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Cheap flights from Chicago to Boston from $109

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Boston departing on 5/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Find the cheapest flights from Chicago to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
9:35 am - 4:43 pm
ORD
-
ORH
6h 08m
1 stop
Delta Logo
5:24 pm - 10:19 pm
ORH
-
ORD
5h 55m
1 stop
$192Delta
Wed, Apr 29 - Wed, May 6
Delta Logo
8:52 am - 4:43 pm
ORD
-
ORH
6h 51m
2 stops
Delta Logo
5:24 pm - 10:15 pm
ORH
-
ORD
5h 51m
1 stop
$202Delta
Wed, Apr 29 - Tue, May 5
Delta Logo
7:05 am - 3:33 pm
ORD
-
ORH
7h 28m
1 stop
Delta Logo
4:15 pm - 8:46 pm
ORH
-
ORD
5h 31m
1 stop
$207Delta
Thu, May 28 - Tue, Jun 2
Delta Logo
5:15 am - 4:43 pm
ORD
-
ORH
10h 28m
2 stops
Delta Logo
5:24 pm - 10:15 pm
ORH
-
ORD
5h 51m
1 stop
$212Delta
Thu, Apr 30 - Tue, May 5
American Airlines Logo
5:00 am - 4:53 pm
ORD
-
ORH
10h 53m
1 stop
American Airlines Logo
5:18 pm - 7:02 am
ORH
-
ORD
14h 44m
2 stops
$217American Airlines
Thu, May 28 - Tue, Jun 2
American Airlines Logo
5:00 am - 4:53 pm
ORD
-
ORH
10h 53m
1 stop
American Airlines Logo
5:18 pm - 7:02 am
ORH
-
ORD
14h 44m
2 stops
$237American Airlines
Thu, May 28 - Tue, Jun 2
American Airlines Logo
5:00 am - 4:53 pm
ORD
-
ORH
10h 53m
1 stop
American Airlines Logo
5:18 pm - 11:31 pm
ORH
-
ORD
7h 13m
1 stop
$247American Airlines
Wed, Jun 10 - Sat, Jun 13
American Airlines Logo
5:00 am - 4:53 pm
ORD
-
ORH
10h 53m
1 stop
American Airlines Logo
5:18 pm - 11:23 pm
ORH
-
ORD
7h 05m
2 stops
$257American Airlines
Wed, Jun 10 - Sat, Jun 13
American Airlines Logo
6:00 am - 4:53 pm
ORD
-
ORH
9h 53m
2 stops
American Airlines Logo
5:18 pm - 11:59 pm
ORH
-
ORD
7h 41m
2 stops
$262American Airlines
Wed, Jun 10 - Sat, Jun 13
Delta Logo
7:05 am - 3:33 pm
ORD
-
ORH
7h 28m
1 stop
Delta Logo
4:15 pm - 10:36 pm
ORH
-
ORD
7h 21m
1 stop
$267Delta
Sun, May 10 - Tue, May 12

American Airlines flights from Chicago to Worcester, Massachusetts

Our best American Airlines deals on Chicago to Worcester, Massachusetts flight tickets
American Airlines
May 28
ORD5:00 amChicago O'Hare Intl
10h 53m
1 stop
ORH4:53 pmWorcester
Jun 2
ORH5:18 pmWorcester
14h 44m
2 stops
ORD7:02 amChicago O'Hare Intl
$217
American Airlines
Apr 21
ORD6:40 amChicago O'Hare Intl
6h 34m
1 stop
ORH2:14 pmWorcester
Apr 25
ORH2:39 pmWorcester
10h 19m
1 stop
ORD11:58 pmChicago O'Hare Intl
$220
American Airlines
Apr 21
ORD6:40 amChicago O'Hare Intl
6h 34m
1 stop
ORH2:14 pmWorcester
Apr 25
ORH2:39 pmWorcester
5h 57m
1 stop
ORD7:36 pmChicago O'Hare Intl
$226

Delta flights from Chicago to Worcester, Massachusetts

Our best Delta deals on Chicago to Worcester, Massachusetts flight tickets
Delta
Apr 29
ORD9:35 amChicago O'Hare Intl
6h 08m
1 stop
ORH4:43 pmWorcester
May 6
ORH5:24 pmWorcester
5h 55m
1 stop
ORD10:19 pmChicago O'Hare Intl
$192
Delta
Apr 29
ORD8:52 amChicago O'Hare Intl
6h 51m
2 stops
ORH4:43 pmWorcester
May 5
ORH5:24 pmWorcester
5h 51m
1 stop
ORD10:15 pmChicago O'Hare Intl
$202
Delta
May 28
ORD7:05 amChicago O'Hare Intl
7h 28m
1 stop
ORH3:33 pmWorcester
Jun 2
ORH4:15 pmWorcester
5h 31m
1 stop
ORD8:46 pmChicago O'Hare Intl
$207

