$57 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, Jun 20 - Wed, Jun 25
ORD
O'Hare Intl.
BOS
Logan Intl.
$206 Roundtrip, just found
$206
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Jun 20 from O'Hare Intl. to Logan Intl., returning Wed, Jun 25, priced at $206 just found
Fri, Jun 20 - Mon, Jun 23
MDW
Midway Intl.
BOS
Logan Intl.
$226 Roundtrip, found 2 days ago
$226
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Fri, Jun 20 from Midway Intl. to Logan Intl., returning Mon, Jun 23, priced at $226 found 2 days ago
Sun, Jun 22 - Mon, Jun 23
ORD
O'Hare Intl.
ORH
Worcester Regional
$653 Roundtrip, found 6 days ago
$653
Roundtrip
found 6 days ago
Select Delta flight, departing Sun, Jun 22 from O'Hare Intl. to Worcester Regional, returning Mon, Jun 23, priced at $653 found 6 days ago

Airfares from $57 One Way, $114 Round Trip from Chicago to Worcester

Prices starting at $114 for return flights and $57 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, Jul 8 - Wed, Jul 9
ORD
Chicago
BOS
Boston
$114 Roundtrip, found 4 hours ago
$114
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Tue, Jul 8 from Chicago to Boston, returning Wed, Jul 9, priced at $114 found 4 hours ago
Thu, Sep 11 - Mon, Sep 15
MDW
Chicago
BOS
Boston
$125 Roundtrip, found 3 hours ago
$125
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Thu, Sep 11 from Chicago to Boston, returning Mon, Sep 15, priced at $125 found 3 hours ago
Wed, Aug 20 - Thu, Aug 21
ORD
Chicago
BOS
Boston
$125 Roundtrip, found 3 days ago
$125
Roundtrip
found 3 days ago
Select Delta flight, departing Wed, Aug 20 from Chicago to Boston, returning Thu, Aug 21, priced at $125 found 3 days ago
Thu, Sep 11 - Sun, Sep 14
ORD
Chicago
BOS
Boston
$143 Roundtrip, found 3 hours ago
$143
Roundtrip
found 3 hours ago
Select United flight, departing Thu, Sep 11 from Chicago to Boston, returning Sun, Sep 14, priced at $143 found 3 hours ago
Sat, Jun 28 - Sat, Jul 5
ORD
Chicago
BOS
Boston
$210 Roundtrip, found 3 hours ago
$210
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Sat, Jun 28 from Chicago to Boston, returning Sat, Jul 5, priced at $210 found 3 hours ago

Worcester economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sea Mist Resort
3.0-star property

Sea Mist Resort

8.8/10 Excellent! (124 reviews)

Jul 24 - Jul 27

3 night stay

Chicago (ORD) to Boston (BOS)

United • 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

Encore Boston Harbor
5.0-star property

Encore Boston Harbor

9.6/10 Exceptional! (2,977 reviews)

Jul 31 - Aug 7

7 night stay

Chicago (CHI) to Boston (BOS)

Southwest Airlines • Coach

Boston (BOS) to Chicago (CHI)

American Airlines • Coach
Save 100% on your flight
per person
found 1 day ago
No microwave at all!!

Reviewed on May 18, 2025

Holly Tree Resort
3.0-star property

Holly Tree Resort

9/10 Wonderful! (343 reviews)

Jul 24 - Jul 27

3 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
good value for money

Reviewed on Oct 21, 2022

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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
JAL, Icelandair, Delta Air Lines, Air New Zealand, United Airlines, El Al, SAS, Iberia, Korean Air, WestJet, American Airlines, KLM, Qatar Airways, Emirates, Alaska Airlines, Etihad Airways, JetBlue, Cathay Pacific, Avianca, Royal Jordanian, Hawaiian Airlines, ANA, TAP Air Portugal, Virgin Atlantic, British Airways
Earliest Flight Arrival
1:56PM UTC
Latest Flight Arrival
4:59AM UTC

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.