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?

American Airlines and Delta 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.

$75 Cheap Flights from Worcester to Chicago in 2025/26

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Find the cheapest flights from Worcester, Massachusetts to Chicago

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

1:47 pm - 10:03 am

ORH

ORD

21h 16m1 stop

6:46 pm - 1:17 pm

ORD

ORH

17h 31m1 stop

$154American Airlines

Thu, Jan 1 - Sun, Jan 4

1:47 pm - 7:30 am

ORH

ORD

18h 43m2 stops

8:45 pm - 1:17 pm

ORD

ORH

15h 32m1 stop

$164American Airlines

Thu, Jan 1 - Sun, Jan 4

2:18 pm - 8:31 am

ORH

ORD

19h 13m2 stops

7:56 pm - 1:53 pm

ORD

ORH

16h 57m2 stops

$169American Airlines

Tue, Jan 6 - Tue, Jan 13

1:40 pm - 10:30 am

ORH

ORD

21h 50m1 stop

6:48 pm - 1:15 pm

ORD

ORH

17h 27m1 stop

$173American Airlines

Fri, Feb 13 - Tue, Feb 17

1:40 pm - 10:30 am

ORH

ORD

21h 50m1 stop

8:55 pm - 1:15 pm

ORD

ORH

15h 20m2 stops

$183American Airlines

Fri, Feb 13 - Tue, Feb 17

1:40 pm - 7:20 am

ORH

ORD

18h 40m2 stops

7:35 pm - 1:15 pm

ORD

ORH

16h 40m2 stops

$188American Airlines

Thu, Feb 12 - Tue, Feb 17

4:16 pm - 8:47 pm

ORH

ORD

5h 31m1 stop

7:10 am - 3:36 pm

ORD

ORH

7h 26m1 stop

$192Delta

Fri, Jan 9 - Sun, Jan 11

1:45 pm - 7:01 am

ORH

ORD

18h 16m1 stop

6:40 am - 1:17 pm

ORD

ORH

5h 37m1 stop

$193American Airlines

Fri, Dec 26 - Tue, Dec 30

4:30 pm - 11:56 pm

ORH

ORD

8h 26m2 stops

9:35 am - 3:48 pm

ORD

ORH

5h 13m1 stop

$202Delta

Mon, Mar 23 - Tue, Mar 24

4:30 pm - 11:56 pm

ORH

ORD

8h 26m2 stops

5:40 am - 3:48 pm

ORD

ORH

9h 08m2 stops

$207Delta

Mon, Mar 23 - Tue, Mar 24

Delta flights from Worcester, Massachusetts to Chicago

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

Delta

Jan 9

ORH4:16 pmWorcester

5h 31m

1 stop

ORD8:47 pmChicago O'Hare Intl

Jan 11

ORD7:10 amChicago O'Hare Intl

7h 26m

1 stop

ORH3:36 pmWorcester

$192

Find similar

Delta

Jan 23

ORH4:16 pmWorcester

7h 18m

1 stop

ORD10:34 pmChicago O'Hare Intl

Jan 27

ORD5:30 amChicago O'Hare Intl

9h 06m

2 stops

ORH3:36 pmWorcester

$202

Find similar

Delta

Mar 23

ORH4:30 pmWorcester

8h 26m

2 stops

ORD11:56 pmChicago O'Hare Intl

Mar 24

ORD5:40 amChicago O'Hare Intl

9h 08m

2 stops

ORH3:48 pmWorcester

$207

Find similar

American Airlines flights from Worcester, Massachusetts to Chicago

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

American Airlines

Dec 14

ORH3:34 pmWorcester

6h 00m

1 stop

ORD8:34 pmChicago O'Hare Intl

Dec 16

ORD6:35 pmChicago O'Hare Intl

19h 30m

1 stop

ORH3:05 pmWorcester

$154

Find similar

American Airlines

Dec 14

ORH3:34 pmWorcester

9h 12m

2 stops

ORD11:46 pmChicago O'Hare Intl

Dec 16

ORD6:35 pmChicago O'Hare Intl

19h 30m

1 stop

ORH3:05 pmWorcester

$164

Find similar

American Airlines

Dec 14

ORH3:34 pmWorcester

16h 45m

2 stops

ORD7:19 amChicago O'Hare Intl

Dec 16

ORD8:40 pmChicago O'Hare Intl

17h 25m

2 stops

ORH3:05 pmWorcester

$169

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

Thu 1/1

1:47 pm-10:03 am

1 stop21h 16m

Chicago O'Hare Intl

Sun 1/4

6:46 pm-1:17 pm

1 stop17h 31m

$154

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 1/1

1:47 pm-7:30 am

2 stops18h 43m

Chicago O'Hare Intl

Sun 1/4

8:45 pm-1:17 pm

1 stop15h 32m

$164

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 1/6

2:18 pm-8:31 am

2 stops19h 13m

Chicago O'Hare Intl

Tue 1/13

7:56 pm-1:53 pm

2 stops16h 57m

$169

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 2/13

1:40 pm-10:30 am

1 stop21h 50m

Chicago O'Hare Intl

Tue 2/17

6:48 pm-1:15 pm

1 stop17h 27m

$173

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 2/13

1:40 pm-10:30 am

1 stop21h 50m

Chicago O'Hare Intl

Tue 2/17

8:55 pm-1:15 pm

2 stops15h 20m

$183

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 2/12

1:40 pm-7:20 am

2 stops18h 40m

Chicago O'Hare Intl

Tue 2/17

7:35 pm-1:15 pm

2 stops16h 40m

$188

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 1/9

4:16 pm-8:47 pm

1 stop5h 31m

Chicago O'Hare Intl

Sun 1/11

7:10 am-3:36 pm

1 stop7h 26m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 12/26

1:45 pm-7:01 am

1 stop18h 16m

Chicago O'Hare Intl

Tue 12/30

6:40 am-1:17 pm

1 stop5h 37m

$193

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 3/23

4:30 pm-11:56 pm

2 stops8h 26m

Chicago O'Hare Intl

Tue 3/24

9:35 am-3:48 pm

1 stop5h 13m

$202

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 3/23

4:30 pm-11:56 pm

2 stops8h 26m

Chicago O'Hare Intl

Tue 3/24

5:40 am-3:48 pm

2 stops9h 08m

$207

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 $317. 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 $423.

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 $349.

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 31m
Direct flights	None

The fastest flight from Worcester, Massachusetts to Chicago takes 5h 31m

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

Search flight deals

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.