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Cheap flights from Halifax to Chicago Midway Airport from C$ 296

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 30/1. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — MDW
17 Jan — 24 Jan1
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 18 December 2025.

Sat 27/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Wed 31/1211:00 a.m.MDW - YHZ
2 stops8h 29mPorter Airlines
Deal found 15/12C$ 878
Sat 27/126:00 a.m.YHZ - MDW
2 stops28h 49mWestJet
Fri 2/16:08 p.m.MDW - YHZ
2 stops29h 33mWestJet
Deal found 17/12C$ 902
Fri 26/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Fri 2/111:00 a.m.MDW - YHZ
2 stops8h 05mPorter Airlines
Deal found 16/12C$ 938
Fri 26/126:00 a.m.YHZ - MDW
2 stops31h 06mWestJet
Fri 2/111:48 a.m.MDW - YHZ
2 stops35h 53mWestJet
Deal found 17/12C$ 1,029
Sat 27/128:25 a.m.YHZ - MDW
1 stop8h 55mPorter Airlines
Fri 2/111:00 a.m.MDW - YHZ
2 stops8h 05mPorter Airlines
Deal found 16/12C$ 1,071
Thu 25/126:10 p.m.YHZ - MDW
2 stops42h 56mWestJet
Thu 1/19:50 a.m.MDW - YHZ
2 stops37h 51mWestJet
Deal found 16/12C$ 1,090
Fri 26/126:00 a.m.YHZ - MDW
2 stops31h 06mWestJet
Thu 1/19:50 a.m.MDW - YHZ
2 stops37h 51mWestJet
Deal found 17/12C$ 1,091

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 18 December 2025.

Round-trip from

C$ 328

One-way from

C$ 296

Popular in

July

Cheapest in

September

Average price

C$ 426
Porter Airlines
  • Porter Airlines
  • 14/4-15/4
  • 3 total stops
  • 17h 25m total
  • Halifax to Chicago
Search Deals
30/1
  • 30/1
  • 1 total stop
  • 13h 07m total
  • Halifax to Chicago
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 207 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 18 December 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

Tue 14/4

7:00 a.m.-3:20 p.m.

2 stops10h 20m

Chicago Midway

Wed 15/4

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

1 stop7h 05m

C$ 338

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 2/4

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

2 stops8h 55m

Chicago Midway

Sun 5/4

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

1 stop7h 05m

C$ 488

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 21/1

7:05 p.m.-10:05 a.m.

2 stops17h 00m

Chicago Midway

Sat 24/1

12:45 p.m.-8:10 p.m.

1 stop5h 25m

C$ 539

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 21/1

6:00 a.m.-5:55 p.m.

2 stops13h 55m

Chicago Midway

Sat 24/1

9:33 a.m.-1:41 a.m.

2 stops14h 08m

C$ 543

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 16/1

8:45 a.m.-11:47 p.m.

2 stops17h 02m

Chicago Midway

Mon 19/1

11:05 a.m.-8:10 p.m.

1 stop7h 05m

C$ 543

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 30/1

8:45 a.m.-7:52 p.m.

1 stop13h 07m

C$ 296

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 2/3

1:20 p.m.-7:07 p.m.

3 stops31h 47m

C$ 311

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 30/1

6:00 a.m.-5:55 p.m.

2 stops13h 55m

C$ 338

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 24/12

9:00 a.m.-9:58 p.m.

1 stop14h 58m

C$ 360

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 23/12

6:55 a.m.-2:37 p.m.

3 stops33h 42m

C$ 442

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/12

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.

Toronto (YTZ) is the most affordable 1-stop option, with an average round-trip price of C$ 499.

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 10h 20m. 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

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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

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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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