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Cheap flights from Worcester, Massachusetts to Chicago from $109

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 6/9. 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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Find the cheapest flights from Worcester, Massachusetts to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
5:40 pm - 10:24 pm
ORH
-
ORD
5h 44m
1 stop
Delta Logo
9:30 am - 5:00 pm
ORD
-
ORH
6h 30m
1 stop
$220Delta
Tue, Aug 4 - Tue, Aug 11
Delta Logo
5:43 pm - 10:34 pm
ORH
-
ORD
5h 51m
1 stop
Delta Logo
9:35 am - 5:03 pm
ORD
-
ORH
6h 28m
1 stop
$222Delta
Tue, Jun 9 - Wed, Jun 10
Delta Logo
5:43 pm - 10:34 pm
ORH
-
ORD
5h 51m
1 stop
Delta Logo
5:30 am - 5:03 pm
ORD
-
ORH
10h 33m
2 stops
$230Delta
Wed, Jun 24 - Mon, Jun 29
American Airlines Logo
5:18 pm - 7:10 am
ORH
-
ORD
14h 52m
1 stop
American Airlines Logo
5:00 am - 4:53 pm
ORD
-
ORH
10h 53m
1 stop
$232American Airlines
Mon, Jun 1 - Thu, Jun 4
American Airlines Logo
5:18 pm - 11:30 pm
ORH
-
ORD
7h 12m
2 stops
American Airlines Logo
6:04 am - 4:53 pm
ORD
-
ORH
9h 49m
2 stops
$235American Airlines
Wed, Jun 24 - Tue, Jun 30
Delta Logo
5:43 pm - 10:48 pm
ORH
-
ORD
6h 05m
1 stop
Delta Logo
9:35 am - 5:03 pm
ORD
-
ORH
6h 28m
1 stop
$236Delta
Mon, Jun 29 - Wed, Jul 1
American Airlines Logo
5:18 pm - 11:58 pm
ORH
-
ORD
7h 40m
2 stops
American Airlines Logo
6:00 am - 4:53 pm
ORD
-
ORH
9h 53m
2 stops
$237American Airlines
Tue, Jun 9 - Wed, Jun 10
Delta Logo
5:43 pm - 10:34 pm
ORH
-
ORD
5h 51m
1 stop
Delta Logo
10:35 am - 5:03 pm
ORD
-
ORH
5h 28m
1 stop
$240Delta
Mon, Jun 15 - Wed, Jun 17
American Airlines Logo
5:18 pm - 7:25 am
ORH
-
ORD
15h 07m
2 stops
American Airlines Logo
6:29 am - 4:53 pm
ORD
-
ORH
9h 24m
1 stop
$242American Airlines
Mon, Jun 1 - Thu, Jun 4
Delta Logo
5:40 pm - 10:24 pm
ORH
-
ORD
5h 44m
1 stop
Delta Logo
9:30 am - 5:00 pm
ORD
-
ORH
6h 30m
1 stop
$246Delta
Wed, Aug 5 - Wed, Aug 12

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
Jun 5
ORH5:18 pmWorcester
16h 48m
1 stop
ORD9:06 amChicago O'Hare Intl
Jun 9
ORD5:00 amChicago O'Hare Intl
10h 53m
1 stop
ORH4:53 pmWorcester
$220
American Airlines
Jun 5
ORH5:18 pmWorcester
16h 48m
1 stop
ORD9:06 amChicago O'Hare Intl
Jun 9
ORD6:04 amChicago O'Hare Intl
9h 49m
2 stops
ORH4:53 pmWorcester
$230
American Airlines
Jun 1
ORH5:18 pmWorcester
14h 52m
1 stop
ORD7:10 amChicago O'Hare Intl
Jun 4
ORD5:00 amChicago O'Hare Intl
10h 53m
1 stop
ORH4:53 pmWorcester
$232

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
Aug 4
ORH5:40 pmWorcester
5h 44m
1 stop
ORD10:24 pmChicago O'Hare Intl
Aug 11
ORD9:30 amChicago O'Hare Intl
6h 30m
1 stop
ORH5:00 pmWorcester
$220
Delta
Jun 9
ORH5:43 pmWorcester
5h 51m
1 stop
ORD10:34 pmChicago O'Hare Intl
Jun 10
ORD9:35 amChicago O'Hare Intl
6h 28m
1 stop
ORH5:03 pmWorcester
$222
Delta
Jun 24
ORH5:43 pmWorcester
5h 51m
1 stop
ORD10:34 pmChicago O'Hare Intl
Jun 29
ORD5:30 amChicago O'Hare Intl
10h 33m
2 stops
ORH5:03 pmWorcester
$230

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 May 23, 2026.
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

Cheapest round-trip

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 8/4

5:40 pm-10:24 pm

1 stop5h 44m

Chicago O'Hare Intl

Tue 8/11

9:30 am-5:00 pm

1 stop6h 30m

$220

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 6/9

5:43 pm-10:34 pm

1 stop5h 51m

Chicago O'Hare Intl

Wed 6/10

9:35 am-5:03 pm

1 stop6h 28m

$222

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 6/24

5:43 pm-10:34 pm

1 stop5h 51m

Chicago O'Hare Intl

Mon 6/29

5:30 am-5:03 pm

2 stops10h 33m

$230

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 6/1

5:18 pm-7:10 am

1 stop14h 52m

Chicago O'Hare Intl

Thu 6/4

5:00 am-4:53 pm

1 stop10h 53m

$232

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 6/24

5:18 pm-11:30 pm

2 stops7h 12m

Chicago O'Hare Intl

Tue 6/30

6:04 am-4:53 pm

2 stops9h 49m

$235

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 6/29

5:43 pm-10:48 pm

1 stop6h 05m

Chicago O'Hare Intl

Wed 7/1

9:35 am-5:03 pm

1 stop6h 28m

$236

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 6/9

5:18 pm-11:58 pm

2 stops7h 40m

Chicago O'Hare Intl

Wed 6/10

6:00 am-4:53 pm

2 stops9h 53m

$237
Quickest round-trip

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 6/15

5:43 pm-10:34 pm

1 stop5h 51m

Chicago O'Hare Intl

Wed 6/17

10:35 am-5:03 pm

1 stop5h 28m

$240

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 6/1

5:18 pm-7:25 am

2 stops15h 07m

Chicago O'Hare Intl

Thu 6/4

6:29 am-4:53 pm

1 stop9h 24m

$242

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 8/5

5:40 pm-10:24 pm

1 stop5h 44m

Chicago O'Hare Intl

Wed 8/12

9:30 am-5:00 pm

1 stop6h 30m

$246

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 $315. 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 $407.

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 $271 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $384. 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 44m

Direct flights

None
The fastest flight from Worcester, Massachusetts to Chicago O'Hare Intl Airport takes 5h 44m
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

Frequently asked questions about flying from Worcester, Massachusetts to Chicago O'Hare Intl Airport

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

    Chicago O'Hare Intl is 823.6 mi away from Worcester. 5h 44m 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
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South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Rosemont
Naperville
Orland Park
New Buffalo
Oak Brook
Kenosha
Joliet
Aurora
Racine
Janesville
Hammond
Evanston
Elgin
Tinley Park

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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