Cheap Flights from Worcester to Chicago

Compare Worcester to Chicago flight deals

Find the cheapest month or even day of the year to fly to Chicago

Book the best Chicago fare with no extra fees

Flight deals from Worcester 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 $570. Find the lowest prices on one-way and return tickets right here.

Chicago.$346 per passenger.Departing Tue, 18 Aug, returning Wed, 19 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Worcester on Tue, 18 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Wed, 19 Aug, arriving in Worcester.Price includes taxes and charges.From $346, select.

Chicago.$420 per passenger.Departing Thu, 22 Oct, returning Mon, 26 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Worcester on Thu, 22 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Mon, 26 Oct, arriving in Worcester.Price includes taxes and charges.From $420, select.

Chicago.$441 per passenger.Departing Fri, 18 Sep, returning Tue, 6 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Worcester on Fri, 18 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Tue, 6 Oct, arriving in Worcester.Price includes taxes and charges.From $441, select.

Chicago.$461 per passenger.Departing Wed, 9 Sep, returning Sun, 13 Sep.Return flight with Delta.Outbound indirect flight with Delta, departs from Worcester on Wed, 9 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sun, 13 Sep, arriving in Worcester.Price includes taxes and charges.From $461, select.

Chicago.$570 per passenger.Departing Mon, 13 Jul, returning Fri, 17 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Worcester on Mon, 13 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago Midway on Fri, 17 Jul, arriving in Worcester.Price includes taxes and charges.From $570, select.

Chicago.$805 per passenger.Departing Wed, 25 Nov, returning Sat, 28 Nov.Return flight with Delta.Outbound indirect flight with Delta, departs from Worcester on Wed, 25 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago O'Hare International on Sat, 28 Nov, arriving in Worcester.Price includes taxes and charges.From $805, select.

Chicago.$1,167 per passenger.Departing Thu, 30 Jul, returning Mon, 3 Aug.Return flight with Delta.Outbound indirect flight with Delta, departs from Worcester on Thu, 30 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 3 Aug, arriving in Worcester.Price includes taxes and charges.From $1,167, 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 August.

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Jan

Feb

Mar

Apr

May

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.

Worcester to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$346
Cheapest month to fly	August

Finding cheap flights from Worcester to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Worcester to Chicago?

The best price we found for a return flight from Worcester to Chicago is $346. 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.

Which airlines fly direct from Worcester to Chicago?

Currently, there are no airlines that fly direct from Worcester to Chicago. But we found flights with one or more stops from $346.

How many flights are there a week from Worcester to Chicago?

As of June 2026, there are no flights flying from Worcester to Chicago.

When is the cheapest time to fly from Worcester to Chicago?

The cheapest month to fly from Worcester to Chicago is usually August.

Which is the cheapest airport to fly into in Chicago?

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 $346.

Which upcoming date is cheapest to fly from Worcester Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Worcester Airport to Chicago on Tuesday, 18 August 2026.

Can I get a direct flight from Worcester Airport to Chicago?

No airlines currently offer direct flights between Worcester Airport and Chicago. Most routes have one or more stops.

How can I get the best flight deal from Worcester Airport to Chicago?

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.

When is the best time to book flights to Chicago?

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.

What’s the weather like in Chicago?

In June, the average temperature is usually around 19°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.

Which is the cheapest airline to fly from Worcester Airport to Chicago with?

Currently, Delta offers the cheapest flight tickets to Chicago.

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

Chicago is one hour behind Worcester, where Worcester Regional Airport is located. Chicago observes the UTC-6 timezone.
Allow plenty of time to make your ORH to Chicago flight. A good rule of thumb is to arrive two hours before international departures and an hour ahead for domestic flights.
During popular months such as March, it's wise to get to the airport earlier than usual. Arrive two hours before domestic departures and four hours ahead for an international flight whenever you're flying during a peak period in general.
Located around 6 kilometres from the centre of Worcester, ORH can be reached in about 10 minutes by car. The journey on public transport will take roughly 25 minutes.
Want a stress-free start to your journey? Stay near ORH. Whether you have an early flight from Worcester Regional Airport to Chicago or don't want departure day to feel hectic, these hotels put convenience first:
74% of flights that leave from Worcester Regional Airport touch down at their destination on schedule.
You'll find ORH at 375 Airport Drive.

