Which airlines fly to Chicago?

Air Canada, United Airlines and Porter Airlines are the top three most popular airlines that fly to Chicago from Halifax according to our data. Air Canada is the first choice among our users, with 61% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

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$ 271.

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.

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

As of June 2026, there are 14 flights per week flying from Halifax to Chicago. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

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

2 flights are operational daily from Halifax to Chicago as of June 2026. The most popular departure time for this route is 4:00p.m., with 100% of flights per day taking off in the afternoon.

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

Air Canada 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 3 as of June 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$ 240 Cheap Flights from Halifax to Chicago in 2026

Q: 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$ 665 to C$ 520. The lowest price recently found on this route was C$ 427.

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Halifax to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

6:25 a.m. - 10:16 a.m.

YHZ

ORD

5h 51m

1 stop

8:45 a.m. - 6:16 p.m.

ORD

YHZ

7h 31m

1 stop

C$ 427Air Canada

Tue, 25 Aug - Sat, 29 Aug

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

YHZ

MDW

9h 35m

2 stops

3:15 p.m. - 11:44 p.m.

MDW

YHZ

6h 29m

2 stops

C$ 489Porter Airlines

Sun, 16 Aug - Thu, 20 Aug

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

YHZ

MDW

8h 35m

1 stop

3:15 p.m. - 11:44 p.m.

MDW

YHZ

6h 29m

2 stops

C$ 496Porter Airlines

Sun, 16 Aug - Thu, 20 Aug

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

YHZ

ORD

8h 35m

1 stop

11:45 a.m. - 11:44 p.m.

ORD

YHZ

9h 59m

2 stops

C$ 497Porter Airlines

Thu, 24 Sep - Mon, 28 Sep

6:25 a.m. - 10:16 a.m.

YHZ

ORD

5h 51m

1 stop

8:45 a.m. - 6:16 p.m.

ORD

YHZ

7h 31m

1 stop

C$ 500Air Canada

Tue, 25 Aug - Sat, 29 Aug

6:25 a.m. - 10:16 a.m.

YHZ

ORD

5h 51m

1 stop

3:40 p.m. - 12:36 a.m.

ORD

YHZ

6h 56m

1 stop

C$ 503Air Canada

Tue, 25 Aug - Sat, 29 Aug

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

YHZ

MDW

8h 35m

1 stop

10:20 a.m. - 11:44 p.m.

MDW

YHZ

11h 24m

2 stops

C$ 503Porter Airlines

Wed, 29 Jul - Sun, 2 Aug

7:15 a.m. - 1:22 p.m.

YHZ

ORD

8h 07m

2 stops

8:45 a.m. - 4:07 p.m.

ORD

YHZ

5h 22m

1 stop

C$ 504Air Canada

Sun, 26 Jul - Sun, 2 Aug

7:00 a.m. - 12:59 p.m.

YHZ

ORD

7h 59m

1 stop

10:55 a.m. - 11:55 p.m.

ORD

YHZ

11h 00m

1 stop

C$ 510United Airlines

Wed, 23 Sep - Sat, 26 Sep

7:00 a.m. - 10:58 a.m.

YHZ

ORD

5h 58m

1 stop

12:05 p.m. - 11:55 p.m.

ORD

YHZ

9h 50m

1 stop

C$ 511United Airlines

Wed, 23 Sep - Sat, 26 Sep

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American Airlines flights from Halifax to Chicago

