$114+ Cheap flights from Worcester, MA (ORH) to Chicago (CHI)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/22. Fares are subject to change and may not be available on all flights or dates of travel.
ORH — CHI
Sep 25 — Oct 21
Round-trip
1 adult, Economy
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Find cheap flights from Worcester to Chicago with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Worcester to Chicago
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Cheapest flights from Worcester to ChicagoExplore the most affordable flight options available from Worcester to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 26, 2026.
Explore the most affordable flight options available from Worcester to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 26, 2026.
This American Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:19 pm -
1 stop6h 11m
Mon 10/266:29 am -
1 stop9h 20m
Deal found 8/23![American Airlines logo]()
$232
This American Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:16 pm -
1 stop15h 09m
Fri 10/306:29 am -
1 stop9h 20m
Deal found 8/23![American Airlines logo]()
$241
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/244:20 pm -
1 stop5h 11m
Wed 9/306:40 am -
2 stops7h 57m
Deal found 8/25![Delta logo]()
$242
This American Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/105:16 pm -
1 stop6h 19m
Tue 9/156:29 am -
1 stop9h 20m
Deal found 8/23![American Airlines logo]()
$246
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/185:16 pm -
1 stop18h 40m
Sun 9/206:29 am -
1 stop9h 20m
Deal found 8/24![American Airlines logo]()
$255
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:20 pm -
1 stop5h 11m
Mon 9/146:40 am -
2 stops7h 57m
Deal found 8/24![Delta logo]()
$256
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/95:16 pm -
1 stop7h 40m
Sun 9/136:29 am -
1 stop9h 20m
Deal found 8/24![American Airlines logo]()
$260
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/134:00 pm -
1 stop5h 45m
Sun 11/157:05 am -
2 stops7h 18m
Deal found 8/22![Delta logo]()
$265
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/94:20 pm -
1 stop6h 58m
Sun 9/135:30 am -
2 stops9h 07m
Deal found 8/25![Delta logo]()
$270
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/145:16 pm -
1 stop15h 09m
Fri 10/166:29 am -
1 stop9h 20m
Deal found 8/24![American Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/144:15 pm -
1 stop7h 02m
Thu 10/157:00 am -
1 stop6h 58m
Deal found 8/24![Delta logo]()
$282
Best flights from Worcester to ChicagoDiscover carefully curated flight deals from Worcester to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 26, 2026.
Discover carefully curated flight deals from Worcester to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 26, 2026.
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/204:15 pm -
1 stop5h 28m
Wed 10/218:36 am -
1 stop5h 22m
Deal found 8/22![Delta logo]()
$232
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:16 pm -
1 stop18h 49m
Fri 10/309:00 pm -
1 stop18h 49m
Deal found 8/26![American Airlines logo]()
$241
This JetBlue deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:00 pm -
1 stop7h 08m
Sun 10/46:00 am -
1 stop8h 54m
Deal found 8/23![JetBlue logo]()
$318
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/153:18 pm -
1 stop7h 17m
Mon 1/187:00 am -
1 stop6h 37m
Deal found 8/23![Delta logo]()
$241
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:20 pm -
2 stops8h 39m
Sun 9/135:30 am -
2 stops9h 07m
Deal found 8/25![Delta logo]()
$275
This JetBlue deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/205:00 pm -
1 stop7h 08m
Sun 9/276:00 am -
1 stop8h 24m
Deal found 8/22![JetBlue logo]()
$318
This JetBlue deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/175:00 pm -
1 stop7h 08m
Sun 9/206:00 am -
1 stop8h 24m
Deal found 8/22![JetBlue logo]()
$364
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/24:20 pm -
2 stops8h 39m
Mon 10/56:40 am -
2 stops7h 57m
Deal found 8/25![Delta logo]()
$336
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/174:20 pm -
1 stop6h 58m
Mon 9/217:05 am -
2 stops7h 32m
Deal found 8/24![Delta logo]()
$342
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/54:20 pm -
1 stop6h 58m
Sun 10/116:15 am -
1 stop7h 43m
Deal found 8/24![Delta logo]()
$342
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/64:15 pm -
2 stops8h 42m
Sat 10/105:40 pm -
1 stop20h 18m
Deal found 8/24![Delta logo]()
$352
Last-minute flights from Worcester to ChicagoDiscover last-minute flight deals from Worcester to Chicago. Data last updated August 26, 2026 and is based on user searches.
Discover last-minute flight deals from Worcester to Chicago. Data last updated August 26, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/15:40 pm -
1 stop5h 44m
Wed 9/210:30 am -
1 stop5h 30m
Deal found 8/22![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:40 pm -
1 stop5h 44m
Fri 9/46:40 am -
2 stops9h 20m
Deal found 8/25![Delta logo]()
$332
This American Airlines deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:23 pm -
1 stop7h 21m
Mon 9/75:00 am -
1 stop10h 58m
Deal found 8/23![American Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:40 pm -
1 stop5h 44m
Wed 9/99:30 am -
1 stop5h 07m
Deal found 8/22![Delta logo]()
$326
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:40 pm -
1 stop5h 44m
Thu 9/107:05 am -
2 stops7h 32m
Deal found 8/21![Delta logo]()
$336
This American Airlines deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:23 pm -
1 stop7h 21m
Thu 9/108:45 am -
1 stop7h 04m
Deal found 8/21![American Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/45:40 pm -
1 stop5h 44m
Sun 9/69:30 am -
1 stop6h 30m
Deal found 8/22![Delta logo]()
$362
One-way flights from Worcester to ChicagoSearch for one-way flight options from Worcester to Chicago. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
Search for one-way flight options from Worcester to Chicago. Find affordable one-way fares based on user searches. Data last updated August 26, 2026.
