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CA $390 Cheap Flights from St. John's (YYT) to Chicago (ORD)

View CA $390 flight on Wed, Sep 2, 2026Opens in a new window

Popular airlines from St. John's Intl. Airport (YYT) to Chicago O'Hare International Airport (ORD)

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Cheap flights from St. John's (YYT) to Chicago (ORD)

Prices were available within the past 7 days and start at CA $390 for one-way flights and CA $623 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

American Airlines
Tue, Sep 1 - Sat, Sep 12
YYT
St. John's
ORD
Chicago
CA $623 Roundtrip, found 9 hours ago
CA $623
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Sep 1 from St. John's to Chicago, returning Sat, Sep 12, priced at CA $623 found 9 hours ago
American Airlines
Tue, Sep 1 - Wed, Sep 9
YYT
St. John's
ORD
Chicago
CA $663 Roundtrip, found 9 hours ago
CA $663
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Sep 1 from St. John's to Chicago, returning Wed, Sep 9, priced at CA $663 found 9 hours ago
American Airlines
Tue, Sep 1 - Thu, Sep 17
YYT
St. John's
ORD
Chicago
CA $674 Roundtrip, found 11 hours ago
CA $674
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Sep 1 from St. John's to Chicago, returning Thu, Sep 17, priced at CA $674 found 11 hours ago
American Airlines
Tue, Sep 1 - Fri, Sep 11
YYT
St. John's
ORD
Chicago
CA $684 Roundtrip, found 9 hours ago
CA $684
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Tue, Sep 1 from St. John's to Chicago, returning Fri, Sep 11, priced at CA $684 found 9 hours ago
American Airlines
Wed, Sep 2 - Wed, Sep 9
YYT
St. John's
ORD
Chicago
CA $703 Roundtrip, found 9 hours ago
CA $703
Roundtrip
found 9 hours ago
Select American Airlines flight, departing Wed, Sep 2 from St. John's to Chicago, returning Wed, Sep 9, priced at CA $703 found 9 hours ago
American Airlines
Fri, Aug 28 - Wed, Sep 2
YYT
St. John's
ORD
Chicago
CA $706 Roundtrip, found 2 days ago
CA $706
Roundtrip
found 2 days ago
Select American Airlines flight, departing Fri, Aug 28 from St. John's to Chicago, returning Wed, Sep 2, priced at CA $706 found 2 days ago
Air Canada
Thu, Sep 3 - Wed, Sep 9
YYT
St. John's
ORD
Chicago
CA $780 Roundtrip, found 9 hours ago
CA $780
Roundtrip
found 9 hours ago
Select Air Canada flight, departing Thu, Sep 3 from St. John's to Chicago, returning Wed, Sep 9, priced at CA $780 found 9 hours ago
Porter Airlines
Thu, Sep 3 - Sun, Sep 6
YYT
St. John's
ORD
Chicago
CA $781 Roundtrip, found 9 hours ago
CA $781
Roundtrip
found 9 hours ago
Select Porter Airlines flight, departing Thu, Sep 3 from St. John's to Chicago, returning Sun, Sep 6, priced at CA $781 found 9 hours ago
United
Thu, Aug 6 - Mon, Aug 10
YYT
St. John's
ORD
Chicago
CA $881 Roundtrip, found 22 hours ago
CA $881
Roundtrip
found 22 hours ago
Select United flight, departing Thu, Aug 6 from St. John's to Chicago, returning Mon, Aug 10, priced at CA $881 found 22 hours ago
WestJet
Fri, Sep 18 - Mon, Sep 21
YYT
St. John's
ORD
Chicago
CA $1,153 Roundtrip, found 8 hours ago
CA $1,153
Roundtrip
found 8 hours ago
Select WestJet flight, departing Fri, Sep 18 from St. John's to Chicago, returning Mon, Sep 21, priced at CA $1,153 found 8 hours ago

Alternative airports near Chicago

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

Select flight to Midway Intl. MDW. Closest option available. Average driving time to city centre is 16 minutes. Flights from CA $782
MDW
Midway Intl.
Closest
Average driving time to city centre16 min
Flights from CA $782

