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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 2/25. 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
2:18 pm - 9:32 pm
ORH
-
ORD
8h 14m
1 stop
American Airlines Logo
3:55 pm - 1:53 pm
ORD
-
ORH
20h 58m
1 stop
$155American Airlines
Thu, Feb 5 - Mon, Feb 9
American Airlines Logo
2:18 pm - 9:32 pm
ORH
-
ORD
8h 14m
1 stop
American Airlines Logo
8:18 pm - 1:53 pm
ORD
-
ORH
16h 35m
2 stops
$164American Airlines
Thu, Feb 5 - Mon, Feb 9
American Airlines Logo
2:18 pm - 7:22 am
ORH
-
ORD
18h 04m
2 stops
American Airlines Logo
8:07 pm - 1:53 pm
ORD
-
ORH
16h 46m
2 stops
$170American Airlines
Thu, Feb 5 - Mon, Feb 9
American Airlines Logo
2:23 pm - 11:27 pm
ORH
-
ORD
10h 04m
2 stops
American Airlines Logo
8:18 pm - 1:05 pm
ORD
-
ORH
15h 47m
2 stops
$184American Airlines
Sat, Feb 7 - Wed, Feb 11
Delta Logo
4:30 pm - 10:05 pm
ORH
-
ORD
6h 35m
1 stop
Delta Logo
7:10 am - 3:33 pm
ORD
-
ORH
7h 23m
1 stop
$193Delta
Fri, Feb 27 - Tue, Mar 3
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
$202Delta
Fri, Feb 27 - Tue, Mar 3
Delta Logo
4:16 pm - 8:47 pm
ORH
-
ORD
5h 31m
1 stop
Delta Logo
7:10 am - 3:33 pm
ORD
-
ORH
7h 23m
1 stop
$218Delta
Wed, Feb 11 - Fri, Feb 13
American Airlines Logo
1:30 pm - 12:16 am
ORH
-
ORD
11h 46m
2 stops
American Airlines Logo
6:40 am - 1:05 pm
ORD
-
ORH
5h 25m
1 stop
$223American Airlines
Thu, Feb 19 - Thu, Feb 26
American Airlines Logo
1:44 pm - 10:00 am
ORH
-
ORD
21h 16m
1 stop
American Airlines Logo
8:55 pm - 1:19 pm
ORD
-
ORH
15h 24m
1 stop
$224American Airlines
Tue, Mar 31 - Thu, Apr 2
Delta Logo
4:16 pm - 11:56 pm
ORH
-
ORD
8h 40m
2 stops
Delta Logo
7:10 am - 3:33 pm
ORD
-
ORH
7h 23m
1 stop
$227Delta
Wed, Feb 11 - Fri, Feb 13

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 27
ORH4:30 pmWorcester
6h 35m
1 stop
ORD10:05 pmChicago O'Hare Intl
Mar 3
ORD7:10 amChicago O'Hare Intl
7h 23m
1 stop
ORH3:33 pmWorcester
$193
Delta
Feb 27
ORH4:30 pmWorcester
6h 35m
1 stop
ORD10:05 pmChicago O'Hare Intl
Mar 3
ORD5:25 amChicago O'Hare Intl
9h 08m
2 stops
ORH3:33 pmWorcester
$202
Delta
Feb 11
ORH4:16 pmWorcester
5h 31m
1 stop
ORD8:47 pmChicago O'Hare Intl
Feb 13
ORD7:10 amChicago O'Hare Intl
7h 23m
1 stop
ORH3:33 pmWorcester
$218

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 5
ORH2:18 pmWorcester
8h 14m
1 stop
ORD9:32 pmChicago O'Hare Intl
Feb 9
ORD3:55 pmChicago O'Hare Intl
20h 58m
1 stop
ORH1:53 pmWorcester
$155
American Airlines
Feb 5
ORH2:18 pmWorcester
8h 14m
1 stop
ORD9:32 pmChicago O'Hare Intl
Feb 9
ORD8:18 pmChicago O'Hare Intl
16h 35m
2 stops
ORH1:53 pmWorcester
$164
American Airlines
Feb 5
ORH2:18 pmWorcester
18h 04m
2 stops
ORD7:22 amChicago O'Hare Intl
Feb 9
ORD8:07 pmChicago O'Hare Intl
16h 46m
2 stops
ORH1:53 pmWorcester
$170

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 January 24, 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

Thu 2/5

2:18 pm-9:32 pm

1 stop8h 14m

Chicago O'Hare Intl

Mon 2/9

3:55 pm-1:53 pm

1 stop20h 58m

$155

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 2/5

2:18 pm-9:32 pm

1 stop8h 14m

Chicago O'Hare Intl

Mon 2/9

8:18 pm-1:53 pm

2 stops16h 35m

$164

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 2/5

2:18 pm-7:22 am

2 stops18h 04m

Chicago O'Hare Intl

Mon 2/9

8:07 pm-1:53 pm

2 stops16h 46m

$170

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 2/7

2:23 pm-11:27 pm

2 stops10h 04m

Chicago O'Hare Intl

Wed 2/11

8:18 pm-1:05 pm

2 stops15h 47m

$184

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 2/27

4:30 pm-10:05 pm

1 stop6h 35m

Chicago O'Hare Intl

Tue 3/3

7:10 am-3:33 pm

1 stop7h 23m

$193

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 2/27

4:30 pm-10:05 pm

1 stop6h 35m

Chicago O'Hare Intl

Tue 3/3

5:25 am-3:33 pm

2 stops9h 08m

$202

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 2/11

4:16 pm-8:47 pm

1 stop5h 31m

Chicago O'Hare Intl

Fri 2/13

7:10 am-3:33 pm

1 stop7h 23m

$218

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 2/19

1:30 pm-12:16 am

2 stops11h 46m

Chicago O'Hare Intl

Thu 2/26

6:40 am-1:05 pm

1 stop5h 25m

$223

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 3/31

1:44 pm-10:00 am

1 stop21h 16m

Chicago O'Hare Intl

Thu 4/2

8:55 pm-1:19 pm

1 stop15h 24m

$224

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 2/11

4:16 pm-11:56 pm

2 stops8h 40m

Chicago O'Hare Intl

Fri 2/13

7:10 am-3:33 pm

1 stop7h 23m

$227

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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 $314. 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 $412.

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 $370. 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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Naperville
Rosemont
New Buffalo
Kenosha
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Hammond
Janesville
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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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