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Cheap flights from Halifax to Chicago from C$ 263

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Halifax to Chicago departing on 14/6. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

Find the cheapest flights from Halifax to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.
YHZ
-
MDW
9h 35m
2 stops
Porter Airlines Logo
3:20 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 24m
2 stops
C$ 535Porter Airlines
Fri, 19 Jun - Mon, 22 Jun
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.
YHZ
-
MDW
9h 35m
2 stops
Porter Airlines Logo
10:15 a.m. - 11:44 p.m.
MDW
-
YHZ
11h 29m
2 stops
C$ 540Porter Airlines
Mon, 1 Jun - Mon, 8 Jun
Delta Logo
1:27 p.m. - 10:17 p.m.
YHZ
-
MDW
10h 50m
2 stops
Delta Logo
9:54 a.m. - 11:07 p.m.
MDW
-
YHZ
11h 13m
2 stops
C$ 543Delta
Wed, 10 Jun - Sat, 20 Jun
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
3:20 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 24m
2 stops
C$ 546Porter Airlines
Sun, 14 Jun - Sun, 21 Jun
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
2 stops
Porter Airlines Logo
3:20 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 24m
2 stops
C$ 547Porter Airlines
Sun, 14 Jun - Sun, 21 Jun
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.
YHZ
-
MDW
9h 35m
2 stops
Porter Airlines Logo
3:20 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 24m
2 stops
C$ 567Porter Airlines
Fri, 19 Jun - Mon, 22 Jun
Multiple Airlines Logo
11:00 p.m. - 9:40 a.m.
YHZ
-
MDW
12h 40m
1 stop
Multiple Airlines Logo
10:25 a.m. - 10:45 a.m.
MDW
-
YHZ
22h 20m
1 stop
C$ 569Multiple Airlines
Sat, 20 Jun - Sat, 27 Jun
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
10:15 a.m. - 9:14 p.m.
MDW
-
YHZ
8h 59m
2 stops
C$ 573Porter Airlines
Mon, 1 Jun - Mon, 8 Jun
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
10:15 a.m. - 11:44 p.m.
MDW
-
YHZ
11h 29m
2 stops
C$ 574Porter Airlines
Mon, 8 Jun - Thu, 11 Jun
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
3:20 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 24m
2 stops
C$ 575Porter Airlines
Fri, 19 Jun - Mon, 22 Jun

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Porter Airlines flights from Halifax to Chicago Midway Airport

Our best Porter Airlines deals on Halifax to Chicago Midway Airport flight tickets
Porter Airlines
19 Jun
YHZ7:00 a.m.Halifax Intl
9h 35m
2 stops
MDW2:35 p.m.Chicago Midway
22 Jun
MDW3:20 p.m.Chicago Midway
6h 24m
2 stops
YHZ11:44 p.m.Halifax Intl
C$ 535
Porter Airlines
1 Jun
YHZ7:00 a.m.Halifax Intl
9h 35m
2 stops
MDW2:35 p.m.Chicago Midway
8 Jun
MDW10:15 a.m.Chicago Midway
11h 29m
2 stops
YHZ11:44 p.m.Halifax Intl
C$ 540
Porter Airlines
14 Jun
YHZ8:00 a.m.Halifax Intl
8h 35m
1 stop
MDW2:35 p.m.Chicago Midway
21 Jun
MDW3:20 p.m.Chicago Midway
6h 24m
2 stops
YHZ11:44 p.m.Halifax Intl
C$ 546

Delta flights from Halifax to Chicago Midway Airport

Our best Delta deals on Halifax to Chicago Midway Airport flight tickets
Delta
10 Jun
YHZ1:27 p.m.Halifax Intl
10h 50m
2 stops
MDW10:17 p.m.Chicago Midway
20 Jun
MDW9:54 a.m.Chicago Midway
11h 13m
2 stops
YHZ11:07 p.m.Halifax Intl
C$ 543
Delta
10 Jun
YHZ3:30 p.m.Halifax Intl
5h 01m
1 stop
MDW6:31 p.m.Chicago Midway
20 Jun
MDW1:21 p.m.Chicago Midway
6h 24m
1 stop
YHZ9:45 p.m.Halifax Intl
C$ 601
Delta
29 May
YHZ3:30 p.m.Halifax Intl
5h 03m
1 stop
MDW6:33 p.m.Chicago Midway
3 Jun
MDW1:22 p.m.Chicago Midway
6h 18m
1 stop
YHZ9:40 p.m.Halifax Intl
C$ 603

momondo Fare Finder

 
Customize your flight search to find flights from Halifax to Chicago Midway Airport 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, momondo users made 96,600 searches. Data last updated 5 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

Fri 19/6

7:00 a.m.-2:35 p.m.

