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CA $286 Cheap Flights from Halifax (YHZ) to Chicago (MDW)

View CA $286 flight on Wed, Aug 19, 2026Opens in a new window

Popular airlines from Stanfield Intl. Airport (YHZ) to Chicago Midway Airport (MDW)

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Cheap flights from Halifax (YHZ) to Chicago (MDW)

Prices were available within the past 7 days and start at CA $286 for one-way flights and CA $428 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Tue, Aug 11 - Fri, Aug 14
YHZ
Halifax
MDW
Chicago
CA $428 Roundtrip, found 4 days ago
CA $428
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Tue, Aug 11 from Halifax to Chicago, returning Fri, Aug 14, priced at CA $428 found 4 days ago
Porter Airlines
Tue, Aug 4 - Wed, Aug 5
YHZ
Halifax
MDW
Chicago
CA $433 Roundtrip, found 5 days ago
CA $433
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Tue, Aug 4 from Halifax to Chicago, returning Wed, Aug 5, priced at CA $433 found 5 days ago
Porter Airlines
Tue, Sep 1 - Sun, Sep 6
YHZ
Halifax
MDW
Chicago
CA $487 Roundtrip, found 3 days ago
CA $487
Roundtrip
found 3 days ago
Select Porter Airlines flight, departing Tue, Sep 1 from Halifax to Chicago, returning Sun, Sep 6, priced at CA $487 found 3 days ago
Delta
Sat, Sep 19 - Mon, Sep 21
YHZ
Halifax
MDW
Chicago
CA $497 Roundtrip, found 5 days ago
CA $497
Roundtrip
found 5 days ago
Select Delta flight, departing Sat, Sep 19 from Halifax to Chicago, returning Mon, Sep 21, priced at CA $497 found 5 days ago
Porter Airlines
Tue, Aug 11 - Fri, Aug 14
YHZ
Halifax
MDW
Chicago
CA $502 Roundtrip, found 4 days ago
CA $502
Roundtrip
found 4 days ago
Select Porter Airlines flight, departing Tue, Aug 11 from Halifax to Chicago, returning Fri, Aug 14, priced at CA $502 found 4 days ago
Porter Airlines
Thu, Jul 23 - Wed, Jul 29
YHZ
Halifax
MDW
Chicago
CA $502 Roundtrip, found 6 days ago
CA $502
Roundtrip
found 6 days ago
Select Porter Airlines flight, departing Thu, Jul 23 from Halifax to Chicago, returning Wed, Jul 29, priced at CA $502 found 6 days ago
Porter Airlines
Wed, Aug 19 - Tue, Aug 25
YHZ
Halifax
MDW
Chicago
CA $504 Roundtrip, found 15 hours ago
CA $504
Roundtrip
found 15 hours ago
Select Porter Airlines flight, departing Wed, Aug 19 from Halifax to Chicago, returning Tue, Aug 25, priced at CA $504 found 15 hours ago
Porter Airlines
Tue, Aug 4 - Wed, Aug 5
YHZ
Halifax
MDW
Chicago
CA $506 Roundtrip, found 5 days ago
CA $506
Roundtrip
found 5 days ago
Select Porter Airlines flight, departing Tue, Aug 4 from Halifax to Chicago, returning Wed, Aug 5, priced at CA $506 found 5 days ago
Delta
Sat, Aug 8 - Sun, Aug 16
YHZ
Halifax
MDW
Chicago
CA $510 Roundtrip, found 4 days ago
CA $510
Roundtrip
found 4 days ago
Select Delta flight, departing Sat, Aug 8 from Halifax to Chicago, returning Sun, Aug 16, priced at CA $510 found 4 days ago
WestJet
Sun, Aug 30 - Sat, Sep 5
YHZ
Halifax
MDW
Chicago
CA $1,022 Roundtrip, found 10 hours ago
CA $1,022
Roundtrip
found 10 hours ago
Select WestJet flight, departing Sun, Aug 30 from Halifax to Chicago, returning Sat, Sep 5, priced at CA $1,022 found 10 hours ago

