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Cheap flights from Worcester, Massachusetts to Chicago from $104

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 10/13. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Worcester, Massachusetts to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
4:15 pm - 8:43 pm
ORH
-
ORD
5h 28m
1 stop
Delta Logo
8:36 am - 2:59 pm
ORD
-
ORH
5h 23m
1 stop
$212Delta
Wed, Oct 14 - Tue, Oct 20
American Airlines Logo
5:16 pm - 9:10 am
ORH
-
ORD
16h 54m
1 stop
American Airlines Logo
6:37 am - 4:51 pm
ORD
-
ORH
9h 14m
1 stop
$230American Airlines
Fri, Jul 31 - Tue, Aug 4
American Airlines Logo
5:23 pm - 11:08 am
ORH
-
ORD
18h 45m
1 stop
American Airlines Logo
6:45 am - 4:58 pm
ORD
-
ORH
9h 13m
1 stop
$232American Airlines
Fri, Aug 28 - Wed, Sep 2
Delta Logo
5:40 pm - 10:36 pm
ORH
-
ORD
5h 56m
1 stop
Delta Logo
6:35 am - 5:00 pm
ORD
-
ORH
9h 25m
2 stops
$240Delta
Tue, Jul 28 - Wed, Jul 29
Delta Logo
4:15 pm - 10:12 pm
ORH
-
ORD
6h 57m
1 stop
Delta Logo
8:36 am - 2:59 pm
ORD
-
ORH
5h 23m
1 stop
$252Delta
Fri, Oct 16 - Mon, Oct 19
Delta Logo
5:40 pm - 10:24 pm
ORH
-
ORD
5h 44m
1 stop
Delta Logo
10:30 am - 5:00 pm
ORD
-
ORH
5h 30m
1 stop
$262Delta
Tue, Aug 11 - Thu, Aug 13
Delta Logo
5:40 pm - 10:36 pm
ORH
-
ORD
5h 56m
1 stop
Delta Logo
10:30 am - 5:00 pm
ORD
-
ORH
5h 30m
1 stop
$266Delta
Tue, Jul 28 - Tue, Aug 4
Delta Logo
5:40 pm - 10:36 pm
ORH
-
ORD
5h 56m
1 stop
Delta Logo
6:40 am - 5:00 pm
ORD
-
ORH
9h 20m
2 stops
$272Delta
Sun, Aug 2 - Wed, Aug 5
American Airlines Logo
5:16 pm - 12:29 am
ORH
-
ORD
8h 13m
1 stop
American Airlines Logo
5:00 am - 4:51 pm
ORD
-
ORH
10h 51m
1 stop
$273American Airlines
Tue, Jul 28 - Sat, Aug 1
Delta Logo
5:40 pm - 10:36 pm
ORH
-
ORD
5h 56m
1 stop
Delta Logo
5:30 am - 5:00 pm
ORD
-
ORH
10h 30m
2 stops
$276Delta
Tue, Jul 28 - Tue, Aug 4

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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
Jul 31
ORH5:16 pmWorcester
16h 54m
1 stop
ORD9:10 amChicago O'Hare Intl
Aug 4
ORD6:37 amChicago O'Hare Intl
9h 14m
1 stop
ORH4:51 pmWorcester
$230
American Airlines
Aug 28
ORH5:23 pmWorcester
18h 45m
1 stop
ORD11:08 amChicago O'Hare Intl
Sep 2
ORD6:45 amChicago O'Hare Intl
9h 13m
1 stop
ORH4:58 pmWorcester
$232
American Airlines
Jul 28
ORH5:16 pmWorcester
8h 13m
1 stop
ORD12:29 amChicago O'Hare Intl
Aug 1
ORD5:00 amChicago O'Hare Intl
10h 51m
1 stop
ORH4:51 pmWorcester
$273

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 14
ORH4:15 pmWorcester
5h 28m
1 stop
ORD8:43 pmChicago O'Hare Intl
Oct 20
ORD8:36 amChicago O'Hare Intl
5h 23m
1 stop
ORH2:59 pmWorcester
$212
Delta
Jul 28
ORH5:40 pmWorcester
5h 56m
1 stop
ORD10:36 pmChicago O'Hare Intl
Jul 29
ORD6:35 amChicago O'Hare Intl
9h 25m
2 stops
ORH5:00 pmWorcester
$240
Delta
Oct 16
ORH4:15 pmWorcester
6h 57m
1 stop
ORD10:12 pmChicago O'Hare Intl
Oct 19
ORD8:36 amChicago O'Hare Intl
5h 23m
1 stop
ORH2:59 pmWorcester
$252

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 July 18, 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
Quickest round-trip

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 10/14

4:15 pm-8:43 pm

1 stop5h 28m

Chicago O'Hare Intl

Tue 10/20

8:36 am-2:59 pm

1 stop5h 23m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 7/31

5:16 pm-9:10 am

1 stop16h 54m

Chicago O'Hare Intl

Tue 8/4

6:37 am-4:51 pm

1 stop9h 14m

$230

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 8/28

5:23 pm-11:08 am

1 stop18h 45m

Chicago O'Hare Intl

Wed 9/2

6:45 am-4:58 pm

1 stop9h 13m

$232

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 7/28

5:40 pm-10:36 pm

1 stop5h 56m

Chicago O'Hare Intl

Wed 7/29

6:35 am-5:00 pm

2 stops9h 25m

$240

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 10/16

4:15 pm-10:12 pm

1 stop6h 57m

Chicago O'Hare Intl

Mon 10/19

8:36 am-2:59 pm

1 stop5h 23m

$252

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 8/11

5:40 pm-10:24 pm

1 stop5h 44m

Chicago O'Hare Intl

Thu 8/13

10:30 am-5:00 pm

1 stop5h 30m

$262

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 7/28

5:40 pm-10:36 pm

1 stop5h 56m

Chicago O'Hare Intl

Tue 8/4

10:30 am-5:00 pm

1 stop5h 30m

$266

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sun 8/2

5:40 pm-10:36 pm

1 stop5h 56m

Chicago O'Hare Intl

Wed 8/5

6:40 am-5:00 pm

2 stops9h 20m

$272

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 7/28

5:16 pm-12:29 am

1 stop8h 13m

Chicago O'Hare Intl

Sat 8/1

5:00 am-4:51 pm

1 stop10h 51m

$273

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 7/28

5:40 pm-10:36 pm

1 stop5h 56m

Chicago O'Hare Intl

Tue 8/4

5:30 am-5:00 pm

2 stops10h 30m

$276

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 $311. 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 $410.

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 $270 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $387. 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 28m

Direct flights

None
The fastest flight from Worcester, Massachusetts to Chicago O'Hare Intl Airport takes 5h 28m
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 28m 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?

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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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