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

Toronto (YYZ) was the most common stop: 80% 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 Montreal (YUL) have the shortest average one-way travel time: 6h 06m.

How many flights depart from Halifax to Chicago on average per week?

As of October 2025, there are 2 flights per week flying from Halifax to Chicago. The most common day of the week flights depart is Sat, with 100% of flights taking off on this day.

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

Flights via Montreal (YUL) offer the lowest average round-trip price of C$ 272.

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

Montreal (YUL) has the shortest average layover time for this route: 2h 19m.

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

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

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 2 as of October 2025.

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$ 157 Cheap Flights from Halifax to Chicago in 2025/26

1 adult

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Find the cheapest flights from Halifax to Chicago

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One-way

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Cheap round-trip flights

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5:55 a.m. - 10:18 a.m.YHZ-ORD

6h 23m1 stop

7:05 a.m. - 3:47 p.m.ORD-YHZ

6h 42m1 stop

C$ 231Air Canada

Find Deal

Sun, 2 Nov - Sat, 8 Nov

5:35 a.m. - 1:01 p.m.YHZ-ORD

9h 26m2 stops

7:05 a.m. - 3:47 p.m.ORD-YHZ

6h 42m1 stop

C$ 233Air Canada

Find Deal

Sun, 2 Nov - Sat, 8 Nov

5:35 a.m. - 1:01 p.m.YHZ-ORD

9h 26m2 stops

2:00 p.m. - 12:06 a.m.ORD-YHZ

8h 06m2 stops

C$ 241Air Canada

Find Deal

Sun, 2 Nov - Sat, 8 Nov

6:55 a.m. - 11:18 a.m.YHZ-ORD

6h 23m1 stop

7:15 a.m. - 3:47 p.m.ORD-YHZ

6h 32m1 stop

C$ 247Air Canada

Find Deal

Wed, 17 Dec - Wed, 7 Jan

8:25 a.m. - 11:50 a.m.YHZ-MDW

5h 25m1 stop

12:45 p.m. - 11:49 p.m.MDW-YHZ

9h 04m2 stops

C$ 325Porter Airlines

Find Deal

Sat, 15 Nov - Sat, 22 Nov

7:00 a.m. - 1:01 p.m.YHZ-ORD

8h 01m1 stop

1:55 p.m. - 12:06 a.m.ORD-YHZ

8h 11m2 stops

C$ 342Multiple Airlines

Find Deal

Wed, 17 Dec - Wed, 7 Jan

3:15 p.m. - 11:32 p.m.YHZ-ORD

10h 17m1 stop

3:55 p.m. - 11:04 a.m.ORD-YHZ

17h 09m2 stops

C$ 348Multiple Airlines

Find Deal

Thu, 4 Dec - Mon, 8 Dec

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

8h 55m1 stop

11:00 a.m. - 9:20 p.m.MDW-YHZ

8h 20m2 stops

C$ 353Porter Airlines

Find Deal

Mon, 17 Nov - Tue, 18 Nov

11:55 a.m. - 11:43 p.m.YHZ-ORD

13h 48m2 stops

6:05 a.m. - 8:10 p.m.ORD-YHZ

12h 05m2 stops

C$ 422United Airlines

Find Deal

Wed, 17 Dec - Wed, 7 Jan

8:20 a.m. - 5:19 p.m.YHZ-MDW

34h 59m2 stops

5:59 p.m. - 7:28 a.m.MDW-YHZ

35h 29m2 stops

C$ 774WestJet

Find Deal

Fri, 26 Dec - Mon, 29 Dec

Air Canada flights from Halifax to Chicago

