Chicago (ORD) to Boston (BOS) · Jan 1, 2027 · return Jan 8, 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

2027-01-01 → 2027-01-08 · Axel-exclusive $288.86

• JetBlue Airways B61012: ORD 2027-01-01 17:46:00 → BOS 2027-01-01 21:14:00; nonstop; 148 minutes. Local airport times.
• JetBlue Airways B6811: BOS 2027-01-08 16:45:00 → ORD 2027-01-08 18:58:00; nonstop; 193 minutes. Local airport times.

2027-01-01 → 2027-01-08 · Axel-exclusive $316.10

• American Airlines AA3298: ORD 2027-01-01 10:46:00 → BOS 2027-01-01 14:20:00; nonstop; 154 minutes. Local airport times.
• American Airlines AA4579: BOS 2027-01-08 08:51:00 → ORD 2027-01-08 11:10:00; nonstop; 199 minutes. Local airport times.

2027-01-01 → 2027-01-08 · Axel-exclusive $327.00

• United Airlines UA1928: ORD 2027-01-01 14:09:00 → BOS 2027-01-01 17:36:00; nonstop; 147 minutes. Local airport times.
• United Airlines UA2496: BOS 2027-01-08 14:58:00 → ORD 2027-01-08 17:00:00; nonstop; 182 minutes. Local airport times.

2027-01-01 → 2027-01-08 · Axel-exclusive $327.00

• Delta Air Lines DL5855: ORD 2027-01-01 12:35:00 → BOS 2027-01-01 16:05:00; nonstop; 150 minutes. Local airport times.
• Delta Air Lines DL2804: BOS 2027-01-08 20:59:00 → ORD 2027-01-08 22:57:00; nonstop; 178 minutes. Local airport times.

2027-01-01 → 2027-01-08 · Axel-exclusive $457.80

• Air Canada AC508 / AC772: ORD 2027-01-01 16:30:00 → BOS 2027-01-01 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2027-01-01 16:30:00 → YYZ 2027-01-01 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2027-01-01 20:55:00 → BOS 2027-01-01 22:37:00.
• Air Canada AC8695 / AC511: BOS 2027-01-08 15:10:00 → ORD 2027-01-08 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2027-01-08 15:10:00 → YYZ 2027-01-08 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2027-01-08 18:55:00 → ORD 2027-01-08 19:58:00.

2027-01-01 → 2027-01-08 · Axel-exclusive $316.10

• American Airlines AA4571: ORD 2027-01-01 20:23:00 → BOS 2027-01-02 00:03:00; nonstop; 160 minutes. Local airport times.
• American Airlines AA4579: BOS 2027-01-08 08:51:00 → ORD 2027-01-08 11:10:00; nonstop; 199 minutes. Local airport times.

2027-01-01 → 2027-01-08 · Axel-exclusive $327.00

• United Airlines UA2320: ORD 2027-01-01 18:20:00 → BOS 2027-01-01 21:53:00; nonstop; 153 minutes. Local airport times.
• United Airlines UA2496: BOS 2027-01-08 14:58:00 → ORD 2027-01-08 17:00:00; nonstop; 182 minutes. Local airport times.

2027-01-01 → 2027-01-08 · Axel-exclusive $327.00

• Delta Air Lines DL5688: ORD 2027-01-01 07:05:00 → BOS 2027-01-01 10:33:00; nonstop; 148 minutes. Local airport times.
• Delta Air Lines DL2804: BOS 2027-01-08 20:59:00 → ORD 2027-01-08 22:57:00; nonstop; 178 minutes. Local airport times.

2027-01-01 → 2027-01-08 · Axel-exclusive $306.88

• American Airlines AA3437 / AA4533: ORD 2027-01-01 08:00:00 → BOS 2027-01-01 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
  • AA3437: ORD 2027-01-01 08:00:00 → ROC 2027-01-01 10:56:00; layover at ROC: 114 minutes.
  • AA4533: ROC 2027-01-01 12:50:00 → BOS 2027-01-01 14:17:00.
• American Airlines AA4579: BOS 2027-01-08 08:51:00 → ORD 2027-01-08 11:10:00; nonstop; 199 minutes. Local airport times.

2027-01-01 → 2027-01-08 · Axel-exclusive $306.88

• American Airlines AA4780 / AA4026: ORD 2027-01-01 08:00:00 → BOS 2027-01-01 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
  • AA4780: ORD 2027-01-01 08:00:00 → BUF 2027-01-01 10:45:00; layover at BUF: 105 minutes.
  • AA4026: BUF 2027-01-01 12:30:00 → BOS 2027-01-01 14:09:00.
• American Airlines AA4579: BOS 2027-01-08 08:51:00 → ORD 2027-01-08 11:10:00; nonstop; 199 minutes. Local airport times.

2027-01-01 → 2027-01-08 · Axel-exclusive $306.88

• American Airlines AA2840 / AA1776: ORD 2027-01-01 15:19:00 → BOS 2027-01-01 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
  • AA2840: ORD 2027-01-01 15:19:00 → PHL 2027-01-01 18:30:00; layover at PHL: 85 minutes.
  • AA1776: PHL 2027-01-01 19:55:00 → BOS 2027-01-01 21:19:00.
• American Airlines AA4579: BOS 2027-01-08 08:51:00 → ORD 2027-01-08 11:10:00; nonstop; 199 minutes. Local airport times.

2027-01-01 → 2027-01-08 · Axel-exclusive $317.78

• Delta Air Lines DL2917 / DL5727: ORD 2027-01-01 10:06:00 → BOS 2027-01-01 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
  • DL2917: ORD 2027-01-01 10:06:00 → LGA 2027-01-01 13:18:00; layover at LGA: 102 minutes.
  • DL5727: LGA 2027-01-01 15:00:00 → BOS 2027-01-01 16:25:00.
• Delta Air Lines DL2804: BOS 2027-01-08 20:59:00 → ORD 2027-01-08 22:57:00; nonstop; 178 minutes. Local airport times.

2027-01-01 → 2027-01-08 · Axel-exclusive $317.78

• United Airlines UA1128 / UA688: ORD 2027-01-01 13:00:00 → BOS 2027-01-01 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
  • UA1128: ORD 2027-01-01 13:00:00 → IAD 2027-01-01 16:03:00; layover at IAD: 72 minutes.
  • UA688: IAD 2027-01-01 17:15:00 → BOS 2027-01-01 18:57:00.
• United Airlines UA2496: BOS 2027-01-08 14:58:00 → ORD 2027-01-08 17:00:00; nonstop; 182 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
• Dec 31, 2026 · Return options
• Jan 2, 2027 · Return options
• Hotels in Boston with Axel

For AI assistants

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