Latest deals
Insights
When to book
FAQs
Price Alerts

Cheap flights from Worcester, Massachusetts to Chicago from $75

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 9/30. 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
0 bags

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Worcester, Massachusetts to Chicago

Cheap round-trip flights

American Airlines Logo
3:25 pm - 8:45 amORH-ORD
18h 20m1 stop
American Airlines Logo
9:45 am - 2:53 pmORD-ORH
4h 08m1 stop
$154American Airlines
Find Deal
Thu, Jan 22 - Mon, Jan 26
American Airlines Logo
3:25 pm - 8:22 amORH-ORD
17h 57m2 stops
American Airlines Logo
8:25 pm - 2:53 pmORD-ORH
17h 28m1 stop
$164American Airlines
Find Deal
Thu, Jan 22 - Mon, Jan 26
American Airlines Logo
4:23 pm - 11:12 pmORH-ORD
7h 49m2 stops
American Airlines Logo
8:11 am - 3:50 pmORD-ORH
6h 39m2 stops
$169American Airlines
Find Deal
Fri, Oct 3 - Tue, Oct 7
American Airlines Logo
4:23 pm - 10:36 amORH-ORD
19h 13m1 stop
American Airlines Logo
6:44 pm - 3:58 pmORD-ORH
20h 14m1 stop
$171American Airlines
Find Deal
Fri, Oct 3 - Sat, Oct 4
American Airlines Logo
4:23 pm - 10:36 amORH-ORD
19h 13m1 stop
American Airlines Logo
9:06 pm - 3:58 pmORD-ORH
17h 52m2 stops
$181American Airlines
Find Deal
Fri, Oct 3 - Sat, Oct 4
American Airlines Logo
4:23 pm - 6:51 amORH-ORD
15h 28m2 stops
American Airlines Logo
5:00 am - 3:56 pmORD-ORH
9h 56m2 stops
$186American Airlines
Find Deal
Thu, Sep 25 - Mon, Sep 29
Delta Logo
3:18 pm - 7:25 pmORH-ORD
5h 07m1 stop
Delta Logo
6:00 am - 1:58 pmORD-ORH
6h 58m1 stop
$212Delta
Find Deal
Tue, Oct 28 - Thu, Nov 6
Delta Logo
3:18 pm - 7:25 pmORH-ORD
5h 07m1 stop
Delta Logo
6:00 am - 1:58 pmORD-ORH
6h 58m1 stop
$222Delta
Find Deal
Fri, Oct 24 - Thu, Nov 6
American Airlines Logo
4:05 pm - 7:25 amORH-ORD
16h 20m1 stop
American Airlines Logo
6:50 am - 3:02 pmORD-ORH
7h 12m1 stop
$224American Airlines
Find Deal
Sat, Oct 25 - Mon, Nov 3
American Airlines Logo
4:23 pm - 12:20 pmORH-ORD
20h 57m1 stop
American Airlines Logo
7:00 am - 3:56 pmORD-ORH
7h 56m1 stop
$226American Airlines
Find Deal
Thu, Sep 25 - Mon, Sep 29

American Airlines flights from Worcester, Massachusetts to Chicago O'Hare Intl Airport

Our best American Airlines deals on Worcester, Massachusetts to Chicago O'Hare Intl Airport flight tickets
American Airlines
Jan 22
ORH3:25 pmWorcester
18h 20m
1 stop
ORD8:45 amChicago O'Hare Intl
Jan 26
ORD9:45 amChicago O'Hare Intl
4h 08m
1 stop
ORH2:53 pmWorcester
$154
Find similar
American Airlines
Jan 22
ORH3:25 pmWorcester
17h 57m
2 stops
ORD8:22 amChicago O'Hare Intl
Jan 26
ORD8:25 pmChicago O'Hare Intl
17h 28m
1 stop
ORH2:53 pmWorcester
$164
Find similar
American Airlines
Oct 3
ORH4:23 pmWorcester
7h 49m
2 stops
ORD11:12 pmChicago O'Hare Intl
Oct 7
ORD8:11 amChicago O'Hare Intl
6h 39m
2 stops
ORH3:50 pmWorcester
$169
Find similar

Delta flights from Worcester, Massachusetts to Chicago O'Hare Intl Airport

Our best Delta deals on Worcester, Massachusetts to Chicago O'Hare Intl Airport flight tickets
Delta
Oct 28
ORH3:18 pmWorcester
5h 07m
1 stop
ORD7:25 pmChicago O'Hare Intl
Nov 6
ORD6:00 amChicago O'Hare Intl
6h 58m
1 stop
ORH1:58 pmWorcester
$212
Find similar
Delta
Oct 24
ORH3:18 pmWorcester
5h 07m
1 stop
ORD7:25 pmChicago O'Hare Intl
Nov 6
ORD6:00 amChicago O'Hare Intl
6h 58m
1 stop
ORH1:58 pmWorcester
$222
Find similar
Delta
Oct 29
ORH3:18 pmWorcester
9h 40m
2 stops
ORD11:58 pmChicago O'Hare Intl
Nov 5
ORD7:10 amChicago O'Hare Intl
5h 48m
2 stops
ORH1:58 pmWorcester
$227
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Worcester, Massachusetts to Chicago O'Hare Intl Airport 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 September 11, 2025.
Use the filters below to find and compare flights from Worcester, Massachusetts to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 1/22

