$264 Cheap Flights from Worcester (ORH) to Chicago (MDW)

View $264 flight on Fri, Nov 7, 2025Opens in a new window

Popular airlines from Worcester, MA (ORH-Worcester Regional) to Chicago Midway Airport (MDW)

Cheap Flights from Worcester to Chicago (ORH-MDW)

Prices were available within the past 7 days and start at $264 for one-way flights and $227 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Tue, Nov 11 - Wed, Nov 12
ORH
Worcester
MDW
Chicago
$227 Roundtrip, found 5 days ago
$227
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 11 from Worcester to Chicago, returning Wed, Nov 12, priced at $227 found 5 days ago
Delta
Tue, Nov 11 - Wed, Nov 12
ORH
Worcester
MDW
Chicago
$297 Roundtrip, found 5 days ago
$297
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 11 from Worcester to Chicago, returning Wed, Nov 12, priced at $297 found 5 days ago
Delta
Mon, Nov 10 - Mon, Nov 17
ORH
Worcester
MDW
Chicago
$304 Roundtrip, found 5 days ago
$304
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Nov 10 from Worcester to Chicago, returning Mon, Nov 17, priced at $304 found 5 days ago
Delta
Mon, Nov 10 - Tue, Nov 11
ORH
Worcester
MDW
Chicago
$324 Roundtrip, found 5 days ago
$324
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Nov 10 from Worcester to Chicago, returning Tue, Nov 11, priced at $324 found 5 days ago
Delta
Fri, Nov 14 - Mon, Nov 17
ORH
Worcester
MDW
Chicago
$341 Roundtrip, found 5 days ago
$341
Roundtrip
found 5 days ago
Select Delta flight, departing Fri, Nov 14 from Worcester to Chicago, returning Mon, Nov 17, priced at $341 found 5 days ago
Delta
Thu, Oct 30 - Sat, Nov 8
ORH
Worcester
MDW
Chicago
$351 Roundtrip, found 3 days ago
$351
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Oct 30 from Worcester to Chicago, returning Sat, Nov 8, priced at $351 found 3 days ago
Delta
Mon, Nov 10 - Wed, Nov 19
ORH
Worcester
MDW
Chicago
$352 Roundtrip, found 5 days ago
$352
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Nov 10 from Worcester to Chicago, returning Wed, Nov 19, priced at $352 found 5 days ago
Delta
Thu, Nov 13 - Mon, Nov 17
ORH
Worcester
MDW
Chicago
$354 Roundtrip, found 5 days ago
$354
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Nov 13 from Worcester to Chicago, returning Mon, Nov 17, priced at $354 found 5 days ago
Delta
Mon, Nov 10 - Sat, Nov 15
ORH
Worcester
MDW
Chicago
$376 Roundtrip, found 5 days ago
$376
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Nov 10 from Worcester to Chicago, returning Sat, Nov 15, priced at $376 found 5 days ago
Delta
Mon, Nov 10 - Wed, Nov 12
ORH
Worcester
MDW
Chicago
$379 Roundtrip, found 5 days ago
$379
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Nov 10 from Worcester to Chicago, returning Wed, Nov 12, priced at $379 found 5 days ago
Delta
Tue, Nov 11 - Wed, Nov 12
ORH
Worcester
MDW
Chicago
$387 Roundtrip, found 5 days ago
$387
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 11 from Worcester to Chicago, returning Wed, Nov 12, priced at $387 found 5 days ago
Delta
Thu, Oct 30 - Sun, Nov 9
ORH
Worcester
MDW
Chicago
$389 Roundtrip, found 3 days ago
$389
Roundtrip
found 3 days ago
Select Delta flight, departing Thu, Oct 30 from Worcester to Chicago, returning Sun, Nov 9, priced at $389 found 3 days ago
Delta
Sun, Nov 9 - Mon, Nov 17
ORH
Worcester
MDW
Chicago
$392 Roundtrip, found 5 days ago
$392
Roundtrip
found 5 days ago
Select Delta flight, departing Sun, Nov 9 from Worcester to Chicago, returning Mon, Nov 17, priced at $392 found 5 days ago
Delta
Wed, Oct 29 - Mon, Nov 10
ORH
Worcester
MDW
Chicago
$394 Roundtrip, found 3 days ago
$394
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Oct 29 from Worcester to Chicago, returning Mon, Nov 10, priced at $394 found 3 days ago
Delta
Tue, Nov 11 - Wed, Nov 12
ORH
Worcester
MDW
Chicago
$399 Roundtrip, found 5 days ago
$399
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 11 from Worcester to Chicago, returning Wed, Nov 12, priced at $399 found 5 days ago
Delta
Thu, Nov 13 - Wed, Nov 19
ORH
Worcester
MDW
Chicago
$402 Roundtrip, found 5 days ago
$402
Roundtrip
found 5 days ago
Select Delta flight, departing Thu, Nov 13 from Worcester to Chicago, returning Wed, Nov 19, priced at $402 found 5 days ago