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

$161 is currently the lowest price for a one-way Worcester Regional Airport to Chicago flight. A return plane ticket starts at $346. These fares can change depending on demand.
To pick up cheap flights from ORH to Chicago, book early. Airlines tend to offer lower prices when flights first go on sale.
If you're flexible with your trip dates, check out the 'Whole month' tool. It'll show you the cheapest price across each month when searching for your Worcester Regional Airport to Chicago ticket.
Finding a cheap flight from ORH to Chicago couldn't be easier with Price Alerts. Simply create one of these automatic notifications and we'll let you know when a lower fare pops up.
Tailor your trip with filters. Pick your arrival and departure times, airlines and total journey duration. You can also sort the results by 'Best,' 'Cheapest' or 'Fastest' flights from Worcester Regional Airport to Chicago.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport (ORD) is around 27 kilometres from the centre of Chicago. If you're opting for a ride-share or a taxi, the drive will take roughly 30 minutes.
If you're travelling on public transport, expect a journey time of around 45 minutes.
The last thing you need is a long 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:
Reserving your vehicle from Chicago O'Hare International Airport around four weeks ahead of your flight from ORH to Chicago can help you lock in the lowest rate.
ORD is located at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

After your flight from Worcester Regional Airport to Chicago has hit the tarmac, you can get to the city centre in around 25 minutes by car. Central Chicago is roughly 16 kilometres from Chicago Midway International Airport (MDW).
If you travel by public transport, the journey will take you 30 minutes or so.
You'll find some great places to park your luggage (and yourself) near MDW. Tuck yourself in and get cosy after your ORH to Chicago flight at one of these well-located options:
Avoid potential price surges. Securing your ride four weeks before your arrival at MDW will save you money.
The address for Chicago Midway International Airport is 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Head to the city centre after your flight from Worcester Regional Airport to Chicago has landed. Central Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and takes roughly 1 hour 40 minutes to reach by car.
The journey will take you about 2 hours if you use public transport.
Reserve a hotel near RFD and get from baggage claim to your bed in a snap. Whether you're coming in on a late ORH to Chicago flight or just want a stress-free arrival, these accommodation options offer a quick route to a good night's sleep:
Booking at least a few weeks ahead of your flight from Worcester Regional Airport to Chicago is always smart. As well as better deals, you'll likely have a better variety of makes and models to choose from at RFD.
Chicago Rockford International Airport can be found at 2 Airport Cir.

Best time to go to Chicago

January is the quietest month for flights from Worcester Regional Airport to Chicago, while July is the most popular. Figure out the ideal time to go to Chicago based on whether you prefer a laid-back vibe or a more bustling atmosphere.
The warmest month in Chicago is July, with temperatures ranging between 16ºC and 28ºC. Lock in your Worcester Regional Airport to Chicago plane ticket then if that's your ideal forecast.
January sees average temperatures of between -12ºC and 3ºC. Look for a cheap ticket from ORH to Chicago around that time if you like travelling in cooler conditions.

More about Chicago

When it comes to looking for somewhere to rest your head, you'll find the most popular stays in Chicago right here. Check out these options as soon as you've booked your flight from Worcester Regional Airport to Chicago:
Art Institute of Chicago and Millennium Park are a couple of top attractions to put on your Chicago to-do list. Continue your sightseeing adventures at Willis Tower.

Explore more of the United States

You've visited Chicago, now it's time to discover other corners of the United States. Travel about 451 kilometres southeast to Columbus to tick off its must-visit sights. From Franklin Park Conservatory and Botanical Gardens to Whetstone Park / Park of Roses and Ohio Theatre, you'll have a packed itinerary ahead.
Around 257 kilometres southeast of Chicago, Indianapolis is another favourite stop in the United States. Start your sightseeing at Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis.