$121+ Cheap flights from White Plains (HPN) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/29. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — CHI
may. 7 — may. 141
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from White Plains to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheapflights Tip: The best prices from White Plains Westchester County to Chicago are usually found in January or September, booked 86 days in advance, depart on a Saturday or Tuesday and return on a Wednesday
Cheap flight deals from White Plains to Chicago
Cheapest
Best
Last-minute
One-way
Cheapest flights from White Plains to ChicagoExplore the most affordable flight options available from White Plains to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 7, 2026.
Explore the most affordable flight options available from White Plains to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on abril 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/412:08 pm
HPN
- ORD
1 stop11h 58m
Multiple Airlines
mié. 5/61:59 pm
ORD
- HPN
2 stops30h 00m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$373
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/2012:08 pm
HPN
- ORD
1 stop11h 58m
Multiple Airlines
dom. 4/265:50 am
ORD
- HPN
2 stops28h 38m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$388
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/15:45 pm
HPN
- ORD
Nonstop2h 55m
American Airlines
sáb. 8/88:18 am
ORD
- HPN
Nonstop2h 10m
American Airlines
Deal found 4/5![American Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/2112:08 pm
HPN
- ORD
2 stops25h 52m
Multiple Airlines
dom. 4/262:10 pm
ORD
- HPN
1 stop20h 18m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/266:00 am
HPN
- MDW
1 stop6h 56m
Delta
sáb. 5/309:22 am
MDW
- HPN
1 stop5h 27m
Delta
Deal found 4/3![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/16:29 am
HPN
- ORD
1 stop7h 08m
Delta
sáb. 8/87:01 am
ORD
- HPN
1 stop3h 52m
Delta
Deal found 4/5![Delta logo]()
$415
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/2012:08 pm
HPN
- ORD
1 stop11h 58m
Multiple Airlines
mar. 4/2110:31 am
ORD
- HPN
2 stops25h 16m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$417
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/266:40 pm
HPN
- ORD
2 stops16h 49m
Delta
sáb. 5/307:00 am
ORD
- HPN
1 stop3h 51m
Delta
Deal found 4/3![Delta logo]()
$424
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/275:48 pm
HPN
- ORD
Nonstop2h 48m
American Airlines
mié. 7/112:40 pm
ORD
- HPN
Nonstop2h 19m
American Airlines
Deal found 4/6![American Airlines logo]()
$425
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/221:27 pm
HPN
- ORD
2 stops23h 05m
Multiple Airlines
dom. 4/262:10 pm
ORD
- HPN
1 stop20h 18m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/96:35 pm
HPN
- ORD
Nonstop2h 55m
American Airlines
lun. 5/116:36 pm
ORD
- HPN
Nonstop2h 23m
American Airlines
Deal found 4/6![American Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/812:45 pm
HPN
- MDW
1 stop6h 46m
Delta
sáb. 9/196:00 am
MDW
- HPN
1 stop5h 13m
Delta
Deal found 4/7![Delta logo]()
$435
Best flights from White Plains to ChicagoDiscover carefully curated flight deals from White Plains to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated abril 7, 2026.
Discover carefully curated flight deals from White Plains to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated abril 7, 2026.
