$93 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 30 - Sun, Jun 7
ORD
O'Hare Intl.
BOS
Logan Intl.
$262 Roundtrip, found 1 hour ago
$262
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sat, May 30 from O'Hare Intl. to Logan Intl., returning Sun, Jun 7, priced at $262 found 1 hour ago
Sun, May 31 - Sun, Jun 7
MDW
Midway Intl.
BOS
Logan Intl.
$378 Roundtrip, found 1 day ago
$378
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sun, May 31 from Midway Intl. to Logan Intl., returning Sun, Jun 7, priced at $378 found 1 day ago

Airfares from $93 One Way, $192 Round Trip from Chicago to Worcester

Prices starting at $192 for return flights and $93 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, Jun 9 - Wed, Jun 10
ORD
Chicago
BOS
Boston
$192 Roundtrip, found 19 hours ago
$192
Roundtrip
found 19 hours ago
Select JetBlue Airways flight, departing Tue, Jun 9 from Chicago to Boston, returning Wed, Jun 10, priced at $192 found 19 hours ago
Sun, Jun 7 - Wed, Jun 10
MDW
Chicago
BOS
Boston
$192 Roundtrip, found 1 day ago
$192
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sun, Jun 7 from Chicago to Boston, returning Wed, Jun 10, priced at $192 found 1 day ago
Wed, Jun 10 - Sat, Jun 13
ORD
Chicago
BOS
Boston
$196 Roundtrip, just found
$196
Roundtrip
just found
Select American Airlines flight, departing Wed, Jun 10 from Chicago to Boston, returning Sat, Jun 13, priced at $196 just found
Wed, Jun 10 - Sat, Jun 13
RFD
Rockford
BOS
Boston
$200 Roundtrip, found 5 days ago
$200
Roundtrip
found 5 days ago
Select American Airlines flight, departing Wed, Jun 10 from Rockford to Boston, returning Sat, Jun 13, priced at $200 found 5 days ago
Mon, Jun 8 - Mon, Jun 15
ORD
Chicago
ORH
Worcester
$226 Roundtrip, found 1 day ago
$226
Roundtrip
found 1 day ago
Select American Airlines flight, departing Mon, Jun 8 from Chicago to Worcester, returning Mon, Jun 15, priced at $226 found 1 day ago

Worcester economy flight packages

Price found within the past 48 hours. Click for updated prices.
By the Sea Guests Bed & Breakfast & Suites
3.5-star property

By the Sea Guests Bed & Breakfast & Suites

9.2/10 Wonderful! (185 reviews)

Jul 20 - Jul 24

4 night stay

Chicago (CHI) to Boston (BOS)

Delta • Coach

Boston (BOS) to Chicago (CHI)

JetBlue Airways • Coach
Save 100% on your flight
Price was $968, price is now $641 per person
$641
per person
found 1 day ago
The property was quite large and roomy. We were there off-season but the property was excellently maintained. Would love to go back in the spring or fall.

Reviewed on Mar 24, 2019

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,001 reviews)

Jul 17 - Jul 20

3 night stay

Chicago (CHI) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,739, price is now $1,060 per person
$1,060
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

The Inn at Hastings Park, Relais & Chateaux - Boston
4.0-star property

The Inn at Hastings Park, Relais & Chateaux - Boston

9.6/10 Exceptional! (256 reviews)

Jul 14 - Jul 21

7 night stay

Chicago (CHI) to Boston (BOS)

Delta • Roundtrip • Coach
Save 100% on your flight
Price was $2,454, price is now $1,512 per person
$1,512
per person
found 9 hours ago
The heater in Room 37 did not maintain a steady, dependable temperature (it varied \- by 5 degrees F). Otherwise, superb restaurant onsite and superb continental breakfast.

Reviewed on Feb 13, 2025

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Worcester first class flight packages

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

Encore Boston Harbor

9.6/10 Exceptional! (3,765 reviews)

Jul 2 - Jul 6

4 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,673, price is now $1,276 per person
$1,276
per person
found 1 day ago
Beautiful views, helpful staff, gorgeous room, and perfect location.

Reviewed on Apr 22, 2026

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,001 reviews)

Jul 2 - Jul 6

4 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,845, price is now $2,118 per person
$2,118
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

The Langham, Boston
5.0-star property

The Langham, Boston

9.6/10 Exceptional! (1,008 reviews)

Jul 2 - Jul 6

4 night stay

Chicago (CHI) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,262, price is now $1,714 per person
$1,714
per person
found 1 day ago
No complaints , everything . I would go back again and again.

Reviewed on Jan 12, 2026

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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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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.