3:25 pm-8:45 am

1 stop18h 20m

Chicago O'Hare Intl

Mon 1/26

9:45 am-2:53 pm

1 stop4h 08m

$154

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 1/22

3:25 pm-8:22 am

2 stops17h 57m

Chicago O'Hare Intl

Mon 1/26

8:25 pm-2:53 pm

1 stop17h 28m

$164

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 10/3

4:23 pm-11:12 pm

2 stops7h 49m

Chicago O'Hare Intl

Tue 10/7

8:11 am-3:50 pm

2 stops6h 39m

$169

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 10/3

4:23 pm-10:36 am

1 stop19h 13m

Chicago O'Hare Intl

Sat 10/4

6:44 pm-3:58 pm

1 stop20h 14m

$171

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 10/3

4:23 pm-10:36 am

1 stop19h 13m

Chicago O'Hare Intl

Sat 10/4

9:06 pm-3:58 pm

2 stops17h 52m

$181

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 9/25

4:23 pm-6:51 am

2 stops15h 28m

Chicago O'Hare Intl

Mon 9/29

5:00 am-3:56 pm

2 stops9h 56m

$186

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Tue 10/28

3:18 pm-7:25 pm

1 stop5h 07m

Chicago O'Hare Intl

Thu 11/6

6:00 am-1:58 pm

1 stop6h 58m

$212

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Fri 10/24

3:18 pm-7:25 pm

1 stop5h 07m

Chicago O'Hare Intl

Thu 11/6

6:00 am-1:58 pm

1 stop6h 58m

$222

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Sat 10/25

4:05 pm-7:25 am

1 stop16h 20m

Chicago O'Hare Intl

Mon 11/3

6:50 am-3:02 pm

1 stop7h 12m

$224

WorcesterChicago

ORH - ORD

ORHORD

Worcester

Thu 9/25

4:23 pm-12:20 pm

1 stop20h 57m

Chicago O'Hare Intl

Mon 9/29

7:00 am-3:56 pm

1 stop7h 56m

$226

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Worcester, Massachusetts to Chicago O'Hare Intl Airport

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 O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $318. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Worcester, Massachusetts because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $426.

What is the cheapest time of day to depart on your flight to Chicago O'Hare Intl Airport?

Flying to Chicago O'Hare Intl Airport from Worcester, Massachusetts in the evening is the least expensive time of day to depart. momondo users have found prices as low as $265 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $351. Of course, these prices can vary depending on the time of year and what airport you fly to.

When to book flights from Worcester, Massachusetts to Chicago O'Hare Intl Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Worcester, Massachusetts to Chicago O'Hare Intl Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Worcester, Massachusetts to Chicago O'Hare Intl Airport (ORH to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Worcester, Massachusetts to Chicago O'Hare Intl Airport

Direct flights

None
There are no direct flights from Worcester, Massachusetts to Chicago O'Hare Intl Airport. There are no popular flight routes from Worcester, Massachusetts to Chicago O'Hare Intl Airport.
Search flight deals

  • How far is Worcester to Chicago O'Hare Intl by plane?

    Chicago O'Hare Intl is 823.6 mi away from Worcester. 5h 07m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Worcester Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Worcester Airport to Chicago O'Hare Intl Airport are refreshed on a daily basis.

  • How old do you have to be to fly from Worcester Airport to Chicago O'Hare Intl Airport?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Worcester Airport to Chicago O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The required travel and health documents for your Chicago O'Hare Intl Airport trip may vary depending on your itinerary and personal circumstances. As a general rule, you should carry multiple documents, including a national ID card or driver's license and a passport valid for six months after your intended arrival at Chicago O'Hare Intl Airport. We recommend that you seek guidance from your airline or a reliable third party such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
South Haven
Rockford
Schaumburg
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Racine
Hammond
Orland Park
Tinley Park
Elgin
Aurora
Janesville
Benton Harbor

Why use momondo?

Why should I use momondo to find a flight deal from Worcester to Chicago?

Finding the right flight to Chicago from Worcester is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Worcester to Chicago with flexible booking policies on momondo?

Flights from Worcester to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Worcester to Chicago?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Chicago from Worcester.

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.

An easier way to manage your Chicago O'Hare Intl Airport trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Sat 10/11
Sat 10/18
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago