$75 Cheap Flights from Worcester (ORH) to Chicago (ORD)

View $75 flight on Wed, Feb 25, 2026Opens in a new window

Popular airlines from Worcester, MA (ORH-Worcester Regional) to Chicago O'Hare Intl. Airport (ORD)

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Cheap Flights from Worcester to Chicago (ORH-ORD)

Prices were available within the past 7 days and start at $75 for one-way flights and $154 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Fri, Dec 5 - Sun, Dec 7
ORH
Worcester
ORD
Chicago
$154 Roundtrip, found 4 days ago
$154
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Dec 5 from Worcester to Chicago, returning Sun, Dec 7, priced at $154 found 4 days ago
Delta
Fri, Dec 5 - Sun, Dec 7
ORH
Worcester
ORD
Chicago
$173 Roundtrip, found 4 days ago
$173
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Dec 5 from Worcester to Chicago, returning Sun, Dec 7, priced at $173 found 4 days ago
Delta
Wed, Feb 25 - Sun, Mar 1
ORH
Worcester
ORD
Chicago
$175 Roundtrip, found 4 days ago
$175
Roundtrip
found 4 days ago
Select Delta flight, departing Wed, Feb 25 from Worcester to Chicago, returning Sun, Mar 1, priced at $175 found 4 days ago
American Airlines
Thu, Dec 11 - Sun, Dec 14
ORH
Worcester
ORD
Chicago
$179 Roundtrip, found 5 days ago
$179
Roundtrip
found 5 days ago
Select American Airlines flight, departing Thu, Dec 11 from Worcester to Chicago, returning Sun, Dec 14, priced at $179 found 5 days ago
Delta
Mon, Nov 10 - Tue, Nov 11
ORH
Worcester
ORD
Chicago
$192 Roundtrip, just found
$192
Roundtrip
just found
Select Delta flight, departing Mon, Nov 10 from Worcester to Chicago, returning Tue, Nov 11, priced at $192 just found
American Airlines
Thu, Apr 16 - Mon, Apr 20
ORH
Worcester
ORD
Chicago
$193 Roundtrip, found 2 days ago
$193
Roundtrip
found 2 days ago
Select American Airlines flight, departing Thu, Apr 16 from Worcester to Chicago, returning Mon, Apr 20, priced at $193 found 2 days ago
Delta
Tue, Nov 11 - Mon, Nov 24
ORH
Worcester
ORD
Chicago
$197 Roundtrip, found 6 days ago
$197
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Nov 11 from Worcester to Chicago, returning Mon, Nov 24, priced at $197 found 6 days ago
American Airlines
Fri, Dec 5 - Sun, Dec 7
ORH
Worcester
ORD
Chicago
$204 Roundtrip, found 4 days ago
$204
Roundtrip
found 4 days ago
Select American Airlines flight, departing Fri, Dec 5 from Worcester to Chicago, returning Sun, Dec 7, priced at $204 found 4 days ago
Delta
Fri, Dec 5 - Sun, Dec 7
ORH
Worcester
ORD
Chicago
$208 Roundtrip, found 4 days ago
$208
Roundtrip
found 4 days ago
Select Delta flight, departing Fri, Dec 5 from Worcester to Chicago, returning Sun, Dec 7, priced at $208 found 4 days ago
JetBlue Airways
Thu, Feb 19 - Sun, Feb 22
ORH
Worcester
ORD
Chicago
$1,317 Roundtrip, found 2 days ago
$1,317
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Thu, Feb 19 from Worcester to Chicago, returning Sun, Feb 22, priced at $1,317 found 2 days ago

Find the cheapest month to fly from Worcester (ORH) to Chicago (ORD)

September is typically the cheapest month to fly

From $154 - $324 per traveler.

