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$81+ Cheap flights from Worcester, MA (ORH) 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 2/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — CHI
Dec 20 — Dec 271
Sat 12/20
Sat 12/27
1 adult, Economy
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Find flight deals from Worcester to Chicago

Cheapest flights from Worcester to Chicago
Explore the most affordable flight options available from Worcester to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on November 20, 2025.

This American Airlines deal was found by Cheapflights users on 11/18. 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.
Wed 12/241:36 pmORH - ORD
1 stop20h 06mAmerican Airlines
Sat 1/37:19 pmORD - ORH
1 stop16h 58mAmerican Airlines
Deal found 11/18$173
This Delta deal was found by Cheapflights users on 11/19. 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.
Thu 12/44:05 pmORH - ORD
1 stop7h 25mDelta
Mon 12/89:40 amORD - ORH
1 stop4h 45mDelta
Deal found 11/19$192
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Tue 12/23:17 pmORH - ORD
1 stop6h 09mAmerican Airlines
Thu 12/45:00 amORD - ORH
2 stops9h 09mAmerican Airlines
Deal found 11/19$202
This Delta deal was found by Cheapflights users on 11/19. 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.
Fri 12/54:05 pmORH - ORD
1 stop5h 33mDelta
Mon 12/89:40 amORD - ORH
1 stop4h 45mDelta
Deal found 11/19$212
This American Airlines deal was found by Cheapflights users on 11/18. 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.
Wed 12/241:36 pmORH - ORD
2 stops19h 50mAmerican Airlines
Sun 1/48:45 pmORD - ORH
1 stop15h 32mAmerican Airlines
Deal found 11/18$217
This American Airlines deal was found by Cheapflights users on 11/19. 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.
Fri 12/191:47 pmORH - ORD
1 stop18h 14mAmerican Airlines
Thu 12/256:00 amORD - ORH
1 stop6h 11mAmerican Airlines
Deal found 11/19$224
This KAYAK deal was found by Cheapflights users on 11/19. 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.
Mon 12/84:05 pmORH - ORD
1 stop5h 33mDelta
Tue 12/99:40 amORD - ORH
1 stop4h 45mDelta
Deal found 11/19$228
This American Airlines deal was found by Cheapflights users on 11/18. 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.
Thu 12/251:36 pmORH - ORD
2 stops18h 54mAmerican Airlines
Tue 12/306:40 amORD - ORH
1 stop5h 37mAmerican Airlines
Deal found 11/18$234

Cheap flight deals from Worcester to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Worcester (ORH) 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 November 20, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$154
(American Airlines)

One-way from

$81
(American Airlines)

Popular in

March

Cheapest in

September

Average price

$247
Provider with most accurate pricing for Worcester-Chicago (CHI) flight deals.
Search Deals
Provider most trusted by Cheapflights users for Worcester-Chicago (CHI) flights.
Search Deals
From Worcester to Chicago (CHI)
Search Deals
One-way flight from Worcester to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 7% potential increase in price ($19 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Worcester 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 November 20, 2025.
Use the filters below to find and compare flights from Worcester to Chicago that are best for you.

Fly from

Worcester

Fly to

Chicago

Route

Depart

Return

Price

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 1/23

2:18 pm-9:04 am

1 stop19h 46m

Chicago O'Hare Intl

Tue 1/27

5:26 pm-1:53 pm

1 stop19h 27m

$154

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 1/22

2:18 pm-9:04 am

1 stop19h 46m

Chicago O'Hare Intl

Tue 1/27

5:26 pm-1:53 pm

1 stop19h 27m

$154

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 12/24

1:36 pm-8:42 am

1 stop20h 06m

Chicago O'Hare Intl

Sat 1/3

7:19 pm-1:17 pm

1 stop16h 58m

$173

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 12/4

4:05 pm-10:30 pm

1 stop7h 25m

Chicago O'Hare Intl

Mon 12/8

9:40 am-3:25 pm

1 stop4h 45m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 1/22

4:16 pm-10:34 pm

1 stop7h 18m

Chicago O'Hare Intl

Tue 1/27

7:10 am-3:36 pm

1 stop7h 26m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 2/12

1:44 pm-10:10 am

1 stop21h 26m

$81

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 12/9

3:34 pm-7:35 pm

1 stop5h 01m

$84

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 12/26

1:45 pm-7:01 am

1 stop18h 16m

$131

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 11/26

3:17 pm-10:56 pm

1 stop8h 39m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/18

Compare providers for flights from Worcester 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 Worcester to Chicago in November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Worcester, Massachusetts-Chicago flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Worcester, Massachusetts-Chicago flight deals on Cheapflights vs. eDreams >95% of the time. Price accuracy is based on data collected from Worcester, Massachusetts-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Worcester, Massachusetts-Chicago flights, Cheapflights users trust eDreams the most. eDreams 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 Worcester, Massachusetts-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 Worcester to Chicago

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

What is the cheapest month to book a flight from Worcester, Massachusetts to Chicago?

Currently, April is the cheapest month in which you can book a flight from Worcester, Massachusetts to Chicago (average of $89). Flying from Worcester, Massachusetts to Chicago in February is currently the most expensive (average of $124). 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 ORH to CHI?

Find hourly flight availability from Worcester 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 November 20, 2025.

Unlike in the afternoon, when flights are generally more expensive, you can save up to 81% on flights from Worcester, Massachusetts to Chicago by exploring options for tickets in the evening.

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 November 20, 2025.
See what other customers who have flown with Delta from Worcester to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,004 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,004 reviews
Delta
7.9
Good
8,004 reviews

Boarding

8.1

Overall

7.9

Crew

8.5

Comfort

7.9

Entertainment

7.9

Food

7.3

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

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

  • What airport do you fly from for flights from Worcester to Chicago?

    Most people fly from Worcester (ORH) if they book a flight from Worcester to Chicago. On average, Worcester has 0 outbound flights to Chicago per day from 0 airlines. Worcester is conveniently located just 3.8 mi from Worcester’s city center.

  • How long is the flight from Worcester, Massachusetts to Chicago?

    There are many flights that can get you from Worcester, Massachusetts to Chicago in 19h 46m. Fly via American Airlines to get the fastest option. There are 820 mi between Worcester, Massachusetts and Chicago.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Worcester 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 Worcester, Massachusetts to Chicago?

    Currently, April is the cheapest month in which you can book a flight from Worcester, Massachusetts to Chicago (average of $89). Flying from Worcester, Massachusetts to Chicago in February is currently the most expensive (average of $124). 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
Lansing
Hammond
Porter
Benton Harbor
Merrillville

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