$49 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.

Sat, May 3 - Tue, May 6
ORD
O'Hare Intl.
ORH
Worcester Regional
$226 Roundtrip, found 6 days ago
$226
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, May 3 from O'Hare Intl. to Worcester Regional, returning Tue, May 6, priced at $226 found 6 days ago
Sat, May 3 - Wed, May 7
ORD
O'Hare Intl.
BOS
Logan Intl.
$332 Roundtrip, just found
$332
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 3 from O'Hare Intl. to Logan Intl., returning Wed, May 7, priced at $332 just found
Sat, May 3 - Sun, May 4
MDW
Midway Intl.
BOS
Logan Intl.
$367 Roundtrip, found 3 days ago
$367
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, May 3 from Midway Intl. to Logan Intl., returning Sun, May 4, priced at $367 found 3 days ago

Airfares from $49 One Way, $109 Round Trip from Chicago to Worcester

Prices starting at $109 for return flights and $49 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.

Wed, Jun 4 - Sun, Jun 8
ORD
Chicago
BOS
Boston
$109 Roundtrip, found 1 hour ago
$109
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Jun 4 from Chicago to Boston, returning Sun, Jun 8, priced at $109 found 1 hour ago
Thu, Oct 16 - Thu, Oct 23
ORD
Chicago
BOS
Boston
$109 Roundtrip, just found
$109
Roundtrip
just found
Select Spirit Airlines flight, departing Thu, Oct 16 from Chicago to Boston, returning Thu, Oct 23, priced at $109 just found
Fri, Aug 8 - Mon, Aug 11
ORD
Chicago
BOS
Boston
$117 Roundtrip, just found
$117
Roundtrip
just found
Select United flight, departing Fri, Aug 8 from Chicago to Boston, returning Mon, Aug 11, priced at $117 just found
Wed, Jul 16 - Wed, Jul 23
ORD
Chicago
BOS
Boston
$117 Roundtrip, found 5 hours ago
$117
Roundtrip
found 5 hours ago
Select Delta flight, departing Wed, Jul 16 from Chicago to Boston, returning Wed, Jul 23, priced at $117 found 5 hours ago
Sat, Jul 12 - Sat, Jul 19
ORD
Chicago
BOS
Boston
$117 Roundtrip, just found
$117
Roundtrip
just found
Select American Airlines flight, departing Sat, Jul 12 from Chicago to Boston, returning Sat, Jul 19, priced at $117 just found

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 21 hours ago
Room hd strong smell of a lavender? cleaner very strong very basic room the AC worked fine.

Reviewed on Aug 4, 2019

Courtyard by Marriott Boston Waltham
3.0-star property

Courtyard by Marriott Boston Waltham

9.2/10 Wonderful! (1,003 reviews)

Jun 27 - Jun 30

3 night stay

Chicago (ORD) to Boston (BOS)

Frontier Airlines • Non-stop • Coach

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Non-stop • Coach
per person
found 20 hours ago
Very Clean, big room, great pool and area. Highly recommended

Reviewed on Apr 3, 2025

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 1 day 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

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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

Chicago to Worcester flights are offered at fantastic discount by Orbitz. Book air tickets now and cut those extra costs out of your travel budget to ensure a rewarding travel experience. With guaranteed low prices like these, can you afford to miss this discount?

Book cheap flights from Chicago to Worcester

Cheap airfares are available on flights from Chicago to Worcester. Use Orbitz to find the best flights that suit both your budget and the travel times that you need. Travelers who are looking for discounted rates on domestic or international flights need to look no further than Orbitz.

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As the world of technology rapidly expands around us, we are continuously finding new ways to improve our services, communications, and accessibility. With our cutting-edge mobile tools now available on Android, iPhone, and tablets, you can access detailed information on your bookings for flights from Chicago to Worcester at any time or anywhere. See your itinerary for your Chicago to Worcester flights, baggage and gate claim details, as well as hotel deals with our easy-to-use apps.

Get a great package with your Chicago to Worcester flights

With frequent updates on your flight status, including delays and changes in bookings, traveling becomes more hassle-free than ever. Not only do we offer huge discounted deals on flights from Chicago to Worcester, we also have fantastic savings on vacation packages, hotel room, cruises, activities, and car rentals so you can pick and choose and create the best travel package for you.

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.