$153 Flight Deals from Worcester to Chicago

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Stops

Up to 1 stop
$357
Up to 2 stops
$291

Airlines

American Airlines
$291

Cabin Class

Economy
$291

Departure Airports

Worcester Regional Airport
$291

Arrival Airports

Chicago O Hare Airport
$291

Layover Airports

Charlotte Douglas International Airport
$291
General Edward Lawrence Logan International Airport
$291
Philadelphia International Airport
$291
Reagan Washington National Airport
$291

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Exclusively for Priceline Members
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On average save $240 per traveler

American Airlines

07/29/25

3:29pm

ORH

9h 28m

PHL

CLT

07/29/25

11:57pm

ORD

American Airlines

08/05/25

8:41pm

ORD

17h 14m

PHL

08/06/25

2:55pm

ORH

^$291

American Airlines

07/29/25

3:29pm

ORH

9h 28m

PHL

CLT

07/29/25

11:57pm

ORD

American Airlines

08/05/25

7:45pm

ORD

18h 10m

PHL

08/06/25

2:55pm

ORH

^$291

American Airlines

07/29/25

3:29pm

ORH

20h 8m

PHL

CLT

07/30/25

10:37am

ORD

American Airlines

08/05/25

7:00am

ORD

7h 4m

PHL

08/05/25

3:04pm

ORH

^$291

American Airlines

07/29/25

3:29pm

ORH

19h 6m

PHL

CLT

07/30/25

9:35am

ORD

American Airlines

08/05/25

7:00am

ORD

7h 4m

PHL

08/05/25

3:04pm

ORH

^$291

American Airlines

07/29/25

3:29pm

ORH

19h 53m

PHL

DCA

07/30/25

10:22am

ORD

American Airlines

08/05/25

8:37am

ORD

5h 27m

PHL

08/05/25

3:04pm

ORH

^$291

American Airlines

07/29/25

3:29pm

ORH

16h 29m

PHL

BOS

07/30/25

6:58am

ORD

American Airlines

08/05/25

7:00am

ORD

7h 4m

PHL

08/05/25

3:04pm

ORH

^$291

American Airlines

07/29/25

3:29pm

ORH

9h 28m

PHL

CLT

07/29/25

11:57pm

ORD

American Airlines

08/05/25

5:00am

ORD

9h 4m

PHL

08/05/25

3:04pm

ORH

^$291

American Airlines

07/29/25

3:29pm

ORH

16h 29m

PHL

BOS

07/30/25

6:58am

ORD

American Airlines

08/05/25

5:00am

ORD

9h 4m

PHL

08/05/25

3:04pm

ORH

^$291

American Airlines

07/29/25

3:29pm

ORH

19h 53m

PHL

DCA

07/30/25

10:22am

ORD

American Airlines

08/05/25

7:00am

ORD

7h 4m

PHL

08/05/25

3:04pm

ORH

^$291

American Airlines

07/29/25

3:29pm

ORH

16h 29m

PHL

BOS

07/30/25

6:58am

ORD

American Airlines

08/05/25

8:37am

ORD

5h 27m

PHL

08/05/25

3:04pm

ORH

^$291

American Airlines

07/29/25

3:29pm

ORH

19h 6m

PHL

CLT

07/30/25

9:35am

ORD

American Airlines

08/05/25

8:37am

ORD

5h 27m

PHL

08/05/25

3:04pm

ORH

^$291

American Airlines

07/29/25

3:29pm

ORH

9h 28m

PHL

CLT

07/29/25

11:57pm

ORD

American Airlines

08/05/25

6:25am

ORD

7h 39m

BOS

PHL

08/05/25

3:04pm

ORH

^$296

American Airlines

07/29/25

3:29pm

ORH

5h 53m

PHL

07/29/25

8:22pm

ORD

American Airlines

08/05/25

8:37am

ORD

5h 27m

PHL

08/05/25

3:04pm

ORH

^$357

Top Deals on flights from Worcester to Chicago

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines

Jul 28

3:29pm

ORH

21h 21m

PHL

DCA

Jul 29

11:50am

ORD

as low as

^$153

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines

Jul 28

3:29pm

ORH

23h 10m

PHL

BOS

Jul 29

1:39pm

ORD

as low as

^$153

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines

Jul 28

3:29pm

ORH

23h

PHL

DCA

Jul 29

1:29pm

ORD

as low as

^$153

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines

Jul 28

3:29pm

ORH

19h 6m

PHL

CLT

Jul 29

9:35am

ORD

as low as

^$153

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines

Jul 28

3:29pm

ORH

23h 46m

PHL

CLT

Jul 29

2:15pm

ORD

as low as

^$153

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines

Jul 28

3:29pm

ORH

20h 8m

PHL

CLT

Jul 29

10:37am

ORD

as low as

^$153

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines

Jul 28

3:29pm

ORH

19h 53m

PHL

DCA

Jul 29

10:22am

ORD

as low as

^$153

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines

Jul 28

3:29pm

ORH

16h 29m

PHL

BOS

Jul 29

6:58am

ORD

as low as

^$159

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines

Jul 28

3:29pm

ORH

18h 36m

PHL

BOS

Jul 29

9:05am

ORD

as low as

^$177

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines

Jul 28

3:29pm

ORH

8h 22m

PHL

Jul 28

10:51pm

ORD

as low as

^$204

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines

Jul 28

3:29pm

ORH

5h 53m

PHL

Jul 28

8:22pm

ORD

as low as

^$238

Worcester, US (ORH) - Chicago, US (CHI)

American Airlines

Jul 28

3:29pm

ORH

PHL

DCA

Jul 28

11:29pm

ORD

as low as

^$283

Frequently Asked Questions

What is the cheapest and fastest flight from Worcester to Chicago?

The cheapest flight is $291 with American Airlines, taking 19 hours 6 minutes. The fastest flight is $357 with American Airlines, taking 5 hours 53 minutes.

What are all possible destination arrival airports?

The possible destination arrival airport is Chicago O'Hare Airport. Layover airports include Philadelphia International Airport and Charlotte Douglas International Airport.

What is the time difference between destination and arrival?

The time difference between Worcester and Chicago is typically one hour, with Chicago being one hour behind Worcester.

Is there a direct flight from Worcester to Chicago?

There is no direct flight from Worcester to Chicago. The cheapest flight is offered by American Airlines for $291 with 2 stops, and a 1 stop flight is also available for $357.

Are there convenient layover flights from Worcester to Chicago?

Yes, there are convenient layover flights from Worcester to Chicago. American Airlines offers a 1 stop flight for $357 with a layover in Philadelphia. Additionally, a 2 stops flight is available for $291, with layovers in Philadelphia and Charlotte.

What are the most convenient layover airports for my flight?

For your flight from Worcester to Chicago, consider convenient layover airports such as Philadelphia International Airport and Charlotte Douglas International Airport.

Flight Deals from Worcester to Chicago from $153

Stops

Airlines

Cabin Class

Departure Airports

Arrival Airports

Layover Airports

Best Price. GUARANTEED.

Top Deals on flights from Worcester to Chicago

Frequently Asked Questions

Flights to Chicago