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Cheap flights from Halifax to Chicago Midway Airport from C$ 270

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 14/6. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — MDW
22 Jun — 29 Jun1
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 23 May 2026.

Fri 12/66:20 a.m.
YHZ
-
MDW
1 stop10h 15m
Porter Airlines
Mon 15/63:20 p.m.
MDW
-
YHZ
1 stop19h 04m
Porter Airlines
Deal found 22/5C$ 559
Thu 4/68:00 a.m.
YHZ
-
MDW
1 stop8h 35m
Porter Airlines
Wed 10/610:15 a.m.
MDW
-
YHZ
1 stop24h 09m
Porter Airlines
Deal found 20/5C$ 581
Fri 19/63:30 p.m.
YHZ
-
MDW
1 stop5h 01m
Delta
Mon 22/61:26 p.m.
MDW
-
YHZ
1 stop6h 14m
Delta
Deal found 22/5C$ 604
Thu 11/68:00 a.m.
YHZ
-
MDW
1 stop8h 35m
Porter Airlines
Wed 17/610:15 a.m.
MDW
-
YHZ
2 stops11h 29m
Porter Airlines
Deal found 19/5C$ 606
Sun 21/68:00 a.m.
YHZ
-
MDW
1 stop27h 40m
Porter Airlines
Thu 25/63:20 p.m.
MDW
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 21/5C$ 611
Fri 19/63:30 p.m.
YHZ
-
MDW
1 stop5h 01m
Delta
Fri 26/61:26 p.m.
MDW
-
YHZ
1 stop6h 14m
Delta
Deal found 22/5C$ 657
Tue 25/86:30 a.m.
YHZ
-
MDW
2 stops14h 03m
Delta
Sun 6/99:24 a.m.
MDW
-
YHZ
2 stops11h 54m
Delta
Deal found 23/5C$ 669
Fri 3/73:30 p.m.
YHZ
-
MDW
1 stop5h 01m
Delta
Fri 10/71:18 p.m.
MDW
-
YHZ
1 stop6h 22m
Delta
Deal found 21/5C$ 679

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 23 May 2026.

Round-trip from

C$ 559

One-way from

C$ 270

Popular in

January

Cheapest in

September

Average price

C$ 766
Porter Airlines
  • Porter Airlines
  • 12/6-15/6
  • 2 total stops
  • 29h 19m total
  • Halifax to Chicago
Search Deals
14/6
  • 14/6
  • 1 total stop
  • 12h 35m total
  • Halifax to Chicago
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in May 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 23 May 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

Thu 4/6

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

1 stop8h 35m

Chicago Midway

Wed 10/6

10:15 a.m.-12:24 p.m.

1 stop24h 09m

C$ 581
Quickest round-trip

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 19/6

3:30 p.m.-6:31 p.m.

1 stop5h 01m

Chicago Midway

Mon 22/6

1:26 p.m.-9:40 p.m.

1 stop6h 14m

C$ 639

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 19/6

3:30 p.m.-6:31 p.m.

1 stop5h 01m

Chicago Midway

Fri 26/6

1:26 p.m.-9:40 p.m.

1 stop6h 14m

C$ 657

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 25/8

6:30 a.m.-4:15 p.m.

2 stops11h 45m

Chicago Midway

Thu 10/9

10:35 a.m.-9:45 p.m.

2 stops9h 10m

C$ 682

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 29/8

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

1 stop5h 03m

Chicago Midway

Sat 12/9

1:00 p.m.-9:45 p.m.

1 stop6h 45m

C$ 682

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 3/7

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

1 stop8h 35m

Chicago Midway

Fri 10/7

3:15 p.m.-6:28 p.m.

2 stops25h 13m

C$ 689

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 20/6

8:30 a.m.-6:11 p.m.

2 stops11h 41m

Chicago Midway

Sat 27/6

1:26 p.m.-9:45 p.m.

1 stop6h 19m

C$ 704

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 18/6

8:30 a.m.-6:31 p.m.

2 stops12h 01m

Chicago Midway

Thu 25/6

1:26 p.m.-9:45 p.m.

1 stop6h 19m

C$ 705
Cheapest one-way

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sun 14/6

11:00 p.m.-9:35 a.m.

1 stop12h 35m

C$ 270

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 9/6

8:00 a.m.-9:35 a.m.

1 stop27h 35m

C$ 277

Flights are sorted by cheapest round-trip flights first.

Deals found on 20/5

Showing 1-10 of 17 resultsSorted by cheapest first
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.

Montreal (YUL) is the most affordable 1-stop option, with an average round-trip price of C$ 880.

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.

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 23 May 2026.
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
439 reviews
Check prices

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
439 reviews
Porter Airlines
8.0
Very good
439 reviews
Check prices

Comfort

8.0

Boarding

8.2

Overall

8.0

Crew

8.6

Entertainment

7.0

Food

7.6

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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.

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

    Porter Airlines and Delta can get you from Halifax to Chicago Midway Airport in just under 5h 01m. Your travel time can differ by up to 3h 34m. Airlines will cover a distance of 1981 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

  • 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$ 467.

  • 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

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 23 May 2026.
AirlineCheapestAverageFlexibilityOn-time
Porter AirlinesCheapestC$ 467AverageC$ 666FlexibilityNo 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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