S$154 Cheap Flights to Woodstock

View S$154 flight on Sat, 25 Oct, 2025Opens in a new window

Popular airlines to Woodstock

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Cheap round-trip flights to Woodstock

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 5 Nov - Sat, 8 Nov
LAX
Los Angeles
ORD
Chicago
S$279 Return, found 2 days ago
S$279
Return
found 2 days ago
Select Delta flight, departing Wed, 5 Nov from Los Angeles to Chicago, returning Sat, 8 Nov, priced at S$279 found 2 days ago
Air Canada
Sat, 1 Nov - Mon, 3 Nov
YYZ
Toronto
ORD
Chicago
S$343 Return, found 15 hours ago
S$343
Return
found 15 hours ago
Select Air Canada flight, departing Sat, 1 Nov from Toronto to Chicago, returning Mon, 3 Nov, priced at S$343 found 15 hours ago
United
Mon, 10 Nov - Mon, 17 Nov
YYZ
Toronto
ORD
Chicago
S$344 Return, found 5 hours ago
S$344
Return
found 5 hours ago
Select United flight, departing Mon, 10 Nov from Toronto to Chicago, returning Mon, 17 Nov, priced at S$344 found 5 hours ago
American Airlines
Sat, 25 Oct - Sat, 1 Nov
LAX
Los Angeles
ORD
Chicago
S$384 Return, found 18 hours ago
S$384
Return
found 18 hours ago
Select American Airlines flight, departing Sat, 25 Oct from Los Angeles to Chicago, returning Sat, 1 Nov, priced at S$384 found 18 hours ago
All Nippon Airways
Tue, 21 Oct - Mon, 27 Oct
SIN
Singapore
ORD
Chicago
S$1,088 Return, found 19 hours ago
S$1,088
Return
found 19 hours ago
Select All Nippon Airways flight, departing Tue, 21 Oct from Singapore to Chicago, returning Mon, 27 Oct, priced at S$1,088 found 19 hours ago

Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD)

July is typically the cheapest month to fly

From S$99 - S$336 per traveller.

Frequently asked questions

What is the name of Woodstock's airport?
Organise a flight to Woodstock and you'll be touching down at O'Hare Intl. Airport (ORD).
What airport is best to fly into Woodstock?
A flight to Woodstock means landing at O'Hare Intl. Airport (ORD). Get off the plane, gather your bags and you'll be 56 kilometres from the downtown area.
How many airlines fly to Woodstock?
There are a total of 49 airlines connecting Woodstock with 224 airports across the world.
Which airlines fly to Woodstock?
Most often, travellers opt to fly with United Airlines, American Airlines and Delta when heading off to Woodstock. The majority of these flights come from New York, with United Airlines operating this route the most.
How many nonstop flights are there to Woodstock?
With roughly 6,379 direct flights running each week, you'll be hitting the tarmac in Woodstock before you can ask, "Are we there yet?"
Where are the most popular flights to Woodstock departing from?
Flights to Woodstock departing from New York, Washington and Dallas airports are highly sought after.
How long is the flight to Woodstock Airport?
If you're going to Woodstock from New York, you're looking at a flight time of 2 hours and 48 minutes. Those departing from Washington should expect to be airborne for around 2 hours and 18 minutes. From Dallas it's approximately 2 hours and 23 minutes away.
How to book the cheapest flight to Woodstock?
Don't leave booking your flight to Woodstock until the last moment. That's one trick seasoned jet-setters use to get the best prices. Booking well in advance means more choices and cheaper flights. Another fantastic way to pick up the best price is to compare all options. If your destination has multiple airports, research the cost of flying into a smaller terminal. And finally, don't forget that the early bird catches the worm. Familiarise yourself with airfare costs and have your credit card ready to reserve your seat as soon as you spot an unbeatable bargain. The best deals never last long.
Do you have any tips for my flight to Woodstock?
If you're poorly prepared, travelling can be overwhelming. But there's no need to hit the panic button just yet. Follow these useful tips and enjoy a pain-free start to your holiday in Woodstock. What to pack in your hand luggage:

  • The secret to having a pain-free flight experience is to plan ahead. So, let's start with the essentials: passport, travel documents, cash and any vital medications. Next, take on board items that'll help pass the time, like some electronic gadgets or a good read. It's also wise to bring your chargers, a comfy neck pillow and a pair of earplugs. Last but not least, don't forget to pop in toiletries like a toothbrush, cleansing wipes and a spare change of clothes.

