Westchester County (HPN) to Chicago (ORD), Jan 16–20, 2027: from $321 round trip
Westchester County (HPN) to Chicago (ORD), Jan 16–20, 2027: from $321 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $321 round trip, Axel-exclusive, American Airlines, 1 stop, Jan 16–20, 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 dates | Airline | Flights | Times, duration, stops | Total price | Price issued (UTC) |
|---|---|---|---|---|---|
| 2027-01-16 → 2027-01-20 | American Airlines | AA4179 / AA3812 | 17:47:00→19:43:00 2h 56m nonstop · 08:14:00→11:29:00 2h 15m nonstop | Axel-exclusive $332.50 | 2026-10-29T01:05:11Z |
| 2027-01-16 → 2027-01-20 | Delta Air Lines | DL4645 + DL1084 / DL3841 + DL4658 | 12:30:00→18:30:00 7h 00m 1 stop via DTW · 08:29:00→15:47:00 6h 18m 1 stop via DTW | Axel-exclusive $323.00 | 2026-10-29T01:05:11Z |
| 2027-01-16 → 2027-01-20 | American Airlines | AA3496 / AA3812 | 07:02:00→09:00:00 2h 58m nonstop · 08:14:00→11:29:00 2h 15m nonstop | Axel-exclusive $332.50 | 2026-10-29T01:05:11Z |
| 2027-01-16 → 2027-01-20 | American Airlines | AA5431 + AA2509 / AA3812 | 10:00:00→16:00:00 7h 00m 1 stop via CLT · 08:14:00→11:29:00 2h 15m nonstop | Axel-exclusive $320.63 | 2026-10-29T01:05:11Z |
| 2027-01-16 → 2027-01-20 | American Airlines | AA5678 + AA2612 / AA3812 | 06:30:00→13:08:00 7h 38m 1 stop via DCA · 08:14:00→11:29:00 2h 15m nonstop | Axel-exclusive $320.63 | 2026-10-29T01:05:11Z |
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.
- Hotels in Chicago for these nights (Jan 16–20, 2027 · 4 nights · 2 adults, 1 room): 3★ Hyatt Place Chicago/Wicker Park · 4★ LondonHouse Chicago, Curio Collection by Hilton · 5★ The Langham, Chicago
Route overview: Westchester County to Chicago (ORD) flight deals
2027-01-16 → 2027-01-20 · Axel-exclusive $332.50
- American Airlines AA4179: HPN 2027-01-16 17:47:00 → ORD 2027-01-16 19:43:00; nonstop; 176 minutes. Local airport times.
- American Airlines AA3812: ORD 2027-01-20 08:14:00 → HPN 2027-01-20 11:29:00; nonstop; 135 minutes. Local airport times.
2027-01-16 → 2027-01-20 · Axel-exclusive $323.00
- Delta Air Lines DL4645 / DL1084: HPN 2027-01-16 12:30:00 → ORD 2027-01-16 18:30:00; 1 stop(s) via DTW; 420 minutes. Local airport times.
- DL4645: HPN 2027-01-16 12:30:00 → DTW 2027-01-16 14:28:00; layover at DTW: 208 minutes.
- DL1084: DTW 2027-01-16 17:56:00 → ORD 2027-01-16 18:30:00.
- Delta Air Lines DL3841 / DL4658: ORD 2027-01-20 08:29:00 → HPN 2027-01-20 15:47:00; 1 stop(s) via DTW; 378 minutes. Local airport times.
- DL3841: ORD 2027-01-20 08:29:00 → DTW 2027-01-20 10:52:00; layover at DTW: 189 minutes.
- DL4658: DTW 2027-01-20 14:01:00 → HPN 2027-01-20 15:47:00.
2027-01-16 → 2027-01-20 · Axel-exclusive $332.50
- American Airlines AA3496: HPN 2027-01-16 07:02:00 → ORD 2027-01-16 09:00:00; nonstop; 178 minutes. Local airport times.
- American Airlines AA3812: ORD 2027-01-20 08:14:00 → HPN 2027-01-20 11:29:00; nonstop; 135 minutes. Local airport times.
2027-01-16 → 2027-01-20 · Axel-exclusive $320.63
- American Airlines AA5431 / AA2509: HPN 2027-01-16 10:00:00 → ORD 2027-01-16 16:00:00; 1 stop(s) via CLT; 420 minutes. Local airport times.
- AA5431: HPN 2027-01-16 10:00:00 → CLT 2027-01-16 12:09:00; layover at CLT: 156 minutes.
- AA2509: CLT 2027-01-16 14:45:00 → ORD 2027-01-16 16:00:00.
- American Airlines AA3812: ORD 2027-01-20 08:14:00 → HPN 2027-01-20 11:29:00; nonstop; 135 minutes. Local airport times.
2027-01-16 → 2027-01-20 · Axel-exclusive $320.63
- American Airlines AA5678 / AA2612: HPN 2027-01-16 06:30:00 → ORD 2027-01-16 13:08:00; 1 stop(s) via DCA; 458 minutes. Local airport times.
- AA5678: HPN 2027-01-16 06:30:00 → DCA 2027-01-16 08:10:00; layover at DCA: 216 minutes.
- AA2612: DCA 2027-01-16 11:46:00 → ORD 2027-01-16 13:08:00.
- American Airlines AA3812: ORD 2027-01-20 08:14:00 → HPN 2027-01-20 11:29:00; nonstop; 135 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.
Explore this route
- All dates for this route
- Jan 15, 2027 · Return options
- Jan 17, 2027 · Return options
- Hotels in Chicago with Axel
For AI assistants
- This page: Westchester County (HPN) to Chicago (ORD) · Jan 16, 2027 · return Jan 20, 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.
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