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Cheap flights from Worcester to Chicago

Compare Worcester to Chicago flight deals

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Flight deals from Worcester Airport to Chicago

Looking for a cheap last-minute deal or the best return flight from Worcester Airport to Chicago? If you want to travel next month, return fares start from P27,890. Find the lowest prices on one-way and return tickets right here.
Chicago.P11,347 per passenger.Departing Tue, 12 May, returning Wed, 3 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Worcester on Tue, 12 May, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Wed, 3 Jun, arriving in Worcester.Price includes taxes and charges.From P11,347, select.
Chicago.P16,610 per passenger.Departing Fri, 8 May, returning Sun, 10 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Worcester on Fri, 8 May, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sun, 10 May, arriving in Worcester.Price includes taxes and charges.From P16,610, select.
Chicago.P18,450 per passenger.Departing Fri, 20 Nov, returning Sun, 22 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Worcester on Fri, 20 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sun, 22 Nov, arriving in Worcester.Price includes taxes and charges.From P18,450, select.
Chicago.P23,757 per passenger.Departing Sun, 14 Jun, returning Wed, 17 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Worcester on Sun, 14 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Wed, 17 Jun, arriving in Worcester.Price includes taxes and charges.From P23,757, select.
Chicago.P27,890 per passenger.Departing Wed, 1 Apr, returning Sun, 5 Apr.Return flight with Delta.Outbound indirect flight with Delta, departs from Worcester on Wed, 1 Apr, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sun, 5 Apr, arriving in Worcester.Price includes taxes and charges.From P27,890, select.
Chicago.P28,561 per passenger.Departing Wed, 18 Mar, returning Sun, 22 Mar.Return flight with Delta.Outbound indirect flight with Delta, departs from Worcester on Wed, 18 Mar, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sun, 22 Mar, arriving in Worcester.Price includes taxes and charges.From P28,561, select.

Find the cheapest month to fly from Worcester to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Worcester to Chicago flights are currently cheapest in May.
Mar
from P28,638
Apr
from P27,965
May
from P16,655
Jun
from P23,821
Jul
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Aug
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Sep
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Oct
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Nov
from P18,500
Dec
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Jan
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Feb
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Alternative Worcester to Chicago routes

Looking for the cheapest, fastest or easiest route from Worcester to Chicago? You could fly into the following airports instead.

Chicago Midway

14km from central Chicago
Closest
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from P11,377
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
Search flights

Worcester to Chicago: Flight information

The things to know before you go.
Cheapest flight foundP11,377
Cheapest month to flyMay

Finding cheap flights from Worcester to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Worcester to Chicago is P11,377. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Worcester to Chicago. But we found flights with one or more stops from P11,377.
As of March 2026, there are no flights flying from Worcester to Chicago.
The cheapest month to fly from Worcester to Chicago is usually May.
If you're flying from Worcester Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from P11,377.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Worcester Airport to Chicago on Tuesday, 12 May 2026.
No airlines currently offer direct flights between Worcester Airport and Chicago. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In March, the average temperature is usually around 3°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, Delta offers the cheapest flight tickets to Chicago.

Flying from Worcester Regional Airport (ORH) to Chicago: what you need to know

  • Worcester Regional Airport is located in Worcester. Following the UTC-5 timezone, Chicago is one hour behind Worcester.

  • For a stress-free journey, arrive at the airport two hours ahead of international flights and an hour before domestic departures. This ensures you have enough time to board your ORH to Chicago flight.

  • Taking off during a peak time like public or school holidays? Expect longer lines at check-in and security. Give yourself extra leeway and arrive up to four hours before international flights and two hours before domestic departures.

  • ORH is about 6 kilometres from central Worcester. If you're catching a cab, driving or ride-sharing from the centre, it'll take 15 minutes or so to get there, depending on traffic. If you're planning to take public transport, expect the travel time to be around 1 hour 20 minutes.

  • Spending the night in a hotel can take the hassle out of arriving at the airport on time. If you're looking for a place to stay before your flight from Worcester Regional Airport to Chicago, consider Grand Worcester Getaway With Large Private Yard!. It's an easy drive from ORH.

  • Of the departures from Worcester Regional Airport, 73.01% land on schedule at their destination.

