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 is the most popular carrier 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.

$165 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.

3:27 pm - 11:58 pmORH-ORD

9h 31m2 stops

6:46 am - 3:02 pmORD-ORH

7h 16m2 stops

$169American Airlines

Find Deal

Sat, Nov 8 - Tue, Nov 11

4:05 pm - 8:21 amORH-ORD

17h 16m2 stops

8:45 pm - 3:02 pmORD-ORH

17h 17m1 stop

$183American Airlines

Find Deal

Sat, Nov 1 - Sat, Nov 8

4:05 pm - 10:08 amORH-ORD

19h 03m1 stop

8:45 pm - 3:02 pmORD-ORH

17h 17m1 stop

$188American Airlines

Find Deal

Sat, Nov 1 - Sat, Nov 8

4:17 pm - 7:25 amORH-ORD

16h 08m1 stop

9:45 am - 4:28 pmORD-ORH

5h 43m1 stop

$192American Airlines

Find Deal

Thu, Oct 23 - Tue, Oct 28

4:17 pm - 7:25 amORH-ORD

16h 08m1 stop

7:10 am - 4:28 pmORD-ORH

8h 18m2 stops

$202American Airlines

Find Deal

Thu, Oct 23 - Tue, Oct 28

4:17 pm - 11:50 pmORH-ORD

8h 33m2 stops

6:05 am - 4:28 pmORD-ORH

9h 23m2 stops

$207American Airlines

Find Deal

Thu, Oct 23 - Tue, Oct 28

4:17 pm - 7:25 amORH-ORD

16h 08m1 stop

8:45 am - 3:50 pmORD-ORH

6h 05m1 stop

$222American Airlines

Find Deal

Fri, Oct 17 - Tue, Oct 21

4:17 pm - 9:04 amORH-ORD

17h 47m1 stop

8:11 am - 3:50 pmORD-ORH

6h 39m2 stops

$232American Airlines

Find Deal

Fri, Oct 17 - Tue, Oct 21

3:18 pm - 7:25 pmORH-ORD

5h 07m1 stop

5:20 am - 1:58 pmORD-ORH

7h 38m2 stops

$283Delta

Find Deal

Fri, Oct 31 - Sun, Nov 2

3:18 pm - 11:59 pmORH-ORD

9h 41m2 stops

5:20 am - 1:58 pmORD-ORH

7h 38m2 stops

$288Delta

Find Deal

Fri, Oct 31 - Sun, Nov 2

American Airlines flights from Worcester, Massachusetts to Chicago

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

American Airlines

Nov 8

ORH3:27 pmWorcester

9h 31m

2 stops

ORD11:58 pmChicago O'Hare Intl

Nov 11

ORD6:46 amChicago O'Hare Intl

7h 16m

2 stops

ORH3:02 pmWorcester

$169

Find similar

American Airlines

Nov 1

ORH4:05 pmWorcester

17h 16m

2 stops

ORD8:21 amChicago O'Hare Intl

Nov 8

ORD8:45 pmChicago O'Hare Intl

17h 17m

1 stop

ORH3:02 pmWorcester

$183

Find similar

American Airlines

Nov 1

ORH4:05 pmWorcester

19h 03m

1 stop

ORD10:08 amChicago O'Hare Intl

Nov 8

ORD8:45 pmChicago O'Hare Intl

17h 17m

1 stop

ORH3:02 pmWorcester

$188

Find similar

Delta flights from Worcester, Massachusetts to Chicago

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

Delta

Oct 31

ORH3:18 pmWorcester

5h 07m

1 stop

ORD7:25 pmChicago O'Hare Intl

Nov 2

ORD5:20 amChicago O'Hare Intl

7h 38m

2 stops

ORH1:58 pmWorcester

$283

Find similar

Delta

Oct 31

ORH3:18 pmWorcester

9h 41m

2 stops

ORD11:59 pmChicago O'Hare Intl

Nov 2

ORD5:20 amChicago O'Hare Intl

7h 38m

2 stops

ORH1:58 pmWorcester

$288

Find similar

Delta

Oct 17

ORH3:18 pmWorcester

9h 40m

2 stops

ORD11:58 pmChicago O'Hare Intl

Oct 21

ORD5:20 amChicago O'Hare Intl

7h 38m

2 stops

ORH1:58 pmWorcester

$298

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

Sat 11/8

3:27 pm-11:58 pm

2 stops9h 31m

Chicago O'Hare Intl

Tue 11/11

6:46 am-3:02 pm

2 stops7h 16m

$169

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 11/1

4:05 pm-8:21 am

2 stops17h 16m

Chicago O'Hare Intl

Sat 11/8

8:45 pm-3:02 pm

1 stop17h 17m

$183

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 11/1

4:05 pm-10:08 am

1 stop19h 03m

Chicago O'Hare Intl

Sat 11/8

8:45 pm-3:02 pm

1 stop17h 17m

$188

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 10/23

4:17 pm-7:25 am

1 stop16h 08m

Chicago O'Hare Intl

Tue 10/28

9:45 am-4:28 pm

1 stop5h 43m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 10/23

4:17 pm-7:25 am

1 stop16h 08m

Chicago O'Hare Intl

Tue 10/28

7:10 am-4:28 pm

2 stops8h 18m

$202

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 10/23

4:17 pm-11:50 pm

2 stops8h 33m

Chicago O'Hare Intl

Tue 10/28

6:05 am-4:28 pm

2 stops9h 23m

$207

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 10/17

4:17 pm-7:25 am

1 stop16h 08m

Chicago O'Hare Intl

Tue 10/21

8:45 am-3:50 pm

1 stop6h 05m

$222

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 10/17

4:17 pm-9:04 am

1 stop17h 47m

Chicago O'Hare Intl

Tue 10/21

8:11 am-3:50 pm

2 stops6h 39m

$232

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 10/31

3:18 pm-7:25 pm

1 stop5h 07m

Chicago O'Hare Intl

Sun 11/2

5:20 am-1:58 pm

2 stops7h 38m

$283

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 10/31

3:18 pm-11:59 pm

2 stops9h 41m

Chicago O'Hare Intl

Sun 11/2

5:20 am-1:58 pm

2 stops7h 38m

$288

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 16 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 Friday 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 $427.

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 $273. 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.

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 07m.
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

Lansing

Portage

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.