$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.

Sat, Jul 5 - Wed, Jul 23
ORD
O'Hare Intl.
ORH
Worcester Regional
$278 Roundtrip, found 2 days ago
$278
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Jul 5 from O'Hare Intl. to Worcester Regional, returning Wed, Jul 23, priced at $278 found 2 days ago
Fri, Jul 4 - Mon, Jul 7
ORD
O'Hare Intl.
BOS
Logan Intl.
$308 Roundtrip, just found
$308
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jul 4 from O'Hare Intl. to Logan Intl., returning Mon, Jul 7, priced at $308 just found
Sat, Jul 5 - Sun, Jul 13
MDW
Midway Intl.
BOS
Logan Intl.
$338 Roundtrip, found 1 day ago
$338
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Sat, Jul 5 from Midway Intl. to Logan Intl., returning Sun, Jul 13, priced at $338 found 1 day ago

Airfares from $57 One Way, $127 Round Trip from Chicago to Worcester

Prices starting at $127 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.

Wed, Jul 23 - Tue, Jul 29
ORD
Chicago
BOS
Boston
$127 Roundtrip, just found
$127
Roundtrip
just found
Select JetBlue Airways flight, departing Wed, Jul 23 from Chicago to Boston, returning Tue, Jul 29, priced at $127 just found
Tue, Jul 22 - Wed, Jul 23
ORD
Chicago
BOS
Boston
$128 Roundtrip, found 2 hours ago
$128
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Tue, Jul 22 from Chicago to Boston, returning Wed, Jul 23, priced at $128 found 2 hours ago
Wed, Jul 9 - Wed, Jul 16
MDW
Chicago
BOS
Boston
$137 Roundtrip, found 6 hours ago
$137
Roundtrip
found 6 hours ago
Select Southwest Airlines flight, departing Wed, Jul 9 from Chicago to Boston, returning Wed, Jul 16, priced at $137 found 6 hours ago
Mon, Sep 15 - Tue, Sep 16
ORD
Chicago
BOS
Boston
$137 Roundtrip, found 1 hour ago
$137
Roundtrip
found 1 hour ago
Select Delta flight, departing Mon, Sep 15 from Chicago to Boston, returning Tue, Sep 16, priced at $137 found 1 hour ago
Thu, Sep 18 - Sun, Sep 21
ORD
Chicago
BOS
Boston
$137 Roundtrip, just found
$137
Roundtrip
just found
Select United flight, departing Thu, Sep 18 from Chicago to Boston, returning Sun, Sep 21, priced at $137 just found

Worcester economy flight packages

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

Riverview Resort

9.2/10 Wonderful! (158 reviews)

Aug 17 - Aug 20

3 night stay

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Non-stop • Coach

Boston (BOS) to Chicago (ORD)

American Airlines • Non-stop • Coach
per person
found 4 hours ago
Very clean and we'll maintained property. No continental breakfast, just coffee ready 1 HR before checkout. Nice employees. Pleasant stay.

Reviewed on Jun 17, 2019

The Coach House
2.0-star property

The Coach House

9.6/10 Exceptional! (125 reviews)

Aug 14 - Aug 17

3 night stay

Chicago (ORD) to Boston (BOS)

United • Coach

Boston (BOS) to Chicago (ORD)

Southwest Airlines • Coach
Save 100% on your flight
per person
found 20 hours ago
The room was a good size. Very clean. The staff was courteous and very helpful. They served a cute little box of fruits and bakery at your door for breakfast. I would highly recommend.

Reviewed on Sep 16, 2024

Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,005 reviews)

Aug 4 - Aug 6

2 night stay

Chicago (CHI) to Boston (BOS)

United • Coach

Boston (BOS) to Chicago (CHI)

JetBlue Airways • 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

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Worcester packages with premium economy flights

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

Holly Tree Resort

9/10 Wonderful! (344 reviews)

Aug 4 - Aug 9

5 night stay

Chicago (ORD) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 22 hours ago
good value for money

Reviewed on Oct 21, 2022

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat
3.0-star property

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

10/10 Exceptional! (8 reviews)

Aug 4 - Aug 9

5 night stay

Chicago (ORD) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
per person
found 22 hours ago
Centerboard
2.0-star property

Centerboard

9.6/10 Exceptional! (66 reviews)

Aug 4 - Aug 9

5 night stay

Chicago (ORD) to Boston (BOS)

Delta • Non-stop roundtrip • PremiumEconomy
per person
found 22 hours ago
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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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Not only does booking with us ensure guaranteed low prices, but Orbitz does the hard work, leaving you to relax. Just tell us what you want, from Chicago to Worcester flights, to great deals on hotels and car rental, and activities and tours, and we will do all the rest.

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.