What is the cheapest airline that flies from Halifax Intl to Chicago?

Air Canada, Porter Airlines, and United Airlines are the most popular carriers operating from Halifax Intl to Chicago

Which layover airport has the shortest connection time from Halifax to Chicago?

Toronto (YYZ) has the shortest average layover time for this route: 2h 09m.

Which layover airport offers the lowest fares from Halifax to Chicago?

Flights via Montreal (YUL) offer the lowest average round-trip price of C$ 268.

Which airport is the most popular layover for flights between Halifax and Chicago?

Toronto (YYZ) was the most common stop: 86% of momondo users choosing one-stop flights on this route connected there.

Which layover airport has the shortest travel time from Halifax to Chicago?

Flights connecting via Toronto (YYZ) have the shortest average one-way travel time: 6h 05m.

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

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

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

The number of operators available for flights from Halifax Intl Airport to Chicago is 1 as of September 2026.

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

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Halifax Intl Airport to Chicago.

What documentation or ID do you need to fly to Chicago?

The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

C$ 248 Cheap Flights from Halifax to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Halifax to Chicago

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5:10 a.m. - 11:07 a.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

7h 57m1 stop Montreal Pierre Elliott Trudeau Intl

3:45 p.m. - 11:55 p.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

6h 10m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 414Air Canada

Sat, 13 Feb - Mon, 15 Feb

6:05 a.m. - 11:07 a.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

7h 02m1 stop Montreal Pierre Elliott Trudeau Intl

3:45 p.m. - 12:55 a.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

7h 10m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 414Air Canada

Sun, 17 Jan - Fri, 22 Jan

6:25 a.m. - 10:22 a.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

5h 57m1 stop Montreal Pierre Elliott Trudeau Intl

8:45 a.m. - 4:02 p.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

5h 17m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 429Air Canada

Fri, 16 Oct - Sun, 18 Oct

5:10 a.m. - 11:07 a.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

7h 57m1 stop Montreal Pierre Elliott Trudeau Intl

7:05 a.m. - 3:55 p.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

6h 50m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 429Air Canada

Sat, 21 Nov - Sat, 28 Nov

6:05 a.m. - 11:07 a.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

7h 02m1 stop Montreal Pierre Elliott Trudeau Intl

3:45 p.m. - 12:15 a.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

6h 30m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 429Air Canada

Fri, 13 Nov - Mon, 16 Nov

5:10 a.m. - 11:07 a.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

7h 57m1 stop Montreal Pierre Elliott Trudeau Intl

3:45 p.m. - 11:55 p.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

6h 10m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 430Air Canada

Sat, 13 Feb - Mon, 15 Feb

5:00 a.m. - 9:23 a.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

6h 23m1 stop Toronto Pearson Intl

7:05 a.m. - 3:55 p.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

6h 50m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 436Air Canada

Mon, 9 Nov - Sat, 14 Nov

5:00 a.m. - 9:23 a.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

6h 23m1 stop Toronto Pearson Intl

3:45 p.m. - 12:15 a.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

6h 30m1 stop Montreal Pierre Elliott Trudeau Intl

C$ 436Air Canada

Mon, 16 Nov - Sat, 21 Nov

6:40 a.m. - 11:40 a.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

7h 00m2 stops Ottawa Toronto Island

12:20 p.m. - 11:45 p.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

9h 25m2 stops Toronto Island Ottawa

C$ 469Porter Airlines

Fri, 13 Nov - Mon, 16 Nov

2:50 p.m. - 11:21 p.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

10h 31m1 stop Newark

9:48 p.m. - 1:24 p.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

13h 36m1 stop Newark

C$ 487United Airlines

Thu, 22 Oct - Sun, 25 Oct

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Porter Airlines flights from Halifax to Chicago

