Cheap Flights to Oswego , IL from CA $166

View CA $166 flight on Sat, Nov. 1, 2025Opens in a new window

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How much is the cheapest flight to Oswego?

Prices were available within the past 7 days and start at CA $166 for one-way flights and CA $245 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Sat, Nov. 1 - Mon, Nov. 3
YYZ
Toronto
ORD
Chicago
CA $245 Roundtrip, found 3 hours ago
CA $245
Roundtrip
found 3 hours ago
Select Air Canada flight, departing Sat, Nov. 1 from Toronto to Chicago, returning Mon, Nov. 3, priced at CA $245 found 3 hours ago
United
Thu, Nov. 20 - Fri, Nov. 28
YYZ
Toronto
ORD
Chicago
CA $245 Roundtrip, found 1 hour ago
CA $245
Roundtrip
found 1 hour ago
Select United flight, departing Thu, Nov. 20 from Toronto to Chicago, returning Fri, Nov. 28, priced at CA $245 found 1 hour ago
American Airlines
Sat, Nov. 1 - Fri, Nov. 7
YYZ
Toronto
ORD
Chicago
CA $261 Roundtrip, just found
CA $261
Roundtrip
just found
Select American Airlines flight, departing Sat, Nov. 1 from Toronto to Chicago, returning Fri, Nov. 7, priced at CA $261 just found
WestJet
Fri, Nov. 21 - Mon, Nov. 24
YYC
Calgary
ORD
Chicago
CA $288 Roundtrip, found 3 hours ago
CA $288
Roundtrip
found 3 hours ago
Select WestJet flight, departing Fri, Nov. 21 from Calgary to Chicago, returning Mon, Nov. 24, priced at CA $288 found 3 hours ago
Delta
Tue, Sep. 9 - Fri, Sep. 26
YUL
Montreal
MDW
Chicago
CA $296 Roundtrip, found 2 days ago
CA $296
Roundtrip
found 2 days ago
Select Delta flight, departing Tue, Sep. 9 from Montreal to Chicago, returning Fri, Sep. 26, priced at CA $296 found 2 days ago

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

June is typically the cheapest month to fly

From CA $106 - CA $340 per traveller.

Graph displaying average flight prices per month

Expedia.ca gives you the best tools to secure great deals on flights to Oswego. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Oswego. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Oswego.

Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Oswego flights with full confidence knowing that you've found the best deal online.

Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Oswego.

Looking to save even more? Get additional savings by bundling your Oswego flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Oswego trip!

Frequently asked questions

What is the name of Oswego's airport?
O'Hare Intl. Airport (ORD) is the main airport in Oswego.
How far is ORD from central Oswego?
Long commutes aren't a big deal if you work out your strategy ahead of time. Downtown Oswego is 48 kilometres from ORD, so it's smart to know how you'll get into the city before you touchdown.
What airport is best to fly into Oswego?
There are two major airports that connect the world with Oswego. O'Hare Airport is approximately 48 kilometres from the central area, while MDW is approximately 48 kilometres away. After you take a look at prices and figure out where you're staying, you'll have a better idea of which one to head to.
How many airlines fly to Oswego?
There are 51 airlines that jet into Oswego from 237 airports around the world.
Which airlines fly to Oswego?
In general, travellers opt to fly with United Airlines, American Airlines and Delta when going to Oswego. The largest number of these flights come from New York, with United Airlines flying this route the most.
How many nonstop flights are there to Oswego?
Flying to somewhere new is much more fun when there aren't any annoying stopovers to slow you down. If you're off to Oswego, the awesome news is that there are approximately 7,564 direct flights operating every week.
Where are the most popular flights to Oswego departing from?
Flights to Oswego departing from New York, Washington and Dallas airports are in high demand.
How long is the flight to Oswego Airport?
If you're flying to Oswego from New York, you'll have a flight time of 2 hours and 44 minutes. Those setting off from Washington should expect to be airborne for around 2 hours and 15 minutes. From Dallas it's around 2 hours and 18 minutes away.
How to book the cheapest flight to Oswego?
If you want to save some cash on your trip to Oswego, listen up! As every experienced traveller will tell you, avoid booking at the last minute. Airfares are generally more expensive just prior to the departure date. Also, shop around and compare your options. If your destination has a few airports, you may be able to nab an excellent price by flying into one that's farther away. And finally, don't forget that the early bird catches the worm. Know what a typical airfare costs and have your credit card ready to reserve your seat as soon as you spot an unbeatable bargain. The sweetest deals never last long.
Do you have any tips for my flight to Oswego?
We've pulled together all the info you need to make your journey as enjoyable as possible. Follow our tips and tricks and you'll be speeding through airport security and having a ball in Oswego before you know it. What to pack in your hand luggage:

  • Flying can be a pleasure if you take the right stuff. Firstly, you'll want some basic toiletry items, such as a toothbrush and some deodorant, a spare set of clothes and a good book. Secondly, make room in your bag for your phone and charger, your important medications and perhaps a quality neck pillow too. Lastly, remember to bring your passport, travel documents and some cash.

Do not pack the following items in your hand luggage:

  • Double-check that you don't have a pocket knife lurking in one of the compartments of your hand luggage. Other restricted items include explosive or flammable substances, such as fuel and matches, and liquids and gels in containers with a capacity of more than 3.4 ounces (100 millilitres).

What to wear on a flight:

  • Comfort should be your highest priority when choosing what to wear on board. Loose clothing is a wise option, as are flat, closed-toe shoes.
  • Deep vein thrombosis (DVT) can pose a risk on long-distance flights. It results from blood clots forming due to inactivity and poor circulation, so do some gentle leg and foot exercises in your seat and consider wearing compression socks or tights.

How to get through airport security fast when flying to Oswego?
A little pre-planning before you get to the airport will help make your trip to Oswego a pleasure. Below are some useful tips and tricks for a swift journey past security:

  • Airport security personnel first need to verify that you have a valid passport and travel documents before anything else. Keep them close by.
  • Next up, both you and your carry-on bag must be X-rayed. To make the process quick and painless, take off anything that might set the alarms off. Personal belongings like your coat, belt and headphones will be required to go through the machine.
  • All electronic gadgets, including your laptop and phone, will also need to be separately scanned.
  • Remove liquids and gels from your carry-on bag. They often need to be sent through the X-ray separately. Each product should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit in a quart-size (one litre), clear zip-lock bag.
  • There's a possibility that you'll be required to remove your shoes to be X-rayed, so wearing slip-on sneakers is always a clever idea.
  • Sharp items such as knives and scissors can't be taken on board. They'll be confiscated at security, so put them in your checked baggage.

Flights to Oswego information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $244

Trending flights to Oswego

Prices were available within the past 7 days and start at CA $166 for one-way flights and CA $245 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Sat, Nov. 1 - Mon, Nov. 3
YYZ
Toronto
ORD
Chicago
CA $245 Roundtrip, found 3 hours ago
CA $245
Roundtrip
found 3 hours ago
Select Air Canada flight, departing Sat, Nov. 1 from Toronto to Chicago, returning Mon, Nov. 3, priced at CA $245 found 3 hours ago
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