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/266:40 pm
HPN
- MDW
2 stops15h 03m
Delta
sáb. 5/309:22 am
MDW
- HPN
1 stop5h 27m
Delta
Deal found 4/3![Delta logo]()
$424
This KAYAK deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/44:30 pm
HPN
- ORD
Nonstop2h 55m
American Airlines
jue. 5/74:17 pm
ORD
- HPN
1 stop5h 43m
American Airlines
Deal found 4/3![American Airlines logo]()
$823
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/1312:35 pm
HPN
- MDW
1 stop6h 31m
Delta
lun. 6/156:05 am
MDW
- HPN
1 stop7h 23m
Delta
Deal found 4/5![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/612:31 pm
HPN
- MDW
1 stop7h 02m
Delta
lun. 6/86:05 am
MDW
- HPN
1 stop5h 04m
Delta
Deal found 4/6![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/254:19 pm
HPN
- MDW
1 stop6h 27m
Delta
mié. 9/309:20 am
MDW
- HPN
1 stop6h 20m
Delta
Deal found 4/6![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/44:19 pm
HPN
- ORD
1 stop6h 01m
Delta
mar. 9/89:30 am
ORD
- HPN
1 stop6h 10m
Delta
Deal found 4/2![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/912:30 pm
HPN
- ORD
1 stop4h 59m
Delta
lun. 5/117:00 am
ORD
- HPN
1 stop3h 50m
Delta
Deal found 4/5![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/612:31 pm
HPN
- ORD
1 stop4h 58m
Delta
dom. 6/77:01 am
ORD
- HPN
1 stop3h 54m
Delta
Deal found 4/6![Delta logo]()
$449
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/3112:35 pm
HPN
- MDW
1 stop6h 50m
Delta
sáb. 8/19:49 am
MDW
- HPN
1 stop5h 43m
Delta
Deal found 4/7![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/54:29 pm
HPN
- MDW
1 stop5h 40m
Delta
mié. 6/109:17 am
MDW
- HPN
1 stop5h 32m
Delta
Deal found 4/7![Delta logo]()
$469
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/2212:30 pm
HPN
- MDW
1 stop6h 28m
Delta
sáb. 4/256:00 am
MDW
- HPN
1 stop7h 29m
Delta
Deal found 4/5![Delta logo]()
$475
This KAYAK deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/196:35 pm
HPN
- ORD
Nonstop2h 55m
American Airlines
jue. 5/215:00 am
ORD
- HPN
1 stop4h 30m
American Airlines
Deal found 4/3![American Airlines logo]()
$1,047
This Delta deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 9/114:19 pm
HPN
- MDW
1 stop6h 27m
Delta
lun. 9/149:30 am
MDW
- HPN
1 stop6h 03m
Delta
Deal found 4/5![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/115:10 pm
HPN
- ORD
1 stop4h 21m
Delta
dom. 6/147:01 am
ORD
- HPN
1 stop3h 54m
Delta
Deal found 4/3![Delta logo]()
$483
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/174:29 pm
HPN
- MDW
1 stop6h 59m
Delta
sáb. 4/189:46 am
MDW
- HPN
1 stop5h 54m
Delta
Deal found 4/4![Delta logo]()
$509
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 6/2512:35 pm
HPN
- MDW
1 stop6h 56m
Delta
sáb. 6/279:17 am
MDW
- HPN
1 stop5h 32m
Delta
Deal found 4/4![Delta logo]()
$517
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/2312:30 pm
HPN
- MDW
1 stop6h 28m
Delta
lun. 4/279:27 am
MDW
- HPN
1 stop5h 22m
Delta
Deal found 4/6![Delta logo]()
$543
This KAYAK deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/412:30 pm
HPN
- ORD
1 stop9h 10m
Delta
jue. 5/76:24 am
ORD
- HPN
1 stop9h 11m
Delta
Deal found 4/3![Delta logo]()
$756
This KAYAK deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/204:29 pm
HPN
- ORD
1 stop5h 56m
Delta
jue. 4/2311:19 am
ORD
- HPN
1 stop5h 57m
Delta
Deal found 4/5![Delta logo]()
$787
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/2812:30 pm
HPN
- ORD
1 stop4h 48m
Delta
mié. 4/295:15 am
ORD
- HPN
1 stop5h 45m
Delta
Deal found 4/2![Delta logo]()
$897
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/2112:45 pm
HPN
- ORD
1 stop6h 56m
Delta
dom. 8/237:10 am
ORD
- HPN
1 stop3h 34m
Delta
Deal found 4/4![Delta logo]()
$991
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/212:30 pm
HPN
- ORD
2 stops8h 22m
Delta
sáb. 5/99:25 am
ORD
- HPN
1 stop5h 24m
Delta
Deal found 4/4![Delta logo]()
$1,129
Last-minute flights from White Plains to ChicagoDiscover last-minute flight deals from White Plains to Chicago. Data last updated abril 7, 2026 and is based on user searches.
