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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.
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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
5:18 pm - 12:34 am
ORH
-
ORD
8h 16m
1 stop
American Airlines Logo
5:00 am - 4:53 pm
ORD
-
ORH
10h 53m
1 stop
$220American Airlines
Mon, Jun 15 - Mon, Jun 22
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
$246Delta
Wed, Jun 10 - Wed, Jun 24
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
$256Delta
Wed, Jun 24 - Tue, Jun 30
American Airlines Logo
5:16 pm - 6:38 am
ORH
-
ORD
14h 22m
1 stop
American Airlines Logo
6:37 am - 4:51 pm
ORD
-
ORH
9h 14m
1 stop
$261American Airlines
Thu, Jul 9 - Sun, Jul 12
American Airlines Logo
5:18 pm - 12:34 am
ORH
-
ORD
8h 16m
1 stop
American Airlines Logo
5:00 am - 4:53 pm
ORD
-
ORH
10h 53m
1 stop
$268American Airlines
Tue, Jun 9 - Fri, Jun 12
American Airlines Logo
5:16 pm - 7:04 am
ORH
-
ORD
14h 48m
2 stops
American Airlines Logo
6:37 am - 4:51 pm
ORD
-
ORH
9h 14m
1 stop
$271American Airlines
Thu, Jul 9 - Sun, Jul 12
American Airlines Logo
5:16 pm - 6:38 am
ORH
-
ORD
14h 22m
1 stop
American Airlines Logo
6:37 am - 4:51 pm
ORD
-
ORH
9h 14m
1 stop
$273American Airlines
Wed, Jul 15 - Fri, Jul 17
Delta Logo
5:43 pm - 10:48 pm
ORH
-
ORD
6h 05m
1 stop
Delta Logo
7:05 pm - 5:00 pm
ORD
-
ORH
20h 55m
1 stop
$274Delta
Fri, Jul 3 - Tue, Jul 7
American Airlines Logo
5:18 pm - 6:58 am
ORH
-
ORD
14h 40m
2 stops
American Airlines Logo
5:00 am - 4:53 pm
ORD
-
ORH
10h 53m
1 stop
$278American Airlines
Tue, Jun 9 - Fri, Jun 12
American Airlines Logo
5:18 pm - 6:57 am
ORH
-
ORD
14h 39m
1 stop
American Airlines Logo
5:00 am - 4:53 pm
ORD
-
ORH
10h 53m
1 stop
$281American Airlines
Wed, Jun 24 - Tue, Jun 30

JetBlue flights from Worcester, Massachusetts to Chicago

Our best JetBlue deals on Worcester, Massachusetts to Chicago flight tickets
JetBlue
Jul 29
ORH4:45 pmWorcester
7h 59m
1 stop
ORD11:44 pmChicago O'Hare Intl
Aug 3
ORD7:00 amChicago O'Hare Intl
7h 50m
1 stop
ORH3:50 pmWorcester
$414
JetBlue
Jul 22
ORH4:45 pmWorcester
7h 59m
1 stop
ORD11:44 pmChicago O'Hare Intl
Jul 25
ORD7:00 amChicago O'Hare Intl
7h 50m
1 stop
ORH3:50 pmWorcester
$424
JetBlue
Aug 3
ORH4:45 pmWorcester
7h 59m
1 stop
ORD11:44 pmChicago O'Hare Intl
Aug 6
ORD7:00 amChicago O'Hare Intl
7h 50m
1 stop
ORH3:50 pmWorcester
$433