Our best Air Canada deals on Halifax to Chicago flight tickets

Air Canada

2 Nov

YHZ5:55 a.m.Halifax Intl

6h 23m

1 stop

ORD10:18 a.m.Chicago O'Hare Intl

8 Nov

ORD7:05 a.m.Chicago O'Hare Intl

6h 42m

1 stop

YHZ3:47 p.m.Halifax Intl

C$ 231

Find similar

Air Canada

2 Nov

YHZ5:35 a.m.Halifax Intl

9h 26m

2 stops

ORD1:01 p.m.Chicago O'Hare Intl

8 Nov

ORD7:05 a.m.Chicago O'Hare Intl

6h 42m

1 stop

YHZ3:47 p.m.Halifax Intl

C$ 233

Find similar

Air Canada

2 Nov

YHZ5:35 a.m.Halifax Intl

9h 26m

2 stops

ORD1:01 p.m.Chicago O'Hare Intl

8 Nov

ORD2:00 p.m.Chicago O'Hare Intl

8h 06m

2 stops

YHZ12:06 a.m.Halifax Intl

C$ 241

Find similar

United Airlines flights from Halifax to Chicago

Our best United Airlines deals on Halifax to Chicago flight tickets

United Airlines

17 Dec

YHZ11:55 a.m.Halifax Intl

13h 48m

2 stops

ORD11:43 p.m.Chicago O'Hare Intl

7 Jan

ORD6:05 a.m.Chicago O'Hare Intl

12h 05m

2 stops

YHZ8:10 p.m.Halifax Intl

C$ 422

Find similar

United Airlines

23 Oct

YHZ1:35 p.m.Halifax Intl

7h 49m

1 stop

ORD7:24 p.m.Chicago O'Hare Intl

27 Oct

ORD9:10 p.m.Chicago O'Hare Intl

16h 01m

2 stops

YHZ3:11 p.m.Halifax Intl

C$ 627

Find similar

United Airlines

22 Oct

YHZ12:05 p.m.Halifax Intl

10h 10m

2 stops

ORD8:15 p.m.Chicago O'Hare Intl

26 Oct

ORD7:15 a.m.Chicago O'Hare Intl

5h 16m

1 stop

YHZ2:31 p.m.Halifax Intl

C$ 655

Find similar

Fly from

Fly to

Route

Depart

Return

Price

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sun 2/11

5:55 a.m.-10:18 a.m.

1 stop6h 23m

Chicago O'Hare Intl

Sat 8/11

7:05 a.m.-3:47 p.m.

1 stop6h 42m

C$ 231

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sun 2/11

5:35 a.m.-1:01 p.m.

2 stops9h 26m

Chicago O'Hare Intl

Sat 8/11

7:05 a.m.-3:47 p.m.

1 stop6h 42m

C$ 233

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sun 2/11

5:35 a.m.-1:01 p.m.

2 stops9h 26m

Chicago O'Hare Intl

Sat 8/11

2:00 p.m.-12:06 a.m.

2 stops8h 06m

C$ 241

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 17/12

6:55 a.m.-11:18 a.m.

1 stop6h 23m

Chicago O'Hare Intl

Wed 7/1

7:15 a.m.-3:47 p.m.

1 stop6h 32m

C$ 247

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 15/11

8:25 a.m.-11:50 a.m.

1 stop5h 25m

Chicago Midway

Sat 22/11

12:45 p.m.-11:49 p.m.

2 stops9h 04m

C$ 325

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 17/12

7:00 a.m.-1:01 p.m.

1 stop8h 01m

Chicago O'Hare Intl

Wed 7/1

1:55 p.m.-12:06 a.m.

2 stops8h 11m

C$ 342

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 4/12

3:15 p.m.-11:32 p.m.

1 stop10h 17m

Chicago O'Hare Intl

Mon 8/12

3:55 p.m.-11:04 a.m.

2 stops17h 09m

C$ 348

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 17/11

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

1 stop8h 55m

Chicago Midway

Tue 18/11

11:00 a.m.-9:20 p.m.

2 stops8h 20m

C$ 353

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 17/12

11:55 a.m.-11:43 p.m.

