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Cheap flights from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Boston departing on 9/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to Boston

Cheap round-trip flights

American Airlines Logo
9:37 pm - 3:59 pmORD-ORH
17h 22m1 stop
American Airlines Logo
4:23 pm - 12:20 pmORH-ORD
20h 57m1 stop
$154American Airlines
Find Deal
Mon, Sep 29 - Fri, Oct 3
American Airlines Logo
9:37 pm - 3:59 pmORD-ORH
17h 22m1 stop
American Airlines Logo
4:23 pm - 11:48 pmORH-ORD
8h 25m2 stops
$164American Airlines
Find Deal
Mon, Sep 29 - Fri, Oct 3
American Airlines Logo
8:29 pm - 3:59 pmORD-ORH
18h 30m2 stops
American Airlines Logo
4:24 pm - 11:48 pmORH-ORD
8h 24m2 stops
$169American Airlines
Find Deal
Tue, Sep 30 - Sat, Oct 4
American Airlines Logo
7:09 pm - 3:50 pmORD-ORH
19h 41m1 stop
American Airlines Logo
4:05 pm - 7:25 amORH-ORD
16h 20m1 stop
$171American Airlines
Find Deal
Sat, Oct 11 - Sat, Oct 18
American Airlines Logo
7:09 pm - 3:50 pmORD-ORH
19h 41m1 stop
American Airlines Logo
4:05 pm - 11:50 pmORH-ORD
8h 45m2 stops
$181American Airlines
Find Deal
Sat, Oct 11 - Sat, Oct 18
American Airlines Logo
5:00 am - 3:56 pmORD-ORH
9h 56m2 stops
American Airlines Logo
4:23 pm - 6:51 amORH-ORD
15h 28m2 stops
$203American Airlines
Find Deal
Mon, Sep 29 - Fri, Oct 3
Delta Logo
7:00 am - 2:38 pmORD-ORH
6h 38m1 stop
Delta Logo
3:18 pm - 8:37 pmORH-ORD
6h 19m1 stop
$212Delta
Find Deal
Thu, Oct 2 - Tue, Oct 7
Delta Logo
7:00 am - 2:38 pmORD-ORH
6h 38m1 stop
Delta Logo
3:18 pm - 8:37 pmORH-ORD
6h 19m1 stop
$222Delta
Find Deal
Thu, Oct 2 - Mon, Oct 6
American Airlines Logo
6:45 am - 3:50 pmORD-ORH
8h 05m1 stop
American Airlines Logo
3:27 pm - 10:55 pmORH-ORD
8h 28m1 stop
$223American Airlines
Find Deal
Fri, Oct 31 - Sun, Nov 2
American Airlines Logo
8:35 am - 3:58 pmORD-ORH
6h 23m1 stop
American Airlines Logo
4:17 pm - 7:25 amORH-ORD
16h 08m1 stop
$224American Airlines
Find Deal
Sat, Oct 4 - Mon, Oct 6

American Airlines flights from Chicago O'Hare Intl Airport to Worcester, Massachusetts

Our best American Airlines deals on Chicago O'Hare Intl Airport to Worcester, Massachusetts flight tickets
American Airlines
Sep 29
ORD9:37 pmChicago O'Hare Intl
17h 22m
1 stop
ORH3:59 pmWorcester
Oct 3
ORH4:23 pmWorcester
20h 57m
1 stop
ORD12:20 pmChicago O'Hare Intl
$154
Find similar
American Airlines
Sep 29
ORD9:37 pmChicago O'Hare Intl
17h 22m
1 stop
ORH3:59 pmWorcester
Oct 3
ORH4:23 pmWorcester
8h 25m
2 stops
ORD11:48 pmChicago O'Hare Intl
$164
Find similar
American Airlines
Sep 30
ORD8:29 pmChicago O'Hare Intl
18h 30m
2 stops
ORH3:59 pmWorcester
Oct 4
ORH4:24 pmWorcester
8h 24m
2 stops
ORD11:48 pmChicago O'Hare Intl
$169
Find similar