Discover last-minute flight deals from White Plains to Chicago. Data last updated abril 7, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/2012:08 pm
HPN
- ORD
1 stop11h 58m
Multiple Airlines
dom. 4/265:50 am
ORD
- HPN
2 stops28h 38m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$388
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/2012:08 pm
HPN
- ORD
1 stop11h 58m
Multiple Airlines
mar. 4/2110:31 am
ORD
- HPN
2 stops25h 16m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$417
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/2112:08 pm
HPN
- ORD
2 stops25h 52m
Multiple Airlines
dom. 4/262:10 pm
ORD
- HPN
1 stop20h 18m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$413
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/221:27 pm
HPN
- ORD
2 stops23h 05m
Multiple Airlines
dom. 4/262:10 pm
ORD
- HPN
1 stop20h 18m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/2912:00 pm
HPN
- ORD
Nonstop2h 43m
American Airlines
mié. 5/66:36 pm
ORD
- HPN
Nonstop2h 23m
American Airlines
Deal found 4/6![American Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/26:00 am
HPN
- MDW
1 stop5h 14m
Delta
sáb. 5/910:45 am
MDW
- HPN
1 stop6h 15m
Delta
Deal found 4/4![Delta logo]()
$445
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/412:08 pm
HPN
- ORD
1 stop11h 58m
Multiple Airlines
mié. 5/61:59 pm
ORD
- HPN
2 stops30h 00m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$373
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/96:35 pm
HPN
- ORD
Nonstop2h 55m
American Airlines
lun. 5/116:36 pm
ORD
- HPN
Nonstop2h 23m
American Airlines
Deal found 4/6![American Airlines logo]()
$429
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/234:30 pm
HPN
- ORD
Nonstop2h 48m
American Airlines
mar. 5/2612:40 pm
ORD
- HPN
Nonstop2h 19m
American Airlines
Deal found 4/7![American Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/266:00 am
HPN
- MDW
1 stop6h 56m
Delta
sáb. 5/309:22 am
MDW
- HPN
1 stop5h 27m
Delta
Deal found 4/3![Delta logo]()
$415
This Delta deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 5/266:40 pm
HPN
- ORD
2 stops16h 49m
Delta
sáb. 5/307:00 am
ORD
- HPN
1 stop3h 51m
Delta
Deal found 4/3![Delta logo]()
$424
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 5/2712:50 pm
HPN
- ORD
1 stop6h 51m
Delta
sáb. 5/308:10 am
ORD
- HPN
1 stop5h 19m
Delta
Deal found 4/6![Delta logo]()
$415
One-way flights from White Plains to ChicagoSearch for one-way flight options from White Plains to Chicago. Find affordable one-way fares based on user searches. Data last updated abril 7, 2026.
Search for one-way flight options from White Plains to Chicago. Find affordable one-way fares based on user searches. Data last updated abril 7, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 5/296:09 pm
HPN
- ORD
2 stops30h 04m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$121
This Kiwi.com deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/16:09 pm
HPN
- ORD
3 stops43h 28m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 6/56:09 pm
HPN
- ORD
3 stops19h 28m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 6/612:00 pm
HPN
- ORD
2 stops44h 55m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/116:09 pm
HPN
- ORD
2 stops38h 46m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/98:00 am
HPN
- ORD
2 stops16h 13m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$145
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 8/308:00 am
HPN
- MDW
2 stops28h 09m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/291:27 pm
HPN
- MDW
2 stops33h 52m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$166
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 7/2912:00 pm
HPN
- MDW
2 stops35h 11m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/151:27 pm
HPN
- MDW
3 stops33h 52m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/98:00 am
HPN
- MDW
3 stops28h 09m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 4/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 6/156:09 pm
HPN
- MDW
3 stops18h 03m
Multiple Airlines
Deal found 4/3![Multiple Airlines logo]()
$223
Find flight deals from White Plains to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from White Plains (HPN) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated abril 7, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $373 (Kiwi.com) |
One-way from | $121 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $486 |
Good round-trip deal | $462 or less |
Good one-way deal | $265 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from White Plains to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated abril 7, 2026.
