$51 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, Aug 22 - Mon, Aug 25
ORD
O'Hare Intl.
ORH
Worcester Regional
$228 Roundtrip, found 2 days ago
$228
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Aug 22 from O'Hare Intl. to Worcester Regional, returning Mon, Aug 25, priced at $228 found 2 days ago
Sat, Aug 23 - Mon, Aug 25
MDW
Midway Intl.
BOS
Logan Intl.
$231 Roundtrip, found 1 day ago
$231
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Aug 23 from Midway Intl. to Logan Intl., returning Mon, Aug 25, priced at $231 found 1 day ago
Sat, Aug 23 - Sat, Sep 6
ORD
O'Hare Intl.
BOS
Logan Intl.
$238 Roundtrip, found 2 hours ago
$238
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Aug 23 from O'Hare Intl. to Logan Intl., returning Sat, Sep 6, priced at $238 found 2 hours ago

Airfares from $51 One Way, $99 Round Trip from Chicago to Worcester

Prices starting at $99 for return flights and $51 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.

Tue, Nov 18 - Fri, Nov 21
MDW
Chicago
BOS
Boston
$99 Roundtrip, found 3 days ago
$99
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Tue, Nov 18 from Chicago to Boston, returning Fri, Nov 21, priced at $99 found 3 days ago
Tue, Sep 9 - Tue, Sep 16
ORD
Chicago
BOS
Boston
$114 Roundtrip, just found
$114
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Sep 9 from Chicago to Boston, returning Tue, Sep 16, priced at $114 just found
Sat, Aug 30 - Sat, Sep 6
ORD
Chicago
BOS
Boston
$129 Roundtrip, found 10 hours ago
$129
Roundtrip
found 10 hours ago
Select United flight, departing Sat, Aug 30 from Chicago to Boston, returning Sat, Sep 6, priced at $129 found 10 hours ago
Wed, Sep 3 - Sun, Sep 7
ORD
Chicago
BOS
Boston
$130 Roundtrip, just found
$130
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Sep 3 from Chicago to Boston, returning Sun, Sep 7, priced at $130 just found
Fri, Oct 17 - Tue, Oct 21
ORD
Chicago
BOS
Boston
$137 Roundtrip, found 1 hour ago
$137
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Oct 17 from Chicago to Boston, returning Tue, Oct 21, priced at $137 found 1 hour ago

Worcester economy flight packages

Price found within the past 48 hours. Click for updated prices.
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,014 reviews)

Sep 26 - Sep 28

2 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Coach

Boston (BOS) to Chicago (CHI)

American Airlines • Coach
Save 100% on your flight
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

Sesuit Harbor House
3.0-star property

Sesuit Harbor House

9.6/10 Exceptional! (158 reviews)

Sep 24 - Sep 30

6 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Excellent stay. Everything you could want in a Cape Cod vacation. Beautiful pool, close to the beach, lovely breakfast, fire pit for s'mores, and even on site GOATS! The owners are great and super accommodating. Will be back!

Reviewed on Aug 9, 2022

The Hotel Salem
3.0-star property

The Hotel Salem

9.2/10 Wonderful! (1,013 reviews)

Sep 30 - Oct 3

3 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Coach

Boston (BOS) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
Great location in the middle of everything! Staff was super nice, room was good very comfortable.

Reviewed on Jun 20, 2025

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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

Low Cost Flights From Chicago to Worcester

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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.