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 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 offers the lowest fares from Halifax to Chicago?

Flights via Montreal (YUL) offer the lowest average round-trip price of C$ 270.

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

As of August 2026, there are 4 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 has the shortest travel time from Halifax to Chicago?

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

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

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 August 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$ 267 Cheap Flights from Halifax to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Halifax to Chicago

Round-trip

One-way

Last minute

Direct

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Enter your travel dates to find the best prices.

6:25 a.m. - 10:15 a.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

5h 50m1 stop Montreal Pierre Elliott Trudeau Intl

5:35 p.m. - 1:54 a.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

6h 19m1 stop Toronto Pearson Intl

C$ 498Air Canada

Fri, 25 Sep - Mon, 5 Oct

5:15 a.m. - 9:00 a.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

5h 45m1 stop Toronto Pearson Intl

3:45 p.m. - 12:49 a.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

7h 04m1 stop Toronto Pearson Intl

C$ 503Air Canada

Fri, 25 Sep - Mon, 5 Oct

6:25 a.m. - 10:17 a.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

5h 52m1 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$ 514Air Canada

Sun, 11 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

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$ 514Air 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

12:50 p.m. - 10:38 p.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

7h 48m1 stop Toronto Pearson Intl

C$ 521Air 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$ 523Air Canada

Sat, 13 Feb - Mon, 15 Feb

7:00 a.m. - 2:35 p.m.YHZ Halifax Intl-MDW Chicago Midway

9h 35m2 stops Ottawa Toronto Island

3:20 p.m. - 11:49 p.m.MDW Chicago Midway-YHZ Halifax Intl

6h 29m2 stops Toronto Island Ottawa

C$ 527Porter Airlines

Fri, 25 Sep - Mon, 5 Oct

7:00 a.m. - 2:35 p.m.YHZ Halifax Intl-MDW Chicago Midway

9h 35m2 stops Ottawa Toronto Island

3:20 p.m. - 11:49 p.m.MDW Chicago Midway-YHZ Halifax Intl

6h 29m2 stops Toronto Island Ottawa

C$ 528Porter Airlines

Fri, 25 Sep - Mon, 5 Oct

7:00 a.m. - 2:35 p.m.YHZ Halifax Intl-MDW Chicago Midway

9h 35m2 stops Ottawa Toronto Island

3:20 p.m. - 11:49 p.m.MDW Chicago Midway-YHZ Halifax Intl

6h 29m2 stops Toronto Island Ottawa

C$ 530Porter Airlines

Fri, 25 Sep - Mon, 5 Oct

2:50 p.m. - 12:28 a.m.YHZ Halifax Intl-ORD Chicago O'Hare Intl

11h 38m1 stop Newark

1:30 p.m. - 11:55 p.m.ORD Chicago O'Hare Intl-YHZ Halifax Intl

8h 25m1 stop Newark

C$ 532United Airlines

Tue, 15 Sep - Wed, 16 Sep

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Delta flights from Halifax to Chicago

