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Cheap flights from Worcester, Massachusetts to Chicago from $75

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Worcester, Massachusetts to Chicago departing on 1/10. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
1:45 pm - 8:42 amORH-ORD
19h 57m1 stop
American Airlines Logo
8:45 pm - 1:17 pmORD-ORH
15h 32m1 stop
$163American Airlines
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Sat, Dec 20 - Sun, Dec 28
American Airlines Logo
3:30 pm - 8:26 pmORH-ORD
5h 56m1 stop
American Airlines Logo
8:50 pm - 3:02 pmORD-ORH
17h 12m1 stop
$182American Airlines
Find Deal
Wed, Dec 10 - Sun, Dec 14
American Airlines Logo
3:30 pm - 11:39 pmORH-ORD
9h 09m2 stops
American Airlines Logo
8:50 pm - 3:02 pmORD-ORH
17h 12m1 stop
$192American Airlines
Find Deal
Wed, Dec 10 - Sun, Dec 14
American Airlines Logo
1:45 pm - 8:42 amORH-ORD
19h 57m1 stop
American Airlines Logo
8:45 pm - 1:17 pmORD-ORH
15h 32m1 stop
$193American Airlines
Find Deal
Sat, Dec 20 - Sun, Dec 28
American Airlines Logo
3:27 pm - 7:19 amORH-ORD
16h 52m2 stops
American Airlines Logo
8:40 pm - 3:05 pmORD-ORH
17h 25m2 stops
$197American Airlines
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Mon, Dec 15 - Tue, Dec 16
American Airlines Logo
1:45 pm - 7:29 amORH-ORD
18h 44m2 stops
American Airlines Logo
8:45 pm - 1:17 pmORD-ORH
15h 32m1 stop
$203American Airlines
Find Deal
Sat, Dec 20 - Sun, Dec 28
American Airlines Logo
3:37 pm - 9:07 amORH-ORD
18h 30m1 stop
American Airlines Logo
8:50 pm - 3:02 pmORD-ORH
17h 12m1 stop
$212American Airlines
Find Deal
Sat, Dec 13 - Sun, Dec 14
American Airlines Logo
1:47 pm - 8:42 amORH-ORD
19h 55m1 stop
American Airlines Logo
8:45 pm - 1:17 pmORD-ORH
15h 32m1 stop
$224American Airlines
Find Deal
Thu, Jan 1 - Sun, Jan 4
American Airlines Logo
3:37 pm - 7:40 amORH-ORD
17h 03m2 stops
American Airlines Logo
8:50 pm - 3:02 pmORD-ORH
17h 12m1 stop
$232American Airlines
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Sat, Dec 13 - Sun, Dec 14
American Airlines Logo
12:19 pm - 8:47 amORH-ORD
21h 28m2 stops
American Airlines Logo
6:46 pm - 1:17 pmORD-ORH
17h 31m1 stop
$234American Airlines
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Wed, Dec 31 - Sun, Jan 4

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

Our best American Airlines deals on Worcester, Massachusetts to Chicago O'Hare Intl Airport flight tickets
American Airlines
Dec 20
ORH1:45 pmWorcester
19h 57m
1 stop
ORD8:42 amChicago O'Hare Intl
Dec 28
ORD8:45 pmChicago O'Hare Intl
15h 32m
1 stop
ORH1:17 pmWorcester
$163
Find similar
American Airlines
Dec 10
ORH3:30 pmWorcester
5h 56m
1 stop
ORD8:26 pmChicago O'Hare Intl
Dec 14
ORD8:50 pmChicago O'Hare Intl
17h 12m
1 stop
ORH3:02 pmWorcester
$182
Find similar
American Airlines
Dec 10
ORH3:30 pmWorcester
9h 09m
2 stops
ORD11:39 pmChicago O'Hare Intl
Dec 14
ORD8:50 pmChicago O'Hare Intl
17h 12m
1 stop
ORH3:02 pmWorcester
$192
Find similar

