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Cheap flights from Halifax to Chicago Midway Airport from C$ 151

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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — MDW
17 Oct — 24 Oct1
1 adult
1 adult, Economy

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 September 2025.

Round-trip from

C$ 303

One-way from

C$ 151

Popular in

October

Cheapest in

January

Average price

C$ 560
Porter Airlines
  • Porter Airlines
  • 22/10-29/10
  • 4 total stops
  • 20h 03m total
  • Halifax to Chicago
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Porter Airlines
  • Porter Airlines
  • 1/10
  • 2 total stops
  • 9h 09m total
  • Halifax to Chicago
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Highest demand for flights based on searches. 6% potential increase in price (C$ 53 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 22 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Halifax to Midway

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 September 2025.

Sun 23/118:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Sun 30/1111:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 17/9C$ 329
Fri 7/118:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Tue 11/1111:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 16/9C$ 359
Thu 13/118:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Mon 17/1111:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 16/9C$ 370
Thu 13/118:30 a.m.YHZ - MDW
1 stop8h 50mMultiple Airlines
Mon 17/119:27 a.m.MDW - YHZ
2 stops24h 45mMultiple Airlines
Deal found 16/9C$ 455
Thu 2/106:10 a.m.YHZ - MDW
2 stops12h 14mPorter Airlines
Mon 6/109:35 a.m.MDW - YHZ
2 stops12h 05mPorter Airlines
Deal found 17/9C$ 470
Thu 2/106:10 a.m.YHZ - MDW
2 stops12h 14mMultiple Airlines
Mon 6/109:35 a.m.MDW - YHZ
1 stop24h 00mMultiple Airlines
Deal found 17/9C$ 473
Fri 31/107:00 a.m.YHZ - MDW
2 stops10h 20mPorter Airlines
Fri 7/1111:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 15/9C$ 501
Tue 21/109:15 a.m.YHZ - MDW
2 stops9h 09mPorter Airlines
Sun 26/1011:00 a.m.MDW - YHZ
2 stops6h 51mPorter Airlines
Deal found 17/9C$ 531

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 September 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 23/11

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

1 stop8h 50m

Chicago Midway

Sun 30/11

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

1 stop7h 05m

C$ 329

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 7/11

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

2 stops8h 55m

Chicago Midway

Tue 11/11

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

1 stop7h 05m

C$ 359

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 13/11

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

1 stop8h 50m

Chicago Midway

Mon 17/11

9:27 a.m.-12:12 p.m.

2 stops24h 45m

C$ 455

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 2/10

6:10 a.m.-4:24 p.m.

2 stops12h 14m

Chicago Midway

Mon 6/10

9:35 a.m.-11:35 a.m.

1 stop24h 00m

C$ 473

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 21/10

9:15 a.m.-4:24 p.m.

2 stops9h 09m

Chicago Midway

Sun 26/10

11:00 a.m.-7:51 p.m.

2 stops6h 51m

C$ 531

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 16/10

3:20 p.m.-8:39 a.m.

1 stop19h 19m

Chicago Midway

Sun 19/10

9:35 a.m.-10:39 p.m.

1 stop11h 04m

C$ 571

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 13/11

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

2 stops8h 55m

Chicago Midway

Mon 17/11

11:00 a.m.-7:51 p.m.

2 stops6h 51m

C$ 629

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 16/10

6:10 a.m.-4:24 p.m.

2 stops12h 14m

Chicago Midway

Sun 19/10

5:20 p.m.-1:52 p.m.

2 stops18h 32m

C$ 636

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 31/10

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

1 stop8h 50m

Chicago Midway

Fri 7/11

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

1 stop7h 05m

C$ 725

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 1/10

9:15 a.m.-4:24 p.m.

2 stops9h 09m

C$ 151

Flights are sorted by cheapest round-trip flights first.

Deals found on 16/9

Showing 1-10 of 18 results
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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.

  • What is the cheapest month to book a flight from Halifax to Chicago Midway Airport?

    Currently, September is the cheapest month in which you can book a flight from Halifax to Chicago Midway Airport (average of C$ 207). Flying from Halifax to Chicago Midway Airport in November is currently the most expensive (average of C$ 312). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

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

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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