Cheap Flights From Westchester County (HPN) To O'Hare Intl. (ORD)

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Cheapest Flights from White Plains (HPN) to Chicago (ORD)

The cheapest flights to O'Hare Intl. found within the past 7 days were CA $791 round trip and one way. Prices and availability subject to change. Additional terms may apply.

Thu, Aug 13 - Tue, Sep 1
HPN
White Plains
ORD
Chicago
CA $791 Roundtrip, found 5 days ago
CA $791
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Thu, Aug 13 from White Plains to Chicago, returning Tue, Sep 1, priced at CA $791 found 5 days ago
Thu, Aug 13 - Tue, Sep 1
HPN
White Plains
ORD
Chicago
CA $849 Roundtrip, found 5 days ago
CA $849
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Thu, Aug 13 from White Plains to Chicago, returning Tue, Sep 1, priced at CA $849 found 5 days ago
Thu, Aug 13 - Tue, Sep 1
HPN
White Plains
ORD
Chicago
CA $1,070 Roundtrip, found 5 days ago
CA $1,070
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Thu, Aug 13 from White Plains to Chicago, returning Tue, Sep 1, priced at CA $1,070 found 5 days ago
Thu, Aug 13 - Tue, Sep 1
HPN
White Plains
ORD
Chicago
CA $1,158 Roundtrip, found 5 days ago
CA $1,158
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Thu, Aug 13 from White Plains to Chicago, returning Tue, Sep 1, priced at CA $1,158 found 5 days ago
Thu, Aug 13 - Tue, Sep 1
HPN
White Plains
ORD
Chicago
CA $1,199 Roundtrip, found 5 days ago
CA $1,199
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Thu, Aug 13 from White Plains to Chicago, returning Tue, Sep 1, priced at CA $1,199 found 5 days ago
Thu, Aug 13 - Tue, Sep 1
HPN
White Plains
ORD
Chicago
CA $1,463 Roundtrip, found 5 days ago
CA $1,463
Roundtrip
found 5 days ago
Select Cape Air flight, departing Thu, Aug 13 from White Plains to Chicago, returning Tue, Sep 1, priced at CA $1,463 found 5 days ago
Thu, Aug 13 - Tue, Sep 1
HPN
White Plains
ORD
Chicago
CA $1,619 Roundtrip, found 5 days ago
CA $1,619
Roundtrip
found 5 days ago
Select Cape Air flight, departing Thu, Aug 13 from White Plains to Chicago, returning Tue, Sep 1, priced at CA $1,619 found 5 days ago

O'Hare Intl. flight + hotel packages - economy flights

Price found within the past 48 hours. Click for updated prices.
Eaglewood Resort and Spa

Eaglewood Resort and Spa

4 out of 5
Price was CA $691, price is now CA $586 per person
CA $586
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
Price was CA $708, price is now CA $601 per person
CA $601
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Wyndham Garden Elk Grove Village/O'Hare

Wyndham Garden Elk Grove Village/O'Hare

3 out of 5
Price was CA $686, price is now CA $596 per person
CA $596
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Chicago Marriott Suites Deerfield

Chicago Marriott Suites Deerfield

4 out of 5
Price was CA $673, price is now CA $586 per person
CA $586
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
Price was CA $769, price is now CA $685 per person
CA $685
per person
Aug 21 - Aug 24
found 1 day ago
Roundtrip flight included
New York (JFK) to Chicago (ORD)
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Frequently asked questions

Are there direct flights from White Plains Airport to ORD?
Your next grand adventure is on the other side of a single flight. You can travel direct from HPN to O'Hare Intl. Airport (ORD) with multiple airlines, including United Airlines and American Airlines.
What airlines fly from HPN to ORD?
There are several airlines that advertise direct flights from White Plains Airport to ORD. United Airlines (UA) is one of the most reputable, offering approximately 60 flights every month. Don't forget to also browse the deals available through American Airlines (AA). Another leading airline, it operates 30 flights every month on the Westchester County to Chicago route. Compare the two to score the best fare.
What is the best day to buy a plane ticket?
Airfares offered on Friday tend to be the cheapest, according to flight demand on Travelocity.ca in 2021. Purchasing your airfares on a Thursday or Saturday can also provide better value, however our advice if you're looking to save money is to avoid booking on a Wednesday or Sunday. Our data shows that those two days have the highest ticket values on average, so keep this in mind if you're browsing flight deals.
What are the cheapest days to fly?
Frequent travellers may already know this, but earlier in the week is often the cheapest time to fly. Flights departing on a Monday are the cheapest of the week. Since flights towards the middle of the week tend to be more popular, this causes the prices to rise. This is why, on average, airfares booked on Travelocity.ca in 2021 were most expensive for Wednesday departures.
How far in advance can you book a flight?
Here's the deal: It is typically possible to start comparing international airfares on Travelocity.ca up to 12 months in advance. However, it does depend on the carrier as not all airlines release their prices that far out. According to our 2021 flight demand trends, last minute planners can still bag a bargain with some of the cheapest fares appearing 2-4 weeks prior to their travel dates.*According to flight demand on Travelocity.ca from January to December 2021. Savings are subject to change and may vary depending on selections made.

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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.