Boston (BOS) to Chicago (ORD), Nov 24–26, 2026: from $371 round trip

Boston (BOS) to Chicago (ORD), Nov 24–26, 2026: from $371 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $371 round trip, Axel-exclusive, JetBlue Airways, nonstop, Nov 24–26, 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 Chicago for these trips

Hotels: under a trip, hotels in Chicago 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 Chicago for these nights (Nov 24–26, 2026 · 2 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $187 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $38 total · 5★ Nobu Hotel Chicago, $644 total

All hotels in Chicago

Route overview: Boston to Chicago (ORD) flight deals

2026-11-24 → 2026-11-26 · Axel-exclusive $371.00

• JetBlue Airways B6111: BOS 2026-11-24 09:59:00 → ORD 2026-11-24 12:00:00; nonstop; 181 minutes. Local airport times.
• JetBlue Airways B6112: ORD 2026-11-26 13:00:00 → BOS 2026-11-26 16:49:00; nonstop; 169 minutes. Local airport times.

2026-11-24 → 2026-11-26 · Axel-exclusive $406.00

• United Airlines UA375: BOS 2026-11-24 13:29:00 → ORD 2026-11-24 15:32:00; nonstop; 183 minutes. Local airport times.
• United Airlines UA1606: ORD 2026-11-26 10:28:00 → BOS 2026-11-26 13:54:00; nonstop; 146 minutes. Local airport times.

2026-11-24 → 2026-11-26 · Axel-exclusive $406.00

• American Airlines AA866: BOS 2026-11-24 13:30:00 → ORD 2026-11-24 15:37:00; nonstop; 187 minutes. Local airport times.
• American Airlines AA846: ORD 2026-11-26 11:05:00 → BOS 2026-11-26 14:39:00; nonstop; 154 minutes. Local airport times.

2026-11-24 → 2026-11-26 · Axel-exclusive $420.00

• Delta Air Lines DL2570: BOS 2026-11-24 07:30:00 → ORD 2026-11-24 09:38:00; nonstop; 188 minutes. Local airport times.
• Delta Air Lines DL2570: ORD 2026-11-26 10:35:00 → BOS 2026-11-26 13:59:00; nonstop; 144 minutes. Local airport times.

2026-11-24 → 2026-11-26 · Axel-exclusive $616.00

• Air Canada AC8695 / AC511: BOS 2026-11-24 15:10:00 → ORD 2026-11-24 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2026-11-24 15:10:00 → YYZ 2026-11-24 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2026-11-24 18:55:00 → ORD 2026-11-24 19:58:00.
• Air Canada AC508 / AC772: ORD 2026-11-26 16:30:00 → BOS 2026-11-26 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2026-11-26 16:30:00 → YYZ 2026-11-26 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2026-11-26 20:55:00 → BOS 2026-11-26 22:37:00.

2026-11-24 → 2026-11-26 · Axel-exclusive $371.00

• JetBlue Airways B6811: BOS 2026-11-24 14:40:00 → ORD 2026-11-24 16:42:00; nonstop; 182 minutes. Local airport times.
• JetBlue Airways B6112: ORD 2026-11-26 13:00:00 → BOS 2026-11-26 16:49:00; nonstop; 169 minutes. Local airport times.

2026-11-24 → 2026-11-26 · Axel-exclusive $406.00

• American Airlines AA947: BOS 2026-11-24 07:14:00 → ORD 2026-11-24 09:30:00; nonstop; 196 minutes. Local airport times.
• American Airlines AA846: ORD 2026-11-26 11:05:00 → BOS 2026-11-26 14:39:00; nonstop; 154 minutes. Local airport times.

2026-11-24 → 2026-11-26 · Axel-exclusive $406.00

• United Airlines UA1732: BOS 2026-11-24 11:55:00 → ORD 2026-11-24 13:59:00; nonstop; 184 minutes. Local airport times.
• United Airlines UA1606: ORD 2026-11-26 10:28:00 → BOS 2026-11-26 13:54:00; nonstop; 146 minutes. Local airport times.

