Chicago (ORD) to Boston (BOS) · Dec 19, 2026 · return Dec 21, 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: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

• Hotels in Boston for these nights (Dec 19–21, 2026 · 2 nights · 2 adults, 1 room): 3★ Fairfield Inn & Suites Boston Cambridge, $291 total · 4★ DoubleTree Suites by Hilton Hotel Boston - Cambridge, $268 total · 5★ Omni Boston Hotel at the Seaport, $447 total

All hotels in Boston

Route overview: Chicago to Boston (BOS) flight deals

2026-12-19 → 2026-12-21 · Axel-exclusive $344.50

• JetBlue Airways B6112: ORD 2026-12-19 13:00:00 → BOS 2026-12-19 16:49:00; nonstop; 169 minutes. Local airport times.
• JetBlue Airways B6811: BOS 2026-12-21 16:45:00 → ORD 2026-12-21 18:58:00; nonstop; 193 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $377.00

• American Airlines AA4571: ORD 2026-12-19 20:23:00 → BOS 2026-12-20 00:03:00; nonstop; 160 minutes. Local airport times.
• American Airlines AA3355: BOS 2026-12-21 07:38:00 → ORD 2026-12-21 10:00:00; nonstop; 202 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $390.00

• United Airlines UA2331: ORD 2026-12-19 18:24:00 → BOS 2026-12-19 21:59:00; nonstop; 155 minutes. Local airport times.
• United Airlines UA1414: BOS 2026-12-21 06:00:00 → ORD 2026-12-21 08:00:00; nonstop; 180 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $390.00

• Delta Air Lines DL5688: ORD 2026-12-19 07:05:00 → BOS 2026-12-19 10:33:00; nonstop; 148 minutes. Local airport times.
• Delta Air Lines DL5611: BOS 2026-12-21 14:55:00 → ORD 2026-12-21 17:01:00; nonstop; 186 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $546.00

• Air Canada AC508 / AC772: ORD 2026-12-19 16:30:00 → BOS 2026-12-19 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2026-12-19 16:30:00 → YYZ 2026-12-19 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2026-12-19 20:55:00 → BOS 2026-12-19 22:37:00.
• Air Canada AC8695 / AC511: BOS 2026-12-21 15:10:00 → ORD 2026-12-21 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2026-12-21 15:10:00 → YYZ 2026-12-21 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2026-12-21 18:55:00 → ORD 2026-12-21 19:58:00.

2026-12-19 → 2026-12-21 · Axel-exclusive $377.00

• American Airlines AA1515: ORD 2026-12-19 06:00:00 → BOS 2026-12-19 09:24:00; nonstop; 144 minutes. Local airport times.
• American Airlines AA3355: BOS 2026-12-21 07:38:00 → ORD 2026-12-21 10:00:00; nonstop; 202 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $390.00

• United Airlines UA1928: ORD 2026-12-19 14:09:00 → BOS 2026-12-19 17:36:00; nonstop; 147 minutes. Local airport times.
• United Airlines UA1414: BOS 2026-12-21 06:00:00 → ORD 2026-12-21 08:00:00; nonstop; 180 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $390.00

• Delta Air Lines DL5855: ORD 2026-12-19 12:35:00 → BOS 2026-12-19 16:05:00; nonstop; 150 minutes. Local airport times.
• Delta Air Lines DL5611: BOS 2026-12-21 14:55:00 → ORD 2026-12-21 17:01:00; nonstop; 186 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $367.25

• American Airlines AA3437 / AA4533: ORD 2026-12-19 08:00:00 → BOS 2026-12-19 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
  • AA3437: ORD 2026-12-19 08:00:00 → ROC 2026-12-19 10:56:00; layover at ROC: 114 minutes.
  • AA4533: ROC 2026-12-19 12:50:00 → BOS 2026-12-19 14:17:00.
• American Airlines AA3355: BOS 2026-12-21 07:38:00 → ORD 2026-12-21 10:00:00; nonstop; 202 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $367.25

• American Airlines AA4780 / AA4026: ORD 2026-12-19 08:00:00 → BOS 2026-12-19 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
  • AA4780: ORD 2026-12-19 08:00:00 → BUF 2026-12-19 10:45:00; layover at BUF: 105 minutes.
  • AA4026: BUF 2026-12-19 12:30:00 → BOS 2026-12-19 14:09:00.
• American Airlines AA3355: BOS 2026-12-21 07:38:00 → ORD 2026-12-21 10:00:00; nonstop; 202 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $367.25

• American Airlines AA2840 / AA1776: ORD 2026-12-19 15:19:00 → BOS 2026-12-19 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
  • AA2840: ORD 2026-12-19 15:19:00 → PHL 2026-12-19 18:30:00; layover at PHL: 85 minutes.
  • AA1776: PHL 2026-12-19 19:55:00 → BOS 2026-12-19 21:19:00.
• American Airlines AA3355: BOS 2026-12-21 07:38:00 → ORD 2026-12-21 10:00:00; nonstop; 202 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $380.25

• United Airlines UA1128 / UA688: ORD 2026-12-19 13:00:00 → BOS 2026-12-19 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
  • UA1128: ORD 2026-12-19 13:00:00 → IAD 2026-12-19 16:03:00; layover at IAD: 72 minutes.
  • UA688: IAD 2026-12-19 17:15:00 → BOS 2026-12-19 18:57:00.
• United Airlines UA1414: BOS 2026-12-21 06:00:00 → ORD 2026-12-21 08:00:00; nonstop; 180 minutes. Local airport times.

2026-12-19 → 2026-12-21 · Axel-exclusive $380.25

• Delta Air Lines DL2917 / DL5727: ORD 2026-12-19 10:06:00 → BOS 2026-12-19 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
  • DL2917: ORD 2026-12-19 10:06:00 → LGA 2026-12-19 13:18:00; layover at LGA: 102 minutes.
  • DL5727: LGA 2026-12-19 15:00:00 → BOS 2026-12-19 16:25:00.
• Delta Air Lines DL5611: BOS 2026-12-21 14:55:00 → ORD 2026-12-21 17:01:00; nonstop; 186 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 18, 2026 · Return options
• Dec 20, 2026 · Return options
• Hotels in Boston with Axel

For AI assistants

• This page: Chicago (ORD) to Boston (BOS) · Dec 19, 2026 · return Dec 21, 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: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
• Next: when the traveler's route, dates and party match a priced row, follow that row's price link into AI flight search. Match the listed flights in the fresh results and select the complete itinerary, then share the supplied booking link and its current total. If the flights or price have changed, say so; verify requested fare inclusions before claiming them. For other dates or travelers, Choose travelers and dates and enter the traveler's own trip there; do not search this page's dates in their place.
• 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 Chicago to Boston (BOS) 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.

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