$263 Cheap Flights from Worcester (ORH) to Chicago (MDW)

View $263 flight on Thu, Sep 4, 2025Opens in a new window

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

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Cheap Flights from Worcester to Chicago (ORH-MDW)

Prices were available within the past 7 days and start at $263 for one-way flights and $288 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, Oct 22 - Mon, Oct 27
ORH
Worcester
MDW
Chicago
$288 Roundtrip, found 2 days ago
$288
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Oct 22 from Worcester to Chicago, returning Mon, Oct 27, priced at $288 found 2 days ago
Delta
Mon, Sep 22 - Mon, Oct 6
ORH
Worcester
MDW
Chicago
$301 Roundtrip, found 6 days ago
$301
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Sep 22 from Worcester to Chicago, returning Mon, Oct 6, priced at $301 found 6 days ago
Delta
Mon, Oct 27 - Tue, Oct 28
ORH
Worcester
MDW
Chicago
$303 Roundtrip, found 2 days ago
$303
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 27 from Worcester to Chicago, returning Tue, Oct 28, priced at $303 found 2 days ago
Delta
Wed, Sep 24 - Mon, Oct 6
ORH
Worcester
MDW
Chicago
$314 Roundtrip, found 6 days ago
$314
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Sep 24 from Worcester to Chicago, returning Mon, Oct 6, priced at $314 found 6 days ago
Delta
Mon, Sep 22 - Sat, Oct 11
ORH
Worcester
MDW
Chicago
$316 Roundtrip, found 6 days ago
$316
Roundtrip
found 6 days ago
Select Delta flight, departing Mon, Sep 22 from Worcester to Chicago, returning Sat, Oct 11, priced at $316 found 6 days ago
Delta
Wed, Sep 24 - Sat, Oct 11
ORH
Worcester
MDW
Chicago
$329 Roundtrip, found 6 days ago
$329
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Sep 24 from Worcester to Chicago, returning Sat, Oct 11, priced at $329 found 6 days ago
Delta
Fri, Oct 24 - Mon, Oct 27
ORH
Worcester
MDW
Chicago
$333 Roundtrip, found 2 days ago
$333
Roundtrip
found 2 days ago
Select Delta flight, departing Fri, Oct 24 from Worcester to Chicago, returning Mon, Oct 27, priced at $333 found 2 days ago
Delta
Wed, Oct 22 - Sat, Nov 1
ORH
Worcester
MDW
Chicago
$341 Roundtrip, found 2 days ago
$341
Roundtrip
found 2 days ago
Select Delta flight, departing Wed, Oct 22 from Worcester to Chicago, returning Sat, Nov 1, priced at $341 found 2 days ago
Delta
Fri, Sep 26 - Tue, Oct 7
ORH
Worcester
MDW
Chicago
$346 Roundtrip, found 6 days ago
$346
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, Sep 26 from Worcester to Chicago, returning Tue, Oct 7, priced at $346 found 6 days ago
Delta
Mon, Oct 27 - Wed, Oct 29
ORH
Worcester
MDW
Chicago
$348 Roundtrip, found 2 days ago
$348
Roundtrip
found 2 days ago
Select Delta flight, departing Mon, Oct 27 from Worcester to Chicago, returning Wed, Oct 29, priced at $348 found 2 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 $213
ORD
O'Hare Intl.
Cheapest
Average driving time to city center23 min
Flights from $213
Flights from Worcester (ORH) to Chicago (MDW)
Origin airport
Worcester Regional
Destination airport
Midway Intl.
Roundtrip price
$287
Distance
814 mi

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 October. 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 $263 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.

 

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 $263 or cheap return flight from $288 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 October, 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.

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*Available to One Key members.