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Cheap flights from Chicago to Boston from $80

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 11/6. 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
0 bags

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Cheap round-trip flights

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American Airlines Logo
5:50 am - 2:02 pmORD-ORH
7h 12m1 stop
American Airlines Logo
3:27 pm - 10:55 pmORH-ORD
8h 28m1 stop
$154American Airlines
Find Deal
Sun, Nov 2 - Mon, Nov 10
American Airlines Logo
6:50 am - 3:02 pmORD-ORH
7h 12m1 stop
American Airlines Logo
3:27 pm - 7:04 amORH-ORD
16h 37m1 stop
$155American Airlines
Find Deal
Thu, Nov 6 - Wed, Nov 12
American Airlines Logo
5:50 am - 2:02 pmORD-ORH
7h 12m1 stop
American Airlines Logo
3:27 pm - 11:37 pmORH-ORD
9h 10m2 stops
$164American Airlines
Find Deal
Sun, Nov 2 - Mon, Nov 10
American Airlines Logo
6:50 am - 3:02 pmORD-ORH
7h 12m1 stop
American Airlines Logo
3:27 pm - 7:04 amORH-ORD
16h 37m1 stop
$173American Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
American Airlines Logo
5:00 am - 3:39 pmORD-ORH
9h 39m1 stop
American Airlines Logo
4:17 pm - 10:39 pmORH-ORD
7h 22m1 stop
$192American Airlines
Find Deal
Sat, Oct 18 - Wed, Oct 22
American Airlines Logo
5:20 am - 3:39 pmORD-ORH
9h 19m2 stops
American Airlines Logo
4:17 pm - 12:04 pmORH-ORD
20h 47m1 stop
$202American Airlines
Find Deal
Sat, Oct 18 - Wed, Oct 22
American Airlines Logo
5:00 am - 3:02 pmORD-ORH
9h 02m2 stops
American Airlines Logo
3:27 pm - 11:37 pmORH-ORD
9h 10m2 stops
$204American Airlines
Find Deal
Thu, Nov 6 - Wed, Nov 12
Delta Logo
6:00 am - 1:58 pmORD-ORH
6h 58m1 stop
Delta Logo
3:18 pm - 8:37 pmORH-ORD
6h 19m1 stop
$212Delta
Find Deal
Thu, Oct 23 - Tue, Oct 28
American Airlines Logo
5:00 am - 3:02 pmORD-ORH
9h 02m2 stops
American Airlines Logo
3:27 pm - 7:04 amORH-ORD
16h 37m1 stop
$217American Airlines
Find Deal
Thu, Nov 6 - Sun, Nov 9
Delta Logo
7:00 am - 3:23 pmORD-ORH
7h 23m1 stop
Delta Logo
4:03 pm - 10:35 pmORH-ORD
7h 32m1 stop
$222Delta
Find Deal
Mon, Nov 10 - Wed, Nov 12

American Airlines flights from Chicago to Worcester, Massachusetts

Our best American Airlines deals on Chicago to Worcester, Massachusetts flight tickets
American Airlines
Nov 2
ORD5:50 amChicago O'Hare Intl
7h 12m
1 stop
ORH2:02 pmWorcester
Nov 10
ORH3:27 pmWorcester
8h 28m
1 stop
ORD10:55 pmChicago O'Hare Intl
$154
Find similar
American Airlines
Nov 6
ORD6:50 amChicago O'Hare Intl
7h 12m
1 stop
ORH3:02 pmWorcester
Nov 12
ORH3:27 pmWorcester
16h 37m
1 stop
ORD7:04 amChicago O'Hare Intl
$155
Find similar
American Airlines
Nov 2
ORD5:50 amChicago O'Hare Intl
7h 12m
1 stop
ORH2:02 pmWorcester
Nov 10
ORH3:27 pmWorcester
9h 10m
2 stops
ORD11:37 pmChicago O'Hare Intl
$164
Find similar

Delta flights from Chicago to Worcester, Massachusetts

Our best Delta deals on Chicago to Worcester, Massachusetts flight tickets
Delta
Oct 23
ORD6:00 amChicago O'Hare Intl
6h 58m
1 stop
ORH1:58 pmWorcester
Oct 28
ORH3:18 pmWorcester
6h 19m
1 stop
ORD8:37 pmChicago O'Hare Intl
$212
Find similar
Delta
Nov 10
ORD7:00 amChicago O'Hare Intl
7h 23m
1 stop
ORH3:23 pmWorcester
Nov 12
ORH4:03 pmWorcester
7h 32m
1 stop
ORD10:35 pmChicago O'Hare Intl
$222
Find similar
Delta
Nov 4
ORD7:10 amChicago O'Hare Intl
5h 48m
2 stops
ORH1:58 pmWorcester
Nov 11
ORH4:03 pmWorcester
7h 27m
2 stops
ORD10:30 pmChicago O'Hare Intl
$227
Find similar

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 October 6, 2025.
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

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Sun 11/2

5:50 am-2:02 pm

1 stop7h 12m

Worcester

Mon 11/10

3:27 pm-10:55 pm

1 stop8h 28m

$154

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 11/6

6:50 am-3:02 pm

1 stop7h 12m

Worcester

Wed 11/12

3:27 pm-7:04 am

1 stop16h 37m

$155

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Sun 11/2

5:50 am-2:02 pm

1 stop7h 12m

Worcester

Mon 11/10

3:27 pm-11:37 pm

2 stops9h 10m

$164

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 11/6

6:50 am-3:02 pm

1 stop7h 12m

Worcester

Sun 11/9

3:27 pm-7:04 am

1 stop16h 37m

$173

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Sat 10/18

5:00 am-3:39 pm

1 stop9h 39m

Worcester

Wed 10/22

4:17 pm-10:39 pm

1 stop7h 22m

$192

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Sat 10/18

5:20 am-3:39 pm

2 stops9h 19m

Worcester

Wed 10/22

4:17 pm-12:04 pm

1 stop20h 47m

$202

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 11/6

5:00 am-3:02 pm

2 stops9h 02m

Worcester

Wed 11/12

3:27 pm-11:37 pm

2 stops9h 10m

$204

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 10/23

6:00 am-1:58 pm

1 stop6h 58m

Worcester

Tue 10/28

3:18 pm-8:37 pm

1 stop6h 19m

$212

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 11/6

5:00 am-3:02 pm

2 stops9h 02m

Worcester

Sun 11/9

3:27 pm-7:04 am

1 stop16h 37m

$217

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Mon 11/10

7:00 am-3:23 pm

1 stop7h 23m

Worcester

Wed 11/12

4:03 pm-10:35 pm

1 stop7h 32m

$222

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 day to depart on your flight to Worcester, Massachusetts?

The cheapest day to depart from Chicago to Worcester, Massachusetts is on a Thursday. Travelers who choose to depart for Worcester, Massachusetts on a Thursday will often find tickets for as low as $258. On the other hand, Friday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $270.

What is the cheapest time of day to depart on your flight to Worcester, Massachusetts?

The cheapest time of day to fly to Worcester, Massachusetts is in the morning when flights can be purchased for as low as $228. Flights in the evening are often more expensive with an average ticket price of $295.

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

Direct flights

None
There are no direct flights from Chicago to Worcester, Massachusetts. There are no popular flight routes from Chicago to Worcester, Massachusetts.
Search flight deals

  • How far is Chicago to Worcester by plane?

    Worcester is 810.4 mi away from Chicago. Typically, this will take 5h 05m 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 $212Free CancellationRating
7.9
7,969 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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