$55 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, May 2 - Mon, May 5
ORD
O'Hare Intl.
ORH
Worcester Regional
$226 Roundtrip, found 6 days ago
$226
Roundtrip
found 6 days ago
Select American Airlines flight, departing Fri, May 2 from O'Hare Intl. to Worcester Regional, returning Mon, May 5, priced at $226 found 6 days ago
Sat, May 3 - Tue, May 13
ORD
O'Hare Intl.
BOS
Logan Intl.
$227 Roundtrip, found 1 hour ago
$227
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, May 3 from O'Hare Intl. to Logan Intl., returning Tue, May 13, priced at $227 found 1 hour ago
Fri, May 2 - Mon, May 5
MDW
Midway Intl.
BOS
Logan Intl.
$366 Roundtrip, found 2 hours ago
$366
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Fri, May 2 from Midway Intl. to Logan Intl., returning Mon, May 5, priced at $366 found 2 hours ago

Airfares from $55 One Way, $109 Round Trip from Chicago to Worcester

Prices starting at $109 for return flights and $55 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.

Thu, Oct 30 - Thu, Nov 6
ORD
Chicago
BOS
Boston
$109 Roundtrip, found 2 hours ago
$109
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Thu, Oct 30 from Chicago to Boston, returning Thu, Nov 6, priced at $109 found 2 hours ago
Sat, Aug 9 - Wed, Aug 13
ORD
Chicago
BOS
Boston
$117 Roundtrip, just found
$117
Roundtrip
just found
Select United flight, departing Sat, Aug 9 from Chicago to Boston, returning Wed, Aug 13, priced at $117 just found
Sat, Aug 9 - Wed, Aug 13
ORD
Chicago
BOS
Boston
$117 Roundtrip, just found
$117
Roundtrip
just found
Select Delta flight, departing Sat, Aug 9 from Chicago to Boston, returning Wed, Aug 13, priced at $117 just found
Sat, Aug 9 - Wed, Aug 13
ORD
Chicago
BOS
Boston
$117 Roundtrip, just found
$117
Roundtrip
just found
Select American Airlines flight, departing Sat, Aug 9 from Chicago to Boston, returning Wed, Aug 13, priced at $117 just found
Wed, May 7 - Sat, May 10
MDW
Chicago
BOS
Boston
$119 Roundtrip, found 6 hours ago
$119
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Wed, May 7 from Chicago to Boston, returning Sat, May 10, priced at $119 found 6 hours ago

Worcester economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sunbird ANNEX Resort
2.0-star property

Sunbird ANNEX Resort

7.6/10 Good! (701 reviews)

Jun 20 - Jun 23

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
per person
found 2 hours ago
Room hd strong smell of a lavender? cleaner very strong very basic room the AC worked fine.

Reviewed on Aug 4, 2019

Sea Mist Resort
3.0-star property

Sea Mist Resort

8.8/10 Excellent! (115 reviews)

Jun 18 - Jun 22

4 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 10 hours ago
I liked having 2 floors as it was a townhouse. Having an equipped kitchen and 2 baths was really a nice convenience for a family of 4. Plenty of closet space and a slider out to the back area where you can sit outside and also use their grills. The place does need updating. It is clearly showing wear. The furnishings and amenities like the TV's are out of date. Regardless, we enjoyed our stay and would stay again.

Reviewed on Dec 12, 2024

Eastern Inn
2.0-star property

Eastern Inn

6.4/10 (352 reviews)

Jun 20 - Jun 23

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
per person
found 2 hours ago
Staff needs re-training on cleaning. I hardly got sleep, people loitering in halls. People used the back & side for adult entertainment, condoms left on steps, trash, chicken wings on the floor. Babies left unattended to run up and down the halls. The air quality was horrible in the room, musty smell. I checked ac filter, filthy.

Reviewed on Jul 31, 2023

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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
863 mi
Direct Flight Airlines
American Airlines, Qatar Airways, JAL, Icelandair, Emirates, Delta Air Lines, Air New Zealand, United Airlines, El Al, Alaska Airlines, Etihad Airways, JetBlue, Cathay Pacific, Avianca, SAS, Royal Jordanian, Iberia, Hawaiian Airlines, Korean Air, ANA, WestJet, TAP Air Portugal, Virgin Atlantic, British Airways
Earliest Flight Arrival
2:25PM UTC
Latest Flight Arrival
4:45AM UTC

Chicago to Worcester

Orbitz guarantees you low prices on flights from Chicago to Worcester. In addition to low fares on Chicago to Worcester flights, Orbitz offers fantastic savings on hotels, cruises, vacation packages, and more.

Earn Miles While Saving

Besides helping you fly for the lowest fares, Orbitz lets you earn miles for your frequent flyer program for certain flights from Chicago to Worcester. If you are a member of the frequent flyer or loyalty program offered by the airline you booked through Orbitz or a partner airline’s, simply add your frequent flyer number to your Orbitz reservation to get credit for your Chicago to Worcester flights.

Travel Planning Made Easy

We help take some of the anxiety out of your Chicago to Worcester flights with free flight alerts. We will let you know of flight changes and delays to your flights from Chicago to Worcester by email, voicemail, or text messages to your mobile phone. Alerts can also be sent to up to six other contacts to keep family and business teams informed.

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Orbitz lets you find the best deals on Chicago to Worcester flights while on the go, with our easy-to-use Android and iPhone mobile apps. Easily check flight status, gate numbers, and other flight details all in one place with our app—which is great when you are in a hurry. You can use the apps to access great mobile deals on flights and amazing hotel rooms.

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.

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.