Our best American Airlines deals on Halifax to Chicago flight tickets

American Airlines

25 Aug

YHZ3:04 p.m.Halifax Intl

6h 25m

1 stop

ORD7:29 p.m.Chicago O'Hare Intl

29 Aug

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

6h 32m

1 stop

YHZ2:32 p.m.Halifax Intl

C$ 524

American Airlines

15 Jul

YHZ3:15 p.m.Halifax Intl

8h 20m

1 stop

ORD9:35 p.m.Chicago O'Hare Intl

22 Jul

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

6h 20m

1 stop

YHZ2:20 p.m.Halifax Intl

C$ 532

American Airlines

25 Sep

YHZ3:15 p.m.Halifax Intl

8h 45m

1 stop

ORD10:00 p.m.Chicago O'Hare Intl

28 Sep

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

6h 33m

1 stop

YHZ2:33 p.m.Halifax Intl

C$ 545

United Airlines flights from Halifax to Chicago

Our best United Airlines deals on Halifax to Chicago flight tickets

United Airlines

23 Sep

YHZ7:00 a.m.Halifax Intl

7h 59m

1 stop

ORD12:59 p.m.Chicago O'Hare Intl

26 Sep

ORD10:55 a.m.Chicago O'Hare Intl

11h 00m

1 stop

YHZ11:55 p.m.Halifax Intl

C$ 510

United Airlines

23 Sep

YHZ7:00 a.m.Halifax Intl

7h 08m

1 stop

ORD12:08 p.m.Chicago O'Hare Intl

26 Sep

ORD3:00 p.m.Chicago O'Hare Intl

6h 55m

1 stop

YHZ11:55 p.m.Halifax Intl

C$ 511

United Airlines

15 Jul

YHZ4:50 p.m.Halifax Intl

3h 53m

ORD6:43 p.m.Chicago O'Hare Intl

22 Jul

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

15h 55m

1 stop

YHZ11:55 p.m.Halifax Intl

C$ 601

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 25/8

6:25 a.m.-10:16 a.m.

1 stop5h 51m

Chicago O'Hare Intl

Sat 29/8

8:45 a.m.-6:16 p.m.

1 stop7h 31m

C$ 427

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sun 16/8

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

2 stops9h 35m

Chicago Midway

Thu 20/8

3:15 p.m.-11:44 p.m.

2 stops6h 29m

C$ 489

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sun 16/8

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

1 stop8h 35m

Chicago Midway

Thu 20/8

3:15 p.m.-11:44 p.m.

2 stops6h 29m

C$ 496

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 24/9

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

1 stop8h 35m

Chicago O'Hare Intl

Mon 28/9

11:45 a.m.-11:44 p.m.

2 stops9h 59m

C$ 497

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 25/8

6:25 a.m.-10:16 a.m.

1 stop5h 51m

Chicago O'Hare Intl

Sat 29/8

8:45 a.m.-6:16 p.m.

1 stop7h 31m

C$ 500

Quickest round-trip

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 25/8

6:25 a.m.-10:16 a.m.

1 stop5h 51m

Chicago O'Hare Intl

Sat 29/8

3:40 p.m.-12:36 a.m.

1 stop6h 56m

C$ 503

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 29/7

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

1 stop8h 35m

Chicago Midway

Sun 2/8

10:20 a.m.-11:44 p.m.

2 stops11h 24m

C$ 503

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sun 26/7

7:15 a.m.-1:22 p.m.

2 stops8h 07m

Chicago O'Hare Intl

Sun 2/8

8:45 a.m.-4:07 p.m.

1 stop5h 22m

C$ 504

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 23/9

7:00 a.m.-12:59 p.m.

1 stop7h 59m

Chicago O'Hare Intl

Sat 26/9

10:55 a.m.-11:55 p.m.

1 stop11h 00m

C$ 510

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 23/9

7:00 a.m.-10:58 a.m.

1 stop5h 58m

Chicago O'Hare Intl

Sat 26/9

12:05 p.m.-11:55 p.m.

1 stop9h 50m

C$ 511

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?

What is the cheapest month to fly to Chicago?

The month of December is another great option to travel to Chicago, with average flight prices from Halifax averaging around C$ 203.

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$ 616. 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$ 911. 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$ 767. 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$ 1,204 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 4 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 49% 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 June 2026, prices for Halifax to Chicago flights are approximately 54% 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$ 692
Fastest flight time	3h 53m
Direct flights	Every day
Airports in Chicago	3 airports

The best one-way flight to Chicago from Halifax in the past 72 hours is C$ 692. The best round-trip flight deal from Halifax to Chicago found on momondo in the last 72 hours is C$ 528.

The fastest flight from Halifax to Chicago takes 3h 53m

Direct flights go from Halifax to Chicago every day.

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

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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 53m.
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 3 as of June 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 72.73% of the total bookings. Other popular models include Embraer 175 with 27.27%.
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 24%, WestJet with 15%, and United Airlines with 14%.

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$ 228	Free Cancellation	Rating 7.4 9,809 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 289	Free Cancellation	Rating 7.1 11,165 reviews	Search Air Canada flights
Porter Airlines	PriceFrom C$ 472	Free Cancellation	Rating 8.0 438 reviews	Search Porter Airlines 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$ 228. Generally, United Airlines has 7 flights on this route every week with an average price of C$ 228. United Airlines is rated 7.4/10 by our users.
Air Canada Flights From Halifax to Chicago
Air Canada (7.1/10 from 11,168 reviews) operates around 7 flights from Halifax to Chicago in any given week. The average Air Canada airfare for this route is around C$ 693, with deals from around C$ 289 rare but found on momondo. Referenced prices are for round-trip Halifax to Chicago flight searches in the last 72 hours.

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?

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$ 240

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 25/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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American Airlines flights from Halifax to Chicago

Our best American 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

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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 airlines fly 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 day?

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

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

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

United Airlines Flights From Halifax to Chicago

Air Canada Flights From Halifax to Chicago

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.

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

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