2 stops13h 48m

Chicago O'Hare Intl

Wed 7/1

6:05 a.m.-8:10 p.m.

2 stops12h 05m

C$ 422

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 26/12

8:20 a.m.-5:19 p.m.

2 stops34h 59m

Chicago Midway

Mon 29/12

5:59 p.m.-7:28 a.m.

2 stops35h 29m

C$ 774

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

Other information

What is the cheapest month to fly to Chicago?

The month of January is another great option to travel to Chicago, with average flight prices from Halifax averaging around C$ 374.

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 Monday when prices can be found for as low as C$ 441. 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 Saturday because tickets tend to average around C$ 931. 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 morning is the cheapest time of day to fly from Halifax to Chicago when you can find flight prices for as low as C$ 541. Flying to Chicago in the morning 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$ 1,209 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 Intl to Chicago flights?

There are 3 cabin classes available to choose from on Halifax Intl 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 53% 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 October 2025, prices for Halifax to Chicago flights are approximately 24% cheaper 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

Direct flights	None

There are no direct flights from Halifax to Chicago. There are no popular flight routes from Halifax to Chicago.

Search flight deals

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 5h 25m.
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 2 as of October 2025.
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 80.00% of the total bookings. Other popular models include Embraer 175 with 20.00%.
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 56% of the total bookings. Other popular airlines include Porter Airlines with 25% and United Airlines with 19%.

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
United Airlines	PriceFrom C$ 229	Free Cancellation	Rating 7.4 8,994 reviews		Search United Airlines flights
Air Canada	PriceFrom C$ 347	Free Cancellation	Rating 7.1 10,332 reviews		Search Air Canada flights

United Airlines Flights From Halifax to Chicago
The lowest priced United Airlines flight from Halifax to Chicago from the last 72 hours was C$ 163. Generally, United Airlines has 1 flight on this route every week with an average price of C$ 302. United Airlines is rated 7.4/10 by our users.
Air Canada Flights From Halifax to Chicago
Air Canada (7.1/10 from 10,332 reviews) operates around 1 flight from Halifax to Chicago in any given week. The average Air Canada airfare for this route is around C$ 407, with deals from around C$ 248 rare but found on momondo. Referenced prices are for round-trip Halifax to Chicago flight searches in the last 72 hours.

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?

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

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.

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1 adult

Tue 18/11

Tue 25/11

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Popular Cities in the United States

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Cheap flights from Halifax to Chicago from C$ 157

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 15/11. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Halifax to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last-minute flights

Air Canada flights from Halifax to Chicago

Our best Air Canada 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

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 month to fly to Chicago?

The month of January is another great option to travel to Chicago, with average flight prices from Halifax averaging around C$ 374.

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?

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 Intl to Chicago flights?

There are 3 cabin classes available to choose from on Halifax Intl 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 53% 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 October 2025, prices for Halifax to Chicago flights are approximately 24% cheaper when compared to flights at the same time last year.

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

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

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

Toronto (YYZ) was the most common stop: 80% of momondo users choosing one-stop flights on this route connected there.

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

Flights via Montreal (YUL) offer the lowest average round-trip price of C$ 272.

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

Flights connecting via Montreal (YUL) have the shortest average one-way travel time: 6h 06m.

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

Montreal (YUL) has the shortest average layover time for this route: 2h 19m.

How many flights depart from Halifax to Chicago on average per week?

As of October 2025, there are 2 flights per week flying from Halifax to Chicago. The most common day of the week flights depart is Sat, with 100% of flights taking off on this day.

When to book flights from Halifax to Chicago

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

Direct flights

How far is Halifax Intl to Chicago by plane?

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

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

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

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

What is the most popular plane model from Halifax to Chicago?

What is the most popular airline 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

United Airlines Flights From Halifax to Chicago

Air Canada Flights From Halifax to Chicago

Travelling to a place near Chicago?

Why use momondo?

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

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

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

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

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