Delta flights from Worcester, Massachusetts to Chicago

Our best Delta deals on Worcester, Massachusetts to Chicago flight tickets
Delta
Jun 10
ORH5:43 pmWorcester
5h 51m
1 stop
ORD10:34 pmChicago O'Hare Intl
Jun 24
ORD9:35 amChicago O'Hare Intl
6h 28m
1 stop
ORH5:03 pmWorcester
$246
Delta
Jun 24
ORH5:43 pmWorcester
5h 51m
1 stop
ORD10:34 pmChicago O'Hare Intl
Jun 30
ORD5:30 amChicago O'Hare Intl
10h 33m
2 stops
ORH5:03 pmWorcester
$256
Delta
Jul 3
ORH5:43 pmWorcester
6h 05m
1 stop
ORD10:48 pmChicago O'Hare Intl
Jul 7
ORD7:05 pmChicago O'Hare Intl
20h 55m
1 stop
ORH5:00 pmWorcester
$274

momondo Fare Finder

 
Customize your flight search to find flights from Worcester, Massachusetts to Chicago 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 28, 2026.
Use the filters below to find and compare flights from Worcester, Massachusetts to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 6/15

5:18 pm-12:34 am

1 stop8h 16m

Chicago O'Hare Intl

Mon 6/22

5:00 am-4:53 pm

1 stop10h 53m

$220
Quickest round-trip

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 6/10

5:43 pm-10:34 pm

1 stop5h 51m

Chicago O'Hare Intl

Wed 6/24

9:35 am-5:03 pm

1 stop6h 28m

$246

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 6/24

5:43 pm-10:34 pm

1 stop5h 51m

Chicago O'Hare Intl

Tue 6/30

5:30 am-5:03 pm

2 stops10h 33m

$256

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 7/9

5:16 pm-6:38 am

1 stop14h 22m

Chicago O'Hare Intl

Sun 7/12

6:37 am-4:51 pm

1 stop9h 14m

$261

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 6/9

5:18 pm-12:34 am

1 stop8h 16m

Chicago O'Hare Intl

Fri 6/12

5:00 am-4:53 pm

1 stop10h 53m

$268

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 7/9

5:16 pm-7:04 am

2 stops14h 48m

Chicago O'Hare Intl

Sun 7/12

6:37 am-4:51 pm

1 stop9h 14m

$271

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 7/15

5:16 pm-6:38 am

1 stop14h 22m

Chicago O'Hare Intl

Fri 7/17

6:37 am-4:51 pm

1 stop9h 14m

$273

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 7/3

5:43 pm-10:48 pm

1 stop6h 05m

Chicago O'Hare Intl

Tue 7/7

7:05 pm-5:00 pm

1 stop20h 55m

$274

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 6/9

5:18 pm-6:58 am

2 stops14h 40m

Chicago O'Hare Intl

Fri 6/12

5:00 am-4:53 pm

1 stop10h 53m

$278

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 6/24

5:18 pm-6:57 am

1 stop14h 39m

Chicago O'Hare Intl

Tue 6/30

5:00 am-4:53 pm

1 stop10h 53m

$281

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

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?

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $318. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Worcester, Massachusetts to Chicago for around $412.

What is the cheapest time of day to depart on your flight to Chicago?

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Worcester, Massachusetts to Chicago during this time can be as low as $270. In contrast, the most expensive time of day to depart to Chicago is at noon when prices are around $367.

When to book flights from Worcester, Massachusetts to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Worcester, Massachusetts to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Worcester, Massachusetts to Chicago (ORH to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Worcester, Massachusetts to Chicago

Fastest flight time

5h 44m

Direct flights

None
The fastest flight from Worcester, Massachusetts to Chicago takes 5h 44m
There are no direct flights from Worcester, Massachusetts to Chicago. There are no popular flight routes from Worcester, Massachusetts to Chicago.
Search flight deals

Frequently asked questions about flying from Worcester, Massachusetts to Chicago

  • How far is Worcester to Chicago by plane?

    Chicago is 810.4 mi away from Worcester. In terms of flight time, this usually takes a little over 5h 44m.

  • When did momondo last update prices for flights from Worcester Airport to Chicago?

    Prices for flights from Worcester Airport to Chicago are updated daily.

  • How old do you have to be to fly from Worcester Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Worcester Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Worcester to Chicago?

We help find the flight that best suits your needs, momondo compares prices from hundreds of airlines and travel agents and helps you filter them to find the best flight from Worcester to Chicago for you.

Can I find flights from Worcester to Chicago with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Worcester to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Worcester to Chicago?

Once all potential Worcester to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport