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$127+ Cheap flights from Chicago (CHI) to Newburgh, NY

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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — JFK
Aug 7 — Aug 141
Thu 8/7
Thu 8/14
1 adult, Economy
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Cheap flight deals from Chicago to Newburgh

Keep the following information in mind while searching for Chicago to Newburgh flight deals. Data was last updated August 2, 2025.

Round-trip from

$212
(Mytrip)

One-way from

$127
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$189
From Chicago (CHI) to Newburgh
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One-way flight from Chicago (CHI) to Newburgh
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Highest demand for flights based on searches. 5% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Chicago to Newburgh

Cheapest flights from Chicago to Newburgh
Explore the most affordable flight options available from Chicago to Newburgh. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 2, 2025.

This Mytrip deal was found by Cheapflights users on 7/31. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/26:44 pmORD - SWF
1 stop15h 37mMultiple Airlines
Mon 10/611:01 amSWF - ORD
1 stop12h 47mMultiple Airlines
Deal found 7/31$230
This Mytrip deal was found by Cheapflights users on 7/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/82:46 pmMDW - SWF
2 stops18h 27mMultiple Airlines
Sun 8/107:52 pmSWF - MDW
2 stops19h 04mMultiple Airlines
Deal found 7/30$524

Cheapflights Fare Finder

 
Customize your flight search to find flights from Chicago to Newburgh 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 August 2, 2025.
Use the filters below to find and compare flights from Chicago to Newburgh that are best for you.

Fly from

Chicago

Fly to

Newburgh

Route

Depart

Return

Price

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Thu 10/2

6:44 pm-11:21 am

1 stop15h 37m

New Windsor Stewart

Mon 10/6

11:01 am-10:48 pm

1 stop12h 47m

$230

ChicagoNew Windsor

ORD - SWF

ORDSWF

Chicago O'Hare Intl

Sat 8/30

5:21 pm-11:23 am

1 stop17h 02m

$127

ChicagoNew Windsor

MDW - SWF

MDWSWF

Chicago Midway

Fri 8/15

2:54 pm-10:13 am

2 stops18h 19m

$166

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/31

Best time to book a flight from Chicago to Newburgh

Have a flexible travel schedule? Discover the best time to fly to Newburgh from Chicago with our price prediction graph.
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 Chicago to Newburgh

What is the cheapest month to book a flight from Chicago to Newburgh?

Currently, January is the cheapest month in which you can book a flight from Chicago to Newburgh (average of $236). Flying from Chicago to Newburgh in June is currently the most expensive (average of $313). 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 CHI to N3W?

Find hourly flight availability from Chicago to Newburgh. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 2, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago to Newburgh as you normally would.

What is the cheapest day to fly from Chicago to Newburgh?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Newburgh. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Chicago to Newburgh flight should consider departing on Friday afternoons when fares are most often at their lowest. Friday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Chicago to Newburgh

Explore weekly flight availability from Chicago to Newburgh. 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 August 2, 2025.

The most flights from CHI to N3W are scheduled on a Friday (51 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (30 on average).

Reviews of airlines servicing Newburgh

Get insights into the airlines that provide service to Newburgh. 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 Newburgh. Reviews last updated August 2, 2025.
Read through reviews of airlines operating flights from Chicago to Newburgh, such as Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Allegiant Air
7.2
Good
702 reviews

Entertainment

5.5

Food

5.9

Overall

7.2

Boarding

7.6

Comfort

6.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.
Allegiant Air
7.2
Good
702 reviews
Allegiant Air
7.2
Good
702 reviews

Entertainment

5.5

Food

5.9

Overall

7.2

Boarding

7.6

Comfort

6.8

Crew

8.1

Reviews

1 / 20
10.0
Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.

Related info for your journey

Find useful and relevant information for your journey from Chicago to Newburgh. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the most reliable airlines from Chicago to Newburgh?

    The top 3 most reliable airlines when flying from Chicago to Newburgh are Cathay Pacific (100%), Republic Airways (89%) and Iberia (86%).

  • What are the cheapest flights from Chicago to Newburgh?

    Looking for the cheapest flight from Chicago to Newburgh? While on average our users pay $2,032, our data indicates the cheapest price to be $80. The most popular route (Chicago O'Hare Intl - New Windsor Stewart), is priced around $230.

  • Can I find deals for flights from Chicago to Newburgh that include hotel bookings?

    Yes. In addition to deals on Chicago to Newburgh flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Newburgh?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Newburgh.

  • Can I find deals for business class flights from Chicago to Newburgh?

    Yes. Cheapflights offers flight deals from Chicago to Newburgh by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Chicago to Newburgh?

    Currently, January is the cheapest month in which you can book a flight from Chicago to Newburgh (average of $236). Flying from Chicago to Newburgh in June is currently the most expensive (average of $313). 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.

See more FAQs

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Alternative routes for Chicago to Newburgh

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Chicago to Newburgh

Discover the top 7 airlines that operate flights from Chicago to Newburgh. 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 August 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$59Average$139FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$73Average$218FlexibilityNo cancel feeOn-time62%
FrontierCheapest$79Average$255FlexibilityNo cancel feeOn-time62%
DeltaCheapest$108Average$319FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$136Average$302FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$147Average$280FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$152Average$281FlexibilityNo cancel feeOn-time63%

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