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Cheap Flights from Kingston (YGK) to Chicago (ORD)

View CA $433 flight on Tue, Nov 24, 2026

Photo by by O'Hare Intl Airport

Popular airlines from Kingston, ON (YGK-Norman Rogers) to Chicago O'Hare International Airport (ORD)

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  • Find the cheapest flights on Expedia from Kingston (YGK) to Chicago (ORD). Flight ticket prices change frequently based on availability and demand. We send price‑drop alerts to make air travel simple and flexible. The lowest one-way fare found on Expedia for this route in the past 7 days starts at for travel on .

    Cheap Flights from Kingston to Chicago (YGK-ORD)

    Prices were available within the past 7 days and start at CA $433 for roundtrip flights, for the period specified. Prices and availability are subject to change.

    Roundtrip

    Select Air Canada flight, departing Tue, Nov 24 from Kingston to Chicago, returning Sat, Nov 28, priced at CA $433 Found 3 days ago

    Tue, Nov 24 - Sat, Nov 28 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Tue, Nov 24 from Kingston to Chicago, returning Tue, Dec 1, priced at CA $538 Found 3 days ago

    Tue, Nov 24 - Tue, Dec 1 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Thu, Dec 10 from Kingston to Chicago, returning Tue, Dec 22, priced at CA $600 Found 6 days ago

    Thu, Dec 10 - Tue, Dec 22 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Sat, Nov 21 from Kingston to Chicago, returning Sun, Nov 29, priced at CA $601 Found 6 days ago

    Sat, Nov 21 - Sun, Nov 29 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Fri, Nov 20 from Kingston to Chicago, returning Fri, Nov 27, priced at CA $622 Found 6 days ago

    Fri, Nov 20 - Fri, Nov 27 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Sat, Nov 21 from Kingston to Chicago, returning Sat, Nov 28, priced at CA $633 Found 3 days ago

    Sat, Nov 21 - Sat, Nov 28 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Thu, Dec 10 from Kingston to Chicago, returning Tue, Dec 22, priced at CA $650 Found 6 days ago

    Thu, Dec 10 - Tue, Dec 22 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Fri, Jan 15 from Kingston to Chicago, returning Sun, Jan 17, priced at CA $685 Found 6 days ago

    Fri, Jan 15 - Sun, Jan 17 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Sat, Nov 21 from Kingston to Chicago, returning Wed, Nov 25, priced at CA $687 Found 6 days ago

    Sat, Nov 21 - Wed, Nov 25 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Sun, Dec 13 from Kingston to Chicago, returning Mon, Dec 21, priced at CA $692 Found 6 days ago

    Sun, Dec 13 - Mon, Dec 21 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Tue, Nov 24 from Kingston to Chicago, returning Tue, Dec 1, priced at CA $706 Found 3 days ago

    Tue, Nov 24 - Tue, Dec 1 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Fri, Nov 20 from Kingston to Chicago, returning Tue, Nov 24, priced at CA $708 Found 6 days ago

    Fri, Nov 20 - Tue, Nov 24 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Sat, Dec 12 from Kingston to Chicago, returning Sun, Dec 20, priced at CA $715 Found 6 days ago

    Sat, Dec 12 - Sun, Dec 20 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Fri, Nov 20 from Kingston to Chicago, returning Fri, Nov 27, priced at CA $737 Found 6 days ago

    Fri, Nov 20 - Fri, Nov 27 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Fri, Jan 15 from Kingston to Chicago, returning Sun, Jan 17, priced at CA $740 Found 6 days ago

    Fri, Jan 15 - Sun, Jan 17 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Thu, Dec 10 from Kingston to Chicago, returning Tue, Dec 22, priced at CA $766 Found 6 days ago

    Thu, Dec 10 - Tue, Dec 22 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Sat, Dec 12 from Kingston to Chicago, returning Sun, Dec 20, priced at CA $782 Found 6 days ago

    Sat, Dec 12 - Sun, Dec 20 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Fri, Jan 15 from Kingston to Chicago, returning Sun, Jan 17, priced at CA $800 Found 6 days ago

    Fri, Jan 15 - Sun, Jan 17 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Sat, Dec 12 from Kingston to Chicago, returning Sun, Dec 20, priced at CA $801 Found 6 days ago

    Sat, Dec 12 - Sun, Dec 20 · YGK · ORD · Roundtrip

    Select Air Canada flight, departing Sat, Nov 21 from Kingston to Chicago, returning Wed, Nov 25, priced at CA $802 Found 6 days ago

    Sat, Nov 21 - Wed, Nov 25 · YGK · ORD · Roundtrip

    Alternative airports near Chicago

    Prices were available within the past 7 days. Prices and availability are subject to change.

    Select flight to O'Hare Intl. ORD. Cheapest option available. Average driving time to city centre is 23 minutes. Flights from CA $433

    23 min

    Book with confidence

    Kingston to Chicago Flights

    The easy way to book your flights from Kingston to Chicago

    With Expedia, it’s simple to find and book flights to Chicago from Kingston whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 1 airlines that cover this route. There are nonstop flights to O'Hare Intl., too.

    Choose your preferred carrier and cabin class with the advanced search tool and select your ideal departure time. Then, if you want, you can see just nonstop or refundable flights. And if you’re traveling last minute, just enter the date to check out flights from Kingston to Chicago today, tomorrow, or this week.

