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Cheap flights from Halifax to Chicago Midway Airport from C$ 274

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 22/9. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — MDW
14 Sep — 21 Sep1
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 15 August 2026.

Tue 29/97:00 a.m. -
2 stops9h 35m
Sat 3/1011:45 a.m. -
2 stops9h 59m
Deal found 10/8C$ 460
Sat 12/95:25 p.m. -
2 stops19h 35m
Sat 19/93:20 p.m. -
1 stop18h 15m
Deal found 14/8C$ 504
Sat 12/93:45 p.m. -
1 stop21h 15m
Sat 19/93:20 p.m. -
1 stop18h 15m
Deal found 14/8C$ 506
Sun 6/98:15 a.m. -
2 stops8h 20m
Tue 8/911:45 a.m. -
2 stops9h 59m
Deal found 13/8C$ 513
Mon 14/911:00 p.m. -
1 stop17h 35m
Wed 16/911:45 a.m. -
2 stops9h 48m
Deal found 13/8C$ 524
Fri 25/97:25 a.m. -
2 stops9h 10m
Fri 2/103:20 p.m. -
2 stops6h 24m
Deal found 10/8C$ 564

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 15 August 2026.

Round-trip from

C$ 460

One-way from

C$ 274

Popular in

January

Cheapest in

December

Average price

C$ 476
Porter Airlines
  • Porter Airlines
  • 29/9-3/10
  • 4 total stops
  • 19h 34m total
  • Halifax to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 22/9
  • 2 total stops
  • 23h 10m total
  • Halifax to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 49 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 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 15 August 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 Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Mon 14/9

11:00 p.m.-2:35 p.m.

1 stop17h 35m

Chicago Midway

Wed 16/9

11:45 a.m.-11:33 p.m.

2 stops9h 48m

C$ 524

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Fri 25/9

7:25 a.m.-2:35 p.m.

2 stops9h 10m

Chicago Midway

Fri 2/10

3:20 p.m.-11:44 p.m.

2 stops6h 24m

C$ 564
Quickest round-trip

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Sat 19/9

3:30 p.m.-6:22 p.m.

1 stop4h 52m

Chicago Midway

Sat 26/9

1:19 p.m.-9:10 p.m.

1 stop5h 51m

C$ 613

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Tue 29/9

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

1 stop5h 03m

Chicago Midway

Tue 6/10

9:29 a.m.-9:10 p.m.

1 stop9h 41m

C$ 614

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Wed 16/9

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

1 stop5h 03m

Chicago Midway

Wed 23/9

9:29 a.m.-9:10 p.m.

1 stop9h 41m

C$ 614

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Wed 9/9

3:30 p.m.-10:44 p.m.

2 stops9h 14m

Chicago Midway

Sat 12/9

9:29 a.m.-9:10 p.m.

1 stop9h 41m

C$ 624

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Fri 25/9

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

1 stop5h 03m

Chicago Midway

Fri 2/10

9:29 a.m.-9:10 p.m.

1 stop9h 41m

C$ 640

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Sat 12/9

3:30 p.m.-10:44 p.m.

2 stops9h 14m

Chicago Midway

Sat 19/9

6:05 a.m.-9:10 p.m.

2 stops13h 05m

C$ 658
Cheapest one-way

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Mon 28/9

7:25 a.m.-2:35 p.m.

2 stops9h 10m

C$ 293

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Mon 31/8

8:30 a.m.-10:55 a.m.

3 stops28h 25m

C$ 329

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/8

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.

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 and Delta can get you from Halifax to Chicago Midway Airport in just under 4h 52m. Your travel time can differ by up to 4h 18m. 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.

  • 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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