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Showing 25
of 98
live flights
American Airlines
AA-5401
17:16
05/08/2026
HPN
White Plains Airport
13h 9m
2 Stops
⏱ DCA · 3h 32m DCA Airport ⏱ MKE · 5h 37m MKE Airport
06:25
05/09/2026
+1
ORD
Chicago Airport
₹32,511
per person
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✕ Non-refundable
09:23
05/08/2026
HPN
White Plains Airport
10h 29m
2 Stops
⏱ LEB · 3h 11m LEB Airport ⏱ BOS · 2h 17m BOS Airport
19:52
05/08/2026
ORD
Chicago Airport
₹32,868
per person
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✓ Refundable 🔥 Last 2 seats
09:23
05/08/2026
HPN
White Plains Airport
9h 26m
2 Stops
⏱ LEB · 3h 11m LEB Airport ⏱ BOS · 1h 14m BOS Airport
18:49
05/08/2026
ORD
Chicago Airport
₹32,868
per person
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✓ Refundable 🔥 Last 2 seats
09:23
05/08/2026
HPN
White Plains Airport
12h 37m
2 Stops
⏱ LEB · 3h 11m LEB Airport ⏱ BOS · 4h 32m BOS Airport
22:00
05/08/2026
ORD
Chicago Airport
₹33,391
per person
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✓ Refundable 🔥 Last 2 seats
09:23
05/08/2026
HPN
White Plains Airport
11h 41m
2 Stops
⏱ LEB · 3h 11m LEB Airport ⏱ BOS · 3h 34m BOS Airport
21:04
05/08/2026
ORD
Chicago Airport
₹34,176
per person
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✓ Refundable 🔥 Last 2 seats
07:35
05/08/2026
HPN
White Plains Airport
13h 18m
2 Stops
⏱ MCO · 1h 10m MCO Airport ⏱ BOS · 4h 3m BOS Airport
20:53
05/08/2026
ORD
Chicago Airport
₹35,035
per person
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✕ Non-refundable 5 fare options
18:40
05/08/2026
HPN
White Plains Airport
14h 58m
1 Stop
⏱ ATL · 11h 25m ATL Airport
09:38
05/09/2026
+1
ORD
Chicago Airport
₹35,040
per person
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✕ Non-refundable
09:23
05/08/2026
HPN
White Plains Airport
11h 30m
2 Stops
⏱ LEB · 3h 11m LEB Airport ⏱ BOS · 3h 29m BOS Airport
20:53
05/08/2026
ORD
Chicago Airport
₹35,110
per person
Select →
✕ Non-refundable 🔥 Last 2 seats
American Airlines
AA-5401
17:16
05/08/2026
HPN
White Plains Airport
13h 4m
2 Stops
⏱ DCA · 3h 42m DCA Airport ⏱ CLE · 5h 47m CLE Airport
06:20
05/09/2026
+1
ORD
Chicago Airport
₹36,724
per person
Select →
✕ Non-refundable
American Airlines
AA-5401
17:16
05/08/2026
HPN
White Plains Airport
12h 34m
2 Stops
⏱ DCA · 3h 21m DCA Airport ⏱ GRR · 5h 35m GRR Airport
05:50
05/09/2026
+1
ORD
Chicago Airport
₹38,128
per person
Select →
✕ Non-refundable
17:15
05/08/2026
HPN
White Plains Airport
23h 14m
1 Stop
⏱ DTW · 20h 56m DTW Airport
16:29
05/09/2026
+1
ORD
Chicago Airport
₹39,253
per person
Select →
✕ Non-refundable
12:30
05/08/2026
HPN
White Plains Airport
24h 26m
1 Stop
⏱ DTW · 22h 12m DTW Airport
12:56
05/09/2026
+1
ORD
Chicago Airport
₹39,253
per person
Select →
✕ Non-refundable
16:29
05/08/2026
HPN
White Plains Airport
16h 16m
2 Stops
⏱ ATL · 2h 53m ATL Airport ⏱ DTW · 8h 26m DTW Airport
08:45
05/09/2026
+1
ORD
Chicago Airport
₹40,000
per person
Select →
✕ Non-refundable
18:40
05/08/2026
HPN
White Plains Airport
13h 56m
2 Stops
⏱ ATL · 1h 55m ATL Airport ⏱ MSP · 6h 23m MSP Airport
08:36
05/09/2026
+1
ORD
Chicago Airport
₹41,217
per person
Select →
✕ Non-refundable
12:30
05/08/2026
HPN
White Plains Airport
6h 3m
1 Stop
⏱ DTW · 4h 1m DTW Airport
18:33
05/08/2026
MDW
Chicago Airport
₹41,350
per person
Select →
✕ Non-refundable
American Airlines
AA-5070
17:59
05/08/2026
HPN
White Plains Airport
11h 24m
2 Stops
⏱ CLT · 2h 38m CLT Airport ⏱ DTW · 4h 35m DTW Airport
05:23
05/09/2026
+1
ORD
Chicago Airport
₹42,041
per person
Select →
