027-02-10 07:51:00; nonstop; 186 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $285.00

• Delta Air Lines DL5855: ORD 2027-01-27 12:35:00 → BOS 2027-01-27 16:05:00; nonstop; 150 minutes. Local airport times.
• Delta Air Lines DL5606: BOS 2027-02-10 20:10:00 → ORD 2027-02-10 22:04:00; nonstop; 174 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $268.38

• American Airlines AA2840 / AA1776: ORD 2027-01-27 15:19:00 → BOS 2027-01-27 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
  • AA2840: ORD 2027-01-27 15:19:00 → PHL 2027-01-27 18:30:00; layover at PHL: 85 minutes.
  • AA1776: PHL 2027-01-27 19:55:00 → BOS 2027-01-27 21:19:00.
• American Airlines AA1379: BOS 2027-02-10 05:53:00 → ORD 2027-02-10 08:04:00; nonstop; 191 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $268.38

• American Airlines AA4780 / AA4026: ORD 2027-01-27 08:00:00 → BOS 2027-01-27 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
  • AA4780: ORD 2027-01-27 08:00:00 → BUF 2027-01-27 10:45:00; layover at BUF: 105 minutes.
  • AA4026: BUF 2027-01-27 12:30:00 → BOS 2027-01-27 14:09:00.
• American Airlines AA1379: BOS 2027-02-10 05:53:00 → ORD 2027-02-10 08:04:00; nonstop; 191 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $268.38

• American Airlines AA3437 / AA4533: ORD 2027-01-27 08:00:00 → BOS 2027-01-27 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
  • AA3437: ORD 2027-01-27 08:00:00 → ROC 2027-01-27 10:56:00; layover at ROC: 114 minutes.
  • AA4533: ROC 2027-01-27 12:50:00 → BOS 2027-01-27 14:17:00.
• American Airlines AA1379: BOS 2027-02-10 05:53:00 → ORD 2027-02-10 08:04:00; nonstop; 191 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $277.88

• United Airlines UA1128 / UA688: ORD 2027-01-27 13:00:00 → BOS 2027-01-27 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
  • UA1128: ORD 2027-01-27 13:00:00 → IAD 2027-01-27 16:03:00; layover at IAD: 72 minutes.
  • UA688: IAD 2027-01-27 17:15:00 → BOS 2027-01-27 18:57:00.
• United Airlines UA1414: BOS 2027-02-10 05:45:00 → ORD 2027-02-10 07:51:00; nonstop; 186 minutes. Local airport times.

2027-01-27 → 2027-02-10 · Axel-exclusive $277.88

• Delta Air Lines DL2917 / DL5727: ORD 2027-01-27 10:06:00 → BOS 2027-01-27 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
  • DL2917: ORD 2027-01-27 10:06:00 → LGA 2027-01-27 13:18:00; layover at LGA: 102 minutes.
  • DL5727: LGA 2027-01-27 15:00:00 → BOS 2027-01-27 16:25:00.
• Delta Air Lines DL5606: BOS 2027-02-10 20:10:00 → ORD 2027-02-10 22:04:00; nonstop; 174 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 26, 2027 · Return options
• Jan 28, 2027 · Return options
• Hotels in Boston with Axel

For AI assistants

• This page: Chicago (ORD) to Boston (BOS) · Jan 27, 2027 · return Feb 10, 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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