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Cheap flights from Halifax to Chicago Midway Airport from C$ 247

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — MDW
1 Aug — 8 Aug1
1 adult
1 adult, Economy, 0 bags

Cheap 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 2 July 2026.

Mon 13/77:00 a.m.
YHZ
-
MDW
2 stops9h 35m
Porter Airlines
Wed 22/73:20 p.m.
MDW
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 29/6C$ 413
Wed 12/88:00 a.m.
YHZ
-
MDW
1 stop8h 35m
Porter Airlines
Wed 26/83:15 p.m.
MDW
-
YHZ
2 stops6h 29m
Porter Airlines
Deal found 1/7C$ 426
Fri 24/78:00 a.m.
YHZ
-
MDW
1 stop8h 35m
Porter Airlines
Sun 26/73:20 p.m.
MDW
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 1/7C$ 429
Mon 20/78:00 a.m.
YHZ
-
MDW
1 stop8h 35m
Porter Airlines
Thu 23/73:20 p.m.
MDW
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 30/6C$ 436
Tue 28/77:00 a.m.
YHZ
-
MDW
2 stops9h 35m
Porter Airlines
Tue 4/83:15 p.m.
MDW
-
YHZ
2 stops6h 29m
Porter Airlines
Deal found 28/6C$ 437
Thu 30/77:00 a.m.
YHZ
-
MDW
2 stops9h 35m
Porter Airlines
Thu 6/810:25 a.m.
MDW
-
YHZ
2 stops11h 19m
Porter Airlines
Deal found 1/7C$ 449
Fri 7/87:00 a.m.
YHZ
-
MDW
2 stops9h 35m
Porter Airlines
Mon 10/83:15 p.m.
MDW
-
YHZ
2 stops6h 29m
Porter Airlines
Deal found 29/6C$ 466

Find 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 2 July 2026.

Round-trip from

C$ 413

One-way from

C$ 247

Popular in

January

Cheapest in

September

Average price

C$ 960
Porter Airlines
  • Porter Airlines
  • 13/7-22/7
  • 4 total stops
  • 15h 59m total
  • Halifax to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 12/8
  • 1 total stop
  • 8h 35m total
  • Halifax to Chicago
Search Deals
Highest demand for flights based on searches. 1% potential increase in price (C$ 9 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 47 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
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 2 July 2026.
Use the filters below to find and compare flights from Halifax to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 12/8

8:00 a.m.-2:35 p.m.

1 stop8h 35m

Chicago Midway

Wed 26/8

3:15 p.m.-11:44 p.m.

2 stops6h 29m

C$ 426

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 28/7

8:00 a.m.-2:35 p.m.

1 stop8h 35m

Chicago Midway

Tue 4/8

3:15 p.m.-11:44 p.m.

2 stops6h 29m

C$ 444

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 25/8

8:00 a.m.-2:35 p.m.

1 stop8h 35m

Chicago Midway

Sat 29/8

10:20 a.m.-11:44 p.m.

2 stops11h 24m

C$ 507
Quickest round-trip

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 24/8

3:30 p.m.-6:33 p.m.

1 stop5h 03m

Chicago Midway

Fri 4/9

1:25 p.m.-9:10 p.m.

1 stop5h 45m

C$ 548

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 25/8

3:30 p.m.-6:33 p.m.

1 stop5h 03m

Chicago Midway

Sat 29/8

9:24 a.m.-9:10 p.m.

1 stop9h 46m

C$ 554
Cheapest one-way

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 25/8

8:00 a.m.-2:35 p.m.

1 stop8h 35m

C$ 250

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 3/8

8:00 a.m.-2:35 p.m.

1 stop8h 35m

C$ 251
Quickest one-way

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 10/8

3:30 p.m.-6:33 p.m.

1 stop5h 03m

C$ 315

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 10/11

6:00 a.m.-12:33 p.m.

2 stops8h 33m

C$ 319

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/7

Sorted by cheapest first

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 cheapest layover airport for flights from Halifax to Chicago Midway Airport?

Average round-trip fare for 1-stop flights from Halifax to Chicago Midway Airport, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Montreal (YUL) is the most affordable 1-stop option, with an average round-trip price of C$ 905.

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 Detroit (DTW) have the shortest average one-way travel time for 1-stop routes: 5h 07m.

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 35m. 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

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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.

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