S$76 Cheap Flights to Oswego

View S$76 flight on Mon, 10 Nov, 2025Opens in a new window

Popular airlines to Oswego

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • payments icon

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap round-trip flights to Oswego

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
Tue, 4 Nov - Tue, 11 Nov
BOS
Boston
ORD
Chicago
S$151 Return, found 2 days ago
S$151
Return
found 2 days ago
Select Delta flight, departing Tue, 4 Nov from Boston to Chicago, returning Tue, 11 Nov, priced at S$151 found 2 days ago
American Airlines
Wed, 12 Nov - Wed, 19 Nov
BOS
Boston
ORD
Chicago
S$240 Return, found 4 days ago
S$240
Return
found 4 days ago
Select American Airlines flight, departing Wed, 12 Nov from Boston to Chicago, returning Wed, 19 Nov, priced at S$240 found 4 days ago
United
Fri, 3 Oct - Mon, 6 Oct
BOS
Boston
ORD
Chicago
S$240 Return, found 4 days ago
S$240
Return
found 4 days ago
Select United flight, departing Fri, 3 Oct from Boston to Chicago, returning Mon, 6 Oct, priced at S$240 found 4 days ago
JetBlue Airways
Mon, 6 Oct - Wed, 15 Oct
BOS
Boston
ORD
Chicago
S$267 Return, found 20 hours ago
S$267
Return
found 20 hours ago
Select JetBlue Airways flight, departing Mon, 6 Oct from Boston to Chicago, returning Wed, 15 Oct, priced at S$267 found 20 hours ago
Swiss International Air Lines
Thu, 5 Feb - Fri, 13 Feb
LHR
London
ORD
Chicago
S$705 Return, found 3 days ago
S$705
Return
found 3 days ago
Select Swiss International Air Lines flight, departing Thu, 5 Feb from London to Chicago, returning Fri, 13 Feb, priced at S$705 found 3 days 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 Oswego's airport?
O'Hare Intl. Airport (ORD) is the most frequently used airport in Oswego.
How far is O'Hare Intl. Airport (ORD) from central Oswego?
O'Hare Intl. Airport (ORD) is 48 kilometres from downtown Oswego, so prepare yourself for a bit of a journey into the city centre.
What airport is best to fly into Oswego?
Travellers flying into Oswego can land at two major airports. O'Hare Intl. Airport (ORD) is 48 kilometres away from the centre of town. Midway Intl. Airport (MDW) is 48 kilometres away.
How many airlines fly to Oswego?
There are 51 air carriers that fly to Oswego from 237 airports around the world.
Which airlines fly to Oswego?
Oswego receives most of its flights from United Airlines, American Airlines and Delta with United Airlines being the favourite choice of airline. New York is the most popular city for travellers to take off from.
How many nonstop flights are there to Oswego?
Organising an awesome Oswego holiday is child's play when there are 7,564 direct flights every week to choose from.
Where are the most popular flights to Oswego departing from?
Flights to Oswego from New York, Washington and Dallas airports are very popular.
How long is the flight to Oswego Airport?
Which airport you depart from determines how much of the in-flight entertainment you'll get to enjoy. From New York to Oswego, the average flight time is 2 hours and 44 minutes. From Washington it's roughly 2 hours and 15 minutes, and from Dallas it's 2 hours and 18 minutes.
How to book the cheapest flight to Oswego?
If you want to have some extra spending money on your trip to Oswego, listen up! As every experienced jet-setter will tell you, avoid booking at the last minute. Prices are often highest close to the departure date. Another terrific way to grab an unbeatable deal is to research all options. If where you're headed has more than one airport, don't forget to research the cost of flying into a smaller terminal. Lastly, another simple way to save some money is be ready to book at a moment's notice. If you spot an irresistible bargain, don't hesitate — grab it while you've got the chance.
Do you have any tips for my flight to Oswego?
Wherever you're coming from, flying can be a pleasurable experience if you've prepared well enough. We've compiled a list of handy hints that will help get your Oswego escape started on the right foot. What to pack in your hand luggage:

  • Air travel can be a pleasure if you bring the right things. First of all you'll need toiletry items, such as a toothbrush and some deodorant, a fresh change of clothes and something to read. Next, find room in your carry-on bag for your electronic devices, chargers, any medications and maybe a blow-up neck pillow as well. Lastly, and most importantly, don't forget to bring your passport, travel papers and some money.

Do not pack the following items in your hand luggage:

  • Squeeze all your full-sized bottles of shampoo and hairspray in your checked baggage. Any liquids in your carry-on suitcase larger than 3.4 ounces (100 millilitres) will be confiscated. Sharp objects, like your trusty Swiss Army knife, and dangerous products which are flammable or explosive, such as aerosol cans, spray paint and fireworks, are also restricted.

What to wear on a flight:

  • Comfort should be your top priority when choosing what to wear on your flight. Loose, breathable clothing is a wise choice, as are flat, closed-toe shoes.
  • The result of sustained periods of inactivity, deep vein thrombosis (DVT) is a blood clotting condition that can affect some passengers on long-haul flights. Reduce the risks by staying hydrated, keeping your legs and ankles moving and wearing compression tights or socks.

How to get through airport security fast when flying to Oswego?
Being prepared before you get to the airport will help make your trip to Oswego a pleasure. Below you'll find some handy tips and tricks for a stress-free journey past security:

  • Be sure to keep your ID and travel documents at hand. They'll be the first things you'll be asked to show at airport security.
  • The X-ray machine is up next. Empty your pockets and remove anything that is likely to set off the scanner's alarm. This includes things like earphones or headphones, as well as your coat or jacket. They'll need to be placed on the conveyor belt for screening.
  • For just a few minutes, you'll have to unplug from the digital world. Your laptop, phone and any other electronic devices also need to go through the scanner.
  • Any liquids or gels, such as perfume or hand cream, that you want to bring on board need to be in containers no larger than 3.4 ounces (100 millilitres). They must also all fit inside a quart-size (one litre), clear zip-lock bag.
  • It's also possible you'll be required to remove your shoes for scanning, so wearing slip-on shoes is always a smart idea.
  • Sharp or pointed objects (like knives and scissors) are not allowed in the cabin. They'll be seized at security, so pack them in your checked baggage.

Book with confidence

Book with confidence

Find Your Flights to Oswego CHI

Cheap flights to Oswego (CHI)

Get started finding a cheap flight to Oswego 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 Oswego.

Return prices range from S$151 - S$1,083 and one-ways Oswego start as low as S$76.

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 Oswego (CHI)

You have several options for which airline you choose to travel with to Oswego. There are 10 airlines flying into CHI: Delta, American Airlines, United, JetBlue Airways, Air India, Virgin Atlantic, Swiss International Air Lines. 

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 Oswego (CHI) varies throughout the year based on seasonal demand. You’ll see the lowest rates for return trips to CHI in November and in November 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 Oswego CHI

Travel information

Travel information

Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Return price
S$150

Trending flights to Oswego

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
Mon, 20 Oct - Tue, 28 Oct
SIN
Singapore
ORD
Chicago
S$1,083 Return, found 22 hours ago
S$1,083
Return
found 22 hours ago
Select All Nippon Airways flight, departing Mon, 20 Oct from Singapore to Chicago, returning Tue, 28 Oct, priced at S$1,083 found 22 hours ago

Explore a world of travel with Expedia

Explore a world of travel with Expedia

*Available to Expedia members.