$54 Cheap flight deals from Chicago (CHI) to Worcester (ORH)

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Airfares from $54 One Way, $97 Round Trip from Chicago to Worcester

Prices starting at $97 for return flights and $54 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.

Thu, Oct 30 - Sat, Nov 1
MDW
Chicago
BOS
Boston
$97 Roundtrip, found 6 days ago
$97
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Oct 30 from Chicago to Boston, returning Sat, Nov 1, priced at $97 found 6 days ago
Thu, Oct 30 - Sat, Nov 1
MDW
Chicago
BOS
Boston
$106 Roundtrip, found 6 days ago
$106
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Thu, Oct 30 from Chicago to Boston, returning Sat, Nov 1, priced at $106 found 6 days ago
Tue, Nov 4 - Tue, Nov 11
ORD
Chicago
BOS
Boston
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Nov 4 from Chicago to Boston, returning Tue, Nov 11, priced at $117 found 5 days ago
Sun, Oct 12 - Wed, Oct 15
ORD
Chicago
BOS
Boston
$119 Roundtrip, found 2 hours ago
$119
Roundtrip
found 2 hours ago
Select United flight, departing Sun, Oct 12 from Chicago to Boston, returning Wed, Oct 15, priced at $119 found 2 hours ago
Fri, Dec 5 - Mon, Dec 8
RFD
Rockford
BOS
Boston
$139 Roundtrip, found 4 hours ago
$139
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Fri, Dec 5 from Rockford to Boston, returning Mon, Dec 8, priced at $139 found 4 hours ago

Worcester economy flight packages

Price found within the past 48 hours. Click for updated prices.
Best Western Springfield West Inn
2.5-star property

Best Western Springfield West Inn

7.8/10 Good! (1,008 reviews)

Nov 8 - Nov 10

2 night stay

Chicago (MDW) to Boston (BOS)

Southwest Airlines • Roundtrip • Coach
Price was $297, price is now $218 per person
$218
per person
found 1 day ago
Easy parking and friendly staff.

Reviewed on Feb 8, 2025

D. Hotel Suites & Spa
3.0-star property

D. Hotel Suites & Spa

9.4/10 Exceptional! (2,240 reviews)

Nov 8 - Nov 10

2 night stay

Chicago (MDW) to Boston (BOS)

Southwest Airlines • Roundtrip • Coach
Price was $396, price is now $282 per person
$282
per person
found 1 day ago
The spacious rooms, the indoor pool, hot tub and of course the staff was amazing, especially Jim, he made a disabled young mans Birthday extra special with a simple touch. First time and will be returning soon.

Reviewed on Oct 6, 2024

Hotel AKA Boston Common
4.0-star property

Hotel AKA Boston Common

9/10 Wonderful! (1,273 reviews)

Oct 24 - Oct 26

2 night stay

Chicago (CHI) to Boston (BOS)

United • Coach

Boston (BOS) to Chicago (CHI)

Southwest Airlines • Coach
Save 100% on your flight
Price was $1,620, price is now $1,199 per person
$1,199
per person
found 1 day ago
Wonderful staff, lovely rooms, easy walk to everything we wanted to do.

Reviewed on Feb 26, 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
863 mi
Direct Flight Airlines
JAL, Icelandair, Delta Air Lines, Air New Zealand, United Airlines, SAS, Iberia, Korean Air, WestJet, American Airlines, KLM, Qatar Airways, Air France, Alaska Airlines, Etihad Airways, JetBlue, Avianca, Cathay Pacific, Royal Jordanian, ITA Airways, Hawaiian Airlines, ANA, TAP Air Portugal, Virgin Atlantic, British Airways
Earliest Flight Arrival
1:32PM UTC
Latest Flight Arrival
4:50AM UTC

Chicago to Worcester

If you are looking to find the best deals on Chicago to Worcester flights, look no further than Orbitz. Orbitz offers guaranteed low prices as well as cutting-edge mobile tools to help you book cheap flights from Chicago to Worcester.

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Our mobile apps for Android and iPhone phones as well as tablets and iPads let you find the cheapest flights from Chicago to Worcester—whether you are at home or running errands. Use the apps to also keep track of delays to your Chicago to Worcester flights and baggage claim information.

Get Miles for Your Flights From Chicago to Worcester

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Stay Informed While You Travel

Orbitz keeps you updated on information that’s relevant to your flights from Chicago to Worcester. We can send you and six of your personal contacts free travel alerts via SMS text, voicemail, or email, so you instantly know about flight delays or changes.

Keep More Money in Your Pocket With Discount Flights

Orbitz looks for the best deals on Chicago to Worcester flights for you. Mix and match airlines for your departing and return flights to fit your travel schedule and budget.

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.