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Cheap flights from Halifax to Chicago from C$ 296

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 30/1. 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

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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. - 3:20 p.m.
YHZ
-
MDW
10h 20m2 stops
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 338Porter Airlines
Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
7:00 a.m. - 3:20 p.m.
YHZ
-
MDW
10h 20m2 stops
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 339Porter Airlines
Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 378Porter Airlines
Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 387Porter Airlines
Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 389Porter Airlines
Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
8:25 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 55m2 stops
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 412Porter Airlines
Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
8:25 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 55m2 stops
Porter Airlines Logo
11:00 a.m. - 11:54 p.m.
MDW
-
YHZ
10h 54m2 stops
C$ 462Porter Airlines
Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
7:00 a.m. - 3:20 p.m.
YHZ
-
MDW
10h 20m2 stops
Porter Airlines Logo
11:00 a.m. - 11:54 p.m.
MDW
-
YHZ
10h 54m2 stops
C$ 481Porter Airlines
Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
8:25 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 55m2 stops
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 488Porter Airlines
Thu, 2 Apr - Sun, 5 Apr
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 502Porter Airlines
Thu, 2 Apr - Sun, 5 Apr

WestJet flights from Halifax to Chicago Midway Airport

Our best WestJet deals on Halifax to Chicago Midway Airport flight tickets
WestJet
13 Jan
YHZ6:00 a.m.Halifax Intl
28h 52m
2 stops
MDW8:52 a.m.Chicago Midway
20 Jan
MDW9:32 a.m.Chicago Midway
14h 09m
2 stops
YHZ1:41 a.m.Halifax Intl
C$ 564
Find similar
WestJet
27 Dec
YHZ6:00 a.m.Halifax Intl
28h 49m
2 stops
MDW8:49 a.m.Chicago Midway
2 Jan
MDW6:08 p.m.Chicago Midway
29h 33m
2 stops
YHZ1:41 a.m.Halifax Intl
C$ 875
Find similar
WestJet
27 Dec
YHZ6:00 a.m.Halifax Intl
28h 49m
2 stops
MDW8:49 a.m.Chicago Midway
2 Jan
MDW6:08 p.m.Chicago Midway
29h 33m
2 stops
YHZ1:41 a.m.Halifax Intl
C$ 902
Find similar

Porter Airlines flights from Halifax to Chicago Midway Airport

Our best Porter Airlines deals on Halifax to Chicago Midway Airport flight tickets
Porter Airlines
14 Apr
YHZ7:00 a.m.Halifax Intl
10h 20m
2 stops
MDW3:20 p.m.Chicago Midway
15 Apr
MDW11:00 a.m.Chicago Midway
7h 05m
1 stop
YHZ8:05 p.m.Halifax Intl
C$ 338
Find similar
Porter Airlines
14 Apr
YHZ7:00 a.m.Halifax Intl
10h 20m
2 stops
MDW3:20 p.m.Chicago Midway
15 Apr
MDW11:00 a.m.Chicago Midway
7h 05m
1 stop
YHZ8:05 p.m.Halifax Intl
C$ 339
Find similar
Porter Airlines
14 Apr
YHZ8:30 a.m.Halifax Intl
8h 50m
1 stop
MDW3:20 p.m.Chicago Midway
15 Apr
MDW11:00 a.m.Chicago Midway
7h 05m
1 stop
YHZ8:05 p.m.Halifax Intl
C$ 378
Find similar

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 18 December 2025.
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

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 14/4

7:00 a.m.-3:20 p.m.

2 stops10h 20m

Chicago Midway

Wed 15/4

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

1 stop7h 05m

C$ 338

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 14/4

7:00 a.m.-3:20 p.m.

2 stops10h 20m

Chicago Midway

Wed 15/4

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

1 stop7h 05m

C$ 339

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 14/4

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

1 stop8h 50m

Chicago Midway

Wed 15/4

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

1 stop7h 05m

C$ 378

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 14/4

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

1 stop8h 50m

Chicago Midway

Wed 15/4

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

1 stop7h 05m

C$ 387

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 14/4

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

1 stop8h 50m

Chicago Midway

Wed 15/4

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

1 stop7h 05m

C$ 389

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 14/4

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

2 stops8h 55m

Chicago Midway

Wed 15/4

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

1 stop7h 05m

C$ 412

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 14/4

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

2 stops8h 55m

Chicago Midway

Wed 15/4

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

2 stops10h 54m

C$ 462

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 14/4

7:00 a.m.-3:20 p.m.

2 stops10h 20m

Chicago Midway

Wed 15/4

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

2 stops10h 54m

C$ 481

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 2/4

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

2 stops8h 55m

Chicago Midway

Sun 5/4

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

1 stop7h 05m

C$ 488

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 2/4

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

1 stop8h 50m

Chicago Midway

Sun 5/4

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

1 stop7h 05m

C$ 502

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

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

What is the cheapest day to depart on your flight to Chicago Midway Airport?

The cheapest day to depart on your flight to Chicago Midway Airport is on a Monday when prices can be found for as low as C$ 389. This is often the case because there is less demand to fly during this day of the week. On the other hand, Sunday is the most expensive day to depart from Halifax because it is more convenient for both business and leisure travellers. As a result, prices tend to be around C$ 593.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Our most recent data shows that the best time of day to fly to Chicago Midway Airport is in the afternoon. Flights from Halifax to Chicago Midway Airport during this time can be as low as C$ 509. In contrast, the most expensive time of day to depart to Chicago Midway Airport is in the morning when prices are around C$ 535.

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

You could potentially save up to 30% 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

8h 50m

Direct flights

None
The fastest flight from Halifax to Chicago Midway Airport takes 8h 50m
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

  • 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 8h 50m.

  • 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 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.

Travelling to a place near Chicago?

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

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.

An easier way to manage your Chicago Midway Airport trip

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