Delta flights from Chicago O'Hare Intl Airport to Worcester, Massachusetts

Our best Delta deals on Chicago O'Hare Intl Airport to Worcester, Massachusetts flight tickets
Delta
Oct 2
ORD7:00 amChicago O'Hare Intl
6h 38m
1 stop
ORH2:38 pmWorcester
Oct 7
ORH3:18 pmWorcester
6h 19m
1 stop
ORD8:37 pmChicago O'Hare Intl
$212
Find similar
Delta
Oct 2
ORD7:00 amChicago O'Hare Intl
6h 38m
1 stop
ORH2:38 pmWorcester
Oct 6
ORH3:18 pmWorcester
6h 19m
1 stop
ORD8:37 pmChicago O'Hare Intl
$222
Find similar
Delta
Oct 9
ORD6:00 amChicago O'Hare Intl
6h 58m
1 stop
ORH1:58 pmWorcester
Oct 24
ORH3:18 pmWorcester
9h 40m
2 stops
ORD11:58 pmChicago O'Hare Intl
$232
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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 September 16, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Worcester, Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Mon 9/29

9:37 pm-3:59 pm

1 stop17h 22m

Worcester

Fri 10/3

4:23 pm-12:20 pm

1 stop20h 57m

$154

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Mon 9/29

9:37 pm-3:59 pm

1 stop17h 22m

Worcester

Fri 10/3

4:23 pm-11:48 pm

2 stops8h 25m

$164

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Tue 9/30

8:29 pm-3:59 pm

2 stops18h 30m

Worcester

Sat 10/4

4:24 pm-11:48 pm

2 stops8h 24m

$169

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Sat 10/11

7:09 pm-3:50 pm

1 stop19h 41m

Worcester

Sat 10/18

4:05 pm-7:25 am

1 stop16h 20m

$171

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Sat 10/11

7:09 pm-3:50 pm

1 stop19h 41m

Worcester

Sat 10/18

4:05 pm-11:50 pm

2 stops8h 45m

$181

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Mon 9/29

5:00 am-3:56 pm

2 stops9h 56m

Worcester

Fri 10/3

4:23 pm-6:51 am

2 stops15h 28m

$203

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 10/2

7:00 am-2:38 pm

1 stop6h 38m

Worcester

Tue 10/7

3:18 pm-8:37 pm

1 stop6h 19m

$212

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 10/2

7:00 am-2:38 pm

1 stop6h 38m

Worcester

Mon 10/6

3:18 pm-8:37 pm

1 stop6h 19m

$222

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Fri 10/31

6:45 am-3:50 pm

1 stop8h 05m

Worcester

Sun 11/2

3:27 pm-10:55 pm

1 stop8h 28m

$223

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Sat 10/4

8:35 am-3:58 pm

1 stop6h 23m

Worcester

Mon 10/6

4:17 pm-7:25 am

1 stop16h 08m

$224

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 O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport 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 O'Hare Intl Airport to Worcester, Massachusetts

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

Cheap Chicago O'Hare Intl Airport to Worcester, Massachusetts (ORD to ORH) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Worcester, Massachusetts

Direct flights

None
There are no direct flights from Chicago O'Hare Intl Airport to Worcester, Massachusetts. There are no popular flight routes from Chicago O'Hare Intl Airport to Worcester, Massachusetts.
Search flight deals

  • How far is Chicago O'Hare Intl to Worcester by plane?

    Worcester is 823.6 mi away from Chicago O'Hare Intl. In terms of flight time, this usually takes a little over 5h 37m.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Worcester Airport?

    Prices for flights from Chicago O'Hare Intl Airport to Worcester Airport refresh daily.

  • How many operators does momondo search for flights from Chicago O'Hare Intl Airport to Worcester Airport?

  • How old do you have to be to fly from Chicago O'Hare Intl Airport 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 O'Hare Intl Airport to Worcester Airport.

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

    The travel and health documents you'll need for your trip to Worcester Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Worcester Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Chicago O'Hare Intl Airport to Worcester, Massachusetts?

Best airlines flying from Chicago O'Hare Intl Airport to Worcester, Massachusetts

Compare and see reviews for airlines that fly from Chicago O'Hare Intl Airport to Worcester, Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $212Free CancellationRating
7.9
7,957 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?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Chicago to Worcester for you.

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?

momondo helps you find the best flight between Chicago and Worcester by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Worcester, momondo offers a useful price alert feature which will track prices for flights to Worcester from Chicago and alert you when they change.

An easier way to manage your Worcester, Massachusetts trip

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