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 $733
ORD
O'Hare Intl.
Cheapest
Average driving time to city centre23 min
Flights from CA $733

Frequently asked questions

How much does a flight from Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.) cost?
You can find one-way and return flights from YHZ to MDW 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 YHZ to MDW ticket fares go up or down.
What is the cheapest month to fly from Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.)?
The cheapest months to fly from YHZ to MDW 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 Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.)?
Enter YHZ to MDW and your travel dates, then apply the 'Nonstop' filter to see only direct flights.
How do I find cheap flights from Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.)?
To find a cheap flight from Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway 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 Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway 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 Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are approximately 8 connecting flights per day from Halifax Stanfield International (YHZ) to Chicago Midway International (MDW). Some common connection points include Liberty International (EWR), LaGuardia (LGA), and Pearson International (YYZ).
What is the earliest flight from Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.)?
The earliest flight from Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.) typically departs around 5:05 AM. This service is offered by Air Canada and Delta. This is a seasonal service active 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.
What day of the week has the most flights from Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.)?
You'll typically find the most flights from Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.) on a Monday, with around 8 flights available. This gives you a good selection for your travel plans. Major airlines on this route include Air Canada, Porter Airlines, and United.
What are the most popular departure times for flights from Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.)?
The most popular departure times for flights from Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.) are in the early morning, from 6am to 9am. Many major carriers, including Porter Airlines, United and Air Canada, offer flights during this window. Many travellers prefer this time as it allows for an early start to their travel day, often leading to an earlier arrival at their destination.
How long does it take to fly from Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.)?
There are no nonstop flights from Halifax Stanfield International Airport (YHZ) to Chicago Midway International Airport (MDW). However, you can find one-stop flights that typically take around 5 hours. These flights cover a distance of approximately 1,981 kilometres. Flights with two or more stops will take significantly longer, usually around 13 hours 30 minutes. Keep in mind that actual travel times can vary depending on the specific routing, layover duration, and factors like weather.
Can you fly business or first class from Halifax, NS (YHZ) to Chicago, IL (MDW)?
Select the "Business class" and "First class" filters when looking for Halifax, NS (YHZ) to Chicago, IL (MDW) 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 Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.) flight with Expedia?
It's easy to earn miles on a Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway 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 (MDW) from Halifax, NS (YHZ)?
If you're planning to travel to Chicago from Stanfield Intl. (YHZ), you can fly directly into Midway Intl. (MDW). Some flights may connect through major hubs like LaGuardia (LGA), Pearson Intl. (YYZ), or Pierre Elliott Trudeau Intl. (YUL) 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 Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.) at the last minute?
Typically, booking a last minute flight from Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway 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 Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.) flight and hotel package?
Securing a Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway 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 Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway Intl.)?
If you booked your Halifax, NS (YHZ-Stanfield Intl.) to Chicago, IL (MDW-Midway 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
Stanfield Intl.
Destination airport
Midway Intl.
Airlines serving
Delta, Porter Airlines, WestJet
Roundtrip price
CA $428
Distance
1970 km

Book with confidence

Goffs to Chicago Flights

The easy way to book your flights from Halifax to Chicago 

With Expedia, it’s simple to find and book flights to Chicago from Halifax 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 Midway 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 Halifax to Chicago today, tomorrow, or this week.  

 

Save dollars with cheap flights from Stanfield Intl., YHZ to Midway Intl., MDW 

Sort your search results by price to find great deals on your flight from Halifax to Chicago—you get all your cheapest options first. Grab yourself a bargain now—the lowest price on flights to Chicago from Halifax currently is just CA $428 rising to CA $1,022.  

Here are more money-saving tips: 

  • Fly in August 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 Halifax 

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.

Goffs to Chicago Flights

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*Available to Expedia members.