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$154+ Cheap flights from Worcester, MA (ORH) to Chicago (CHI)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
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 October 30, 2025.

This American Airlines deal was found by Cheapflights users on 10/28. 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 12/33:30 pmORH - ORD
1 stop18h 37mAmerican Airlines
Wed 12/108:50 pmORD - ORH
1 stop17h 19mAmerican Airlines
Deal found 10/28$154
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Sat 11/223:17 pmORH - ORD
1 stop16h 47mAmerican Airlines
Mon 11/246:47 amORD - ORH
1 stop7h 04mAmerican Airlines
Deal found 10/29$208
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/144:03 pmORH - ORD
1 stop5h 41mDelta
Tue 11/187:00 amORD - ORH
1 stop7h 23mDelta
Deal found 10/30$212
This Delta deal was found by Cheapflights users on 10/29. 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.
Sun 11/94:03 pmORH - ORD
1 stop7h 32mDelta
Tue 11/119:30 amORD - ORH
1 stop4h 53mDelta
Deal found 10/29$222
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Sun 11/233:17 pmORH - ORD
2 stops17h 04mAmerican Airlines
Fri 11/285:00 amORD - ORH
2 stops8h 51mAmerican Airlines
Deal found 10/29$237
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/243:17 pmORH - ORD
1 stop18h 51mAmerican Airlines
Fri 11/286:35 pmORD - ORH
1 stop19h 16mAmerican Airlines
Deal found 10/29$244
This American Airlines deal was found by Cheapflights users on 10/28. 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 11/123:27 pmORH - ORD
1 stop16h 37mAmerican Airlines
Sun 11/166:50 amORD - ORH
1 stop7h 12mAmerican Airlines
Deal found 10/28$247
This American Airlines deal was found by Cheapflights users on 10/29. 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.
Sat 11/223:17 pmORH - ORD
1 stop18h 51mAmerican Airlines
Tue 12/25:00 amORD - ORH
1 stop8h 51mAmerican Airlines
Deal found 10/29$253

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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$154
(American Airlines)

Popular in

April

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
Highest demand for flights based on searches. 9% potential increase in price ($24 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 October 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 October 30, 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

Wed 12/3

3:30 pm-9:07 am

1 stop18h 37m

Chicago O'Hare Intl

Wed 12/10

8:50 pm-3:09 pm

1 stop17h 19m

$154

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 2/17

3:18 pm-9:46 pm

1 stop7h 28m

Chicago O'Hare Intl

Wed 2/18

7:00 am-2:37 pm

1 stop6h 37m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 2/17

3:18 pm-9:46 pm

1 stop7h 28m

Chicago O'Hare Intl

Mon 2/23

7:00 am-2:37 pm

1 stop6h 37m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 2/19

3:18 pm-7:25 pm

1 stop5h 07m

Chicago O'Hare Intl

Mon 2/23

7:00 am-2:37 pm

1 stop6h 37m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 2/18

3:18 pm-7:25 pm

1 stop5h 07m

Chicago O'Hare Intl

Mon 2/23

7:00 am-2:37 pm

1 stop6h 37m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 11/14

4:03 pm-8:44 pm

1 stop5h 41m

Chicago O'Hare Intl

Tue 11/18

7:00 am-3:23 pm

1 stop7h 23m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 11/22

3:17 pm-11:40 pm

2 stops9h 23m

Chicago O'Hare Intl

Mon 11/24

5:00 am-2:51 pm

1 stop8h 51m

$218

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sun 11/9

4:03 pm-10:35 pm

1 stop7h 32m

Chicago O'Hare Intl

Tue 11/11

9:30 am-3:23 pm

1 stop4h 53m

$222

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 11/6

3:18 pm-7:25 pm

1 stop5h 07m

$175

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 11/7

3:18 pm-11:58 pm

2 stops9h 40m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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 October.
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, November is the cheapest month in which you can book a flight from Worcester, Massachusetts to Chicago (average of $88). Flying from Worcester, Massachusetts to Chicago in December is currently the most expensive (average of $125). 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 October 30, 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 October 30, 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
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,998 reviews
Delta
7.9
Good
7,998 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 28m. Fly via American Airlines or Delta 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, November is the cheapest month in which you can book a flight from Worcester, Massachusetts to Chicago (average of $88). Flying from Worcester, Massachusetts to Chicago in December is currently the most expensive (average of $125). 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
Porter
Benton Harbor

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