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$108+ 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 9/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — CHI
May 11 — May 181
Mon 5/11
Mon 5/18
1 adult, Economy
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Cheap 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 April 11, 2026.

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.
Tue 5/264:15 pm
ORH
-
ORD
1 stop5h 31m
Delta
Fri 5/297:05 am
ORD
-
ORH
1 stop7h 28m
Delta
Deal found 4/6$207
This American Airlines deal was found by Cheapflights users on 4/10. 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 4/282:39 pm
ORH
-
ORD
1 stop5h 21m
American Airlines
Sat 5/25:00 am
ORD
-
ORH
1 stop8h 14m
American Airlines
Deal found 4/10$211
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.
Wed 5/274:15 pm
ORH
-
ORD
2 stops8h 44m
Delta
Thu 5/287:05 am
ORD
-
ORH
1 stop7h 28m
Delta
Deal found 4/6$217
This Delta deal was found by Cheapflights users on 4/9. 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 4/245:24 pm
ORH
-
ORD
1 stop5h 51m
Delta
Tue 4/289:35 am
ORD
-
ORH
1 stop6h 08m
Delta
Deal found 4/9$227
This American Airlines deal was found by Cheapflights users on 4/10. 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.
Mon 4/272:39 pm
ORH
-
ORD
1 stop21h 02m
American Airlines
Tue 4/2810:42 pm
ORD
-
ORH
2 stops14h 32m
American Airlines
Deal found 4/10$232

Find 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 April 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$207
(Delta)

One-way from

$108
(American Airlines)

Popular in

April

Cheapest in

September

Average price

$252
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. 8% potential increase in price ($22 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 April 2026
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 April 11, 2026.
Use the filters below to find and compare flights from Worcester to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 5/26

4:15 pm-10:36 pm

1 stop7h 21m

Chicago O'Hare Intl

Thu 5/28

7:05 am-3:33 pm

1 stop7h 28m

$207

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 5/27

4:15 pm-11:59 pm

2 stops8h 44m

Chicago O'Hare Intl

Fri 5/29

7:05 am-3:33 pm

1 stop7h 28m

$217

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 5/20

2:39 pm-6:43 am

1 stop17h 04m

Chicago O'Hare Intl

Fri 5/22

6:40 am-4:53 pm

1 stop9h 13m

$220

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 4/24

5:24 pm-10:15 pm

1 stop5h 51m

Chicago O'Hare Intl

Tue 4/28

5:15 am-4:43 pm

2 stops10h 28m

$237
Quickest round-trip

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 4/22

5:24 pm-10:15 pm

1 stop5h 51m

Chicago O'Hare Intl

Mon 4/27

9:35 am-4:43 pm

1 stop6h 08m

$283

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 6/4

5:18 pm-12:38 am

1 stop8h 20m

Chicago O'Hare Intl

Mon 6/8

5:00 am-4:53 pm

1 stop10h 53m

$292

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 9/2

3:18 pm-11:57 pm

2 stops9h 39m

Chicago O'Hare Intl

Sun 9/6

5:30 am-2:39 pm

2 stops8h 09m

$303

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 4/21

5:24 pm-10:15 pm

1 stop5h 51m

Chicago O'Hare Intl

Mon 4/27

9:35 am-4:43 pm

1 stop6h 08m

$307

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 7/2

5:16 pm-12:29 am

1 stop8h 13m

Chicago O'Hare Intl

Mon 7/6

6:40 am-4:51 pm

1 stop9h 11m

$352

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 4/23

5:24 pm-10:15 pm

1 stop5h 51m

Chicago O'Hare Intl

Mon 4/27

9:35 am-4:43 pm

1 stop6h 08m

$354

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/7

Showing 1-10 of 19 resultsSorted by cheapest first
1
2

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Worcester, Massachusetts-Chicago flight deals on Cheapflights vs. FlightHub >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 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 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, February is the cheapest month in which you can book a flight from Worcester, Massachusetts to Chicago (average of $96). Flying from Worcester, Massachusetts to Chicago in January is currently the most expensive (average of $123). 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.

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 7h 21m. Fly via Delta or American Airlines to get the fastest option. There are 820 mi between Worcester, Massachusetts and Chicago. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • 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, February is the cheapest month in which you can book a flight from Worcester, Massachusetts to Chicago (average of $96). Flying from Worcester, Massachusetts to Chicago in January is currently the most expensive (average of $123). 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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