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Cheap flights from Chicago to Boston from $109

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago to Boston departing on 10/24. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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0 bags

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Find the cheapest flights from Chicago to Boston (CHI-ORH)

Cheap round-trip flights

American Airlines Logo
9:11 pm - 3:59 pmORD-ORH
17h 48m1 stop
American Airlines Logo
4:24 pm - 6:51 amORH-ORD
15h 27m2 stops
$164American Airlines
Find Deal
Tue, Sep 2 - Sat, Sep 6
American Airlines Logo
8:34 pm - 3:59 pmORD-ORH
18h 25m2 stops
American Airlines Logo
4:24 pm - 6:51 amORH-ORD
15h 27m2 stops
$169American Airlines
Find Deal
Tue, Sep 2 - Sat, Sep 6
American Airlines Logo
5:00 am - 2:55 pmORD-ORH
8h 55m1 stop
American Airlines Logo
4:24 pm - 8:43 amORH-ORD
17h 19m1 stop
$183American Airlines
Find Deal
Tue, Sep 2 - Sat, Sep 6
Delta Logo
6:00 am - 1:58 pmORD-ORH
6h 58m1 stop
Delta Logo
3:18 pm - 7:25 pmORH-ORD
5h 07m1 stop
$212Delta
Find Deal
Wed, Oct 8 - Tue, Oct 14
Delta Logo
6:00 am - 1:58 pmORD-ORH
6h 58m1 stop
Delta Logo
3:18 pm - 8:37 pmORH-ORD
6h 19m1 stop
$222Delta
Find Deal
Thu, Oct 9 - Tue, Oct 14
American Airlines Logo
7:09 pm - 3:50 pmORD-ORH
19h 41m1 stop
American Airlines Logo
4:17 pm - 7:25 amORH-ORD
16h 08m1 stop
$224American Airlines
Find Deal
Sat, Oct 11 - Tue, Oct 14
American Airlines Logo
6:45 am - 3:50 pmORD-ORH
8h 05m1 stop
American Airlines Logo
3:29 pm - 10:52 pmORH-ORD
8h 23m1 stop
$228American Airlines
Find Deal
Thu, Oct 30 - Sun, Nov 2
Delta Logo
7:10 am - 1:58 pmORD-ORH
5h 48m2 stops
Delta Logo
3:18 pm - 8:37 pmORH-ORD
6h 19m1 stop
$232Delta
Find Deal
Wed, Oct 8 - Tue, Oct 14
American Airlines Logo
7:09 pm - 3:50 pmORD-ORH
19h 41m1 stop
American Airlines Logo
4:17 pm - 8:18 amORH-ORD
17h 01m2 stops
$234American Airlines
Find Deal
Sat, Oct 11 - Wed, Oct 15
Delta Logo
7:10 am - 1:58 pmORD-ORH
5h 48m2 stops
Delta Logo
3:18 pm - 11:57 pmORH-ORD
9h 39m2 stops
$237Delta
Find Deal
Wed, Oct 8 - Wed, Oct 15

Delta flights from Chicago to Worcester, Massachusetts

Our best Delta deals on Chicago to Worcester, Massachusetts flight tickets
Delta
Oct 8
ORD6:00 amChicago O'Hare Intl
6h 58m
1 stop
ORH1:58 pmWorcester
Oct 14
ORH3:18 pmWorcester
5h 07m
1 stop
ORD7:25 pmChicago O'Hare Intl
$212
Find similar
Delta
Oct 9
ORD6:00 amChicago O'Hare Intl
6h 58m
1 stop
ORH1:58 pmWorcester
Oct 14
ORH3:18 pmWorcester
6h 19m
1 stop
ORD8:37 pmChicago O'Hare Intl
$222
Find similar
Delta
Oct 8
ORD7:10 amChicago O'Hare Intl
5h 48m
2 stops
ORH1:58 pmWorcester
Oct 14
ORH3:18 pmWorcester
6h 19m
1 stop
ORD8:37 pmChicago O'Hare Intl
$232
Find similar

American Airlines flights from Chicago to Worcester, Massachusetts

Our best American Airlines deals on Chicago to Worcester, Massachusetts flight tickets
American Airlines
Sep 2
ORD9:11 pmChicago O'Hare Intl
17h 48m
1 stop
ORH3:59 pmWorcester
Sep 6
ORH4:24 pmWorcester
15h 27m
2 stops
ORD6:51 amChicago O'Hare Intl
$164
Find similar
American Airlines
Sep 2
ORD8:34 pmChicago O'Hare Intl
18h 25m
2 stops
ORH3:59 pmWorcester
Sep 6
ORH4:24 pmWorcester
15h 27m
2 stops
ORD6:51 amChicago O'Hare Intl
$169
Find similar
American Airlines
Sep 2
ORD5:00 amChicago O'Hare Intl
8h 55m
1 stop
ORH2:55 pmWorcester
Sep 6
ORH4:24 pmWorcester
17h 19m
1 stop
ORD8:43 amChicago O'Hare Intl
$183
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Chicago to Worcester, Massachusetts 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 August 18, 2025.
Use the filters below to find and compare flights from Chicago to Worcester, Massachusetts that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Tue 9/2

