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Cheap flights from Worcester, Massachusetts to Chicago from $92

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 5/7. 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

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Find the cheapest flights from Worcester, Massachusetts to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
2:39 pm - 8:54 am
ORH
-
ORD
19h 15m
1 stop
American Airlines Logo
5:45 pm - 2:14 pm
ORD
-
ORH
19h 29m
1 stop
$192American Airlines
Tue, Apr 28 - Sat, May 2
American Airlines Logo
2:39 pm - 11:54 pm
ORH
-
ORD
10h 15m
2 stops
American Airlines Logo
7:15 pm - 2:14 pm
ORD
-
ORH
17h 59m
1 stop
$202American Airlines
Tue, Apr 28 - Sat, May 2
Delta Logo
4:33 pm - 10:12 pm
ORH
-
ORD
6h 39m
1 stop
Delta Logo
10:45 am - 3:50 pm
ORD
-
ORH
4h 05m
1 stop
$206Delta
Wed, Apr 8 - Thu, Apr 9
American Airlines Logo
2:39 pm - 11:54 pm
ORH
-
ORD
10h 15m
2 stops
American Airlines Logo
5:00 am - 2:14 pm
ORD
-
ORH
8h 14m
2 stops
$208American Airlines
Tue, Apr 28 - Sat, May 2
American Airlines Logo
2:39 pm - 7:00 pm
ORH
-
ORD
5h 21m
1 stop
American Airlines Logo
6:40 am - 2:14 pm
ORD
-
ORH
6h 34m
1 stop
$212American Airlines
Wed, Apr 8 - Sat, Apr 11
American Airlines Logo
2:39 pm - 11:54 pm
ORH
-
ORD
10h 15m
2 stops
American Airlines Logo
8:30 am - 2:14 pm
ORD
-
ORH
4h 44m
1 stop
$216American Airlines
Wed, Apr 8 - Sat, Apr 11
Delta Logo
4:33 pm - 10:12 pm
ORH
-
ORD
6h 39m
1 stop
Delta Logo
10:45 am - 3:50 pm
ORD
-
ORH
4h 05m
1 stop
$220Delta
Tue, Apr 7 - Thu, Apr 9
American Airlines Logo
2:39 pm - 8:54 am
ORH
-
ORD
19h 15m
1 stop
American Airlines Logo
5:00 am - 2:14 pm
ORD
-
ORH
8h 14m
2 stops
$222American Airlines
Wed, Apr 8 - Sat, Apr 11
Delta Logo
4:15 pm - 10:36 pm
ORH
-
ORD
7h 21m
1 stop
Delta Logo
7:00 am - 3:33 pm
ORD
-
ORH
7h 33m
2 stops
$226Delta
Mon, Jun 1 - Tue, Jun 2
American Airlines Logo
2:39 pm - 11:54 pm
ORH
-
ORD
10h 15m
2 stops
American Airlines Logo
6:05 am - 2:14 pm
ORD
-
ORH
7h 09m
2 stops
$227American Airlines
Wed, Apr 8 - Sat, Apr 11

American Airlines flights from Worcester, Massachusetts to Chicago

Our best American Airlines deals on Worcester, Massachusetts to Chicago flight tickets
American Airlines
Apr 28
ORH2:39 pmWorcester
19h 15m
1 stop
ORD8:54 amChicago O'Hare Intl
May 2
ORD5:45 pmChicago O'Hare Intl
19h 29m
1 stop
ORH2:14 pmWorcester
$192
American Airlines
Apr 28
ORH2:39 pmWorcester
10h 15m
2 stops
ORD11:54 pmChicago O'Hare Intl
May 2
ORD7:15 pmChicago O'Hare Intl
17h 59m
1 stop
ORH2:14 pmWorcester
$202
American Airlines
Apr 2
ORH1:44 pmWorcester
21h 16m
1 stop
ORD10:00 amChicago O'Hare Intl
Apr 10
ORD6:40 amChicago O'Hare Intl
6h 34m
1 stop
ORH2:14 pmWorcester
$206

Delta flights from Worcester, Massachusetts to Chicago

Our best Delta deals on Worcester, Massachusetts to Chicago flight tickets
Delta
Apr 10
ORH4:33 pmWorcester
4h 57m
1 stop
ORD8:30 pmChicago O'Hare Intl
Apr 14
ORD10:45 amChicago O'Hare Intl
4h 58m
1 stop
ORH4:43 pmWorcester
$192
Delta
Apr 10
ORH4:33 pmWorcester
4h 57m
1 stop
ORD8:30 pmChicago O'Hare Intl
Apr 14
ORD8:15 amChicago O'Hare Intl
7h 28m
2 stops
ORH4:43 pmWorcester
$202
Delta
Apr 8
ORH4:33 pmWorcester
6h 39m
1 stop
ORD10:12 pmChicago O'Hare Intl
Apr 9
ORD10:45 amChicago O'Hare Intl
4h 05m
1 stop
ORH3:50 pmWorcester
$206

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 March 27, 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

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 4/28

2:39 pm-8:54 am

1 stop19h 15m

Chicago O'Hare Intl

Sat 5/2

5:45 pm-2:14 pm

1 stop19h 29m

$192

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 4/28

2:39 pm-11:54 pm

2 stops10h 15m

Chicago O'Hare Intl

Sat 5/2

7:15 pm-2:14 pm

1 stop17h 59m

$202
Quickest round-trip

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 4/8

4:33 pm-10:12 pm

1 stop6h 39m

Chicago O'Hare Intl

Thu 4/9

10:45 am-3:50 pm

1 stop4h 05m

$206

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 4/28

2:39 pm-11:54 pm

2 stops10h 15m

Chicago O'Hare Intl

Sat 5/2

5:00 am-2:14 pm

2 stops8h 14m

$208

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 4/8

2:39 pm-7:00 pm

1 stop5h 21m

Chicago O'Hare Intl

Sat 4/11

6:40 am-2:14 pm

1 stop6h 34m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 4/8

2:39 pm-11:54 pm

2 stops10h 15m

Chicago O'Hare Intl

Sat 4/11

8:30 am-2:14 pm

1 stop4h 44m

$216

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 4/7

4:33 pm-10:12 pm

1 stop6h 39m

Chicago O'Hare Intl

Thu 4/9

10:45 am-3:50 pm

1 stop4h 05m

$220

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 4/8

2:39 pm-8:54 am

1 stop19h 15m

Chicago O'Hare Intl

Sat 4/11

5:00 am-2:14 pm

2 stops8h 14m

$222

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Mon 6/1

4:15 pm-10:36 pm

1 stop7h 21m

Chicago O'Hare Intl

Tue 6/2

7:00 am-3:33 pm

2 stops7h 33m

$226

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Wed 4/8

2:39 pm-11:54 pm

2 stops10h 15m

Chicago O'Hare Intl

Sat 4/11

6:05 am-2:14 pm

2 stops7h 09m

$227

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 19 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 Wednesday when prices can be found for as low as $310. 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 $401.

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 $267. 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

4h 57m

Direct flights

None
The fastest flight from Worcester, Massachusetts to Chicago takes 4h 57m
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 4h 57m.

  • 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?

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Schererville
Munster
Crown Point
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.

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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