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Worcester, Massachusetts that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated April 12, 2026.
Use the filters below to find and compare flights from Chicago to Worcester, Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 4/29

9:35 am-4:43 pm

1 stop6h 08m

Worcester

Wed 5/6

5:24 pm-10:19 pm

1 stop5h 55m

$192

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 4/29

8:52 am-4:43 pm

2 stops6h 51m

Worcester

Tue 5/5

5:24 pm-10:15 pm

1 stop5h 51m

$202

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 5/28

7:05 am-3:33 pm

1 stop7h 28m

Worcester

Tue 6/2

4:15 pm-8:46 pm

1 stop5h 31m

$207

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 4/30

5:15 am-4:43 pm

2 stops10h 28m

Worcester

Tue 5/5

5:24 pm-10:15 pm

1 stop5h 51m

$212

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 5/28

5:00 am-4:53 pm

1 stop10h 53m

Worcester

Tue 6/2

5:18 pm-7:02 am

2 stops14h 44m

$217

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 5/28

5:00 am-4:53 pm

1 stop10h 53m

Worcester

Tue 6/2

5:18 pm-7:02 am

2 stops14h 44m

$237

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 6/10

5:00 am-4:53 pm

1 stop10h 53m

Worcester

Sat 6/13

5:18 pm-11:31 pm

1 stop7h 13m

$247

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 6/10

5:00 am-4:53 pm

1 stop10h 53m

Worcester

Sat 6/13

5:18 pm-11:23 pm

2 stops7h 05m

$257

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 6/10

6:00 am-4:53 pm

2 stops9h 53m

Worcester

Sat 6/13

5:18 pm-11:59 pm

2 stops7h 41m

$262

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Sun 5/10

7:05 am-3:33 pm

1 stop7h 28m

Worcester

Tue 5/12

4:15 pm-10:36 pm

1 stop7h 21m

$267

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Chicago to Worcester, Massachusetts

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Chicago to Worcester?

American Airlines and Delta are the most popular carriers operating from Chicago to Worcester

What airlines fly to Worcester, Massachusetts?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Worcester, Massachusetts from Chicago according to our data. American Airlines is the first choice among our users, with 39% of people opting to fly with this airline when traveling to Worcester, Massachusetts. Keep in mind that there are 6 different airlines that fly to Worcester, Massachusetts on a routine basis, so you have a few additional options to choose from.

When to book flights from Chicago to Worcester, Massachusetts

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago to Worcester, Massachusetts according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago to Worcester, Massachusetts (CHI to ORH) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Worcester, Massachusetts

Fastest flight time

4h 58m

Direct flights

None
The fastest flight from Chicago to Worcester, Massachusetts takes 4h 58m
There are no direct flights from Chicago to Worcester, Massachusetts. There are no popular flight routes from Chicago to Worcester, Massachusetts.
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Frequently asked questions about flying from Chicago to Worcester, Massachusetts

  • How far is Chicago to Worcester by plane?

    Worcester is 810.4 mi away from Chicago. Typically, this will take 4h 58m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago to Worcester Airport?

    Prices for flights from Chicago to Worcester Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Worcester Airport?

  • How old do you have to be to fly from Chicago to Worcester Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Worcester Airport.

  • What documentation or ID do you need to fly to Worcester Airport?

    The travel and health documents required for your trip to Worcester Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Worcester Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Chicago to Worcester, Massachusetts

Compare and see reviews for airlines that fly from Chicago to Worcester, Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $207Free CancellationRating
7.9
8,408 reviews
Search Delta flights

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Winchester

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Worcester?

Finding the right flight to Worcester from Chicago is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Worcester quick and easy, saving you time and money.

Can I find flights from Chicago to Worcester with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Worcester from Chicago with this policy.

How can momondo help me find flights from Chicago to Worcester?

Once you have performed a search for Chicago to Worcester flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Worcester right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Worcester now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Worcester and let you know when they change.

An easier way to manage your Worcester, Massachusetts trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
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