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Cheap flights from Worcester, Massachusetts to Chicago from $94

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 10/26. 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 pmORH  Worcester-ORD Chicago O'Hare Intl
5h 28m1 stop New York LaGuardia
Delta Logo
7:00 am - 2:58 pmORD  Chicago O'Hare Intl-ORH Worcester
6h 58m1 stop New York LaGuardia
$192Delta
Wed, Oct 21 - Mon, Oct 26
Delta Logo
4:15 pm - 10:32 pmORH  Worcester-ORD Chicago O'Hare Intl
7h 17m1 stop New York LaGuardia
Delta Logo
7:00 am - 2:52 pmORD  Chicago O'Hare Intl-ORH Worcester
6h 52m1 stop New York LaGuardia
$192Delta
Wed, Nov 4 - Wed, Nov 11
American Airlines Logo
5:16 pm - 12:18 pmORH  Worcester-ORD Chicago O'Hare Intl
20h 02m1 stop Philadelphia
American Airlines Logo
6:29 am - 4:49 pmORD  Chicago O'Hare Intl-ORH Worcester
9h 20m1 stop Philadelphia
$192American Airlines
Wed, Oct 21 - Mon, Oct 26
American Airlines Logo
5:16 pm - 9:30 pmORH  Worcester-ORD Chicago O'Hare Intl
5h 14m1 stop Philadelphia
American Airlines Logo
6:29 am - 4:49 pmORD  Chicago O'Hare Intl-ORH Worcester
9h 20m1 stop Philadelphia
$192American Airlines
Wed, Sep 23 - Mon, Sep 28
Delta Logo
4:20 pm - 8:31 pmORH  Worcester-ORD Chicago O'Hare Intl
5h 11m1 stop New York LaGuardia
Delta Logo
9:30 am - 3:37 pmORD  Chicago O'Hare Intl-ORH Worcester
5h 07m1 stop New York LaGuardia
$192Delta
Wed, Sep 23 - Wed, Sep 30
American Airlines Logo
5:19 pm - 10:30 pmORH  Worcester-ORD Chicago O'Hare Intl
6h 11m1 stop Philadelphia
American Airlines Logo
6:29 am - 4:49 pmORD  Chicago O'Hare Intl-ORH Worcester
9h 20m1 stop Philadelphia
$192American Airlines
Sat, Oct 24 - Thu, Oct 29
American Airlines Logo
5:16 pm - 11:56 pmORH  Worcester-ORD Chicago O'Hare Intl
7h 40m1 stop Philadelphia
American Airlines Logo
8:45 am - 4:49 pmORD  Chicago O'Hare Intl-ORH Worcester
7h 04m1 stop Philadelphia
$192American Airlines
Sat, Sep 19 - Tue, Sep 22
American Airlines Logo
5:16 pm - 11:56 pmORH  Worcester-ORD Chicago O'Hare Intl
7h 40m1 stop Philadelphia
American Airlines Logo
6:29 am - 4:49 pmORD  Chicago O'Hare Intl-ORH Worcester
9h 20m1 stop Philadelphia
$193American Airlines
Thu, Sep 10 - Thu, Sep 17
Delta Logo
4:15 pm - 11:52 pmORH  Worcester-ORD Chicago O'Hare Intl
8h 37m2 stops New York LaGuardia Atlanta Hartsfield-Jackson
Delta Logo
8:36 am - 2:58 pmORD  Chicago O'Hare Intl-ORH Worcester
5h 22m1 stop New York LaGuardia
$202Delta
Wed, Oct 21 - Mon, Oct 26
Delta Logo
4:15 pm - 10:32 pmORH  Worcester-ORD Chicago O'Hare Intl
7h 17m1 stop New York LaGuardia
Delta Logo
5:30 am - 2:52 pmORD  Chicago O'Hare Intl-ORH Worcester
8h 22m2 stops Atlanta Hartsfield-Jackson New York LaGuardia
$202Delta
Wed, Nov 4 - Wed, Nov 11

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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
Sep 10
ORH5:16 pmWorcester
7h 40m
1 stop
ORD11:56 pmChicago O'Hare Intl
Sep 17
ORD6:29 amChicago O'Hare Intl
9h 20m
1 stop
ORH4:49 pmWorcester
$193
American Airlines
Sep 18
ORH5:16 pmWorcester
18h 40m
1 stop
ORD10:56 amChicago O'Hare Intl
Sep 22
ORD8:45 amChicago O'Hare Intl
7h 04m
1 stop
ORH4:49 pmWorcester
$208
American Airlines
Aug 28
ORH5:23 pmWorcester
15h 07m
1 stop
ORD7:30 amChicago O'Hare Intl
Sep 1
ORD8:19 amChicago O'Hare Intl
7h 39m
1 stop
ORH4:58 pmWorcester
$226