Do not pack the following items in your hand luggage:

  • While the list of prohibited items differs between air carriers, the general guide to follow is avoid carrying anything flammable, sharp or explosive. This includes things like screwdrivers, drills, aerosol cans and bleaching agents. Sports equipment like hockey sticks, and objects that could injure passengers, such as pepper spray and firearms, aren't allowed in the cabin either.

What to wear on a flight:

  • You'll want to go for comfort over style. Prepare for temperature changes by wearing layers, and pick easy-to-remove footwear like slip-ons.
  • Deep vein thrombosis (DVT) is a potential risk on long-haul flights. It's the result of blood clots forming due to poor circulation and inactivity, so do some gentle foot and leg exercises in your seat and consider wearing compression socks or tights.

How to get through airport security fast when flying to Woodstock?
Being organised before you get to the airport will make your trip to Woodstock a piece of cake. Check out our handy tips and tricks for a swift journey through security:

  • Airport security personnel first need to verify that you have a valid passport and boarding pass before anything else. Keep them within easy reach.
  • Time to strip down. Well sort of. Your jacket, belt, keys and other items in your pocket, like your headphones, will need to go through the X-ray machine. Make your life easier by removing them before your turn arrives.
  • Your electronic devices like laptops and phones will also need to go on a tray to be scanned. Don't worry though, you'll be back online soon enough.
  • Want to bring along your favourite hand cream? No problem. As long as the volume is no greater than 3.4 ounces (100 millilitres) and it's stored in a clear zip-close bag, you're permitted to bring it with you in your carry-on bag.
  • Slip-on shoes are a great footwear choice as you're less likely to be required to remove them when going through security. Safety boots and heavier-style shoes are often subjected to additional screening.
  • Airlines will not allow any sharp objects in the cabin. If you need to bring these kinds of items, check them in.

Book with confidence

Book with confidence

Find Your Flights to Woodstock CHI

Cheap flights to Woodstock (CHI)

Get started finding a cheap flight to Woodstock on Expedia by either choosing a deal on this page or using the search bar to enter your travel dates, origin airport and whether you want a return or one-way airfare. You can filter for flexibility, number of stops, airline and departure/arrival times to find the best flight for you.

We recommend using the ‘Flexible Dates’ calendar at the top of the page to see the price of plane tickets on the surrounding dates. This allows you to pick the cheapest days to fly if your trip allows flexibility and score cheap flight deals to Woodstock.

Return prices range from S$279 - S$1,088 and one-ways Woodstock start as low as S$154.

Be aware that choosing a non-stop flight can sometimes be more expensive while saving you time. And routes with connections may be available at a cheaper rate.

 

Airlines that fly to Woodstock (CHI)

You have several options for which airline you choose to travel with to Woodstock. There are 10 airlines flying into CHI: Delta, United, American Airlines, Air Canada, Alaska Airlines, All Nippon Airways. 

Cheap plane tickets may be available from different airlines at different times and with unique terms. It’s best to understand the details of each airline’s offer before judging its value.

For example, if you plan to check in a bag or bring hand baggage, it's worth checking whether the cheap airfare deal includes a baggage allowance. If not, verify whether the baggage fee is higher than the difference of other airline plane ticket deals offering free checked in/hand baggage in exchange for a slightly higher airfare. 

Additionally, your preferred frequent flyer membership programmes may influence your choice of cheap airline. Expedia allows you to enter your membership numbers during checkout to earn points from your airline and Expedia Rewards—all while getting a great deal and planning all your travel on one online platform.

 

Find the best deals

At Expedia, we source many flight deals from multiple providers, so you can easily find the best deals that are right for you. A great strategy for getting the best deals can be to make sure you book and travel at optimal times. Airfare to Woodstock (CHI) varies throughout the year based on seasonal demand. You’ll see the lowest rates for return trips to CHI in November and in October for one-ways.

 

Cancellation & flexibility

To change or cancel eligible flights, go to ‘My Trips’ and navigate to your itinerary. If you booked within the last 24 hours, you might be able to cancel your flight for free. Learn more about flight changes or cancellations from our customer service portal. Some plane tickets are available with no change fees, which you can filter for during your search.

Find Your Flights to Woodstock CHI

Travel information

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
S$271

Trending flights to Woodstock

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

All Nippon Airways
Tue, 21 Oct - Mon, 27 Oct
SIN
Singapore
ORD
Chicago
S$1,088 Return, found 19 hours ago
S$1,088
Return
found 19 hours ago
Select All Nippon Airways flight, departing Tue, 21 Oct from Singapore to Chicago, returning Mon, 27 Oct, priced at S$1,088 found 19 hours ago

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Explore a world of travel with Expedia

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