This Delta deal was found by Cheapflights users on 8/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:15 pm -
1 stop7h 02m
Deal found 8/21![Delta logo]()
$114
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/234:15 pm -
1 stop7h 02m
Deal found 8/24![Delta logo]()
$123
This Delta deal was found by Cheapflights users on 8/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/104:20 pm -
1 stop5h 11m
Deal found 8/23![Delta logo]()
$128
This JetBlue deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:00 pm -
1 stop7h 08m
Deal found 8/24![JetBlue logo]()
$157
This Delta deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:40 pm -
1 stop5h 44m
Deal found 8/25![Delta logo]()
$159
This JetBlue deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/254:45 pm -
1 stop8h 12m
Deal found 8/24![JetBlue logo]()
$203
This JetBlue deal was found by Cheapflights users on 8/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:00 pm -
1 stop7h 08m
Deal found 8/25![JetBlue logo]()
$213
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:16 pm -
2 stops17h 54m
Deal found 8/24![American Airlines logo]()
$245
This Delta deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:40 pm -
1 stop5h 53m
Deal found 8/24![Delta logo]()
$259
This JetBlue deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/224:44 pm -
1 stop7h 46m
Deal found 8/24![JetBlue logo]()
$280
Find flight deals from Worcester to Chicago
Discover tips and strategies to find the most affordable flight options for your journey from Worcester (ORH) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated August 26, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $232 (American Airlines) |
One-way from | $114 (Delta) |
Popular in | June |
Cheapest in | January |
Average price | $254 |
Cheapflights Fare Finder
Customize your flight search to find flights from Worcester to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 26, 2026.
Use the filters below to find and compare flights from Worcester to Chicago that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Tue 10/20
4:15 pm-8:43 pm
1 stop5h 28m
Chicago O'Hare Intl
Wed 10/21
8:36 am-2:58 pm
1 stop5h 22m
$232
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Mon 10/26
5:16 pm-11:05 am
1 stop18h 49m
Chicago O'Hare Intl
Fri 10/30
9:00 pm-4:49 pm
1 stop18h 49m
$241
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Fri 1/15
3:18 pm-9:35 pm
1 stop7h 17m
Chicago O'Hare Intl
Mon 1/18
7:00 am-2:37 pm
1 stop6h 37m
$241
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Fri 9/11
4:20 pm-11:59 pm
2 stops8h 39m
Chicago O'Hare Intl
Sun 9/13
5:30 am-3:37 pm
2 stops9h 07m
$275
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Fri 10/2
5:00 pm-11:08 pm
1 stop7h 08m
Chicago O'Hare Intl
Sun 10/4
6:00 am-3:54 pm
1 stop8h 54m
$318
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Sun 9/20
5:00 pm-11:08 pm
1 stop7h 08m
Chicago O'Hare Intl
Sun 9/27
6:00 am-3:24 pm
1 stop8h 24m
$318
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Fri 10/2
4:20 pm-11:59 pm
2 stops8h 39m
Chicago O'Hare Intl
Mon 10/5
6:40 am-3:37 pm
2 stops7h 57m
$336
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Thu 9/17
4:20 pm-10:18 pm
1 stop6h 58m
Chicago O'Hare Intl
Mon 9/21
7:05 am-3:37 pm
2 stops7h 32m
$342
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Mon 10/5
4:20 pm-10:18 pm
1 stop6h 58m
Chicago O'Hare Intl
Sun 10/11
6:15 am-2:58 pm
1 stop7h 43m
$342
WorcesterChicago
ORH Worcester - ORD Chicago O'Hare Intl
ORHORD
Worcester
Tue 10/6
4:15 pm-11:57 pm
2 stops8h 42m
Chicago O'Hare Intl
Sat 10/10
5:40 pm-2:58 pm
1 stop20h 18m
$352
Showing 1-10 of 19 resultsSorted by cheapest first
Compare providers for flights from Worcester to Chicago
Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Worcester to Chicago in August.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Worcester, Massachusetts-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Worcester, Massachusetts-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Worcester, Massachusetts-Chicago flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Worcester, Massachusetts-Chicago flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Worcester, Massachusetts-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Worcester to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Worcester with our price prediction graph.
ORH-CHI
ORH-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Worcester to Chicago
ORH-CHI
ORH-ORD
No data available for this route at this time. Please check back soon.
Related info for your journey
Find useful and relevant information for your journey from Worcester to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsBenton Harbor
Lansing
Merrillville
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Hammond
Saint Joseph
Porter
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