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

Our best JetBlue deals on Worcester, Massachusetts to Chicago O'Hare Intl Airport flight tickets
JetBlue
Sep 5
ORH4:45 pmWorcester
7h 59m
1 stop
ORD11:44 pmChicago O'Hare Intl
Sep 8
ORD7:00 amChicago O'Hare Intl
7h 52m
1 stop
ORH3:52 pmWorcester
$290
JetBlue
Oct 15
ORH4:45 pmWorcester
7h 59m
1 stop
ORD11:44 pmChicago O'Hare Intl
Oct 19
ORD7:00 amChicago O'Hare Intl
7h 47m
1 stop
ORH3:47 pmWorcester
$333
JetBlue
Sep 27
ORH5:00 pmWorcester
7h 08m
1 stop
ORD11:08 pmChicago O'Hare Intl
Oct 4
ORD6:00 amChicago O'Hare Intl
8h 54m
1 stop
ORH3:54 pmWorcester
$376

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 August 14, 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 Worcester - ORD Chicago O'Hare Intl

ORHORD

Worcester

Wed 10/21

4:15 pm-8:43 pm

1 stop5h 28m

Chicago O'Hare Intl

Mon 10/26

7:00 am-2:58 pm

1 stop6h 58m

$192

WorcesterChicago

ORH Worcester - ORD Chicago O'Hare Intl

ORHORD

Worcester

Wed 11/4

4:15 pm-10:32 pm

1 stop7h 17m

Chicago O'Hare Intl

Wed 11/11

7:00 am-2:52 pm

1 stop6h 52m

$192

WorcesterChicago

ORH Worcester - ORD Chicago O'Hare Intl

ORHORD

Worcester

Wed 10/21

5:16 pm-12:18 pm

1 stop20h 02m

Chicago O'Hare Intl

Mon 10/26

6:29 am-4:49 pm

1 stop9h 20m

$192

WorcesterChicago

ORH Worcester - ORD Chicago O'Hare Intl

ORHORD

Worcester

Wed 9/23

5:16 pm-9:30 pm

1 stop5h 14m

Chicago O'Hare Intl

Mon 9/28

6:29 am-4:49 pm

1 stop9h 20m

$192
Quickest round-trip

WorcesterChicago

ORH Worcester - ORD Chicago O'Hare Intl

ORHORD

Worcester

Wed 9/23

4:20 pm-8:31 pm

1 stop5h 11m

Chicago O'Hare Intl

Wed 9/30

9:30 am-3:37 pm

1 stop5h 07m

$192

WorcesterChicago

ORH Worcester - ORD Chicago O'Hare Intl

ORHORD

Worcester

Sat 10/24

5:19 pm-10:30 pm

1 stop6h 11m

Chicago O'Hare Intl

Thu 10/29

6:29 am-4:49 pm

1 stop9h 20m

$192

WorcesterChicago

ORH Worcester - ORD Chicago O'Hare Intl

ORHORD

Worcester

Sat 9/19

5:16 pm-11:56 pm

1 stop7h 40m

Chicago O'Hare Intl

Tue 9/22

8:45 am-4:49 pm

1 stop7h 04m

$192

WorcesterChicago

ORH Worcester - ORD Chicago O'Hare Intl

ORHORD

Worcester

Thu 9/10

5:16 pm-11:56 pm

1 stop7h 40m

Chicago O'Hare Intl

Thu 9/17

6:29 am-4:49 pm

1 stop9h 20m

$193

WorcesterChicago

ORH Worcester - ORD Chicago O'Hare Intl

ORHORD

Worcester

Wed 10/21

4:15 pm-11:52 pm

2 stops8h 37m

Chicago O'Hare Intl

Mon 10/26

8:36 am-2:58 pm

1 stop5h 22m

$202

WorcesterChicago

ORH Worcester - ORD Chicago O'Hare Intl

ORHORD

Worcester

Wed 11/4

4:15 pm-10:32 pm

1 stop7h 17m

Chicago O'Hare Intl

Wed 11/11

5:30 am-2:52 pm

2 stops8h 22m

$202

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 $310. 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 $408.

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 $273 when looking at flights departing in the evening. Try not to purchase tickets at noon because they tend to be around $386. 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 11m

Direct flights

None
The fastest flight from Worcester, Massachusetts to Chicago O'Hare Intl Airport takes 5h 11m
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 11m 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.

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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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