$73 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, Jun 13 - Sat, Jun 27
ORD
O'Hare Intl.
BOS
Logan Intl.
$220 Roundtrip, found 4 hours ago
$220
Roundtrip
found 4 hours ago
Select United flight, departing Sat, Jun 13 from O'Hare Intl. to Logan Intl., returning Sat, Jun 27, priced at $220 found 4 hours ago
Fri, Jun 12 - Sun, Jun 14
RFD
Greater Rockford
BOS
Logan Intl.
$307 Roundtrip, found 18 hours ago
$307
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Fri, Jun 12 from Greater Rockford to Logan Intl., returning Sun, Jun 14, priced at $307 found 18 hours ago
Fri, Jun 12 - Sun, Jun 14
MDW
Midway Intl.
BOS
Logan Intl.
$323 Roundtrip, found 18 hours ago
$323
Roundtrip
found 18 hours ago
Select Delta flight, departing Fri, Jun 12 from Midway Intl. to Logan Intl., returning Sun, Jun 14, priced at $323 found 18 hours ago

Airfares from $73 One Way, $149 Round Trip from Chicago to Worcester

Prices starting at $149 for return flights and $73 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, Sep 2 - Tue, Sep 8
ORD
Chicago
BOS
Boston
$149 Roundtrip, found 9 hours ago
$149
Roundtrip
found 9 hours ago
Select Delta flight, departing Wed, Sep 2 from Chicago to Boston, returning Tue, Sep 8, priced at $149 found 9 hours ago
Wed, Jul 1 - Sat, Jul 4
ORD
Chicago
BOS
Boston
$153 Roundtrip, found 4 hours ago
$153
Roundtrip
found 4 hours ago
Select United flight, departing Wed, Jul 1 from Chicago to Boston, returning Sat, Jul 4, priced at $153 found 4 hours ago
Fri, Jul 31 - Wed, Aug 5
ORD
Chicago
BOS
Boston
$157 Roundtrip, found 3 hours ago
$157
Roundtrip
found 3 hours ago
Select Delta flight, departing Fri, Jul 31 from Chicago to Boston, returning Wed, Aug 5, priced at $157 found 3 hours ago
Wed, Jul 8 - Sat, Jul 11
RFD
Rockford
BOS
Boston
$186 Roundtrip, found 5 hours ago
$186
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Wed, Jul 8 from Rockford to Boston, returning Sat, Jul 11, priced at $186 found 5 hours ago
Fri, Jul 31 - Wed, Aug 5
MDW
Chicago
BOS
Boston
$190 Roundtrip, found 3 hours ago
$190
Roundtrip
found 3 hours ago
Select Southwest Airlines flight, departing Fri, Jul 31 from Chicago to Boston, returning Wed, Aug 5, priced at $190 found 3 hours ago

Worcester economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Atlas Hotel
4.5-star property

The Atlas Hotel

9.4/10 Exceptional! (113 reviews)

Jul 17 - Jul 20

3 night stay

Chicago (CHI) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $836, price is now $542 per person
$542
per person
found 1 day ago
Boston Harbor Hotel
5.0-star property

Boston Harbor Hotel

9.8/10 Exceptional! (1,004 reviews)

Jul 17 - Jul 20

3 night stay

Chicago (CHI) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $1,708, price is now $1,027 per person
$1,027
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

Meco Hotel - Hostel
2.0-star property

Meco Hotel - Hostel

8.6/10 Excellent! (435 reviews)

Jul 15 - Jul 22

7 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • Coach
Save 100% on your flight
Price was $2,793, price is now $1,683 per person
$1,683
per person
found 1 day ago
The staff member was super nice.

Reviewed on Nov 10, 2025

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Worcester packages with premium economy flights

Price found within the past 48 hours. Click for updated prices.
The Westin Boston Seaport District
4.0-star property

The Westin Boston Seaport District

9.2/10 Wonderful! (2,405 reviews)

Jul 9 - Jul 12

3 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • PremiumEconomy
Price was $1,100, price is now $790 per person
$790
per person
found 1 day ago
Food, bars, fitness center all on site and walking distance to great shopping

Reviewed on Apr 14, 2026

The Charles Hotel
4.0-star property

The Charles Hotel

9.4/10 Exceptional! (1,001 reviews)

Jul 9 - Jul 12

3 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • PremiumEconomy
Price was $1,281, price is now $953 per person
$953
per person
found 1 day ago
Great Cambridge hotel. Close to T stop and great location in Harvard Square. Lobby is a great place to read or get some work done. Rooms very comfortable.

Reviewed on Mar 31, 2025

The Whitney Hotel
4.0-star property

The Whitney Hotel

9.6/10 Exceptional! (557 reviews)

Jul 9 - Jul 12

3 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,039, price is now $1,526 per person
$1,526
per person
found 1 day ago
What a gem in Boston! I've been to Boston many times and usually stay closer to the Downtown Crossing area. This time we stayed at the Whitney, choosing to try out that part of town. We loved it! Bigger than a boutique hotel, but small enough to feel intimate. Charles St is a great walking street, and we loved the location. The room was on the ground level (actually partly below ground) but was excellent! Well-appointed room, a good amount of space for Boston, and super professional staff. I'll be back when I come back to Boston

Reviewed on Jul 30, 2024

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Worcester first class flight packages

Price found within the past 48 hours. Click for updated prices.
Sunbird Cape Cod Resort
2.5-star property

Sunbird Cape Cod Resort

7.8/10 Good! (540 reviews)

Jul 23 - Jul 29

6 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,479, price is now $1,098 per person
$1,098
per person
found 1 day ago
The room had a stain on the bed sheet and there was a strange scent to the room

Reviewed on Oct 12, 2025

Sea Crest Beach Resort
3.5-star property

Sea Crest Beach Resort

8/10 Very Good! (284 reviews)

Jul 23 - Jul 29

6 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $3,749, price is now $2,529 per person
$2,529
per person
found 1 day ago
5pm check in- ridiculous 18$ pool cocktails-ridiculous Dirty beaches- extremely ridiculous Mold in bathroom 25$ per night super uncomfortable rollaway bed- ridiculous

Reviewed on Aug 9, 2025

The Cape Club Resort
2.0-star property

The Cape Club Resort

No reviews

Jul 23 - Jul 29

6 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
Price was $1,998, price is now $1,508 per person
$1,508
per person
found 1 day 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

If you are looking to get guaranteed low prices for Chicago to Worcester flights then Orbitz is the place to go. We use cutting edge mobile tools to find the best deals on air tickets and to keep you updated on delays and changes.

Get Package Savings by Booking Flights and Hotels at the Same Time

Using the Orbitz Matrix display, you can see how much you will save on flights from Chicago to Worcester if the discount fare is combined with a hotel. You can also look at hotel reviews, photos and maps of the area, so it will be convenient to make your budget travel plans.

Orbitz for Business Helps Corporations save Money

Orbitz can assist all businesses from the small to major corporations with discounts on flights from Chicago to Worcester. We fine- tune your needs for Chicago to Worcester flights and optimize your plans by assessing your business and coming up with ways for you to save on air tickets.

Using Online Check-In Makes Flying Simple

You can use the Orbitz website to check-in for your flights from Chicago to Worcester. You can also make changes to your schedule or even cancel a flight.

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.