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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 1/23. 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 Worcester, Massachusetts to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
3:34 pm - 10:54 pmORH-ORD
8h 20m1 stop
American Airlines Logo
5:00 am - 3:02 pmORD-ORH
9h 02m1 stop
$154American Airlines
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Thu, Dec 11 - Mon, Dec 15
American Airlines Logo
3:34 pm - 9:07 amORH-ORD
18h 33m1 stop
American Airlines Logo
6:10 am - 3:02 pmORD-ORH
7h 52m2 stops
$164American Airlines
Find Deal
Thu, Dec 11 - Mon, Dec 15
American Airlines Logo
3:34 pm - 7:19 amORH-ORD
16h 45m2 stops
American Airlines Logo
6:10 am - 3:02 pmORD-ORH
7h 52m2 stops
$169American Airlines
Find Deal
Thu, Dec 11 - Mon, Dec 15
American Airlines Logo
4:17 pm - 12:04 pmORH-ORD
20h 47m1 stop
American Airlines Logo
5:50 am - 2:02 pmORD-ORH
7h 12m1 stop
$173American Airlines
Find Deal
Fri, Oct 31 - Sun, Nov 2
American Airlines Logo
4:17 pm - 12:04 pmORH-ORD
20h 47m1 stop
American Airlines Logo
8:04 pm - 3:39 pmORD-ORH
18h 35m2 stops
$183American Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
American Airlines Logo
4:17 pm - 11:50 pmORH-ORD
8h 33m2 stops
American Airlines Logo
7:15 pm - 3:39 pmORD-ORH
19h 24m2 stops
$188American Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
American Airlines Logo
4:17 pm - 10:43 amORH-ORD
19h 26m1 stop
American Airlines Logo
5:00 am - 3:50 pmORD-ORH
9h 50m1 stop
$192American Airlines
Find Deal
Mon, Oct 27 - Fri, Oct 31
American Airlines Logo
4:55 pm - 12:04 pmORH-ORD
20h 09m1 stop
American Airlines Logo
5:20 am - 3:39 pmORD-ORH
9h 19m2 stops
$202American Airlines
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Tue, Oct 28 - Sat, Nov 1
Delta Logo
3:18 pm - 8:37 pmORH-ORD
6h 19m1 stop
Delta Logo
7:00 am - 1:58 pmORD-ORH
5h 58m1 stop
$293Delta
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Fri, Oct 24 - Sun, Oct 26
Delta Logo
3:18 pm - 9:46 pmORH-ORD
7h 28m1 stop
Delta Logo
7:00 am - 2:37 pmORD-ORH
6h 37m1 stop
$337Delta
Find Deal
Tue, Mar 17 - Mon, Mar 23

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 11
ORH3:34 pmWorcester
8h 20m
1 stop
ORD10:54 pmChicago O'Hare Intl
Dec 15
ORD5:00 amChicago O'Hare Intl
9h 02m
1 stop
ORH3:02 pmWorcester
$154
Find similar
American Airlines
Dec 11
ORH3:34 pmWorcester
18h 33m
1 stop
ORD9:07 amChicago O'Hare Intl
Dec 15
ORD6:10 amChicago O'Hare Intl
7h 52m
2 stops
ORH3:02 pmWorcester
$164
Find similar
American Airlines
Dec 11
ORH3:34 pmWorcester
16h 45m
2 stops
ORD7:19 amChicago O'Hare Intl
Dec 15
ORD6:10 amChicago O'Hare Intl
7h 52m
2 stops
ORH3:02 pmWorcester
$169
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
Oct 24
ORH3:18 pmWorcester
6h 19m
1 stop
ORD8:37 pmChicago O'Hare Intl
Oct 26
ORD7:00 amChicago O'Hare Intl
5h 58m
1 stop
ORH1:58 pmWorcester
$293
Find similar
Delta
Mar 17
ORH3:18 pmWorcester
7h 28m
1 stop
ORD9:46 pmChicago O'Hare Intl
Mar 23
ORD7:00 amChicago O'Hare Intl
6h 37m
1 stop
ORH2:37 pmWorcester
$337
Find similar
Delta
Oct 24
ORH3:18 pmWorcester
9h 40m
2 stops
ORD11:58 pmChicago O'Hare Intl
Oct 26
ORD7:10 amChicago O'Hare Intl
5h 48m
2 stops
ORH1:58 pmWorcester
$358
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 October 13, 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

Thu 12/11

3:34 pm-10:54 pm

1 stop8h 20m

Chicago O'Hare Intl

Mon 12/15

5:00 am-3:02 pm

1 stop9h 02m

$154

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 12/11

3:34 pm-9:07 am

1 stop18h 33m

Chicago O'Hare Intl

Mon 12/15

6:10 am-3:02 pm

2 stops7h 52m

$164

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 12/11

3:34 pm-7:19 am

2 stops16h 45m

Chicago O'Hare Intl

Mon 12/15

6:10 am-3:02 pm

2 stops7h 52m

$169

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 10/31

4:17 pm-12:04 pm

1 stop20h 47m

Chicago O'Hare Intl

Sun 11/2

5:50 am-2:02 pm

1 stop7h 12m

$173

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 10/27

4:17 pm-12:04 pm

1 stop20h 47m

Chicago O'Hare Intl

Fri 10/31

8:04 pm-3:39 pm

2 stops18h 35m

$183

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 10/27

4:17 pm-11:50 pm

2 stops8h 33m

Chicago O'Hare Intl

Fri 10/31

7:15 pm-3:39 pm

2 stops19h 24m

$188

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 10/27

4:17 pm-10:43 am

1 stop19h 26m

Chicago O'Hare Intl

Fri 10/31

5:00 am-3:50 pm

1 stop9h 50m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 10/28

4:55 pm-12:04 pm

1 stop20h 09m

Chicago O'Hare Intl

Sat 11/1

5:20 am-3:39 pm

2 stops9h 19m

$202

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 10/24

3:18 pm-8:37 pm

1 stop6h 19m

Chicago O'Hare Intl

Sun 10/26

7:00 am-1:58 pm

1 stop5h 58m

$293

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 3/17

3:18 pm-9:46 pm

1 stop7h 28m

Chicago O'Hare Intl

Mon 3/23

7:00 am-2:37 pm

1 stop6h 37m

$337

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 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 $321. 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 $434.

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 $267 when looking at flights departing in the evening. Try not to purchase tickets in the morning because they tend to be around $352. 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

Direct flights

None
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.
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  • How far is Worcester to Chicago O'Hare Intl by plane?

    Chicago O'Hare Intl is 823.6 mi away from Worcester. 5h 07m 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
Racine
Orland Park
Hammond
Tinley Park
Janesville
Elgin
Aurora
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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