    Save dollars with cheap flights from Norman Rogers, YGK to O'Hare Intl., ORD

    Sort your search results by price to find great deals on your flight from Kingston to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Kingston currently is just CA $433 rising to CA $802.

    Here are more money-saving tips:

    • Fly in November when flight prices are normally at their lowest
    • Book about a month to 6 weeks before you travel for the best prices to Chicago
    • Avoid peak season and weekends when flights can cost more
    • Early morning and late-night flights are sometimes cheaper, so try varying your travel times
    • One surefire way to save money on your flight is to book your flight and hotel together with Expedia. Sometimes, the savings are so large that the flight is basically free!

    Reasons to choose Expedia for your flight to Chicago from Kingston

    Whatever your destination, budget, or reason to travel, in just one quick search, you can choose from loads of flights, airlines, and cabin classes. The filters make it quick and easy to find your ideal flights, and if you choose one of the flexible options, you won’t be charged to change your flight. So book your flight to Chicago with Expedia today.

    Frequently Asked Questions

    How much does a flight from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.) cost?

    You can find one-way and return flights from YGK to ORD with Expedia. Flight prices vary based on the month and day of the week you want to travel, as well as the airline and how far in advance you book your ticket. Filter your search on Expedia by "Price (lowest to highest)" to see our cheapest fares first, and use the Price Tracking tool to receive alerts when YGK to ORD ticket fares go up or down.

    What is the cheapest month to fly from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.)?

    The cheapest months to fly from YGK to ORD are typically during off-peak season when demand is low. Traveling in off-peak or shoulder months is usually a good way to secure cheap tickets, just remember to avoid flying during holidays if you are able to. Use the calendar view in your search to see which months have low fares on this route.

    Which airlines fly direct from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.)?

    Enter YGK to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.

    How do I find cheap flights from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.)?

    To find a cheap flight from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.), be flexible with your dates. Traveling outside of peak vacation months and booking a mid-week flight can help you save. Early morning and late night flights are often more affordable, too. Expedia allows you to compare flight times, airlines and routes all in one place to find low fares. You can also set up Price Tracking and receive alerts when fares go up or down.

    What is the best time to fly from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.)?

    The best time to fly is usually mid-week (Tuesday or Wednesday) and during early morning hours as flights tend to be cheaper, less crowded, and generally more on-time. Avoid major holidays and peak vacation seasons for smoother travel. Combining off-peak days and hours often gives the best combination of cost, comfort, and convenience.

    How many flights per day from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.)?

    There are approximately 4 connecting flights per day from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.). A common connection point is Pearson Intl. (YYZ).

    What is the earliest flight from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.)?

    The earliest flight from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.) typically departs around 4:00 AM local time. This service is offered by Air Canada. This is a seasonal service, active only in December. An early departure like this can help you make the most of your time at your destination. To compare early flights on Expedia, select the "Early Morning" and "Morning" filters in your search.

    How long does it take to fly from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.)?

    There are no nonstop flights from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.). The distance between these two airports is approximately 951 kilometres. Flights with one stop typically take around 9 hours. If your journey involves two or more stops, you can expect the travel time to be longer, usually around 15 hours 48 minutes. Keep in mind that actual flight times can vary due to factors like routing, weather, and wind patterns.

    Can you fly business or first class from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.)?

    Select the "Business class" and "First class" filters when looking for YGK to ORD flights on Expedia. This is the easiest way to compare prices, routes and flight times for your trip.

    How do I earn miles on a Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?

    It's easy to earn miles on a Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.) flight when you book with Expedia. Before you confirm your booking, simply select your frequent flyer program and enter your program number. As a member of One Key™, you can also earn OneKeyCash™* on top of your airline miles when you book with Expedia.

    *Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

    What airports do you fly into for Chicago, IL (ORD) from Kingston, ON (YGK)?

    If you're planning to travel to Chicago from Norman Rogers (YGK), you can fly directly into O'Hare Intl. (ORD). Some flights may connect through major hubs like Pearson Intl. (YYZ) before reaching Chicago. Compare routes and airports on Expedia to find the best flight options for your travel plans.

    Is it cheaper to buy a plane ticket from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?

    Typically, booking a last minute flight from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.) will be more expensive than booking in advance. As the departure date approaches, there are usually fewer seats available which can drive up the cost. However, if there's some wiggle room with your travel dates and times, you could bag a cheap last-minute fare.

    Is it cheaper to book a Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?

    Securing a Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package is usually cheaper than booking separately. With Expedia, you can enjoy the ease of organizing your travels all in one place. Select from our extensive range of stays and then add flights, activities and car rentals to your booking. Bundle everything together, and you could save hundreds of dollars.

    Can I cancel or change the date of my flight from Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.)?

    If you booked your Kingston, ON (YGK-Norman Rogers) to Chicago, IL (ORD-O'Hare Intl.) flight within the last 24 hours, you may be able to modify or cancel it without any fees. Depending on the airline and the type of ticket you have, additional charges may apply for changes beyond this timeframe. Airline policies and contact information can be found in your itinerary or confirmation email. Or, head to our Customer Service portal if you'd like more information.

    Travel information

    Origin airportKingston, ON
    Destination airportChicago O'Hare International Airport
    Distance950 km away
    Roundtrip priceCA $433

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