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$104+ 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — CHI
Jul 30 — Aug 61
Wed 7/30
Wed 8/6
1 adult, Economy
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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 July 25, 2025.

Round-trip from

$154
(American Airlines)

One-way from

$104
(Delta)

Popular in

March

Cheapest in

September

Average price

$225
From Worcester to Chicago (CHI)
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One-way flight from Worcester to Chicago (CHI)
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Highest demand for flights based on searches. 9% potential increase in price ($23 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($3 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 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 July 25, 2025.

This American Airlines deal was found by Cheapflights users on 7/24. 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 8/233:20 pmORH - ORD
1 stop8h 29mAmerican Airlines
Sat 8/305:00 amORD - ORH
1 stop8h 55mAmerican Airlines
Deal found 7/24$154
This Delta deal was found by Cheapflights users on 7/22. 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 8/193:55 pmORH - ORD
1 stop7h 25mDelta
Tue 8/267:15 amORD - ORH
1 stop6h 41mDelta
Deal found 7/22$212

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 July 25, 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

Sat 8/23

3:20 pm-10:49 pm

1 stop8h 29m

Chicago O'Hare Intl

Sat 8/30

5:00 am-2:55 pm

1 stop8h 55m

$154

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 8/6

3:48 pm-8:49 pm

1 stop6h 01m

Chicago O'Hare Intl

Tue 8/12

7:15 am-2:56 pm

1 stop6h 41m

$222

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 8/19

3:55 pm-8:47 pm

1 stop5h 52m

$104

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sun 9/7

4:23 pm-6:51 am

2 stops15h 28m

$119

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/24

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, August is the cheapest month in which you can book a flight from Worcester, Massachusetts to Chicago (average of $245). Flying from Worcester, Massachusetts 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 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 July 25, 2025.

Unlike in the morning, when flights are generally more expensive, you can save up to 31% on flights from Worcester, Massachusetts to Chicago by exploring options for tickets at noon.

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 25, 2025.
See what other customers who have flown with Delta and American Airlines 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
8.0
Very good
7,967 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,967 reviews
Delta
8.0
Very good
7,967 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,967 reviews

Comfort

7.9

Overall

8.0

Food

7.3

Boarding

8.2

Crew

8.5

Entertainment

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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.

  • 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, August is the cheapest month in which you can book a flight from Worcester, Massachusetts to Chicago (average of $245). Flying from Worcester, Massachusetts 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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