9:11 pm-3:59 pm

1 stop17h 48m

Worcester

Sat 9/6

4:24 pm-6:51 am

2 stops15h 27m

$164

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Tue 9/2

8:34 pm-3:59 pm

2 stops18h 25m

Worcester

Sat 9/6

4:24 pm-6:51 am

2 stops15h 27m

$169

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Tue 9/2

5:00 am-2:55 pm

1 stop8h 55m

Worcester

Sat 9/6

4:24 pm-8:43 am

1 stop17h 19m

$183

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 10/8

6:00 am-1:58 pm

1 stop6h 58m

Worcester

Tue 10/14

3:18 pm-7:25 pm

1 stop5h 07m

$212

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 10/9

6:00 am-1:58 pm

1 stop6h 58m

Worcester

Tue 10/14

3:18 pm-8:37 pm

1 stop6h 19m

$222

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Sat 10/11

7:09 pm-3:50 pm

1 stop19h 41m

Worcester

Tue 10/14

4:17 pm-7:25 am

1 stop16h 08m

$224

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Thu 10/30

6:45 am-3:50 pm

1 stop8h 05m

Worcester

Sun 11/2

3:29 pm-10:52 pm

1 stop8h 23m

$228

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 10/8

7:10 am-1:58 pm

2 stops5h 48m

Worcester

Tue 10/14

3:18 pm-8:37 pm

1 stop6h 19m

$232

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Sat 10/11

7:09 pm-3:50 pm

1 stop19h 41m

Worcester

Wed 10/15

4:17 pm-8:18 am

2 stops17h 01m

$234

ChicagoWorcester

ORD - ORH

ORDORH

Chicago O'Hare Intl

Wed 10/8

7:10 am-1:58 pm

2 stops5h 48m

Worcester

Wed 10/15

3:18 pm-11:57 pm

2 stops9h 39m

$237

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 Boston from

How to get the cheapest flight ticket from Chicago to Worcester, Massachusetts

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 Worcester, Massachusetts?

The cheapest day to depart from Chicago to Worcester, Massachusetts is on a Thursday. Travelers who choose to depart for Worcester, Massachusetts on a Thursday will often find tickets for as low as $258. On the other hand, Friday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $270.

What is the cheapest time of day to depart on your flight to Worcester, Massachusetts?

The cheapest time of day to fly to Worcester, Massachusetts is in the morning when flights can be purchased for as low as $228. Flights in the evening are often more expensive with an average ticket price of $295.

When to book flights from Chicago to Worcester, Massachusetts

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

Cheap Chicago to Worcester, Massachusetts (CHI to ORH) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Worcester, Massachusetts

Best Price Found

$109

Fastest flight time

4h 31m

Direct flights

None

Airports in Worcester, Massachusetts

1 airport
The best one-way flight to Worcester, Massachusetts from Chicago in the past 72 hours is $109. The best round-trip flight deal from Chicago to Worcester, Massachusetts found on momondo in the last 72 hours is $164.
The fastest flight from Chicago to Worcester, Massachusetts takes 4h 31m
There are no direct flights from Chicago to Worcester, Massachusetts. Popular non-direct route for this connection is Chicago O'Hare Intl Airport - Worcester Airport.
There is 1 airport near Worcester, Massachusetts: Worcester (ORH)
Search flight deals

  • How far is Chicago to Worcester by plane?

    Worcester is 810.4 mi away from Chicago. Typically, this will take 4h 31m by plane in normal conditions.

  • When did momondo last update prices for flights from Chicago to Worcester Airport?

    Prices for flights from Chicago to Worcester Airport refresh daily.

  • How many operators does momondo search for flights from Chicago to Worcester Airport?

  • How old do you have to be to fly from Chicago to Worcester 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 Chicago to Worcester Airport.

  • What documentation or ID do you need to fly to Worcester Airport?

    The travel and health documents required for your trip to Worcester Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Worcester Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Chicago to Worcester, Massachusetts

Compare and see reviews for airlines that fly from Chicago to Worcester, Massachusetts with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $212Free CancellationRating
8.0
7,981 reviews
Search Delta flights

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Winchester

Why use momondo?

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

Finding the right flight to Worcester from Chicago 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 Worcester quick and easy, saving you time and money.

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

Yes. momondo enables you to select and highlight flights to Worcester from Chicago with this policy.

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

Once you have performed a search for Chicago to Worcester flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Chicago to Worcester right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Chicago to Worcester now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Worcester and let you know when they change.

An easier way to manage your Worcester, Massachusetts 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.
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