How long is the flight from Worcester, Massachusetts to Chicago?

There are many flights that can get you from Worcester, Massachusetts to Chicago in 20h 57m. Fly via American Airlines to get the fastest option. There are 820 mi between Worcester, Massachusetts and Chicago.

What is the cheapest day to fly from Worcester, Massachusetts to Chicago?

Travelers seeking maximum savings on their Worcester, Massachusetts to Chicago flight should consider departing on Friday afternoons when fares are most often at their lowest. Thursday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

What is the cheapest day to fly round-trip from Worcester, Massachusetts to Chicago?

Flights from Worcester, Massachusetts to Chicago are found to be more expensive on Wednesday. This shouldn't discourage you from searching as you can still find great deals by being flexible with your options. Use our search form to find deals on tickets to Chicago.

How far in advance should I book a flight from Worcester, Massachusetts to Chicago?

Users have found that booking a flight from Worcester, Massachusetts to Chicago at least 51 days early can save you up to 63% on average compared to booking a flight this week. If booking 51 days before your flight isn’t an option for you, users have found flights from Worcester, Massachusetts to Chicago for as little as $205 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as $373 for flights departing within the next 3 days.

What is the cheapest month to fly from Worcester, Massachusetts to Chicago?

Flights from Worcester, Massachusetts to Chicago lean towards being more expensive in March. Prices are generally better when you fly from Worcester, Massachusetts to Chicago in September, with the cheapest ticket starting at $64.

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.

$75+ Flights from Worcester, MA to Chicago

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Cheap flight deals from Worcester to Chicago

Round-trip from	$154 (American Airlines)
One-way from	$75 (American Airlines)
Popular in	March
Cheapest in	September
Average price	$184

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. 7% potential increase in price ($20 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 September 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 September 11, 2025.

Wed 9/244:24 pmORH - ORD

1 stop5h 19mAmerican Airlines

Thu 9/257:00 amORD - ORH

1 stop7h 58mAmerican Airlines

Deal found 9/10

$154

Thu 9/254:23 pmORH - ORD

2 stops15h 28mAmerican Airlines

Mon 9/295:00 amORD - ORH

2 stops9h 56mAmerican Airlines

Deal found 9/10

$186

Sat 9/204:24 pmORH - ORD

1 stop17h 19mAmerican Airlines

Mon 9/228:35 amORD - ORH

1 stop6h 21mAmerican Airlines

Deal found 9/10

$192

Tue 10/283:18 pmORH - ORD

1 stop5h 07mDelta

Wed 11/57:00 amORD - ORH

1 stop5h 58mDelta

Deal found 9/11

$212

Fri 10/243:18 pmORH - ORD

1 stop5h 07mDelta

Mon 11/36:00 amORD - ORH

1 stop6h 58mDelta

Deal found 9/11

$222

Sat 10/254:05 pmORH - ORD

1 stop16h 20mAmerican Airlines

Mon 11/36:50 amORD - ORH

1 stop7h 12mAmerican Airlines

Deal found 9/11

$224

Wed 10/293:18 pmORH - ORD

2 stops9h 40mDelta

Wed 11/57:10 amORD - ORH

2 stops5h 48mDelta

Deal found 9/11

$227

Best flights from Worcester to Chicago
Discover carefully curated flight deals from Worcester to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 11, 2025.

Fri 10/34:23 pmORH - ORD

1 stop20h 57mAmerican Airlines

Tue 10/75:00 amORD - ORH

1 stop9h 50mAmerican Airlines

Deal found 9/10

$154

Tue 10/283:18 pmORH - ORD

1 stop6h 19mDelta

Mon 11/36:00 amORD - ORH

1 stop6h 58mDelta

Deal found 9/11

$212

Thu 10/24:23 pmORH - ORD

1 stop7h 16mAmerican Airlines

Tue 10/78:45 amORD - ORH

1 stop6h 05mAmerican Airlines

Deal found 9/10

$154

Thu 9/254:23 pmORH - ORD

2 stops15h 28mAmerican Airlines

Mon 9/295:00 amORD - ORH

2 stops9h 56mAmerican Airlines

Deal found 9/10

$186

Wed 10/293:18 pmORH - ORD

1 stop5h 07mDelta

Thu 11/67:00 amORD - ORH

1 stop5h 58mDelta

Deal found 9/11

$212

Wed 10/293:18 pmORH - ORD

1 stop6h 19mDelta

Wed 11/56:00 amORD - ORH

1 stop6h 58mDelta

Deal found 9/11

$212

Tue 10/283:18 pmORH - ORD

1 stop5h 07mDelta

Tue 11/47:00 amORD - ORH

1 stop5h 58mDelta

Deal found 9/11

$212

Wed 10/293:18 pmORH - ORD

1 stop5h 07mDelta

Tue 11/47:00 amORD - ORH

1 stop5h 58mDelta

Deal found 9/11

$212

Tue 10/283:18 pmORH - ORD

1 stop5h 07mDelta

Thu 11/66:00 amORD - ORH

1 stop6h 58mDelta

Deal found 9/11

$212

Last-minute flights from Worcester to Chicago
Discover last-minute flight deals from Worcester to Chicago. Data last updated September 11, 2025 and is based on user searches.

