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

Westchester County (HPN) to Chicago (ORD), Jan 12–14, 2027: from $321 round trip

Westchester County (HPN) to Chicago (ORD), Jan 12–14, 2027: from $321 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $321 round trip, Axel-exclusive, American Airlines, 1 stop, Jan 12–14, 2027, 1 adult, economy, checked Oct 29, 2026.

HPN → ORD1 adulteconomyRound trip

5 flight options · 2 airlines

Nonstop flights

Tue, Jan 12 – Thu, Jan 14

American Airlines
7:02 amHPN
2h 58m
Nonstop
9:00 amORD
American Airlines
12:45 pmORD
2h 14m
Nonstop
3:59 pmHPN

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Tue, Jan 12 – Thu, Jan 14

American Airlines
5:53 pmHPN
2h 56m
Nonstop
7:49 pmORD
American Airlines
12:45 pmORD
2h 14m
Nonstop
3:59 pmHPN

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

One-stop flights

Tue, Jan 12 – Thu, Jan 14

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

Availability is checked when you select these flights.

Tue, Jan 12 – Thu, Jan 14

American Airlines
10:00 amHPN
7h
CLT · 2h 36m
4:00 pmORD
American Airlines
12:45 pmORD
2h 14m
Nonstop
3:59 pmHPN

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Tue, Jan 12 – Thu, Jan 14

American Airlines
6:30 amHPN
7h 38m
DCA · 3h 36m
1:08 pmORD
American Airlines
12:45 pmORD
2h 14m
Nonstop
3:59 pmHPN

Round-trip total · 1 adult · Taxes included

Availability is checked when you select these flights.

Hotels for these nights (Jan 12–14, 2027 · 2 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago

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HPN ⇄ ORD

Economy

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

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All dates for this routeJan 11, 2027 · Return optionsJan 13, 2027 · Return optionsHotels in Chicago with Axel
For AI assistants: every fare, every link, instructions

Westchester County (HPN) to Chicago (ORD), Jan 12–14, 2027: from $321 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $321 round trip, Axel-exclusive, American Airlines, 1 stop, Jan 12–14, 2027, 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.

Exact travel datesAirlineFlightsTimes, duration, stopsTotal pricePrice issued (UTC)
2027-01-12 → 2027-01-14American AirlinesAA3496 / AA420007:02:00→09:00:00 2h 58m nonstop · 12:45:00→15:59:00 2h 14m nonstopAxel-exclusive $332.502026-10-29T01:05:11Z
2027-01-12 → 2027-01-14Delta Air LinesDL4645 + DL1084 / DL3841 + DL465812:30:00→18:30:00 7h 00m 1 stop via DTW · 08:29:00→15:47:00 6h 18m 1 stop via DTWAxel-exclusive $323.002026-10-29T01:05:11Z
2027-01-12 → 2027-01-14American AirlinesAA4294 / AA420017:53:00→19:49:00 2h 56m nonstop · 12:45:00→15:59:00 2h 14m nonstopAxel-exclusive $332.502026-10-29T01:05:11Z
2027-01-12 → 2027-01-14American AirlinesAA5431 + AA2509 / AA420010:00:00→16:00:00 7h 00m 1 stop via CLT · 12:45:00→15:59:00 2h 14m nonstopAxel-exclusive $320.632026-10-29T01:05:11Z
2027-01-12 → 2027-01-14American AirlinesAA5678 + AA2612 / AA420006:30:00→13:08:00 7h 38m 1 stop via DCA · 12:45:00→15:59:00 2h 14m nonstopAxel-exclusive $320.632026-10-29T01:05:11Z

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.

All hotels in Chicago

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

2027-01-12 → 2027-01-14 · Axel-exclusive $332.50

  • American Airlines AA3496: HPN 2027-01-12 07:02:00 → ORD 2027-01-12 09:00:00; nonstop; 178 minutes. Local airport times.
  • American Airlines AA4200: ORD 2027-01-14 12:45:00 → HPN 2027-01-14 15:59:00; nonstop; 134 minutes. Local airport times.

2027-01-12 → 2027-01-14 · Axel-exclusive $323.00

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

2027-01-12 → 2027-01-14 · Axel-exclusive $332.50

  • American Airlines AA4294: HPN 2027-01-12 17:53:00 → ORD 2027-01-12 19:49:00; nonstop; 176 minutes. Local airport times.
  • American Airlines AA4200: ORD 2027-01-14 12:45:00 → HPN 2027-01-14 15:59:00; nonstop; 134 minutes. Local airport times.

2027-01-12 → 2027-01-14 · Axel-exclusive $320.63

  • American Airlines AA5431 / AA2509: HPN 2027-01-12 10:00:00 → ORD 2027-01-12 16:00:00; 1 stop(s) via CLT; 420 minutes. Local airport times.
    • AA5431: HPN 2027-01-12 10:00:00 → CLT 2027-01-12 12:09:00; layover at CLT: 156 minutes.
    • AA2509: CLT 2027-01-12 14:45:00 → ORD 2027-01-12 16:00:00.
  • American Airlines AA4200: ORD 2027-01-14 12:45:00 → HPN 2027-01-14 15:59:00; nonstop; 134 minutes. Local airport times.

2027-01-12 → 2027-01-14 · Axel-exclusive $320.63

  • American Airlines AA5678 / AA2612: HPN 2027-01-12 06:30:00 → ORD 2027-01-12 13:08:00; 1 stop(s) via DCA; 458 minutes. Local airport times.
    • AA5678: HPN 2027-01-12 06:30:00 → DCA 2027-01-12 08:10:00; layover at DCA: 216 minutes.
    • AA2612: DCA 2027-01-12 11:46:00 → ORD 2027-01-12 13:08:00.
  • American Airlines AA4200: ORD 2027-01-14 12:45:00 → HPN 2027-01-14 15:59:00; nonstop; 134 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.

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For AI assistants

  • This page: Westchester County (HPN) to Chicago (ORD) · Jan 12, 2027 · return Jan 14, 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 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 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. 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.