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 $253
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $253

Frequently asked questions

How much does a flight from Worcester Regional Airport (ORH) to Midway Intl. Airport (MDW) cost?
Get a cheap one-way flight from $264 or cheap return flight from $227 from Worcester Regional Airport (ORH) to Midway Intl. Airport (MDW) with Expedia. Enter your travel dates and sort by "Price (lowest to highest)" to see our cheapest flight deals on this route.
What is the cheapest month to fly from Worcester Regional Airport (ORH) to Midway Intl. Airport (MDW)?
The cheapest month to fly from ORH to MDW is November, when demand is low. Off-peak months are generally when you'll find cheap fares for travel between these airports.
Which airlines fly direct from Worcester Regional Airport (ORH) to Midway Intl. Airport (MDW)?
There aren't any direct flights from Worcester, MA (ORH-Worcester Regional) to Midway Intl. Airport (MDW). However, you'll find other airports offering nonstop flights. Board your plane at Logan Intl. Airport (BOS) and fly straight to Chicago without any detours.
What is the cheapest airline that flies from Worcester Regional Airport (ORH) to Midway Intl. Airport (MDW)?
To find the cheapest airline flying from ORH to MDW, use Expedia's filter tool. Customize your search based on your travel needs, such as preferred carriers and cabin class. You can then sort your results by "Price (lowest to highest)" to discover the cheapest flight right away.
How many flights per day from Worcester Regional Airport (ORH) to Midway Intl. Airport (MDW)?
Direct flights from Worcester Regional Airport (ORH) to Midway Intl. Airport (MDW) aren't available daily, so you'll have to take a flight with a layover. Explore your options with Expedia's filter tool. Enter your travel dates and select either "1 Stop" or "2+ Stops."
What day of the week has the most flights from ORH to MDW?
Friday is usually the busiest day for flights, while Tuesday tends to be the quietest.* Just remember that flight schedules can change depending on various factors, including the time of year and carrier.*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 Midway Intl. Airport (MDW)?
To avoid possible delays on the Worcester Regional Airport (ORH) to Midway Intl. Airport (MDW) route, travel before 3 PM. Later flights are 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 Midway Intl. Airport (MDW) last-minute?
Holding off until right before your break to book a ticket from ORH to MDW often results in higher prices. While you might find some last-minute deals, they're not always guaranteed. Be flexible with your itinerary for the best chance of scoring a bargain.
Is it cheaper to book an ORH to MDW flight and hotel package?
Compared with arranging hotels and flights separately, booking an ORH to MDW flight and hotel package with Expedia could lead to significant savings. What's more, having it all in one place will take the stress out of travel planning. Simply pick your flights and select from our wide range of stays, then tailor your trip with extras like activities, tours and car rentals.
Can I cancel or change the date of my flight from Worcester Regional Airport (ORH) to Midway Intl. Airport (MDW)?
Typically, you're able to reschedule or cancel your ORH to MDW flight. However, additional charges may apply, especially if you made your booking more than 24 hours ago. Double-check your itinerary for the airline's policies and fees on flight changes, or if you'd like further details, head to our Customer Service portal.

Travel information

Origin airport
Worcester Regional
Destination airport
Midway Intl.
Airlines serving
Delta
Roundtrip price
$227
Distance
814 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 November. 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 $264 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

Explore a world of travel with Expedia

*Available to One Key members.