What airlines fly to Chicago?

American Airlines, United Airlines and Delta are the top three most popular airlines that fly to Chicago from Worcester, Massachusetts according to our data. American Airlines is the first choice among our users, with 44% of people opting to fly with this airline when traveling to Chicago. Keep in mind that there are 7 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Worcester to Chicago?

Delta and American Airlines are the most popular carriers operating from Worcester to Chicago

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.

$94 Cheap Flights from Worcester to Chicago in 2025/26

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Find the cheapest flights from Worcester, Massachusetts to Chicago

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One-way

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Cheap round-trip flights

Enter your travel dates to find the best prices.

1:45 pm - 10:03 amORH-ORD

21h 18m1 stop

8:45 pm - 1:17 pmORD-ORH

15h 32m1 stop

$154American Airlines

Find Deal

Sun, Dec 21 - Sun, Dec 28

2:18 pm - 9:05 amORH-ORD

19h 47m2 stops

8:09 am - 1:53 pmORD-ORH

4h 44m1 stop

$164American Airlines

Find Deal

Fri, Jan 23 - Wed, Jan 28

2:18 pm - 9:01 amORH-ORD

19h 43m2 stops

7:56 pm - 1:53 pmORD-ORH

16h 57m2 stops

$169American Airlines

Find Deal

Fri, Jan 23 - Wed, Jan 28

4:05 pm - 10:30 pmORH-ORD

7h 25m1 stop

7:45 am - 3:25 pmORD-ORH

6h 40m1 stop

$192Delta

Find Deal

Fri, Dec 5 - Sun, Dec 7

3:30 pm - 10:54 pmORH-ORD

8h 24m1 stop

8:50 pm - 3:02 pmORD-ORH

17h 12m1 stop

$202American Airlines

Find Deal

Fri, Dec 12 - Sun, Dec 14

3:30 pm - 7:19 amORH-ORD

16h 49m2 stops

8:50 pm - 3:02 pmORD-ORH

17h 12m1 stop

$212American Airlines

Find Deal

Fri, Dec 12 - Sun, Dec 14

1:45 pm - 10:03 amORH-ORD

21h 18m1 stop

8:45 pm - 1:17 pmORD-ORH

15h 32m1 stop

$224American Airlines

Find Deal

Sun, Dec 28 - Sun, Jan 4

3:37 pm - 9:07 amORH-ORD

18h 30m1 stop

8:50 pm - 3:02 pmORD-ORH

17h 12m1 stop

$232American Airlines

Find Deal

Sat, Dec 13 - Sun, Dec 14

1:44 pm - 10:10 amORH-ORD

21h 26m1 stop

6:48 pm - 1:19 pmORD-ORH

17h 31m1 stop

$233American Airlines

Find Deal

Sun, Feb 15 - Sun, Feb 22

1:45 pm - 9:21 amORH-ORD

20h 36m2 stops

6:36 pm - 1:17 pmORD-ORH

17h 41m1 stop

$234American Airlines

Find Deal

Sun, Dec 28 - Fri, Jan 2

American Airlines flights from Worcester, Massachusetts to Chicago

Our best American Airlines deals on Worcester, Massachusetts to Chicago flight tickets

American Airlines

Dec 21

ORH1:45 pmWorcester

21h 18m

1 stop

ORD10:03 amChicago O'Hare Intl

Dec 28

ORD8:45 pmChicago O'Hare Intl

15h 32m

1 stop

ORH1:17 pmWorcester

$154

Find similar

American Airlines

Jan 23

ORH2:18 pmWorcester

19h 47m

2 stops

ORD9:05 amChicago O'Hare Intl

Jan 28

ORD8:09 amChicago O'Hare Intl

4h 44m

1 stop

ORH1:53 pmWorcester

$164

Find similar

American Airlines

Jan 23

ORH2:18 pmWorcester

19h 43m

2 stops

ORD9:01 amChicago O'Hare Intl

Jan 28

ORD7:56 pmChicago O'Hare Intl

16h 57m

2 stops

ORH1:53 pmWorcester

$169

Find similar

Delta flights from Worcester, Massachusetts to Chicago

Our best Delta deals on Worcester, Massachusetts to Chicago flight tickets

Delta

Jan 9

ORH4:16 pmWorcester

7h 18m

1 stop

ORD10:34 pmChicago O'Hare Intl

Jan 12

ORD9:35 amChicago O'Hare Intl

5h 01m

1 stop

ORH3:36 pmWorcester

$192

Find similar

Delta

Jan 9

ORH4:16 pmWorcester

5h 31m

1 stop

ORD8:47 pmChicago O'Hare Intl

Jan 11

ORD5:30 amChicago O'Hare Intl

9h 06m

2 stops

ORH3:36 pmWorcester

$202

Find similar

Delta

Jan 9

ORH4:16 pmWorcester

8h 43m

2 stops

ORD11:59 pmChicago O'Hare Intl

Jan 12

ORD5:30 amChicago O'Hare Intl

9h 06m

2 stops

ORH3:36 pmWorcester

$207

Find similar

momondo Fare Finder

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

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sun 12/21

1:45 pm-10:03 am

1 stop21h 18m

Chicago O'Hare Intl

Sun 12/28

8:45 pm-1:17 pm

1 stop15h 32m

$154

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 1/23

2:18 pm-9:05 am

2 stops19h 47m

Chicago O'Hare Intl

Wed 1/28

8:09 am-1:53 pm

1 stop4h 44m

$164

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 1/23

2:18 pm-9:01 am

2 stops19h 43m

Chicago O'Hare Intl

Wed 1/28

7:56 pm-1:53 pm

2 stops16h 57m

$169

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 12/5

4:05 pm-10:30 pm

1 stop7h 25m

Chicago O'Hare Intl

Sun 12/7

7:45 am-3:25 pm

1 stop6h 40m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 12/12

3:30 pm-10:54 pm

1 stop8h 24m

Chicago O'Hare Intl

Sun 12/14

8:50 pm-3:02 pm

1 stop17h 12m

$202

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 12/12

3:30 pm-7:19 am

2 stops16h 49m

Chicago O'Hare Intl

Sun 12/14

8:50 pm-3:02 pm

1 stop17h 12m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sun 12/28

1:45 pm-10:03 am

1 stop21h 18m

Chicago O'Hare Intl

Sun 1/4

8:45 pm-1:17 pm

1 stop15h 32m

$224

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 12/13

3:37 pm-9:07 am

1 stop18h 30m

Chicago O'Hare Intl

Sun 12/14

8:50 pm-3:02 pm

1 stop17h 12m

$232

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sun 2/15

1:44 pm-10:10 am

1 stop21h 26m

Chicago O'Hare Intl

Sun 2/22

6:48 pm-1:19 pm

1 stop17h 31m

$233

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sun 12/28

1:45 pm-9:21 am

2 stops20h 36m

Chicago O'Hare Intl

Fri 1/2

6:36 pm-1:17 pm

1 stop17h 41m

$234

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first

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

Prices

Airlines

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 Wednesday when prices can be found for as low as $321. 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 $429.

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 $272. In contrast, the most expensive time of day to depart to Chicago is in the morning when prices are around $351.

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

Direct flights	None

There are no direct flights from Worcester, Massachusetts to Chicago. There are no popular flight routes from Worcester, Massachusetts to Chicago.

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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 31m.
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.
What is the most popular airline from Worcester, Massachusetts to Chicago?
Based on momondo bookings for this flight route, the most popular airline on flight routes from Worcester, Massachusetts to Chicago is Delta (100% of total bookings).

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

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.