Find flights
When to book
FAQs

Cheap flights from Halifax to Chicago Midway Airport from C$ 325

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/3. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — MDW
17 Dec — 24 Dec1
1 adult
1 adult, Economy, 0 bags

Find flight deals from Halifax to Midway

Enter your travel dates to find the best prices.

Cheapest flights from Halifax to Midway
Explore the most affordable flight options available from Halifax to Midway. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 17 November 2025.

Tue 23/127:00 a.m.YHZ - MDW
2 stops10h 20mPorter Airlines
Fri 26/1211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 15/11C$ 461
Fri 5/127:00 a.m.YHZ - MDW
2 stops10h 20mPorter Airlines
Sun 14/1211:00 a.m.MDW - YHZ
2 stops8h 20mPorter Airlines
Deal found 16/11C$ 519
Sun 30/118:20 p.m.YHZ - MDW
1 stop15h 45mMultiple Airlines
Tue 2/1211:00 a.m.MDW - YHZ
2 stops8h 20mMultiple Airlines
Deal found 16/11C$ 586
Sat 29/118:25 a.m.YHZ - MDW
1 stop5h 25mMultiple Airlines
Tue 2/1211:00 a.m.MDW - YHZ
1 stop12h 42mMultiple Airlines
Deal found 16/11C$ 647
Fri 26/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Fri 2/111:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 17/11C$ 669
Sun 14/128:25 a.m.YHZ - MDW
1 stop8h 55mPorter Airlines
Sun 21/1211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 16/11C$ 697
Mon 22/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Fri 26/1211:00 a.m.MDW - YHZ
2 stops6h 51mPorter Airlines
Deal found 16/11C$ 698

Cheap flight deals from Halifax to Midway

Discover tips and strategies to find the most affordable flight options for your journey from Halifax (YHZ) to Midway (MDW). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 17 November 2025.

Round-trip from

C$ 325

Popular in

July

Cheapest in

September

Average price

C$ 508
Porter Airlines
  • Porter Airlines
  • 8/3-10/3
  • 2 total stops
  • 15h 55m total
  • Halifax to Chicago
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 214 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Halifax to Midway that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 17 November 2025.
Use the filters below to find and compare flights from Halifax to Chicago Midway Airport that are best for you.

Fly from

Halifax

Fly to

Midway

Route

Depart

Return

Price

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sun 8/3

8:30 a.m.-3:20 p.m.

1 stop8h 50m

Chicago Midway

Tue 10/3

11:00 a.m.-8:05 p.m.

1 stop7h 05m

C$ 325

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 13/4

8:25 a.m.-3:20 p.m.

2 stops8h 55m

Chicago Midway

Thu 16/4

11:00 a.m.-11:54 p.m.

2 stops10h 54m

C$ 450

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 7/1

8:20 p.m.-10:05 a.m.

1 stop15h 45m

Chicago Midway

Thu 15/1

11:00 a.m.-1:41 a.m.

1 stop12h 41m

C$ 454

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 20/2

8:20 p.m.-4:16 p.m.

2 stops21h 56m

Chicago Midway

Sun 1/3

11:00 a.m.-9:05 p.m.

2 stops8h 05m

C$ 505

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 19/12

8:25 a.m.-3:20 p.m.

2 stops8h 55m

C$ 405

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/11

Best time to book a flight from Halifax to Midway

Have a flexible travel schedule? Discover the best time to fly to Midway from Halifax with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Halifax to Chicago Midway Airport

What’s the top layover airport for flights from Halifax to Chicago Midway Airport?

Share of one-stop round-trip flights from Halifax to Chicago Midway Airport chosen by Cheapflights users in the past 12 months, using the same layover each way.

Montreal (YUL) – chosen by Cheapflights users on 50% of one-stop itineraries from Halifax to Chicago Midway Airport on Cheapflights.

What’s the fastest layover option from Halifax to Chicago Midway Airport?

Shortest average travel time for 1-stop one-way flights from Halifax to Chicago Midway Airport, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Toronto (YTZ) have the shortest average one-way travel time for 1-stop routes: 5h 30m.

What’s the fastest layover option from Halifax to Chicago Midway Airport?

Shortest average travel time for 1-stop one-way flights from Halifax to Chicago Midway Airport, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Toronto (YTZ) have the shortest average one-way travel time for 1-stop routes: 5h 30m.

Which airport typically offers the quickest layover for flights from Halifax to Chicago Midway Airport?

Average layover duration for 1-stop one-way flights from Halifax to Chicago Midway Airport, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Montreal (YUL) offer the fastest connection on this route, with an average layover time of 1h 47m.

Related info for your journey

Find useful and relevant information for your journey from Halifax to Midway. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Halifax to Chicago Midway?

    Most people fly from Halifax Intl (YHZ) if they book a flight from Halifax to Chicago Midway. On average, Halifax Intl has 0 outbound flights to Chicago Midway per day from 0 airlines. Halifax Intl is conveniently located just 26.9 km from Halifax’s city centre.

  • How long is the flight from Halifax to Chicago Midway Airport?

    Porter Airlines can get you from Halifax to Chicago Midway Airport in just under 8h 50m. Your travel time can differ by up to . Airlines will cover a distance of 1981 km.

  • Can I find deals for flights from Halifax to Midway that include hotel bookings?

    Yes. In addition to deals on Halifax to Midway flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Halifax to Midway?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Halifax to Midway.

  • Can I find deals for business class flights from Halifax to Midway?

    Yes. Cheapflights offers flight deals from Halifax to Midway by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Halifax to Midway

See prices for flight routes from nearby airports that may be better suited for you.
Halifax to O'Hare Intl flights
Moncton to O'Hare Intl flights
St John to O'Hare Intl flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Halifax to Midway?

Deals for Halifax to Midway flights are sourced from 900+ travel sites when you use Cheapflights. When all flight results come back, Cheapflights lets you sort and filter flights using different criteria to choose better, like price, airport, cabin class, and plenty of other options.

Why should you use Cheapflights to find cheap flight tickets from Halifax to Midway?

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights from Halifax to Midway.

Can Cheapflights find flights from Halifax to Midway with no change fees?

Certainly. Search results for flights to Midway from Halifax shown to you on Cheapflights can be narrowed down with different useful search filters, which includes flexible booking options.

Can Cheapflights notify me if prices for flights from Halifax to Midway become cheaper?

Of course! You can now track prices for flights from Halifax to Midway and get an alert from Cheapflights when they change. Have a valid email address ready and click the bell icon next to the flight deals above to set up your price alerts.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.