Use the filters below to find and compare flights from White Plains to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
mar. 5/26
6:40 pm-8:43 am
2 stops15h 03m
Chicago Midway
sáb. 5/30
9:22 am-3:49 pm
1 stop5h 27m
$424
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
sáb. 6/13
12:35 pm-6:06 pm
1 stop6h 31m
Chicago Midway
lun. 6/15
6:05 am-2:28 pm
1 stop7h 23m
$449
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
sáb. 6/6
12:31 pm-6:33 pm
1 stop7h 02m
Chicago Midway
lun. 6/8
6:05 am-12:09 pm
1 stop5h 04m
$449
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
vie. 9/25
4:19 pm-9:46 pm
1 stop6h 27m
Chicago Midway
mié. 9/30
9:20 am-4:40 pm
1 stop6h 20m
$449
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
vie. 9/4
4:19 pm-9:20 pm
1 stop6h 01m
Chicago O'Hare Intl
mar. 9/8
9:30 am-4:40 pm
1 stop6h 10m
$449
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
sáb. 5/9
12:30 pm-4:29 pm
1 stop4h 59m
Chicago O'Hare Intl
lun. 5/11
7:00 am-11:50 am
1 stop3h 50m
$449
White PlainsChicago
HPN - ORD
HPNORD
White Plains Westchester County
sáb. 6/6
12:31 pm-4:29 pm
1 stop4h 58m
Chicago O'Hare Intl
dom. 6/7
7:01 am-11:55 am
1 stop3h 54m
$449
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
vie. 7/31
12:35 pm-6:25 pm
1 stop6h 50m
Chicago Midway
sáb. 8/1
9:49 am-4:32 pm
1 stop5h 43m
$469
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
vie. 6/5
4:29 pm-9:09 pm
1 stop5h 40m
Chicago Midway
mié. 6/10
9:17 am-3:49 pm
1 stop5h 32m
$469
White PlainsChicago
HPN - MDW
HPNMDW
White Plains Westchester County
mié. 4/22
12:30 pm-5:58 pm
1 stop6h 28m
Chicago Midway
sáb. 4/25
6:00 am-2:29 pm
1 stop7h 29m
$475
Showing 1-10 of 41 resultsSorted by cheapest first
Compare providers for flights from White Plains to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from White Plains to Chicago in April.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on White Plains-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on White Plains-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from White Plains-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on White Plains-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for White Plains-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from White Plains to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from White Plains with our price prediction graph.
HPN-CHI
HPN-MDW
HPN-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from White Plains to Chicago
HPN-CHI
HPN-MDW
HPN-ORD
How far ahead should I book a flight from White Plains to Chicago?
Use this chart to determine the optimal time to book a round-trip flight from White Plains to Chicago. Price data was last updated on April 3, 2026.
The best time to book flights from White Plains to Chicago is 49 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest month to book a flight from White Plains to Chicago?
Currently, December is the cheapest month in which you can book a flight from White Plains to Chicago (average of $48). Flying from White Plains to Chicago in July is currently the most expensive (average of $119). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from HPN to CHI?
Find hourly flight availability from White Plains to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated abril 7, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from White Plains to Chicago as you normally would.
Weekly flight availability from White Plains to Chicago
Explore weekly flight availability from White Plains to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated abril 7, 2026.
The most flights from HPN to CHI are scheduled on a Tuesday (7 on average). You will have fewer flight options on Friday, which is when the least amount of flights are scheduled (4 on average).
How much does it cost to fly round-trip from White Plains to Chicago?
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated abril 7, 2026.
Peruse reviews from past customers who have flown with Delta and American Airlines from White Plains to Chicago to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Food
7.2
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Food
7.2
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Entertainment
7.8
Boarding
8.1
Crew
8.5
Overall
7.9
Food
7.2
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Related info for your journey
Find useful and relevant information for your journey from White Plains to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Chicago flight routes
Complete your trip
Flights by cabin class
Other flight options
Other flights from White Plains
Popular flights
Alternative routes for White Plains to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Other flights to Chicago
Explore flights to Chicago departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on abril 7, 2026.
Complete your trip
Complete your trip to Chicago by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from White Plains to Chicago by cabin class
Find flights from White Plains to Chicago, based on your preferred cabin class, be it economy, premium economy, business, or first class.
White Plains and Chicago flights
Browse other White Plains and Chicago flight options. Last updated on abril 7, 2026.
Other flights from White Plains
Browse through other flights departing from White Plains. Flights are based on user searches made on Cheapflights and were last updated on abril 7, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from White Plains to Chicago
Discover the top airline that operate flights from White Plains to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated abril 7, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$373 | Average$491 | FlexibilityNo cancel fee | On-time71% |