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$99+ Cheap flights from Newburgh, NY 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
JFK — CHI
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheap flight deals from Newburgh to Chicago

Keep the following information in mind while searching for Newburgh to Chicago flight deals. Data was last updated July 31, 2025.

Round-trip from

$218
(Mytrip)

One-way from

$99
(Mytrip)

Popular in

June

Cheapest in

September

Average price

$267
From Newburgh to Chicago (CHI)
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One-way flight from Newburgh to Chicago (CHI)
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Highest demand for flights based on searches. 12% potential increase in price ($32 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 July 2025
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Find flight deals from Newburgh to Chicago

Cheapest flights from Newburgh to Chicago
Explore the most affordable flight options available from Newburgh to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2025.

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 8/225:36 pmSWF - ORD
1 stop17h 55mMultiple Airlines
Sun 8/245:16 pmORD - SWF
1 stop15h 56mMultiple Airlines
Deal found 7/30$218
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.
Mon 8/257:37 pmSWF - RFD
1 stop14h 52mMultiple Airlines
Thu 8/283:06 pmRFD - SWF
2 stops20h 59mMultiple Airlines
Deal found 7/31$256

Cheapflights Fare Finder

 
Customize your flight search to find flights from Newburgh 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 July 31, 2025.
Use the filters below to find and compare flights from Newburgh to Chicago that are best for you.

Fly from

Newburgh

Fly to

Chicago

Route

Depart

Return

Price

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Fri 8/22

5:36 pm-10:31 am

1 stop17h 55m

Chicago O'Hare Intl

Sun 8/24

5:16 pm-10:12 am

1 stop15h 56m

$218

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Mon 8/25

7:37 pm-9:29 am

1 stop14h 52m

Chicago Greater Rockford

Thu 8/28

3:06 pm-1:05 pm

2 stops20h 59m

$256

New WindsorChicago

SWF - ORD

SWFORD

New Windsor Stewart

Mon 8/18

7:37 pm-10:31 am

1 stop15h 54m

$99

New WindsorChicago

SWF - RFD

SWFRFD

New Windsor Stewart

Sun 10/26

7:11 pm-7:54 am

1 stop13h 43m

$102

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Sun 8/17

8:33 pm-6:17 pm

2 stops22h 44m

$201

New WindsorChicago

SWF - MDW

SWFMDW

New Windsor Stewart

Thu 8/7

7:52 pm-1:56 pm

2 stops19h 04m

$414

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Best time to book a flight from Newburgh to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Newburgh 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 Newburgh to Chicago

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

Currently, August is the cheapest month in which you can book a flight from Newburgh to Chicago (average of $245). Flying from Newburgh to Chicago in March is currently the most expensive (average of $321). 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 N3W to CHI?

Find hourly flight availability from Newburgh 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 July 31, 2025.

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

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

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

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

Weekly flight availability from Newburgh to Chicago

Explore weekly flight availability from Newburgh 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 July 31, 2025.

The most flights from N3W to CHI are scheduled on a Thursday (50 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (29 on average).

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 July 31, 2025.
Read through reviews of airlines operating flights from Newburgh to Chicago, 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

Comfort

6.8

Overall

7.2

Boarding

7.6

Crew

8.1

Entertainment

5.5

Food

5.9

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

Comfort

6.8

Overall

7.2

Boarding

7.6

Crew

8.1

Entertainment

5.5

Food

5.9

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 Newburgh to Chicago. 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 popular routes from Newburgh to Chicago?

    Most travelers choose New Windsor Stewart - Chicago O'Hare Intl, New Windsor Stewart - Chicago Greater Rockford or New Windsor Stewart - Chicago Midway when deciding on the best route from Newburgh to Chicago.

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

    Before booking your flight to Chicago from Newburgh, check out the most reliable airlines to get you to your destination on time: Cathay Pacific (100%), China Airlines (83%), LATAM Airlines( 76%).

  • What are the cheapest flights from Newburgh to Chicago?

    The cheapest flight price from Newburgh to Chicago is $84. On average you can expect to pay $651. The most popular route, (New Windsor Stewart - Chicago O'Hare Intl), can usually be booked for $234.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Newburgh to Chicago 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 Newburgh to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Newburgh to Chicago (average of $245). Flying from Newburgh to Chicago in March is currently the most expensive (average of $321). 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

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Alternative routes for Newburgh to Chicago

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

Discover the top 7 airlines that operate flights from Newburgh 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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$66Average$199FlexibilityNo cancel feeOn-time65%
JetBlueCheapest$83Average$229FlexibilityNo cancel feeOn-time62%
United AirlinesCheapest$96Average$330FlexibilityNo cancel feeOn-time69%
FrontierCheapest$98Average$292FlexibilityNo cancel feeOn-time62%
DeltaCheapest$121Average$358FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$137Average$316FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$152Average$253FlexibilityNo cancel feeOn-time63%

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