  • You'll find ORH at 375 Airport Drive.

How to find the cheapest flights from Worcester Regional Airport (ORH) to Chicago

  • The best price we've found for a one-way Worcester Regional Airport to Chicago flight is P10,301. The cheapest price for a return flight is P11,347. Remember fares may change due to availability at the time of booking.

  • Don't leave everything to the last moment. You're more likely to pick up cheap flights from ORH to Chicago if you book early. Airlines often have some amazing early bird deals.

  • Scoring cheap tickets from Worcester Regional Airport to Chicago is easier if you can be flexible with your travel plans. Use the 'Whole month' tool to access the lowest fares across the month and walk away with an incredible deal.

  • Stay on top of deals for cheap flights from ORH to Chicago by creating a Price Alert. You'll receive an email or notification on the app when fares go down.

  • Snag an affordable flight from Worcester Regional Airport to Chicago with the help of our filters. Choose your ideal duration, departure time and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) to central Chicago takes around 35 minutes by car. The centre is roughly 40 kilometres away.

  • Travelling to the centre on public transport will take you around 55 minutes.

  • The last thing you need is a lengthy journey to your hotel if you're arriving on a late flight from Worcester Regional Airport to Chicago. Reserve one of these accommodation options near ORD instead:

  • Travel at your own speed with an O'Hare International Airport rental car. Pick up a set of wheels from Routes Car Rentals, Dollar or Budget and see more of Chicago and beyond.

  • Booking your ride from O'Hare International Airport around four weeks before your flight from ORH to Chicago can help you get the best possible rate.

  • The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • The centre of Chicago is around 19 kilometres from Chicago Midway International Airport (MDW). After your flight from Worcester Regional Airport to Chicago has hit the runway and you've navigated your way to arrivals, the drive should take about 20 minutes.

  • If you're catching public transport, it'll take around 45 minutes.

  • You'll find some comfortable places ready to welcome you near MDW. Settle in and get cosy after your ORH to Chicago flight at one of these well-located options:

  • Forget about public transport schedules or waiting forever for a cab. Pick up a Chicago Midway International Airport rental car and let your trip unfold on your terms. Check out the rates and availability from Dollar, Hertz and Budget.

  • Get what you want, not just what's left over. Booking your ride from MDW four weeks in advance often means better deals and a bigger choice of vehicles.

  • The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Chicago Rockford International Airport (RFD) is about 137 kilometres from the centre of Chicago. It'll take you about 1 hour 25 minutes to reach the city centre by ride-share or cab once you've stepped off your flight from Worcester Regional Airport to Chicago.

  • If you use public transport, the journey time is around 4 hours 15 minutes.

  • If you don't want to make the trip into the centre, find a hotel near RFD. Get settled at one of these options after your ORH to Chicago flight:

  • Take control of the next leg of your trip with a Chicago Rockford International Airport rental car. Budget, Alamo and National are reliable rental providers.

  • Rental agencies sometimes offer deals on early bookings, so reserve your vehicle from RFD well ahead of your flight from Worcester Regional Airport to Chicago. A bit of planning goes a long way in savings.

  • Chicago Rockford International Airport's official address is 2 Airport Cir.

Best time to go to Chicago

  • Carefully consider your trip dates before locking in your flight from Worcester Regional Airport to Chicago. The city buzzes during high season, but rates are generally higher and top attractions can be crowded. Plan your trip to Chicago in the low season for a more relaxed vibe.

  • Before booking a Worcester Regional Airport to Chicago plane ticket, think about what kind of weather works for you. July is the warmest month in Chicago, with temperatures ranging from 15ºC (59ºF) to 29ºC (84ºF).

  • Search for cheap tickets from ORH to Chicago in January if you'd rather travel when it's cooler. Temperatures are at their lowest then, ranging between -12ºC (10ºF) and 3ºC (37ºF) on average.

More about Chicago

Explore more of United States

  • Chicago is always a good idea, but there are so many other parts of United States you'll want to see. About 451 kilometres south-east of Chicago, a visit to Columbus will keep you on the move. Don't miss top attractions like Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • If you're eager to discover another side of United States, head for Indianapolis, roughly 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are key reasons to visit.

Plan the rest of your trip from Worcester to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.