Sat 9/204:24 pmORH - ORD

1 stop17h 19mAmerican Airlines

Mon 9/228:35 amORD - ORH

1 stop6h 21mAmerican Airlines

Deal found 9/10

$192

Wed 9/244:24 pmORH - ORD

1 stop5h 19mAmerican Airlines

Thu 9/257:00 amORD - ORH

1 stop7h 58mAmerican Airlines

Deal found 9/10

$154

Thu 9/254:23 pmORH - ORD

2 stops15h 28mAmerican Airlines

Mon 9/295:00 amORD - ORH

2 stops9h 56mAmerican Airlines

Deal found 9/10

$186

Fri 10/243:18 pmORH - ORD

1 stop5h 07mDelta

Mon 11/36:00 amORD - ORH

1 stop6h 58mDelta

Deal found 9/11

$222

Sat 10/254:05 pmORH - ORD

1 stop16h 20mAmerican Airlines

Mon 11/36:50 amORD - ORH

1 stop7h 12mAmerican Airlines

Deal found 9/11

$224

Tue 10/283:18 pmORH - ORD

1 stop5h 07mDelta

Tue 11/47:00 amORD - ORH

1 stop5h 58mDelta

Deal found 9/11

$212

Wed 10/293:18 pmORH - ORD

2 stops9h 40mDelta

Tue 11/47:10 amORD - ORH

2 stops5h 48mDelta

Deal found 9/11

$227

One-way flights from Worcester to Chicago
Search for one-way flight options from Worcester to Chicago. Find affordable one-way fares based on user searches. Data last updated September 11, 2025.

Tue 9/304:24 pmORH - ORD

1 stop5h 19mAmerican Airlines

Deal found 9/9

$75

Wed 10/14:24 pmORH - ORD

2 stops15h 27mAmerican Airlines

Deal found 9/10

$90

Mon 10/203:18 pmORH - ORD

1 stop5h 07mDelta

Deal found 9/9

$104

Fri 11/73:27 pmORH - ORD

2 stops18h 25mAmerican Airlines

Deal found 9/11

$125

Thu 9/184:23 pmORH - ORD

2 stops8h 25mAmerican Airlines

Deal found 9/11

$139

Sat 11/83:27 pmORH - ORD

1 stop5h 59mAmerican Airlines

Deal found 9/11

$144

Fri 11/73:18 pmORH - ORD

1 stop5h 07mDelta

Deal found 9/11

$165

Fri 9/193:18 pmORH - ORD

1 stop6h 17mDelta

Deal found 9/11

$175

Mon 10/133:18 pmORH - ORD

1 stop17h 44mDelta

Deal found 9/11

$178

Mon 10/204:17 pmORH - ORD

2 stops8h 36mAmerican Airlines

Deal found 9/9

$184

Sun 10/124:17 pmORH - ORD

1 stop16h 08mAmerican Airlines

Deal found 9/10

$185

Fly from

Fly to

Route

Depart

Return

Price

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 10/3

4:23 pm-12:20 pm

1 stop20h 57m

Chicago O'Hare Intl

Tue 10/7

5:00 am-3:50 pm

1 stop9h 50m

$154

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 10/2

4:23 pm-10:39 pm

1 stop7h 16m

Chicago O'Hare Intl

Tue 10/7

8:45 am-3:50 pm

1 stop6h 05m

$154

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 9/25

4:23 pm-6:51 am

2 stops15h 28m

Chicago O'Hare Intl

Mon 9/29

5:00 am-3:56 pm

2 stops9h 56m

$186

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 10/28

3:18 pm-8:37 pm

1 stop6h 19m

Chicago O'Hare Intl

Mon 11/3

6:00 am-1:58 pm

1 stop6h 58m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 10/29

3:18 pm-7:25 pm

1 stop5h 07m

Chicago O'Hare Intl

Thu 11/6

7:00 am-1:58 pm

1 stop5h 58m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 10/29

3:18 pm-8:37 pm

1 stop6h 19m

Chicago O'Hare Intl

Wed 11/5

6:00 am-1:58 pm

1 stop6h 58m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 10/28

3:18 pm-7:25 pm

1 stop5h 07m

Chicago O'Hare Intl

Tue 11/4

7:00 am-1:58 pm

1 stop5h 58m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 10/29

3:18 pm-7:25 pm

1 stop5h 07m

Chicago O'Hare Intl

Tue 11/4

7:00 am-1:58 pm

1 stop5h 58m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 10/28

3:18 pm-7:25 pm

1 stop5h 07m

Chicago O'Hare Intl

Thu 11/6

6:00 am-1:58 pm

1 stop6h 58m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 9/30

4:24 pm-8:43 pm

1 stop5h 19m

$75

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 18 results

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?

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

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

8.0

Very good

7,960 reviews

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

7,960 reviews

Delta

8.0

Very good

7,960 reviews

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

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 20h 57m. Fly via American Airlines to get the fastest option. There are 820 mi between Worcester, Massachusetts and Chicago.
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.

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$75+ 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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Worcester to Chicago with Cheapflights

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2. Select your favorite providers

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Cheap flight deals from Worcester to Chicago

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Worcester to Chicago

Cheapest flights from Worcester to ChicagoExplore 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 September 11, 2025.

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 September 11, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Worcester to Chicago that are best for you.

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.

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?

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 September 11, 2025.

Reviews of airlines servicing Chicago

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.

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?

How long is the flight from Worcester, Massachusetts to Chicago?

Can I find deals for flights from Worcester to Chicago that include hotel bookings?

How can I find direct flights from Worcester to Chicago?

Can I find deals for business class flights from Worcester to Chicago?

What is the cheapest month to book a flight from Worcester, Massachusetts to Chicago?

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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 September 11, 2025.