Chicago (ORD) to Boston (BOS) · Dec 30, 2026 · return Jan 1, 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.

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 30 – Jan 1, 2027 · 2 nights · 2 adults, 1 room): 3★ Aloft by Marriott Boston Seaport District, $309 total · 4★ DoubleTree Suites by Hilton Hotel Boston - Cambridge, $312 total · 5★ Omni Boston Hotel at the Seaport, $523 total

All hotels in Boston

Route overview: Chicago to Boston (BOS) flight deals

2026-12-30 → 2027-01-01 · Axel-exclusive $335.23

• JetBlue Airways B61012: ORD 2026-12-30 17:46:00 → BOS 2026-12-30 21:14:00; nonstop; 148 minutes. Local airport times.
• JetBlue Airways B6811: BOS 2027-01-01 16:45:00 → ORD 2027-01-01 18:58:00; nonstop; 193 minutes. Local airport times.

2026-12-30 → 2027-01-01 · Axel-exclusive $366.85

• American Airlines AA640: ORD 2026-12-30 06:00:00 → BOS 2026-12-30 09:33:00; nonstop; 153 minutes. Local airport times.
• American Airlines AA4579: BOS 2027-01-01 08:51:00 → ORD 2027-01-01 11:10:00; nonstop; 199 minutes. Local airport times.

2026-12-30 → 2027-01-01 · Axel-exclusive $379.50

• Delta Air Lines DL5688: ORD 2026-12-30 07:05:00 → BOS 2026-12-30 10:33:00; nonstop; 148 minutes. Local airport times.
• Delta Air Lines DL2804: BOS 2027-01-01 20:59:00 → ORD 2027-01-01 22:57:00; nonstop; 178 minutes. Local airport times.

2026-12-30 → 2027-01-01 · Axel-exclusive $379.50

• United Airlines UA2213: ORD 2026-12-30 06:50:00 → BOS 2026-12-30 10:17:00; nonstop; 147 minutes. Local airport times.
• United Airlines UA2496: BOS 2027-01-01 14:58:00 → ORD 2027-01-01 17:00:00; nonstop; 182 minutes. Local airport times.

2026-12-30 → 2027-01-01 · Axel-exclusive $531.30

• Air Canada AC508 / AC772: ORD 2026-12-30 16:30:00 → BOS 2026-12-30 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2026-12-30 16:30:00 → YYZ 2026-12-30 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2026-12-30 20:55:00 → BOS 2026-12-30 22:37:00.
• Air Canada AC8695 / AC511: BOS 2027-01-01 15:10:00 → ORD 2027-01-01 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2027-01-01 15:10:00 → YYZ 2027-01-01 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2027-01-01 18:55:00 → ORD 2027-01-01 19:58:00.

2026-12-30 → 2027-01-01 · Axel-exclusive $366.85

• American Airlines AA1457: ORD 2026-12-30 20:00:00 → BOS 2026-12-30 23:32:00; nonstop; 152 minutes. Local airport times.
• American Airlines AA4579: BOS 2027-01-01 08:51:00 → ORD 2027-01-01 11:10:00; nonstop; 199 minutes. Local airport times.

2026-12-30 → 2027-01-01 · Axel-exclusive $379.50

• United Airlines UA1990: ORD 2026-12-30 21:49:00 → BOS 2026-12-31 01:18:00; nonstop; 149 minutes. Local airport times.
• United Airlines UA2496: BOS 2027-01-01 14:58:00 → ORD 2027-01-01 17:00:00; nonstop; 182 minutes. Local airport times.

2026-12-30 → 2027-01-01 · Axel-exclusive $379.50

• Delta Air Lines DL5855: ORD 2026-12-30 12:35:00 → BOS 2026-12-30 16:05:00; nonstop; 150 minutes. Local airport times.
• Delta Air Lines DL2804: BOS 2027-01-01 20:59:00 → ORD 2027-01-01 22:57:00; nonstop; 178 minutes. Local airport times.

2026-12-30 → 2027-01-01 · Axel-exclusive $357.10

• American Airlines AA4780 / AA4026: ORD 2026-12-30 08:00:00 → BOS 2026-12-30 14:09:00; 1 stop(s) via BUF; 309 minutes. Local airport times.
  • AA4780: ORD 2026-12-30 08:00:00 → BUF 2026-12-30 10:45:00; layover at BUF: 105 minutes.
  • AA4026: BUF 2026-12-30 12:30:00 → BOS 2026-12-30 14:09:00.
• American Airlines AA4579: BOS 2027-01-01 08:51:00 → ORD 2027-01-01 11:10:00; nonstop; 199 minutes. Local airport times.

2026-12-30 → 2027-01-01 · Axel-exclusive $357.10

• American Airlines AA2840 / AA1776: ORD 2026-12-30 15:19:00 → BOS 2026-12-30 21:19:00; 1 stop(s) via PHL; 300 minutes. Local airport times.
  • AA2840: ORD 2026-12-30 15:19:00 → PHL 2026-12-30 18:30:00; layover at PHL: 85 minutes.
  • AA1776: PHL 2026-12-30 19:55:00 → BOS 2026-12-30 21:19:00.
• American Airlines AA4579: BOS 2027-01-01 08:51:00 → ORD 2027-01-01 11:10:00; nonstop; 199 minutes. Local airport times.

2026-12-30 → 2027-01-01 · Axel-exclusive $357.10

• American Airlines AA3437 / AA4533: ORD 2026-12-30 08:00:00 → BOS 2026-12-30 14:17:00; 1 stop(s) via ROC; 317 minutes. Local airport times.
  • AA3437: ORD 2026-12-30 08:00:00 → ROC 2026-12-30 10:56:00; layover at ROC: 114 minutes.
  • AA4533: ROC 2026-12-30 12:50:00 → BOS 2026-12-30 14:17:00.
• American Airlines AA4579: BOS 2027-01-01 08:51:00 → ORD 2027-01-01 11:10:00; nonstop; 199 minutes. Local airport times.

2026-12-30 → 2027-01-01 · Axel-exclusive $369.75

• Delta Air Lines DL2917 / DL5727: ORD 2026-12-30 10:06:00 → BOS 2026-12-30 16:25:00; 1 stop(s) via LGA; 319 minutes. Local airport times.
  • DL2917: ORD 2026-12-30 10:06:00 → LGA 2026-12-30 13:18:00; layover at LGA: 102 minutes.
  • DL5727: LGA 2026-12-30 15:00:00 → BOS 2026-12-30 16:25:00.
• Delta Air Lines DL2804: BOS 2027-01-01 20:59:00 → ORD 2027-01-01 22:57:00; nonstop; 178 minutes. Local airport times.

2026-12-30 → 2027-01-01 · Axel-exclusive $369.75

• United Airlines UA1128 / UA688: ORD 2026-12-30 13:00:00 → BOS 2026-12-30 18:57:00; 1 stop(s) via IAD; 297 minutes. Local airport times.
  • UA1128: ORD 2026-12-30 13:00:00 → IAD 2026-12-30 16:03:00; layover at IAD: 72 minutes.
  • UA688: IAD 2026-12-30 17:15:00 → BOS 2026-12-30 18:57:00.
• United Airlines UA2496: BOS 2027-01-01 14:58:00 → ORD 2027-01-01 17:00:00; nonstop; 182 minutes. Local airport times.

Explore this route

• All dates for this route
• Dec 29, 2026 · Return options
• Dec 31, 2026 · Return options
• Hotels in Boston with Axel

For AI assistants

• This page: Chicago (ORD) to Boston (BOS) · Dec 30, 2026 · return Jan 1, 2027: 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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