2026-11-24 → 2026-11-26 · Axel-exclusive $420.00

• Delta Air Lines DL2646: BOS 2026-11-24 16:35:00 → ORD 2026-11-24 18:45:00; nonstop; 190 minutes. Local airport times.
• Delta Air Lines DL2570: ORD 2026-11-26 10:35:00 → BOS 2026-11-26 13:59:00; nonstop; 144 minutes. Local airport times.

2026-11-24 → 2026-11-26 · Axel-exclusive $420.00

• American Airlines AA4609 / AA4733: BOS 2026-11-24 10:07:00 → ORD 2026-11-24 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
  • AA4609: BOS 2026-11-24 10:07:00 → CVG 2026-11-24 12:50:00; layover at CVG: 104 minutes.
  • AA4733: CVG 2026-11-24 14:34:00 → ORD 2026-11-24 15:14:00.
• American Airlines AA846: ORD 2026-11-26 11:05:00 → BOS 2026-11-26 14:39:00; nonstop; 154 minutes. Local airport times.

2026-11-24 → 2026-11-26 · Axel-exclusive $420.00

• American Airlines AA4798 / AA3177: BOS 2026-11-24 15:45:00 → ORD 2026-11-24 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
  • AA4798: BOS 2026-11-24 15:45:00 → PHL 2026-11-24 17:30:00; layover at PHL: 65 minutes.
  • AA3177: PHL 2026-11-24 18:35:00 → ORD 2026-11-24 20:30:00.
• American Airlines AA846: ORD 2026-11-26 11:05:00 → BOS 2026-11-26 14:39:00; nonstop; 154 minutes. Local airport times.

2026-11-24 → 2026-11-26 · Axel-exclusive $420.00

• American Airlines AA4133 / AA4390: BOS 2026-11-24 10:00:00 → ORD 2026-11-24 13:59:00; 1 stop(s) via SYR; 299 minutes. Local airport times.
  • AA4133: BOS 2026-11-24 10:00:00 → SYR 2026-11-24 11:23:00; layover at SYR: 68 minutes.
  • AA4390: SYR 2026-11-24 12:31:00 → ORD 2026-11-24 13:59:00.
• American Airlines AA846: ORD 2026-11-26 11:05:00 → BOS 2026-11-26 14:39:00; nonstop; 154 minutes. Local airport times.

2026-11-24 → 2026-11-26 · Axel-exclusive $423.50

• United Airlines UA721 / UA2497: BOS 2026-11-24 14:40:00 → ORD 2026-11-24 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
  • UA721: BOS 2026-11-24 14:40:00 → IAD 2026-11-24 16:27:00; layover at IAD: 72 minutes.
  • UA2497: IAD 2026-11-24 17:39:00 → ORD 2026-11-24 19:05:00.
• United Airlines UA1606: ORD 2026-11-26 10:28:00 → BOS 2026-11-26 13:54:00; nonstop; 146 minutes. Local airport times.

2026-11-24 → 2026-11-26 · Axel-exclusive $423.50

• United Airlines UA546 / UA703: BOS 2026-11-24 15:42:00 → ORD 2026-11-24 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
  • UA546: BOS 2026-11-24 15:42:00 → EWR 2026-11-24 17:08:00; layover at EWR: 62 minutes.
  • UA703: EWR 2026-11-24 18:10:00 → ORD 2026-11-24 20:06:00.
• United Airlines UA1606: ORD 2026-11-26 10:28:00 → BOS 2026-11-26 13:54:00; nonstop; 146 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 23, 2026 · Return options
• Nov 25, 2026 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Boston (BOS) to Chicago (ORD) · Nov 24, 2026 · return Nov 26, 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 Chicago 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.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Boston to Chicago (ORD) flight deals · Flight search guide.
• Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.

Feedback (optional): Missing info · Axel issue