Frequently asked questions

How much does a flight from St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.) cost?
You can find cheap one-way flights from CA $390 and cheap return flights from CA $623 YYT to ORD with Expedia. One-way flights typically cost between CA$380 and CA$1139, and return flights often range between CA$825 and CA$2440. 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 the cheapest fares first, and use the Price Tracking tool to receive alerts when YYT to ORD ticket fares go up or down.
What is the cheapest month to fly from St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The cheapest months to fly from YYT 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 St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Enter YYT to ORD and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
What is the cheapest airline that flies from St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
Porter Airlines is one of the cheapest airlines offering connecting return flights from St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.), with prices starting from around CA$725 for flights that can be booked for departure within the next year. These flights typically include a layover in Stanfield Intl. (YHZ). Prices are per adult, economy/coach class. Use Expedia's search tool to compare the prices and schedules of airlines that fly this route to find the best option for your plans and budget.
How do I find cheap flights from St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
To find a cheap flight from St. John's, NL (YYT-St. John's Intl.) 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 St. John's, NL (YYT-St. John's Intl.) 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 St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are approximately 12 connecting flights per day from St. John's Intl. (YYT) to O'Hare Intl. (ORD). Some common connection points include Pearson Intl. (YYZ), Pierre Elliott Trudeau Intl. (YUL), and Stanfield Intl. (YHZ).
What is the earliest flight from St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The earliest flight from St. John's International Airport (YYT) to O'Hare International Airport (ORD) typically departs around 5:00 AM local time. This flight is operated by Air Canada. This is a seasonal service, active only in July. 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.
What day of the week has the most flights from St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You'll generally find the most flights from St. John's Intl. (YYT) to O'Hare Intl. (ORD) on a Saturday, with around 18 flights available. This gives you a good selection of options for your travel plans. Major airlines on this route include Air Canada, PAL Airlines, and WestJet. While Saturday is the busiest, flight schedules are fairly consistent throughout the week, so you'll have several flight options no matter which day you choose.
What are the most popular departure times for flights from St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
The most popular departure times for flights from St. John's Intl. (YYT) to O'Hare Intl. (ORD) are in the early morning, from 3am to 6am. Air Canada offers flights during this window. Many travelers prefer this time as it allows for an early arrival at your destination, giving you more of the day to enjoy.
How long does it take to fly from St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
There are no nonstop flights from St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.). For flights with one stop, you can expect the journey to take around 7 hours 18 minutes. If your flight has two or more stops, the travel time typically increases to about 15 hours. The distance between these two airports is approximately 2,820 kilometers. Keep in mind that actual flight times can vary due to factors like layover duration, routing, and weather conditions.
Can you fly business or first class from St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
You can fly business class between YYT and ORD. You can fly business class with Air Canada.
How do I earn miles on a St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight with Expedia?
It's easy to earn miles on a St. John's, NL (YYT-St. John's Intl.) 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 St. John's, NL (YYT)?
If you're planning to travel to Chicago from St. John's Intl. (YYT), you can fly directly into O'Hare Intl. (ORD) which offers international flights and connections. Some flights may connect through major hubs like Pierre Elliott Trudeau Intl. (YUL), Stanfield Intl. (YHZ), or Deer Lake Regional (YDF) 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 St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.) at the last minute?
Typically, booking a last minute flight from St. John's, NL (YYT-St. John's Intl.) 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 St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.) flight and hotel package?
Securing a St. John's, NL (YYT-St. John's Intl.) 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 St. John's, NL (YYT-St. John's Intl.) to Chicago, IL (ORD-O'Hare Intl.)?
If you booked your St. John's, NL (YYT-St. John's Intl.) 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 airport
St. John's Intl.
Destination airport
O'Hare Intl.
Airlines serving
Air Canada, American Airlines, Porter Airlines, United, WestJet
Roundtrip price
CA $623
Distance
2802 km

Book with confidence

St. John's to Chicago Flights

The easy way to book your flights from St. John's to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from St. John's whether you’re traveling for business or pleasure. Enter your travel dates, hit search, and choose your flight from 20 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 St. John's to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from St. John's Intl., YYT to O'Hare Intl., ORD 

Sort your search results by price to find great deals on your flight from St. John's to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from St. John's currently is just CA $623 rising to CA $1,153.  

Here are more money-saving tips: 

  • Fly in September 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 St. John's 

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.

St. John's to Chicago Flights

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