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Route overview: Westchester County to Chicago (ORD) flight deals

Westchester County → Chicago

Dec 21, 2026 · return Jan 4, 2027

HPN → ORD1 adulteconomyRound trip

5 flight options · 2 airlines

Nonstop flights

Mon, Dec 21 – Mon, Jan 4

American Airlines
7:29 amHPN
2h 55m
Nonstop
9:24 amORD
American Airlines
8:13 amORD
2h 16m
Nonstop
11:29 amHPN

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

American Airlines
12:13 pmHPN
2h 46m
Nonstop
1:59 pmORD
American Airlines
8:13 amORD
2h 16m
Nonstop
11:29 amHPN

Round-trip total · 1 adult · Taxes included

One-stop flights

Mon, Dec 21 – Mon, Jan 4

Delta Air Lines
12:30 pmHPN
7h
DTW · 3h 28m
6:30 pmORD
Delta Air Lines
8:29 amORD
6h 18m
DTW · 3h 9m
3:47 pmHPN

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

American Airlines
10:00 amHPN
7h
CLT · 2h 36m
4:00 pmORD
American Airlines
8:13 amORD
2h 16m
Nonstop
11:29 amHPN

Round-trip total · 1 adult · Taxes included

Mon, Dec 21 – Mon, Jan 4

American Airlines
6:30 amHPN
7h 38m
DCA · 3h 36m
1:08 pmORD
American Airlines
8:13 amORD
2h 16m
Nonstop
11:29 amHPN

Round-trip total · 1 adult · Taxes included

Make this trip yours

HPN ⇄ ORD

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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Explore this route

All dates for this routeDec 20, 2026 → Jan 3, 2027Dec 22, 2026 → Jan 5, 2027
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

Route overview: Westchester County to Chicago (ORD) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-12-21 → 2027-01-04American AirlinesAA3496 / AA3812$393.752026-10-29T01:05:11Z
2026-12-21 → 2027-01-04Delta Air LinesDL4645 + DL1084 / DL3841 + DL4658$382.502026-10-29T01:05:11Z
2026-12-21 → 2027-01-04American AirlinesAA3812 / AA3812$393.752026-10-29T01:05:11Z
2026-12-21 → 2027-01-04American AirlinesAA5431 + AA2509 / AA3812$377.502026-10-29T01:05:11Z
2026-12-21 → 2027-01-04American AirlinesAA5678 + AA2612 / AA3812$377.502026-10-29T01:05:11Z

2026-12-21 → 2027-01-04 · $393.75

  • American Airlines AA3496: HPN 2026-12-21 07:29:00 → ORD 2026-12-21 09:24:00; nonstop; 175 minutes. Local airport times.
  • American Airlines AA3812: ORD 2027-01-04 08:13:00 → HPN 2027-01-04 11:29:00; nonstop; 136 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $382.50

  • Delta Air Lines DL4645 / DL1084: HPN 2026-12-21 12:30:00 → ORD 2026-12-21 18:30:00; 1 stop(s) via DTW; 420 minutes. Local airport times.
    • DL4645: HPN 2026-12-21 12:30:00 → DTW 2026-12-21 14:28:00; layover at DTW: 208 minutes.
    • DL1084: DTW 2026-12-21 17:56:00 → ORD 2026-12-21 18:30:00.
  • Delta Air Lines DL3841 / DL4658: ORD 2027-01-04 08:29:00 → HPN 2027-01-04 15:47:00; 1 stop(s) via DTW; 378 minutes. Local airport times.
    • DL3841: ORD 2027-01-04 08:29:00 → DTW 2027-01-04 10:52:00; layover at DTW: 189 minutes.
    • DL4658: DTW 2027-01-04 14:01:00 → HPN 2027-01-04 15:47:00.

2026-12-21 → 2027-01-04 · $393.75

  • American Airlines AA3812: HPN 2026-12-21 12:13:00 → ORD 2026-12-21 13:59:00; nonstop; 166 minutes. Local airport times.
  • American Airlines AA3812: ORD 2027-01-04 08:13:00 → HPN 2027-01-04 11:29:00; nonstop; 136 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $377.50

  • American Airlines AA5431 / AA2509: HPN 2026-12-21 10:00:00 → ORD 2026-12-21 16:00:00; 1 stop(s) via CLT; 420 minutes. Local airport times.
    • AA5431: HPN 2026-12-21 10:00:00 → CLT 2026-12-21 12:09:00; layover at CLT: 156 minutes.
    • AA2509: CLT 2026-12-21 14:45:00 → ORD 2026-12-21 16:00:00.
  • American Airlines AA3812: ORD 2027-01-04 08:13:00 → HPN 2027-01-04 11:29:00; nonstop; 136 minutes. Local airport times.

2026-12-21 → 2027-01-04 · $377.50

  • American Airlines AA5678 / AA2612: HPN 2026-12-21 06:30:00 → ORD 2026-12-21 13:08:00; 1 stop(s) via DCA; 458 minutes. Local airport times.
    • AA5678: HPN 2026-12-21 06:30:00 → DCA 2026-12-21 08:10:00; layover at DCA: 216 minutes.
    • AA2612: DCA 2026-12-21 11:46:00 → ORD 2026-12-21 13:08:00.
  • American Airlines AA3812: ORD 2027-01-04 08:13:00 → HPN 2027-01-04 11:29:00; nonstop; 136 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: Westchester County (HPN) to Chicago (ORD) · Dec 21, 2026 · return Jan 4, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
  • 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 Westchester County 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. Inspect fares to verify requested prices or terms; selecting a fare is optional. Use that fare’s booking link to preserve its Membership price basis. State anything unverified. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and explain what remains unresolved. Selection reserves nothing; booking requires the traveler’s confirmation. 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.