Our best Porter Airlines deals on Halifax to Chicago flight tickets

Porter Airlines

13 Nov

YHZ6:40 a.m.Halifax Intl

7h 00m

2 stops

ORD11:40 a.m.Chicago O'Hare Intl

16 Nov

ORD12:20 p.m.Chicago O'Hare Intl

9h 25m

2 stops

YHZ11:45 p.m.Halifax Intl

C$ 469

Porter Airlines

16 Oct

YHZ7:00 a.m.Halifax Intl

9h 35m

2 stops

MDW2:35 p.m.Chicago Midway

19 Oct

MDW3:20 p.m.Chicago Midway

6h 29m

2 stops

YHZ11:49 p.m.Halifax Intl

C$ 509

Porter Airlines

16 Nov

YHZ6:40 a.m.Halifax Intl

7h 00m

2 stops

ORD11:40 a.m.Chicago O'Hare Intl

21 Nov

ORD12:20 p.m.Chicago O'Hare Intl

9h 25m

2 stops

YHZ11:45 p.m.Halifax Intl

C$ 528

United Airlines flights from Halifax to Chicago

Our best United Airlines deals on Halifax to Chicago flight tickets

United Airlines

22 Oct

YHZ2:50 p.m.Halifax Intl

10h 31m

1 stop

ORD11:21 p.m.Chicago O'Hare Intl

25 Oct

ORD9:48 p.m.Chicago O'Hare Intl

13h 36m

1 stop

YHZ1:24 p.m.Halifax Intl

C$ 487

United Airlines

29 Sep

YHZ7:00 a.m.Halifax Intl

7h 54m

1 stop

ORD12:54 p.m.Chicago O'Hare Intl

30 Sep

ORD6:00 a.m.Chicago O'Hare Intl

15h 55m

1 stop

YHZ11:55 p.m.Halifax Intl

C$ 495

United Airlines

22 Oct

YHZ7:05 a.m.Halifax Intl

9h 21m

2 stops

ORD2:26 p.m.Chicago O'Hare Intl

25 Oct

ORD9:48 p.m.Chicago O'Hare Intl

13h 36m

1 stop

YHZ1:24 p.m.Halifax Intl

C$ 582

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 13/2

5:10 a.m.-11:07 a.m.

1 stop7h 57m

Chicago O'Hare Intl

Mon 15/2

3:45 p.m.-11:55 p.m.

1 stop6h 10m

C$ 414

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sun 17/1

6:05 a.m.-11:07 a.m.

1 stop7h 02m

Chicago O'Hare Intl

Fri 22/1

3:45 p.m.-12:55 a.m.

1 stop7h 10m

C$ 414

Quickest round-trip

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 16/10

6:25 a.m.-10:22 a.m.

1 stop5h 57m

Chicago O'Hare Intl

Sun 18/10

8:45 a.m.-4:02 p.m.

1 stop5h 17m

C$ 429

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 21/11

5:10 a.m.-11:07 a.m.

1 stop7h 57m

Chicago O'Hare Intl

Sat 28/11

7:05 a.m.-3:55 p.m.

1 stop6h 50m

C$ 429

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 13/11

6:05 a.m.-11:07 a.m.

1 stop7h 02m

Chicago O'Hare Intl

Mon 16/11

3:45 p.m.-12:15 a.m.

1 stop6h 30m

C$ 429

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 13/2

5:10 a.m.-11:07 a.m.

1 stop7h 57m

Chicago O'Hare Intl

Mon 15/2

3:45 p.m.-11:55 p.m.

1 stop6h 10m

C$ 430

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Mon 9/11

5:00 a.m.-9:23 a.m.

1 stop6h 23m

Chicago O'Hare Intl

Sat 14/11

7:05 a.m.-3:55 p.m.

1 stop6h 50m

C$ 436

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Mon 16/11

5:00 a.m.-9:23 a.m.

1 stop6h 23m

Chicago O'Hare Intl

Sat 21/11

3:45 p.m.-12:15 a.m.

1 stop6h 30m

C$ 436

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 13/11

6:40 a.m.-11:40 a.m.

2 stops7h 00m

Chicago O'Hare Intl

Mon 16/11

12:20 p.m.-11:45 p.m.

2 stops9h 25m

C$ 469

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Thu 22/10

2:50 p.m.-11:21 p.m.

1 stop10h 31m

Chicago O'Hare Intl

Sun 25/10

9:48 p.m.-1:24 p.m.

1 stop13h 36m

C$ 487

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Halifax to Chicago

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

Prices

Airlines

Layovers

What is the typical price of a round-trip flight between Halifax and Chicago?

Prices are currently low for flights on this route.

Typical prices usually range from C$ 470 to C$ 542.
The lowest price recently found on this route was C$ 414.

What is the cheapest month to fly to Chicago?

The month of September is another great option to travel to Chicago, with average flight prices from Halifax averaging around C$ 496.

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

The cheapest day to depart on your flight to Chicago is on a Sunday when prices can be found for as low as C$ 513. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Tuesday because tickets tend to average around C$ 874. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

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

In the afternoon is the cheapest time of day to fly from Halifax to Chicago when you can find flight prices for as low as C$ 760. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 899 per ticket.

What is the cheapest Halifax Intl to Chicago flight route?

