Boston (BOS) to Chicago (ORD) · Jan 24, 2027 · return Feb 3, 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 Chicago for these trips

Hotels: under a trip, hotels in Chicago 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 Chicago for these nights (Jan 24 – Feb 3, 2027 · 10 nights · 2 adults, 1 room): 3★ The Willows Hotel, $1,046 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $1,406 total · 5★ Nobu Hotel Chicago, $3,614 total

All hotels in Chicago

Route overview: Boston to Chicago (ORD) flight deals

2027-01-24 → 2027-02-03 · Axel-exclusive $251.76

• JetBlue Airways B6111: BOS 2027-01-24 09:59:00 → ORD 2027-01-24 12:00:00; nonstop; 181 minutes. Local airport times.
• JetBlue Airways B61012: ORD 2027-02-03 17:46:00 → BOS 2027-02-03 21:14:00; nonstop; 148 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $275.50

• American Airlines AA2015: BOS 2027-01-24 10:24:00 → ORD 2027-01-24 12:35:00; nonstop; 191 minutes. Local airport times.
• American Airlines AA640: ORD 2027-02-03 06:00:00 → BOS 2027-02-03 09:33:00; nonstop; 153 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $275.50

• United Airlines UA2040: BOS 2027-01-24 16:54:00 → ORD 2027-01-24 19:00:00; nonstop; 186 minutes. Local airport times.
• United Airlines UA1606: ORD 2027-02-03 10:30:00 → BOS 2027-02-03 13:55:00; nonstop; 145 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $285.00

• Delta Air Lines DL2570: BOS 2027-01-24 07:30:00 → ORD 2027-01-24 09:35:00; nonstop; 185 minutes. Local airport times.
• Delta Air Lines DL5688: ORD 2027-02-03 07:05:00 → BOS 2027-02-03 10:33:00; nonstop; 148 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $418.00

• Air Canada AC8695 / AC511: BOS 2027-01-24 15:10:00 → ORD 2027-01-24 19:58:00; 1 stop(s) via YYZ; 348 minutes. Local airport times.
  • AC8695: BOS 2027-01-24 15:10:00 → YYZ 2027-01-24 17:11:00; layover at YYZ: 104 minutes.
  • AC511: YYZ 2027-01-24 18:55:00 → ORD 2027-01-24 19:58:00.
• Air Canada AC508 / AC772: ORD 2027-02-03 16:30:00 → BOS 2027-02-03 22:37:00; 1 stop(s) via YYZ; 307 minutes. Local airport times.
  • AC508: ORD 2027-02-03 16:30:00 → YYZ 2027-02-03 19:10:00; layover at YYZ: 105 minutes.
  • AC772: YYZ 2027-02-03 20:55:00 → BOS 2027-02-03 22:37:00.

2027-01-24 → 2027-02-03 · Axel-exclusive $251.76

• JetBlue Airways B6811: BOS 2027-01-24 16:45:00 → ORD 2027-01-24 18:58:00; nonstop; 193 minutes. Local airport times.
• JetBlue Airways B61012: ORD 2027-02-03 17:46:00 → BOS 2027-02-03 21:14:00; nonstop; 148 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $275.50

• United Airlines UA1414: BOS 2027-01-24 05:45:00 → ORD 2027-01-24 07:51:00; nonstop; 186 minutes. Local airport times.
• United Airlines UA1606: ORD 2027-02-03 10:30:00 → BOS 2027-02-03 13:55:00; nonstop; 145 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $275.50

• American Airlines AA653: BOS 2027-01-24 13:27:00 → ORD 2027-01-24 15:39:00; nonstop; 192 minutes. Local airport times.
• American Airlines AA640: ORD 2027-02-03 06:00:00 → BOS 2027-02-03 09:33:00; nonstop; 153 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $285.00

• Delta Air Lines DL5606: BOS 2027-01-24 20:10:00 → ORD 2027-01-24 22:04:00; nonstop; 174 minutes. Local airport times.
• Delta Air Lines DL5688: ORD 2027-02-03 07:05:00 → BOS 2027-02-03 10:33:00; nonstop; 148 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $285.00

• American Airlines AA4798 / AA3177: BOS 2027-01-24 15:45:00 → ORD 2027-01-24 20:30:00; 1 stop(s) via PHL; 345 minutes. Local airport times.
  • AA4798: BOS 2027-01-24 15:45:00 → PHL 2027-01-24 17:30:00; layover at PHL: 65 minutes.
  • AA3177: PHL 2027-01-24 18:35:00 → ORD 2027-01-24 20:30:00.
• American Airlines AA640: ORD 2027-02-03 06:00:00 → BOS 2027-02-03 09:33:00; nonstop; 153 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $285.00

• American Airlines AA4609 / AA4733: BOS 2027-01-24 10:07:00 → ORD 2027-01-24 15:14:00; 1 stop(s) via CVG; 367 minutes. Local airport times.
  • AA4609: BOS 2027-01-24 10:07:00 → CVG 2027-01-24 12:50:00; layover at CVG: 104 minutes.
  • AA4733: CVG 2027-01-24 14:34:00 → ORD 2027-01-24 15:14:00.
• American Airlines AA640: ORD 2027-02-03 06:00:00 → BOS 2027-02-03 09:33:00; nonstop; 153 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $285.00

• American Airlines AA4133 / AA4390: BOS 2027-01-24 10:00:00 → ORD 2027-01-24 13:59:00; 1 stop(s) via SYR; 299 minutes. Local airport times.
  • AA4133: BOS 2027-01-24 10:00:00 → SYR 2027-01-24 11:23:00; layover at SYR: 68 minutes.
  • AA4390: SYR 2027-01-24 12:31:00 → ORD 2027-01-24 13:59:00.
• American Airlines AA640: ORD 2027-02-03 06:00:00 → BOS 2027-02-03 09:33:00; nonstop; 153 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $287.38

• United Airlines UA546 / UA703: BOS 2027-01-24 15:42:00 → ORD 2027-01-24 20:06:00; 1 stop(s) via EWR; 324 minutes. Local airport times.
  • UA546: BOS 2027-01-24 15:42:00 → EWR 2027-01-24 17:08:00; layover at EWR: 62 minutes.
  • UA703: EWR 2027-01-24 18:10:00 → ORD 2027-01-24 20:06:00.
• United Airlines UA1606: ORD 2027-02-03 10:30:00 → BOS 2027-02-03 13:55:00; nonstop; 145 minutes. Local airport times.

2027-01-24 → 2027-02-03 · Axel-exclusive $287.38

• United Airlines UA721 / UA2497: BOS 2027-01-24 14:40:00 → ORD 2027-01-24 19:05:00; 1 stop(s) via IAD; 325 minutes. Local airport times.
  • UA721: BOS 2027-01-24 14:40:00 → IAD 2027-01-24 16:27:00; layover at IAD: 72 minutes.
  • UA2497: IAD 2027-01-24 17:39:00 → ORD 2027-01-24 19:05:00.
• United Airlines UA1606: ORD 2027-02-03 10:30:00 → BOS 2027-02-03 13:55:00; nonstop; 145 minutes. Local airport times.

Explore this route

• All dates for this route
• Jan 23, 2027 · Return options
• Jan 25, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Boston (BOS) to Chicago (ORD) · Jan 24, 2027 · return Feb 3, 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 Chicago 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.
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• 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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