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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 5/29. 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.
American Airlines Logo
1:30 pm - 9:18 pm
ORH
-
ORD
8h 48m
1 stop
American Airlines Logo
6:40 am - 1:05 pm
ORD
-
ORH
5h 25m
1 stop
$154American Airlines
Mon, Feb 23 - Fri, Feb 27
American Airlines Logo
1:30 pm - 12:06 am
ORH
-
ORD
11h 36m
2 stops
American Airlines Logo
8:54 pm - 1:05 pm
ORD
-
ORH
15h 11m
1 stop
$164American Airlines
Mon, Feb 23 - Fri, Feb 27
American Airlines Logo
1:30 pm - 12:16 am
ORH
-
ORD
11h 46m
2 stops
American Airlines Logo
8:45 pm - 1:05 pm
ORD
-
ORH
15h 20m
2 stops
$189American Airlines
Fri, Feb 27 - Mon, Mar 2
American Airlines Logo
1:30 pm - 12:06 am
ORH
-
ORD
11h 36m
2 stops
American Airlines Logo
8:45 pm - 1:05 pm
ORD
-
ORH
15h 20m
2 stops
$204American Airlines
Mon, Feb 23 - Fri, Feb 27
Delta Logo
5:24 pm - 10:15 pm
ORH
-
ORD
5h 51m
1 stop
Delta Logo
9:35 am - 4:43 pm
ORD
-
ORH
6h 08m
1 stop
$207Delta
Fri, Apr 24 - Mon, Apr 27
Delta Logo
4:30 pm - 10:05 pm
ORH
-
ORD
6h 35m
1 stop
Delta Logo
5:25 am - 3:33 pm
ORD
-
ORH
9h 08m
2 stops
$212Delta
Mon, Mar 2 - Thu, Mar 5
Delta Logo
4:30 pm - 11:56 pm
ORH
-
ORD
8h 26m
2 stops
Delta Logo
5:25 am - 3:33 pm
ORD
-
ORH
9h 08m
2 stops
$217Delta
Mon, Mar 2 - Thu, Mar 5
American Airlines Logo
2:39 pm - 7:39 am
ORH
-
ORD
18h 00m
1 stop
American Airlines Logo
7:15 pm - 2:14 pm
ORD
-
ORH
17h 59m
1 stop
$223American Airlines
Fri, Apr 24 - Sun, Apr 26
Delta Logo
5:35 pm - 10:36 pm
ORH
-
ORD
6h 01m
1 stop
Delta Logo
9:00 am - 4:51 pm
ORD
-
ORH
6h 51m
2 stops
$227Delta
Mon, May 11 - Tue, May 12
American Airlines Logo
2:39 pm - 8:54 am
ORH
-
ORD
19h 15m
1 stop
American Airlines Logo
8:50 pm - 2:14 pm
ORD
-
ORH
16h 24m
1 stop
$243American Airlines
Thu, Apr 16 - Mon, Apr 20

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
Feb 23
ORH1:30 pmWorcester
8h 48m
1 stop
ORD9:18 pmChicago O'Hare Intl
Feb 27
ORD6:40 amChicago O'Hare Intl
5h 25m
1 stop
ORH1:05 pmWorcester
$154
American Airlines
Feb 25
ORH1:30 pmWorcester
8h 48m
1 stop
ORD9:18 pmChicago O'Hare Intl
Mar 3
ORD6:40 amChicago O'Hare Intl
5h 25m
1 stop
ORH1:05 pmWorcester
$162
American Airlines
Feb 23
ORH1:30 pmWorcester
11h 36m
2 stops
ORD12:06 amChicago O'Hare Intl
Feb 27
ORD8:54 pmChicago O'Hare Intl
15h 11m
1 stop
ORH1:05 pmWorcester
$164

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
Feb 25
ORH4:30 pmWorcester
6h 35m
1 stop
ORD10:05 pmChicago O'Hare Intl
Mar 2
ORD7:10 amChicago O'Hare Intl
7h 23m
1 stop
ORH3:33 pmWorcester
$192
Delta
Feb 23
ORH4:30 pmWorcester
6h 35m
1 stop
ORD10:05 pmChicago O'Hare Intl
Mar 4
ORD9:35 amChicago O'Hare Intl
4h 58m
1 stop
ORH3:33 pmWorcester
$197
Delta
Feb 25
ORH4:30 pmWorcester
8h 26m
2 stops
ORD11:56 pmChicago O'Hare Intl
Mar 4
ORD9:35 amChicago O'Hare Intl
4h 58m
1 stop
ORH3:33 pmWorcester
$202

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 February 11, 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

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 2/23

1:30 pm-9:18 pm

1 stop8h 48m

Chicago O'Hare Intl

Fri 2/27

6:40 am-1:05 pm

1 stop5h 25m

$154

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 2/23

1:30 pm-12:06 am

2 stops11h 36m

Chicago O'Hare Intl

Fri 2/27

8:54 pm-1:05 pm

1 stop15h 11m

$164

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 2/27

1:30 pm-12:16 am

2 stops11h 46m

Chicago O'Hare Intl

Mon 3/2

8:45 pm-1:05 pm

2 stops15h 20m

$189

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 2/23

1:30 pm-12:06 am

2 stops11h 36m

Chicago O'Hare Intl

Fri 2/27

8:45 pm-1:05 pm

2 stops15h 20m

$204

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 4/24

5:24 pm-10:15 pm

1 stop5h 51m

Chicago O'Hare Intl

Mon 4/27

9:35 am-4:43 pm

1 stop6h 08m

$207

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 3/2

4:30 pm-10:05 pm

1 stop6h 35m

Chicago O'Hare Intl

Thu 3/5

5:25 am-3:33 pm

2 stops9h 08m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 3/2

4:30 pm-11:56 pm

2 stops8h 26m

Chicago O'Hare Intl

Thu 3/5

5:25 am-3:33 pm

2 stops9h 08m

$217

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 4/24

2:39 pm-7:39 am

1 stop18h 00m

Chicago O'Hare Intl

Sun 4/26

7:15 pm-2:14 pm

1 stop17h 59m

$223

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 5/11

5:35 pm-10:36 pm

1 stop6h 01m

Chicago O'Hare Intl

Tue 5/12

9:00 am-4:51 pm

2 stops6h 51m

$227

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 4/16

2:39 pm-8:54 am

1 stop19h 15m

Chicago O'Hare Intl

Mon 4/20

8:50 pm-2:14 pm

1 stop16h 24m

$243

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 Wednesday 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 $405.

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 $382. 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

4h 57m

Direct flights

None
The fastest flight from Worcester, Massachusetts to Chicago O'Hare Intl Airport takes 4h 57m
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. 4h 57m 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
Rockford
Merrillville
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Naperville
Rosemont
New Buffalo
Kenosha
Oak Brook
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Orland Park
Racine
Hammond
Janesville
Tinley Park
Elgin
Aurora
South Holland

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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