Fly from Halifax Intl to Chicago O'Hare Intl for the best Halifax Intl - Chicago flight prices

What cabin class options are available on Halifax to Chicago flights?

There are 2 cabin classes available to choose from on Halifax to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Halifax to Chicago flights?

You could potentially save up to 58% on your flight if you consider stops on a Halifax to Chicago flight.

How have Halifax to Chicago flight prices changed over time?

As of September 2026, prices for Halifax to Chicago flights are approximately 67% more expensive when compared to flights at the same time last year.

When to book flights from Halifax to Chicago

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

Estimated round-trip price

Cheap Halifax to Chicago (YHZ to CHI) flight deals and tips

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

Best price found	C$ 248
Fastest flight time	3h 45m
Direct flights	Sun
Airports in Chicago	3 airports

The best one-way flight to Chicago from Halifax in the past 72 hours is C$ 248. The best round-trip flight deal from Halifax to Chicago found on momondo in the last 72 hours is C$ 414.

The fastest flight from Halifax to Chicago takes 3h 45m

Direct flights go from Halifax to Chicago on Sunday. There are no airlines offering direct flights.

There are 3 airports in Chicago. From Halifax there are direct flights to Chicago O'Hare Intl (ORD).

Search flight deals

Frequently asked questions about flying from Halifax to Chicago

How far is Halifax Intl to Chicago by plane?
Chicago is 1963.4 km away from Halifax Intl. A reasonable flight in good conditions will take 3h 45m.
When did momondo last update prices for flights from Halifax Intl Airport to Chicago?
Prices for flights from Halifax Intl Airport to Chicago refresh daily.
How many operators does momondo search for flights from Halifax Intl Airport to Chicago?
The number of operators available for flights from Halifax Intl Airport to Chicago is 1 as of September 2026.
How old do you have to be to fly from Halifax Intl Airport to Chicago?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Halifax Intl Airport to Chicago.
What documentation or ID do you need to fly to Chicago?
The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular plane model from Halifax to Chicago?
Based on momondo bookings for flights between Halifax and Chicago, the leading plane model is Embraer 175 (Enhanced Winglets), making up 69.23% of the total bookings. Other popular models include Boeing 737 MAX 8 with 7.69%, De Havilland (Bombardier) DHC-8-400 Dash 8Q with 7.69%, and Embraer 175 with 7.69%.
What is the most popular airline from Halifax to Chicago?
Based on momondo bookings for flights between Halifax and Chicago, the leading airline is Air Canada, making up 48% of the total bookings. Other popular airlines include Porter Airlines with 27%, WestJet with 15%, and United Airlines with 11%.

Best airlines flying from Halifax to Chicago

Compare and see reviews for airlines that fly from Halifax to Chicago with momondo

Airline	Rating	Free Cancellation	Price
Air Canada	PriceFrom C$ 266	Free Cancellation	Rating 7.1 11,608 reviews		Search Air Canada flights

Merrillville

Benton Harbor

Hammond

Munster

Valparaiso

Portage

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?

All flight searches from Halifax to Chicago on momondo can be filtered to show those which offer flexible booking policies.

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?

Price alerts on flights to Chicago from Halifax are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago trip

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Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Cheap flights from Halifax to Chicago from C$ 248

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 7/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Find the cheapest flights from Halifax to Chicago

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Big names, great deals

Big names, great deals

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Porter Airlines flights from Halifax to Chicago

Our best Porter Airlines deals on Halifax to Chicago flight tickets

United Airlines flights from Halifax to Chicago

Our best United Airlines deals on Halifax to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Halifax to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Halifax to Chicago

What is the typical price of a round-trip flight between Halifax and Chicago?

What is the cheapest month to fly to Chicago?

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

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

What is the cheapest Halifax Intl to Chicago flight route?

What cabin class options are available on Halifax to Chicago flights?

Can stopping save me money on Halifax to Chicago flights?

How have Halifax to Chicago flight prices changed over time?

What is the cheapest airline that flies from Halifax Intl to Chicago?

Which airport is the most popular layover for flights between Halifax and Chicago?

Which layover airport offers the lowest fares from Halifax to Chicago?

Which layover airport has the shortest travel time from Halifax to Chicago?

Which layover airport has the shortest connection time from Halifax to Chicago?

When to book flights from Halifax to Chicago

Cheap Halifax to Chicago (YHZ to CHI) flight deals and tips

Best price found

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying from Halifax to Chicago

Best airlines flying from Halifax to Chicago

Compare and see reviews for airlines that fly from Halifax to Chicago with momondo

Travelling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular Cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Halifax

According to popular flight searches on momondo this year

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