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Cheap flights from Halifax to Chicago Midway Airport from C$ 164

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 30/9. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — MDW
19 Aug — 26 Aug1
1 adult

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 14 August 2025.

Round-trip from

C$ 262

One-way from

C$ 164

Popular in

October

Cheapest in

January

Average price

C$ 669
Porter Airlines
  • Porter Airlines
  • 17/11-22/11
  • 3 total stops
  • 16h 00m total
  • Halifax to Chicago
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Porter Airlines
  • Porter Airlines
  • 30/9
  • 2 total stops
  • 12h 14m total
  • Halifax to Chicago
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Highest demand for flights based on searches. 8% potential increase in price (C$ 67 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease (C$ 20 potential savings vs. average RT price).
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Average for round-trip flights in August 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 14 August 2025.

Mon 17/118:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Sat 22/1111:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 11/8C$ 262
Tue 18/118:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Thu 20/1111:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 11/8C$ 274
Mon 17/118:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Fri 21/1111:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 11/8C$ 276
Wed 15/106:10 a.m.YHZ - MDW
2 stops12h 14mPorter Airlines
Sat 18/109:35 a.m.MDW - YHZ
2 stops12h 05mPorter Airlines
Deal found 12/8C$ 292
Thu 20/118:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Sun 23/1111:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 11/8C$ 296
Wed 19/118:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Sat 22/1111:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 11/8C$ 309
Wed 19/118:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Thu 20/1111:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 11/8C$ 317

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 14 August 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

Mon 17/11

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

2 stops8h 55m

Chicago Midway

Sat 22/11

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

1 stop7h 05m

C$ 262

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 18/11

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

2 stops8h 55m

Chicago Midway

Thu 20/11

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

2 stops10h 54m

C$ 274

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 18/11

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

2 stops8h 55m

Chicago Midway

Sat 22/11

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

2 stops6h 51m

C$ 274

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 17/11

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

2 stops8h 55m

Chicago Midway

Thu 20/11

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

2 stops10h 54m

C$ 274

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 17/11

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

2 stops8h 55m

Chicago Midway

Fri 21/11

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

2 stops10h 54m

C$ 276

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 15/10

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

2 stops12h 14m

Chicago Midway

Sat 18/10

9:35 a.m.-11:40 p.m.

2 stops12h 05m

C$ 292

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 15/10

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

2 stops9h 09m

C$ 164

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 30/9

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

2 stops12h 14m

C$ 164

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 24/9

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

2 stops12h 14m

C$ 171

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 28/8

6:45 a.m.-4:24 p.m.

2 stops11h 39m

C$ 237

Flights are sorted by cheapest round-trip flights first.

Deals found on 13/8

Showing 1-10 of 16 results
1
2

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.

Reviews of airlines servicing Midway

Get insights into the airlines that provide service to Midway. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Midway. Reviews last updated 14 August 2025.
Check out reviews from past customers who have flown with Porter Airlines from Halifax to Chicago Midway Airport to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
332 reviews
Check prices

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
332 reviews
Porter Airlines
8.0
Very good
332 reviews
Check prices

Overall

8.0

Entertainment

7.0

Boarding

8.2

Crew

8.7

Comfort

8.0

Food

7.6

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

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 1 airline. Halifax Intl is conveniently located just 26.9 km from Halifax’s city centre.

  • What is the cheapest airline to fly from Halifax to Chicago Midway Airport round-trip?

    Cheapflights users have booked flights from Halifax to Chicago Midway Airport round-trip from C$ 434.

  • 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, June is the cheapest month in which you can book a flight from Halifax to Chicago Midway Airport (average of C$ 233). 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

Top airline flying from Halifax to Midway

Discover the top airline that operate flights from Halifax to Midway. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 629,999 searches. Data last updated 14 August 2025.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 434AverageC$ 613FlexibilityNo cancel feeOn-time52%
Search Porter Airlines 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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