Chicago (ORD) to Boston (BOS), Nov 8–12, 2026: from $265 round trip

Chicago (ORD) to Boston (BOS), Nov 8–12, 2026: from $265 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $265 round trip, Axel-exclusive, JetBlue Airways, nonstop, Nov 8–12, 2026, 1 adult, economy, checked Oct 29, 2026. 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.

Hotels in Boston for these trips

Hotels: under a trip, hotels in Boston for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Boston for these nights (Nov 8–12, 2026 · 4 nights · 2 adults, 1 room): 3★ The Verb Hotel · 4★ The Eliot Hotel · 5★ Boston Harbor Hotel

All hotels in Boston

Route overview: Chicago to Boston (BOS) flight deals

2026-11-08 → 2026-11-12 · Axel-exclusive $265.00

• JetBlue Airways B6112: ORD 2026-11-08 13:00:00 → BOS 2026-11-08 16:49:00; nonstop; 169 minutes. Local airport times.
• JetBlue Airways B6111: BOS 2026-11-12 09:59:00 → ORD 2026-11-12 12:00:00; nonstop; 181 minutes. Local airport times.

2026-11-08 → 2026-11-12 · Axel-exclusive $290.00

• American Airlines AA2054: ORD 2026-11-08 12:06:00 → BOS 2026-11-08 15:39:00; nonstop; 153 minutes. Local airport times.
• American Airlines AA947: BOS 2026-11-12 05:51:00 → ORD 2026-11-12 08:04:00; nonstop; 193 minutes. Local airport times.

2026-11-08 → 2026-11-12 · Axel-exclusive $300.00

• Delta Air Lines DL2570: ORD 2026-11-08 10:35:00 → BOS 2026-11-08 13:59:00; nonstop; 144 minutes. Local airport times.
• Delta Air Lines DL2804: BOS 2026-11-12 20:40:00 → ORD 2026-11-12 22:36:00; nonstop; 176 minutes. Local airport times.

2026-11-08 → 2026-11-12 · Axel-exclusive $300.00

• United Airlines UA2101: ORD 2026-11-08 13:59:00 → BOS 2026-11-08 17:24:00; nonstop; 145 minutes. Local airport times.
• United Airlines UA503: BOS 2026-11-12 10:25:00 → ORD 2026-11-12 12:29:00; nonstop; 184 minutes. Local airport times.

2026-11-08 → 2026-11-12 · Axel-exclusive $420.00

• Air Canada AC508 / AC772: ORD 2026-11-08 16:30:00 → BOS 2026-11-08 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2026-11-08 16:30:00 → YYZ 2026-11-08 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2026-11-08 20:55:00 → BOS 2026-11-08 22:37:00.
• Air Canada AC8695 / AC511: BOS 2026-11-12 15:10:00 → ORD 2026-11-12 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2026-11-12 15:10:00 → YYZ 2026-11-12 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2026-11-12 18:55:00 → ORD 2026-11-12 19:58:00.

2026-11-08 → 2026-11-12 · Axel-exclusive $290.00

• American Airlines AA1951: ORD 2026-11-08 06:00:00 → BOS 2026-11-08 09:29:00; nonstop; 149 minutes. Local airport times.
• American Airlines AA947: BOS 2026-11-12 05:51:00 → ORD 2026-11-12 08:04:00; nonstop; 193 minutes. Local airport times.

2026-11-08 → 2026-11-12 · Axel-exclusive $300.00

• Delta Air Lines DL2816: ORD 2026-11-08 15:05:00 → BOS 2026-11-08 18:36:00; nonstop; 151 minutes. Local airport times.
• Delta Air Lines DL2804: BOS 2026-11-12 20:40:00 → ORD 2026-11-12 22:36:00; nonstop; 176 minutes. Local airport times.

2026-11-08 → 2026-11-12 · Axel-exclusive $300.00

• United Airlines UA1186: ORD 2026-11-08 06:15:00 → BOS 2026-11-08 09:34:00; nonstop; 139 minutes. Local airport times.
• United Airlines UA503: BOS 2026-11-12 10:25:00 → ORD 2026-11-12 12:29:00; nonstop; 184 minutes. Local airport times.

2026-11-08 → 2026-11-12 · Axel-exclusive $282.50

• American Airlines AA3437 / AA4533: ORD 2026-11-08 08:00:00 → BOS 2026-11-08 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
  • AA3437: ORD 2026-11-08 08:00:00 → ROC 2026-11-08 10:56:00; layover at ROC: 114 minutes.
  • AA4533: ROC 2026-11-08 12:50:00 → BOS 2026-11-08 14:17:00.
• American Airlines AA947: BOS 2026-11-12 05:51:00 → ORD 2026-11-12 08:04:00; nonstop; 193 minutes. Local airport times.

2026-11-08 → 2026-11-12 · Axel-exclusive $282.50

• American Airlines AA2840 / AA1776: ORD 2026-11-08 15:19:00 → BOS 2026-11-08 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
  • AA2840: ORD 2026-11-08 15:19:00 → PHL 2026-11-08 18:30:00; layover at PHL: 85 minutes.
  • AA1776: PHL 2026-11-08 19:55:00 → BOS 2026-11-08 21:19:00.
• American Airlines AA947: BOS 2026-11-12 05:51:00 → ORD 2026-11-12 08:04:00; nonstop; 193 minutes. Local airport times.

2026-11-08 → 2026-11-12 · Axel-exclusive $282.50

• American Airlines AA4780 / AA4026: ORD 2026-11-08 08:00:00 → BOS 2026-11-08 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
  • AA4780: ORD 2026-11-08 08:00:00 → BUF 2026-11-08 10:45:00; layover at BUF: 105 minutes.
  • AA4026: BUF 2026-11-08 12:30:00 → BOS 2026-11-08 14:09:00.
• American Airlines AA947: BOS 2026-11-12 05:51:00 → ORD 2026-11-12 08:04:00; nonstop; 193 minutes. Local airport times.

2026-11-08 → 2026-11-12 · Axel-exclusive $292.50

• United Airlines UA1128 / UA688: ORD 2026-11-08 13:00:00 → BOS 2026-11-08 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
  • UA1128: ORD 2026-11-08 13:00:00 → IAD 2026-11-08 16:03:00; layover at IAD: 72 minutes.
  • UA688: IAD 2026-11-08 17:15:00 → BOS 2026-11-08 18:57:00.
• United Airlines UA503: BOS 2026-11-12 10:25:00 → ORD 2026-11-12 12:29:00; nonstop; 184 minutes. Local airport times.

2026-11-08 → 2026-11-12 · Axel-exclusive $292.50

• Delta Air Lines DL2917 / DL5727: ORD 2026-11-08 10:06:00 → BOS 2026-11-08 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
  • DL2917: ORD 2026-11-08 10:06:00 → LGA 2026-11-08 13:18:00; layover at LGA: 102 minutes.
  • DL5727: LGA 2026-11-08 15:00:00 → BOS 2026-11-08 16:25:00.
• Delta Air Lines DL2804: BOS 2026-11-12 20:40:00 → ORD 2026-11-12 22:36:00; nonstop; 176 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
• Nov 7, 2026 · Return options
• Nov 9, 2026 · Return options
• Hotels in Boston with Axel

For AI assistants

• This page: Chicago (ORD) to Boston (BOS) · Nov 8, 2026 · return Nov 12, 2026: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Boston for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
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