Our best Delta deals on Halifax to Chicago flight tickets

Delta

18 Sep

YHZ3:30 p.m.Halifax Intl

7h 00m

1 stop

ORD8:30 p.m.Chicago O'Hare Intl

21 Sep

ORD8:55 a.m.Chicago O'Hare Intl

10h 30m

2 stops

YHZ9:25 p.m.Halifax Intl

C$ 627

Delta

25 Sep

YHZ3:30 p.m.Halifax Intl

5h 03m

1 stop

MDW6:33 p.m.Chicago Midway

5 Oct

MDW9:29 a.m.Chicago Midway

9h 41m

1 stop

YHZ9:10 p.m.Halifax Intl

C$ 641

Delta

25 Sep

YHZ3:30 p.m.Halifax Intl

5h 03m

1 stop

MDW6:33 p.m.Chicago Midway

5 Oct

MDW9:29 a.m.Chicago Midway

9h 41m

1 stop

YHZ9:10 p.m.Halifax Intl

C$ 642

Air Canada flights from Halifax to Chicago

Our best Air Canada deals on Halifax to Chicago flight tickets

Air Canada

25 Sep

YHZ6:25 a.m.Halifax Intl

5h 50m

1 stop

ORD10:15 a.m.Chicago O'Hare Intl

5 Oct

ORD5:35 p.m.Chicago O'Hare Intl

6h 19m

1 stop

YHZ1:54 a.m.Halifax Intl

C$ 498

Air Canada

25 Sep

YHZ5:15 a.m.Halifax Intl

5h 45m

1 stop

ORD9:00 a.m.Chicago O'Hare Intl

5 Oct

ORD3:45 p.m.Chicago O'Hare Intl

7h 04m

1 stop

YHZ12:49 a.m.Halifax Intl

C$ 503

Air Canada

13 Feb

YHZ5:10 a.m.Halifax Intl

7h 57m

1 stop

ORD11:07 a.m.Chicago O'Hare Intl

15 Feb

ORD3:45 p.m.Chicago O'Hare Intl

6h 10m

1 stop

YHZ11:55 p.m.Halifax Intl

C$ 514

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 25/9

6:25 a.m.-10:15 a.m.

1 stop5h 50m

Chicago O'Hare Intl

Mon 5/10

5:35 p.m.-1:54 a.m.

1 stop6h 19m

C$ 498

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 25/9

5:15 a.m.-9:00 a.m.

1 stop5h 45m

Chicago O'Hare Intl

Mon 5/10

3:45 p.m.-12:49 a.m.

1 stop7h 04m

C$ 503

Quickest round-trip

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sun 11/10

6:25 a.m.-10:17 a.m.

1 stop5h 52m

Chicago O'Hare Intl

Sun 18/10

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

1 stop5h 17m

C$ 514

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$ 514

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

12:50 p.m.-10:38 p.m.

1 stop7h 48m

C$ 521

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$ 523

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Fri 25/9

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

2 stops9h 35m

Chicago Midway

Mon 5/10

3:20 p.m.-11:49 p.m.

2 stops6h 29m

C$ 527

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Fri 25/9

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

2 stops9h 35m

Chicago Midway

Mon 5/10

3:20 p.m.-11:49 p.m.

2 stops6h 29m

C$ 528

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Fri 25/9

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

2 stops9h 35m

Chicago Midway

Mon 5/10

3:20 p.m.-11:49 p.m.

2 stops6h 29m

C$ 530

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Tue 15/9

2:50 p.m.-12:28 a.m.

1 stop11h 38m

Chicago O'Hare Intl

Wed 16/9

1:30 p.m.-11:55 p.m.

1 stop8h 25m

C$ 532

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

Prices are currently typical for flights on this route.

Typical prices usually range from C$ 353 to C$ 520.
The lowest price recently found on this route was C$ 498.

What is the cheapest month to fly to Chicago?

The month of November is another great option to travel to Chicago, with average flight prices from Halifax averaging around C$ 460.

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$ 517. 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$ 882. 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$ 775. 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$ 1,730 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 August 2026, prices for Halifax to Chicago flights are approximately 57% 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$ 267
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$ 267. The best round-trip flight deal from Halifax to Chicago found on momondo in the last 72 hours is C$ 498.

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

Direct flights go from Halifax to Chicago on Sunday. The only airline offering direct flights is United Airlines.

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 August 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 26%, WestJet with 14%, and United Airlines with 12%.

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$ 268	Free Cancellation	Rating 7.1 11,555 reviews		Search Air Canada flights

Air Canada Flights From Halifax to Chicago
The lowest priced Air Canada flight from Halifax to Chicago from the last 72 hours was C$ 268. Generally, Air Canada has 1 flight on this route every week with an average price of C$ 611. Air Canada is rated 7.1/10 by our users.

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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.

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Cheap flights from Halifax to Chicago from C$ 267

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 21/9. 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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Delta flights from Halifax to Chicago

Our best Delta deals on Halifax to Chicago flight tickets

Air Canada flights from Halifax to Chicago

Our best Air Canada deals on Halifax to Chicago flight tickets

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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?

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

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

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According to popular flight searches on momondo this year

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