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Cheap flights from Chicago to Boston from $99

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 9/15. 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

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Chicago to Boston

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
5:00 am - 4:51 pm
ORD
-
ORH
10h 51m
1 stop
American Airlines Logo
5:16 pm - 12:29 am
ORH
-
ORD
8h 13m
1 stop
$192American Airlines
Thu, Jul 30 - Sun, Aug 2
Delta Logo
5:30 am - 5:00 pm
ORD
-
ORH
10h 30m
2 stops
Delta Logo
5:40 pm - 10:24 pm
ORH
-
ORD
5h 44m
1 stop
$202Delta
Tue, Aug 11 - Wed, Aug 19
Delta Logo
9:30 am - 5:00 pm
ORD
-
ORH
6h 30m
1 stop
Delta Logo
5:40 pm - 10:24 pm
ORH
-
ORD
5h 44m
1 stop
$208Delta
Wed, Aug 5 - Tue, Aug 11
Delta Logo
10:30 am - 5:00 pm
ORD
-
ORH
5h 30m
1 stop
Delta Logo
5:40 pm - 10:36 pm
ORH
-
ORD
5h 56m
1 stop
$230Delta
Tue, Jul 28 - Sun, Aug 2
Delta Logo
5:30 am - 5:00 pm
ORD
-
ORH
10h 30m
2 stops
Delta Logo
5:40 pm - 10:24 pm
ORH
-
ORD
5h 44m
1 stop
$240Delta
Tue, Aug 11 - Wed, Aug 19
American Airlines Logo
8:30 am - 4:51 pm
ORD
-
ORH
7h 21m
1 stop
American Airlines Logo
5:16 pm - 6:28 am
ORH
-
ORD
14h 12m
1 stop
$249American Airlines
Wed, Jul 22 - Sun, Jul 26
American Airlines Logo
5:00 am - 4:58 pm
ORD
-
ORH
10h 58m
1 stop
American Airlines Logo
5:23 pm - 6:14 am
ORH
-
ORD
13h 51m
2 stops
$277American Airlines
Thu, Aug 6 - Sun, Aug 9
American Airlines Logo
5:00 am - 4:51 pm
ORD
-
ORH
10h 51m
1 stop
American Airlines Logo
5:16 pm - 10:38 am
ORH
-
ORD
18h 22m
1 stop
$310American Airlines
Sat, Jul 25 - Mon, Jul 27
American Airlines Logo
5:00 am - 4:58 pm
ORD
-
ORH
10h 58m
1 stop
American Airlines Logo
5:23 pm - 6:14 am
ORH
-
ORD
13h 51m
2 stops
$314American Airlines
Fri, Aug 21 - Sun, Aug 23
American Airlines Logo
5:00 am - 4:51 pm
ORD
-
ORH
10h 51m
1 stop
American Airlines Logo
5:16 pm - 7:23 am
ORH
-
ORD
15h 07m
2 stops
$315American Airlines
Thu, Jul 30 - Sun, Aug 2

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American Airlines flights from Chicago to Worcester, Massachusetts

Our best American Airlines deals on Chicago to Worcester, Massachusetts flight tickets
American Airlines
Jul 30
ORD5:00 amChicago O'Hare Intl
10h 51m
1 stop
ORH4:51 pmWorcester
Aug 2
ORH5:16 pmWorcester
8h 13m
1 stop
ORD12:29 amChicago O'Hare Intl
$192
American Airlines
Aug 6
ORD5:00 amChicago O'Hare Intl
10h 58m
1 stop
ORH4:58 pmWorcester
Aug 9
ORH5:23 pmWorcester
13h 51m
2 stops
ORD6:14 amChicago O'Hare Intl
$277
American Airlines
Jul 14
ORD9:45 amChicago O'Hare Intl
6h 06m
1 stop
ORH4:51 pmWorcester
Jul 15
ORH5:16 pmWorcester
7h 14m
1 stop
ORD11:30 pmChicago O'Hare Intl
$302

JetBlue flights from Chicago to Worcester, Massachusetts

Our best JetBlue deals on Chicago to Worcester, Massachusetts flight tickets
JetBlue
Aug 19
ORD7:00 amChicago O'Hare Intl
7h 52m
1 stop
ORH3:52 pmWorcester
Aug 24
ORH4:45 pmWorcester
7h 59m
1 stop
ORD11:44 pmChicago O'Hare Intl
$494
JetBlue
Aug 19
ORD7:00 amChicago O'Hare Intl
7h 52m
1 stop
ORH3:52 pmWorcester
Aug 24
ORH4:45 pmWorcester
7h 59m
1 stop
ORD11:44 pmChicago O'Hare Intl
$502
JetBlue
Oct 17
ORD7:00 amChicago O'Hare Intl
7h 47m
1 stop
ORH3:47 pmWorcester
Oct 25
ORH4:45 pmWorcester
7h 59m
1 stop
ORD11:44 pmChicago O'Hare Intl
$509

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 July 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

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 7/30

5:00 am-4:51 pm

1 stop10h 51m

Worcester

Sun 8/2

5:16 pm-12:29 am

1 stop8h 13m

$192

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Tue 8/11

5:30 am-5:00 pm

2 stops10h 30m

Worcester

Wed 8/19

5:40 pm-10:24 pm

1 stop5h 44m

$202

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 8/5

9:30 am-5:00 pm

1 stop6h 30m

Worcester

Tue 8/11

5:40 pm-10:24 pm

1 stop5h 44m

$208
Quickest round-trip

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Tue 7/28

10:30 am-5:00 pm

1 stop5h 30m

Worcester

Sun 8/2

5:40 pm-10:36 pm

1 stop5h 56m

$230

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Tue 8/11

5:30 am-5:00 pm

2 stops10h 30m

Worcester

Wed 8/19

5:40 pm-10:24 pm

1 stop5h 44m

$240

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 7/22

8:30 am-4:51 pm

1 stop7h 21m

Worcester

Sun 7/26

5:16 pm-6:28 am

1 stop14h 12m

$249

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 8/6

5:00 am-4:58 pm

1 stop10h 58m

Worcester

Sun 8/9

5:23 pm-6:14 am

2 stops13h 51m

$277

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Sat 7/25

5:00 am-4:51 pm

1 stop10h 51m

Worcester

Mon 7/27

5:16 pm-10:38 am

1 stop18h 22m

$310

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Fri 8/21

5:00 am-4:58 pm

1 stop10h 58m

Worcester

Sun 8/23

5:23 pm-6:14 am

2 stops13h 51m

$314

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 7/30

5:00 am-4:51 pm

1 stop10h 51m

Worcester

Sun 8/2

5:16 pm-7:23 am

2 stops15h 07m

$315

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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2

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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?

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

What airlines fly to Worcester, Massachusetts?

United Airlines, American Airlines and Delta are the top three most popular airlines that fly to Worcester, Massachusetts from Chicago according to our data. United Airlines is the first choice among our users, with 41% 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

5h 30m

Direct flights

None
The fastest flight from Chicago to Worcester, Massachusetts takes 5h 30m
There are no direct flights from Chicago to Worcester, Massachusetts. There are no popular flight routes from Chicago to Worcester, Massachusetts.
Search flight deals

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 5h 30m 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
7.8
8,458 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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