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 Wednesday mornings 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.

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 50 days early can save you up to 69% on average compared to booking a flight this week. If booking 50 days before your flight isn’t an option for you, users have found flights from Worcester, Massachusetts to Chicago for as little as $211 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 $357 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 May. Prices are generally better when you fly from Worcester, Massachusetts to Chicago in September, with the cheapest ticket starting at $60.

Most accurate provider : When it comes to deals on Worcester, Massachusetts-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Worcester, Massachusetts-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Worcester, Massachusetts-Chicago flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Worcester, Massachusetts-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Worcester, Massachusetts-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 1 airline. 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.

$81+ Flights from Worcester, MA to Chicago

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1. Tell us where you want to go

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2. Select your favorite providers

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Cheap flight deals from Worcester to Chicago

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$154 (American Airlines)
One-way from	$81 (American Airlines)
Popular in	May
Cheapest in	September
Average price	$269

Provider with most accurate pricing for Worcester-Chicago (CHI) flight deals.

Search Deals

Provider most trusted by Cheapflights users for Worcester-Chicago (CHI) flights.

Search Deals

From Worcester to Chicago (CHI)

Search Deals

One-way flight from Worcester to Chicago (CHI)

Search Deals

Highest demand for flights based on searches. 9% potential increase in price ($25 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 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 April 17, 2025.

Fri 5/22:18 pmORH - ORD

1 stop21h 47mAmerican Airlines

Tue 5/64:44 pmORD - ORH

1 stop19h 32mAmerican Airlines

Deal found 4/17

$154

Tue 7/154:00 pmORH - ORD

1 stop5h 49mDelta

Wed 7/237:00 amORD - ORH

1 stop7h 12mDelta

Deal found 4/16

$212

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 April 17, 2025.

Fri 5/22:18 pmORH - ORD

1 stop21h 47mAmerican Airlines

Tue 5/64:44 pmORD - ORH

1 stop19h 32mAmerican Airlines

Deal found 4/17

$154

Tue 7/154:00 pmORH - ORD

1 stop5h 49mDelta

Wed 7/237:00 amORD - ORH

1 stop7h 12mDelta

Deal found 4/16

$212

Last-minute flights from Worcester to Chicago
Discover last-minute flight deals from Worcester to Chicago. Data last updated April 17, 2025 and is based on user searches.

Thu 4/242:18 pmORH - ORD

1 stop21h 47mAmerican Airlines

Fri 4/255:10 pmORD - ORH

1 stop18h 58mAmerican Airlines

Deal found 4/16

$314

Thu 4/244:00 pmORH - ORD

2 stops8h 59mDelta

Fri 4/256:00 amORD - ORH

1 stop8h 06mDelta

Deal found 4/16

$438

Fri 5/22:18 pmORH - ORD

1 stop21h 47mAmerican Airlines

Tue 5/64:44 pmORD - ORH

1 stop19h 32mAmerican Airlines

Deal found 4/17

$154

Tue 5/64:00 pmORH - ORD

1 stop7h 23mDelta

Wed 5/77:00 amORD - ORH

1 stop7h 05mDelta

Deal found 4/16

$212

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 April 17, 2025.

Thu 8/211:40 pmORH - ORD

1 stop20h 33mAmerican Airlines

Deal found 4/16

$81

Wed 8/64:00 pmORH - ORD

1 stop7h 46mDelta

Deal found 4/16

$104

Cheapflights Fare Finder

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

Fly from

Fly to

Route

Depart

Return

Price

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 5/2

2:18 pm-11:05 am

1 stop21h 47m

Chicago O'Hare Intl

Tue 5/6

4:44 pm-1:16 pm

1 stop19h 32m

$154

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 7/15

4:00 pm-10:46 pm

1 stop7h 46m

Chicago O'Hare Intl

Tue 7/22

7:00 am-3:12 pm

1 stop7h 12m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 8/21

1:40 pm-9:13 am

1 stop20h 33m

$81

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 8/6

4:00 pm-10:46 pm

1 stop7h 46m

$104

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/16

Compare providers for flights from Worcester to Chicago

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Worcester to Chicago in April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
eDreams	Price Accuracy3 stars	Trust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

Most accurate provider: When it comes to deals on Worcester, Massachusetts-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Worcester, Massachusetts-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Worcester, Massachusetts-Chicago flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Worcester, Massachusetts-Chicago flights, Cheapflights users trust eDreams the most. eDreams has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Worcester, Massachusetts-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

Rainfall in Chicago by month

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.

Temperature in Chicago by month

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).

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Delta and American Airlines from Worcester to Chicago. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,916 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta

8.0

Very good

7,916 reviews

Delta

8.0

Very good

7,916 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,916 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

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 1 airline. 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

Merrillville

Hammond

Benton Harbor

Porter

Lansing

Valparaiso

Chesterton

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Top airline flying from Worcester to Chicago

Airline	Cheapest	Average	Flexibility	On-time
Delta	Cheapest$193	Average$393	FlexibilityNo cancel fee	On-timeN/A

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$81+ 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 8/21. 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

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Worcester to Chicago

Most accurate provider

Most trusted provider

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 April 17, 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 April 17, 2025.

Cheapflights Fare Finder

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

Compare providers for flights from Worcester to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Worcester to Chicago in April.

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 April 17, 2025.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Read reviews from past customers who have flown Delta and American Airlines from Worcester to Chicago. Reviews also offer insight into each airline's 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?

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?

Traveling to a place near Worcester?

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Alternative routes for Worcester to Chicago

See prices for flight routes from nearby airports that may be better suited for you.

Top airline flying from Worcester to Chicago

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Travel Smart

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 April 17, 2025.