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Cheap flights from Worcester, Massachusetts to Chicago from $104

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 10/13. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Worcester, Massachusetts to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Delta Logo
4:15 pm - 8:43 pm
ORH
-
ORD
5h 28m
1 stop
Delta Logo
8:36 am - 2:59 pm
ORD
-
ORH
5h 23m
1 stop
$212Delta
Wed, Oct 14 - Tue, Oct 20
American Airlines Logo
5:23 pm - 7:30 am
ORH
-
ORD
15h 07m
1 stop
American Airlines Logo
5:00 am - 4:58 pm
ORD
-
ORH
10h 58m
1 stop
$230American Airlines
Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
5:23 pm - 11:08 am
ORH
-
ORD
18h 45m
1 stop
American Airlines Logo
6:45 am - 4:58 pm
ORD
-
ORH
9h 13m
1 stop
$232American Airlines
Fri, Aug 28 - Wed, Sep 2
Delta Logo
5:40 pm - 10:24 pm
ORH
-
ORD
5h 44m
1 stop
Delta Logo
6:59 am - 5:00 pm
ORD
-
ORH
9h 01m
2 stops
$240Delta
Wed, Aug 19 - Tue, Sep 1
Delta Logo
5:40 pm - 10:24 pm
ORH
-
ORD
5h 44m
1 stop
Delta Logo
10:30 am - 5:00 pm
ORD
-
ORH
5h 30m
1 stop
$262Delta
Tue, Aug 11 - Thu, Aug 13
American Airlines Logo
5:16 pm - 11:30 pm
ORH
-
ORD
7h 14m
1 stop
American Airlines Logo
5:00 am - 4:51 pm
ORD
-
ORH
10h 51m
1 stop
$266American Airlines
Sun, Jul 26 - Tue, Jul 28
Delta Logo
5:40 pm - 10:36 pm
ORH
-
ORD
5h 56m
1 stop
Delta Logo
6:40 am - 5:00 pm
ORD
-
ORH
9h 20m
2 stops
$272Delta
Sun, Aug 2 - Wed, Aug 5
Delta Logo
5:40 pm - 10:36 pm
ORH
-
ORD
5h 56m
1 stop
Delta Logo
9:30 am - 5:00 pm
ORD
-
ORH
6h 30m
1 stop
$294Delta
Sun, Aug 2 - Wed, Aug 5
Delta Logo
5:40 pm - 10:24 pm
ORH
-
ORD
5h 44m
1 stop
Delta Logo
5:30 am - 5:00 pm
ORD
-
ORH
10h 30m
2 stops
$296Delta
Thu, Aug 6 - Mon, Aug 10
Delta Logo
5:40 pm - 7:57 pm
ORH
-
ORD
27h 17m
1 stop
Delta Logo
10:30 am - 5:00 pm
ORD
-
ORH
5h 30m
1 stop
$301Delta
Fri, Aug 21 - Tue, Sep 1

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Delta flights from Worcester, Massachusetts to Chicago

Our best Delta deals on Worcester, Massachusetts to Chicago flight tickets
Delta
Oct 14
ORH4:15 pmWorcester
5h 28m
1 stop
ORD8:43 pmChicago O'Hare Intl
Oct 20
ORD8:36 amChicago O'Hare Intl
5h 23m
1 stop
ORH2:59 pmWorcester
$212
Delta
Jul 28
ORH5:40 pmWorcester
5h 56m
1 stop
ORD10:36 pmChicago O'Hare Intl
Jul 29
ORD9:30 amChicago O'Hare Intl
6h 30m
1 stop
ORH5:00 pmWorcester
$230
Delta
Jul 28
ORH5:40 pmWorcester
5h 56m
1 stop
ORD10:36 pmChicago O'Hare Intl
Jul 29
ORD6:35 amChicago O'Hare Intl
9h 25m
2 stops
ORH5:00 pmWorcester
$240

American Airlines flights from Worcester, Massachusetts to Chicago

Our best American Airlines deals on Worcester, Massachusetts to Chicago flight tickets
American Airlines
Aug 6
ORH5:23 pmWorcester
15h 07m
1 stop
ORD7:30 amChicago O'Hare Intl
Aug 10
ORD5:00 amChicago O'Hare Intl
10h 58m
1 stop
ORH4:58 pmWorcester
$230
American Airlines
Aug 28
ORH5:23 pmWorcester
18h 45m
1 stop
ORD11:08 amChicago O'Hare Intl
Sep 2
ORD6:45 amChicago O'Hare Intl
9h 13m
1 stop
ORH4:58 pmWorcester
$232
American Airlines
Jul 26
ORH5:16 pmWorcester
7h 14m
1 stop
ORD11:30 pmChicago O'Hare Intl
Jul 28
ORD5:00 amChicago O'Hare Intl
10h 51m
1 stop
ORH4:51 pmWorcester
$266

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 July 16, 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
Quickest round-trip

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 10/14

4:15 pm-8:43 pm

1 stop5h 28m

Chicago O'Hare Intl

Tue 10/20

8:36 am-2:59 pm

1 stop5h 23m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 8/6

5:23 pm-7:30 am

1 stop15h 07m

Chicago O'Hare Intl

Mon 8/10

5:00 am-4:58 pm

1 stop10h 58m

$230

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 8/28

5:23 pm-11:08 am

1 stop18h 45m

Chicago O'Hare Intl

Wed 9/2

6:45 am-4:58 pm

1 stop9h 13m

$232

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 8/19

5:40 pm-10:24 pm

1 stop5h 44m

Chicago O'Hare Intl

Tue 9/1

6:59 am-5:00 pm

2 stops9h 01m

$240

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 8/11

5:40 pm-10:24 pm

1 stop5h 44m

Chicago O'Hare Intl

Thu 8/13

10:30 am-5:00 pm

1 stop5h 30m

$262

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sun 7/26

5:16 pm-11:30 pm

1 stop7h 14m

Chicago O'Hare Intl

Tue 7/28

5:00 am-4:51 pm

1 stop10h 51m

$266

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sun 8/2

5:40 pm-10:36 pm

1 stop5h 56m

Chicago O'Hare Intl

Wed 8/5

6:40 am-5:00 pm

2 stops9h 20m

$272

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sun 8/2

5:40 pm-10:36 pm

1 stop5h 56m

Chicago O'Hare Intl

Wed 8/5

9:30 am-5:00 pm

1 stop6h 30m

$294

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 8/6

5:40 pm-10:24 pm

1 stop5h 44m

Chicago O'Hare Intl

Mon 8/10

5:30 am-5:00 pm

2 stops10h 30m

$296

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 8/21

5:40 pm-7:57 pm

1 stop27h 17m

Chicago O'Hare Intl

Tue 9/1

10:30 am-5:00 pm

1 stop5h 30m

$301

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 $316. 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 $414.

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 at noon when prices are around $370.

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 28m

Direct flights

None
The fastest flight from Worcester, Massachusetts to Chicago takes 5h 28m
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 28m.

  • 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
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
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