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

Our best Delta deals on Worcester, Massachusetts to Chicago O'Hare Intl Airport flight tickets
Delta
Mar 23
ORH4:30 pmWorcester
6h 42m
1 stop
ORD10:12 pmChicago O'Hare Intl
Mar 28
ORD5:50 pmChicago O'Hare Intl
20h 58m
1 stop
ORH3:48 pmWorcester
$290
Find similar
Delta
Mar 29
ORH4:30 pmWorcester
17h 48m
1 stop
ORD9:18 amChicago O'Hare Intl
Mar 30
ORD2:40 pmChicago O'Hare Intl
24h 08m
1 stop
ORH3:48 pmWorcester
$413
Find similar
Delta
Mar 23
ORH4:30 pmWorcester
21h 46m
2 stops
ORD1:16 pmChicago O'Hare Intl
Mar 28
ORD5:50 pmChicago O'Hare Intl
20h 58m
1 stop
ORH3:48 pmWorcester
$417
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Worcester, Massachusetts to Chicago O'Hare Intl Airport 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 November 26, 2025.
Use the filters below to find and compare flights from Worcester, Massachusetts to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 12/20

1:45 pm-8:42 am

1 stop19h 57m

Chicago O'Hare Intl

Sun 12/28

8:45 pm-1:17 pm

1 stop15h 32m

$163

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 12/10

3:30 pm-8:26 pm

1 stop5h 56m

Chicago O'Hare Intl

Sun 12/14

8:50 pm-3:02 pm

1 stop17h 12m

$182

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 12/10

3:30 pm-11:39 pm

2 stops9h 09m

Chicago O'Hare Intl

Sun 12/14

8:50 pm-3:02 pm

1 stop17h 12m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 12/20

1:45 pm-8:42 am

1 stop19h 57m

Chicago O'Hare Intl

Sun 12/28

8:45 pm-1:17 pm

1 stop15h 32m

$193

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 12/15

3:27 pm-7:19 am

2 stops16h 52m

Chicago O'Hare Intl

Tue 12/16

8:40 pm-3:05 pm

2 stops17h 25m

$197

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 12/20

1:45 pm-7:29 am

2 stops18h 44m

Chicago O'Hare Intl

Sun 12/28

8:45 pm-1:17 pm

1 stop15h 32m

$203

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 12/13

3:37 pm-9:07 am

1 stop18h 30m

Chicago O'Hare Intl

Sun 12/14

8:50 pm-3:02 pm

1 stop17h 12m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 1/1

1:47 pm-8:42 am

1 stop19h 55m

Chicago O'Hare Intl

Sun 1/4

8:45 pm-1:17 pm

1 stop15h 32m

$224

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 12/13

3:37 pm-7:40 am

2 stops17h 03m

Chicago O'Hare Intl

Sun 12/14

8:50 pm-3:02 pm

1 stop17h 12m

$232

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 12/31

12:19 pm-8:47 am

2 stops21h 28m

Chicago O'Hare Intl

Sun 1/4

6:46 pm-1:17 pm

1 stop17h 31m

$234

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Worcester, Massachusetts to Chicago O'Hare Intl Airport

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 Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $323. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Worcester, Massachusetts because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $430.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Worcester, Massachusetts in the evening is the least expensive time of day to depart. momondo users have found prices as low as $269 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $363. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

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

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

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

Fastest flight time

5h 31m

Direct flights

None
The fastest flight from Worcester, Massachusetts to Chicago O'Hare Intl Airport takes 5h 31m
There are no direct flights from Worcester, Massachusetts to Chicago O'Hare Intl Airport. There are no popular flight routes from Worcester, Massachusetts to Chicago O'Hare Intl Airport.
Search flight deals

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

    Chicago O'Hare Intl is 823.6 mi away from Worcester. 5h 56m is a normal flight duration for this route.

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

    Prices for flights from Worcester Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

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

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Tinley Park
Janesville
Aurora
Elgin
Benton Harbor

Why use momondo?

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

Finding the right flight to Chicago from Worcester 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 Chicago quick and easy, saving you time and money.

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

Flights from Worcester to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Worcester.

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

Yes momondo offers price alerts on flights to Chicago from Worcester. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

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