2 stops9h 35m

Chicago Midway

Mon 22/6

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

2 stops6h 24m

C$ 535

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 1/6

7:00 a.m.-2:35 p.m.

2 stops9h 35m

Chicago Midway

Mon 8/6

10:15 a.m.-11:44 p.m.

2 stops11h 29m

C$ 540

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 10/6

1:27 p.m.-10:17 p.m.

2 stops10h 50m

Chicago Midway

Sat 20/6

9:54 a.m.-11:07 p.m.

2 stops11h 13m

C$ 543
Quickest round-trip

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sun 14/6

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

1 stop8h 35m

Chicago Midway

Sun 21/6

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

2 stops6h 24m

C$ 546

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sun 14/6

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

2 stops8h 35m

Chicago Midway

Sun 21/6

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

2 stops6h 24m

C$ 547

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 19/6

7:00 a.m.-2:35 p.m.

2 stops9h 35m

Chicago Midway

Mon 22/6

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

2 stops6h 24m

C$ 567

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 20/6

11:00 p.m.-9:40 a.m.

1 stop12h 40m

Chicago Midway

Sat 27/6

10:25 a.m.-10:45 a.m.

1 stop22h 20m

C$ 569

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 1/6

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

1 stop8h 35m

Chicago Midway

Mon 8/6

10:15 a.m.-9:14 p.m.

2 stops8h 59m

C$ 573

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 8/6

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

1 stop8h 35m

Chicago Midway

Thu 11/6

10:15 a.m.-11:44 p.m.

2 stops11h 29m

C$ 574

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 19/6

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

1 stop8h 35m

Chicago Midway

Mon 22/6

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

2 stops6h 24m

C$ 575

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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How to get the cheapest flight ticket from Halifax to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Can stopping save me money on Halifax to Chicago Midway Airport flights?

You could potentially save up to 31% on your flight if you consider stops on a Halifax to Chicago Midway Airport flight.

When to book flights from Halifax to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Halifax to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Halifax to Chicago Midway Airport (YHZ to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Halifax to Chicago Midway Airport

Fastest flight time

5h 03m

Direct flights

None
The fastest flight from Halifax to Chicago Midway Airport takes 5h 03m
There are no direct flights from Halifax to Chicago Midway Airport. There are no popular flight routes from Halifax to Chicago Midway Airport.
Search flight deals

Frequently asked questions about flying from Halifax to Chicago Midway Airport

  • How far is Halifax Intl to Chicago Midway by plane?

    A flight from Halifax Intl to Chicago Midway will travel around 1975.6 km. By plane, this route typically takes 5h 03m.

  • When did momondo last update prices for flights from Halifax Intl Airport to Chicago Midway Airport?

    Prices for flights from Halifax Intl Airport to Chicago Midway Airport refresh daily.

  • How many operators does momondo search for flights from Halifax Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Halifax Intl Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Halifax Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The necessary travel and health documents for your Chicago Midway Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Halifax to Chicago Midway Airport?

Best airlines flying from Halifax to Chicago Midway Airport

Compare and see reviews for airlines that fly from Halifax to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
Porter AirlinesPriceFrom C$ 460Free CancellationRating
8.0
436 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Munster

Why use momondo?

Why should I use momondo to find a flight deal from Halifax to Chicago?

Finding the right flight to Chicago from Halifax is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Halifax to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Halifax with this policy.

How can momondo help me find flights from Halifax to Chicago?

momondo helps you find the best flight between Halifax and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Halifax to Chicago right now. Can momondo alert me if prices change?

Yes. momondo can track prices for Halifax to Chicago flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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