✕ Non-refundable 5 fare options
12:50
05/08/2026
HPN
White Plains Airport
7h 36m
1 Stop
⏱ ATL · 4h 3m ATL Airport
20:26
05/08/2026
ORD
Chicago Airport
₹42,183
per person
Select →
✕ Non-refundable
American Airlines
AA-3395
06:00
05/08/2026
HPN
White Plains Airport
29h 4m
1 Stop
⏱ MIA · 23h 21m MIA Airport
11:04
05/09/2026
+1
ORD
Chicago Airport
₹42,249
per person
Select →
✕ Non-refundable 5 fare options
12:30
05/08/2026
HPN
White Plains Airport
7h 44m
1 Stop
⏱ DTW · 5h 27m DTW Airport
20:14
05/08/2026
ORD
Chicago Airport
₹42,342
per person
Select →
✕ Non-refundable
American Airlines
AA-5070
17:59
05/08/2026
HPN
White Plains Airport
11h 12m
2 Stops
⏱ CLT · 2h 28m CLT Airport ⏱ GRR · 4h 37m GRR Airport
05:11
05/09/2026
+1
ORD
Chicago Airport
₹42,874
per person
Select →
✕ Non-refundable 5 fare options
06:00
05/08/2026
HPN
White Plains Airport
12h 5m
2 Stops
⏱ ATL · 2h 33m ATL Airport ⏱ DTW · 4h 42m DTW Airport
18:05
05/08/2026
ORD
Chicago Airport
₹43,089
per person
Select →
✕ Non-refundable
06:00
05/08/2026
HPN
White Plains Airport
14h 14m
2 Stops
⏱ ATL · 2h 33m ATL Airport ⏱ DTW · 6h 47m DTW Airport
20:14
05/08/2026
ORD
Chicago Airport
₹43,089
per person
Select →
✕ Non-refundable
12:50
05/08/2026
HPN
White Plains Airport
9h 3m
1 Stop
⏱ ATL · 5h 35m ATL Airport
21:53
05/08/2026
ORD
Chicago Airport
₹43,185
per person
Select →
✕ Non-refundable
10:29
05/08/2026
HPN
White Plains Airport
9h 57m
1 Stop
⏱ ATL · 6h 23m ATL Airport
20:26
05/08/2026
ORD
Chicago Airport
₹43,185
per person
Select →
✕ Non-refundable
06:00
05/08/2026
HPN
White Plains Airport
10h 56m
1 Stop
⏱ ATL · 7h 13m ATL Airport
16:56
05/08/2026
ORD
Chicago Airport
₹43,185
per person
Select →
✕ Non-refundable
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White Plains to Chicago — what to expect when booking
The HPN–ORD route is served by multiple carriers throughout the year.
Fares on this route can move quickly — a price available now may not be there 30 minutes later.
If your dates are flexible, try shifting your departure by a day or two using the date strip above.
Mid-week departures often show lower base fares compared to weekend starts on many routes.
Before you book
Compare nearby dates The date strip above lets you scan nearby fares without restarting the search.
Open full search for more control Route page shows a limited live set. Full search opens the complete inventory with fresh results.
Check fare details Each result shows baggage, refundability and fare details before you proceed.
More flights from White Plains (HPN)
15 routes
More flights from Chicago (ORD)
195 routes
❓ Frequently asked questions — White Plains to Chicago flights
▼ Is it worth booking White Plains to Chicago flights in advance?
Generally yes — fares on most routes are most competitive around 4–6 weeks before departure. Booking earlier usually means better availability and a lower base fare when your dates are fixed.
▼ How far is White Plains from Chicago by air?
The straight-line distance between White Plains,USA (HPN) and Chicago,USA (ORD) is approximately shown in the route details above. Actual flying distance may vary slightly depending on routing.
▼ Are there non-stop flights from HPN to ORD?
Non-stop availability on this route varies by airline schedule and season. Use the filters below to quickly check whether direct options are available on your selected date.
▼ What is the cheapest day to fly from White Plains to Chicago?
Mid-week departures often show lower prices than weekend travel on many routes. Use the date strip above to compare nearby days quickly.