Alternative airports near Chicago

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city center is 23 minutes. Flights from $197
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $197

Frequently asked questions

How much does a flight from Worcester Regional Airport (ORH) to O'Hare Intl. Airport (ORD) cost?
Get a cheap one-way flight from $75 or cheap return flight from $154 from Worcester Regional Airport (ORH) to O'Hare Intl. Airport (ORD) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to find our cheapest flight deals on this route.
What is the cheapest month to fly from Worcester Regional Airport (ORH) to O'Hare Intl. Airport (ORD)?
The cheapest month to fly from ORH to ORD is December, when there's less demand. Off-peak months are usually when airlines offer better prices between these airports.
Which airlines fly direct from Worcester Regional Airport (ORH) to O'Hare Intl. Airport (ORD)?
There aren't any direct flights from Worcester, MA (ORH-Worcester Regional) to O'Hare Intl. Airport (ORD). However, there are other airports that offer nonstop flights. Begin your journey at Logan Intl. Airport (BOS) and travel straight to Chicago without a layover.
What is the cheapest airline that flies from Worcester Regional Airport (ORH) to O'Hare Intl. Airport (ORD)?
Use the filter tool on Expedia to compare different airlines and find the most affordable carrier that'll take you from ORH to ORD. Then, sort your results by "Price (lowest to highest)" to pick up the best deal available.
How many flights per day from Worcester Regional Airport (ORH) to O'Hare Intl. Airport (ORD)?
There are no daily nonstop flights from Worcester Regional Airport (ORH) to O'Hare Intl. Airport (ORD). But you can choose flights with layovers. Filter your search results on Expedia to include one or two stops, and you'll be on your way in no time at all.
What day of the week has the most flights from ORH to ORD?
Friday is typically the busiest day for flights, while Tuesday is often the quietest.* Just remember that flight schedules can change based on a range of factors, such as the carrier and season.*Busiest/quietest day to travel is based on Expedia flight demand through January to December 2024.
What is the best time to fly from Worcester Regional Airport (ORH) to O'Hare Intl. Airport (ORD)?
Choose a flight from Worcester Regional Airport (ORH) to O'Hare Intl. Airport (ORD) that takes off before 3 PM to reduce the likelihood of delays. Departures later than this are on average 22% more likely to be canceled.**Most reliable time of the day and month to travel recommendation is based on January through August 2024 flight status data sourced from OAG's global flight data platform.
Is it cheaper to buy a plane ticket from Worcester Regional Airport (ORH) to O'Hare Intl. Airport (ORD) last-minute?
Booking your flight from ORH to ORD right before your trip is generally more expensive. However, if you're flexible with your itinerary, you could score a cheap last-minute fare.
Is it cheaper to book an ORH to ORD flight and hotel package?
You'll typically save money by securing an ORH to ORD flight and hotel package compared to booking separately. In fact, travelers could save hundreds of dollars by bundling with Expedia. And it's easy to manage everything in one place. Once you've chosen your ideal accommodations and flights, you can add extras such as activities, car rentals and tours.
Can I cancel or change the date of my flight from Worcester Regional Airport (ORH) to O'Hare Intl. Airport (ORD)?
Typically, you're able to reschedule or cancel your ORH to ORD flight. However, there may be additional charges, especially if you booked more than 24 hours ago. Check your itinerary for the airline's fees and guidelines on flight changes, or if you need further details, head to our Customer Service portal.

Travel information

Origin airport
Worcester Regional
Destination airport
O'Hare Intl.
Airlines serving
American Airlines, Delta
Roundtrip price
$154
Distance
820 mi

Book with confidence

Worcester to Chicago Flights

The cheapest times to fly from Worcester to Chicago

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Worcester to Chicago are during the month of December. You can find some of the cheapest flights from Worcester to Chicago with Expedia's search tool and vast selection of airlines.

 

The best time to book a flight from Worcester to Chicago

Sunday is one of the best days to book for cheap flights from Worcester to Chicago: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

 

How to find cheap round-trip tickets from Worcester to Chicago

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Worcester to Chicago in 2025. You can also book with separate airlines for your outbound and return journeys, from $75 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

 

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Worcester to Chicago flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

 

You could also save big by booking one of Expedia's vacation packages. Bundling together your Worcester to Chicago airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

 

*Terms apply.

 

Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023. The percentages you see are averages.

 

Worcester to Chicago Flights

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*Available to One Key members.