$47 Cheap flight deals from Chicago (CHI) to Worcester (ORH)

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This Weekend's Flight Deals from Chicago to Worcester

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Feb 20 - Sun, Feb 22
MDW
Midway Intl.
BOS
Logan Intl.
$233 Roundtrip, found 1 day ago
$233
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Fri, Feb 20 from Midway Intl. to Logan Intl., returning Sun, Feb 22, priced at $233 found 1 day ago
Sat, Feb 21 - Tue, Feb 24
ORD
O'Hare Intl.
BOS
Logan Intl.
$358 Roundtrip, just found
$358
Roundtrip
just found
Select JetBlue Airways flight, departing Sat, Feb 21 from O'Hare Intl. to Logan Intl., returning Tue, Feb 24, priced at $358 just found
Sat, Feb 21 - Mon, Feb 23
RFD
Greater Rockford
BOS
Logan Intl.
$446 Roundtrip, found 5 days ago
$446
Roundtrip
found 5 days ago
Select American Airlines flight, departing Sat, Feb 21 from Greater Rockford to Logan Intl., returning Mon, Feb 23, priced at $446 found 5 days ago

Airfares from $47 One Way, $81 Round Trip from Chicago to Worcester

Prices starting at $81 for return flights and $47 for one-way flights to Worcester were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sun, Apr 19 - Thu, Apr 30
ORD
Chicago
BOS
Boston
$81 Roundtrip, found 1 day ago
$81
Roundtrip
found 1 day ago
Select United flight, departing Sun, Apr 19 from Chicago to Boston, returning Thu, Apr 30, priced at $81 found 1 day ago
Sat, May 2 - Sat, May 9
ORD
Chicago
BOS
Boston
$91 Roundtrip, found 2 days ago
$91
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, May 2 from Chicago to Boston, returning Sat, May 9, priced at $91 found 2 days ago
Wed, Jun 3 - Sat, Jun 6
ORD
Chicago
BOS
Boston
$109 Roundtrip, found 2 days ago
$109
Roundtrip
found 2 days ago
Select JetBlue Airways flight, departing Wed, Jun 3 from Chicago to Boston, returning Sat, Jun 6, priced at $109 found 2 days ago
Sat, Jul 4 - Wed, Jul 8
ORD
Chicago
BOS
Boston
$110 Roundtrip, found 2 days ago
$110
Roundtrip
found 2 days ago
Select Delta flight, departing Sat, Jul 4 from Chicago to Boston, returning Wed, Jul 8, priced at $110 found 2 days ago
Sat, Apr 4 - Wed, Apr 8
MDW
Chicago
BOS
Boston
$120 Roundtrip, found 5 hours ago
$120
Roundtrip
found 5 hours ago
Select Southwest Airlines flight, departing Sat, Apr 4 from Chicago to Boston, returning Wed, Apr 8, priced at $120 found 5 hours ago

Worcester economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Langham, Boston
5.0-star property

The Langham, Boston

9.6/10 Exceptional! (1,004 reviews)

Apr 2 - Apr 5

3 night stay

Chicago (CHI) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,048, price is now $702 per person
$702
per person
found 1 day ago
No complaints , everything . I would go back again and again.

Reviewed on Jan 12, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,005 reviews)

Apr 2 - Apr 5

3 night stay

Chicago (CHI) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,469, price is now $973 per person
$973
per person
found 1 day ago
The staff is VERY attentive to all your needs. It just makes everything easy and more comfortable: room service to concierge to valet parking etc. etc.

Reviewed on Mar 24, 2024

Maverick Suites at 402 Columbus Ave
2.5-star property

Maverick Suites at 402 Columbus Ave

7.8/10 Good! (66 reviews)

Mar 20 - Mar 26

6 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Non-stop • Coach

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Non-stop • Coach
Save 100% on your flight
Price was $1,034, price is now $766 per person
$766
per person
found 1 day ago
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More About Flying To Worcester from Chicago

Route Information for Flights from Chicago to Worcester

Origin Airport IATA Code
CHI
Destination Airport IATA Code
ORH
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to Worcester

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Flight Deals on the Go

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With Orbitz, not do you get amazing low-cost deals on Chicago to Worcester flights, but we can send you flight alerts to your mobile phone or email. Instantly learn about delays to your flights from Chicago to Worcester, so you can plan ahead and make different travel arrangements if you need to.

Guaranteed low prices for Chicago to Worcester flights makes Orbitz the perfect online budget travel source.

Frequently asked questions

Are there non-stop flights from Chicago to Worcester?
There certainly are, so you'll only need to keep track of one flight number. Select from 4 airlines that operate direct flights from O'Hare Airport to Boston, MA (BOS-Logan Intl.), including:

  • United Airlines
  • American Airlines
  • Delta
  • JetBlue

What is the shortest flight from Chicago to Worcester?
If conditions are good and all goes as planned, you could be flying into Logan Intl. Airport (BOS) from Midway Intl. Airport (MDW) in as little as 2 hours and 59 minutes. With such a brief flight time, consider traveling with just carry-on luggage.
What airlines fly from Chicago to Worcester most frequently?
With a nice range of airlines traveling between Chicago and Worcester, you'll have your choice of excellent deals. The airlines servicing this route the most frequently are: United Airlines - (UA) with 208 flights every month American Airlines - (AA) with 199 flights every month Delta - (DL) with 147 flights every month JetBlue - (B6) with 56 flights every month
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won't keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.