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

Delta, Porter Airlines, and American 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 are updated daily.

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

As of November 2025, there is 1 operator available to choose from for flights from Halifax Intl Airport to Chicago.

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

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.

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.

$172 Cheap Flights from Halifax to Chicago in 2025/26

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8:25 am - 11:50 amYHZ-MDW

5h 25m1 stop

11:00 am - 8:10 pmMDW-YHZ

7h 10m1 stop

$199Porter Airlines

Find Deal

Sat, Dec 13 - Mon, Dec 15

8:25 am - 11:50 amYHZ-MDW

5h 25m1 stop

11:00 am - 11:54 pmMDW-YHZ

10h 54m2 stops

$230Porter Airlines

Find Deal

Sat, Dec 13 - Mon, Dec 15

6:00 am - 12:48 pmYHZ-MDW

8h 48m2 stops

1:28 pm - 1:41 amMDW-YHZ

10h 13m2 stops

$289Delta

Find Deal

Tue, Mar 3 - Wed, Mar 4

8:45 am - 9:48 pmYHZ-ORD

15h 03m1 stop

12:09 pm - 5:38 pmORD-YHZ

27h 29m1 stop

$305Multiple Airlines

Find Deal

Sat, Dec 13 - Mon, Dec 15

8:45 am - 9:48 pmYHZ-ORD

15h 03m1 stop

9:14 pm - 5:38 pmORD-YHZ

18h 24m2 stops

$334Multiple Airlines

Find Deal

Sat, Dec 13 - Mon, Dec 15

6:00 am - 12:35 pmYHZ-MDW

8h 35m2 stops

1:00 pm - 1:41 amMDW-YHZ

10h 41m2 stops

$343Delta

Find Deal

Tue, Mar 3 - Wed, Mar 4

1:10 pm - 7:35 pmYHZ-ORD

8h 25m1 stop

11:40 am - 8:44 pmORD-YHZ

7h 04m1 stop

$398American Airlines

Find Deal

Thu, Apr 30 - Mon, May 4

6:30 am - 12:33 pmYHZ-ORD

8h 03m1 stop

3:04 pm - 12:22 amORD-YHZ

7h 18m1 stop

$413American Airlines

Find Deal

Sat, Dec 27 - Mon, Dec 29

5:35 am - 11:18 amYHZ-ORD

7h 43m1 stop

3:35 pm - 12:06 amORD-YHZ

6h 31m1 stop

$460Air Canada

Find Deal

Fri, Dec 26 - Fri, Jan 2

5:35 am - 11:18 amYHZ-ORD

7h 43m1 stop

7:05 am - 3:47 pmORD-YHZ

6h 42m1 stop

$462Air Canada

Find Deal

Thu, Dec 18 - Thu, Dec 25

American Airlines flights from Halifax to Chicago

Our best American Airlines deals on Halifax to Chicago flight tickets

American Airlines

Apr 30

YHZ1:10 pmHalifax Intl

8h 25m

1 stop

ORD7:35 pmChicago O'Hare Intl

May 4

ORD11:40 amChicago O'Hare Intl

7h 04m

1 stop

YHZ8:44 pmHalifax Intl

$398

Find similar

American Airlines

Dec 27

YHZ6:30 amHalifax Intl

8h 03m

1 stop

ORD12:33 pmChicago O'Hare Intl

Dec 29

ORD3:04 pmChicago O'Hare Intl

7h 18m

1 stop

YHZ12:22 amHalifax Intl

$413

Find similar

American Airlines

Dec 27

YHZ6:30 amHalifax Intl

8h 03m

1 stop

ORD12:33 pmChicago O'Hare Intl

Jan 2

ORD3:00 pmChicago O'Hare Intl

7h 22m

1 stop

YHZ12:22 amHalifax Intl

$448

Find similar

Air Canada flights from Halifax to Chicago

Our best Air Canada deals on Halifax to Chicago flight tickets

Air Canada

Dec 26

YHZ5:35 amHalifax Intl

7h 43m

1 stop

ORD11:18 amChicago O'Hare Intl

Jan 2

ORD3:35 pmChicago O'Hare Intl

6h 31m

1 stop

YHZ12:06 amHalifax Intl

$460

Find similar

Air Canada

Dec 18

YHZ5:35 amHalifax Intl

7h 43m

1 stop

ORD11:18 amChicago O'Hare Intl

Dec 25

ORD7:05 amChicago O'Hare Intl

6h 42m

1 stop

YHZ3:47 pmHalifax Intl

$462

Find similar

Air Canada

Dec 25

YHZ9:00 amHalifax Intl

10h 48m

2 stops

ORD5:48 pmChicago O'Hare Intl

Jan 1

ORD3:35 pmChicago O'Hare Intl

6h 31m

1 stop

YHZ12:06 amHalifax Intl

$466

Find similar

Fly from

Fly to

Route

Depart

Return

Price

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 12/13

8:25 am-11:50 am

1 stop5h 25m

Chicago Midway

Mon 12/15

11:00 am-8:10 pm

1 stop7h 10m

$199

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 12/13

8:25 am-11:50 am

1 stop5h 25m

Chicago Midway

Mon 12/15

11:00 am-11:54 pm

2 stops10h 54m

$230

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 3/3

6:00 am-12:48 pm

2 stops8h 48m

Chicago Midway

Wed 3/4

1:28 pm-1:41 am

2 stops10h 13m

$289

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 12/13

8:45 am-9:48 pm

1 stop15h 03m

Chicago O'Hare Intl

Mon 12/15

12:09 pm-5:38 pm

1 stop27h 29m

$305

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 12/13

8:45 am-9:48 pm

1 stop15h 03m

Chicago O'Hare Intl

Mon 12/15

9:14 pm-5:38 pm

2 stops18h 24m

$334

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 3/3

6:00 am-12:35 pm

2 stops8h 35m

Chicago Midway

Wed 3/4

1:00 pm-1:41 am

2 stops10h 41m

$343

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 4/30

1:10 pm-7:35 pm

1 stop8h 25m

Chicago O'Hare Intl

Mon 5/4

11:40 am-8:44 pm

1 stop7h 04m

$398

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 12/27

6:30 am-12:33 pm

1 stop8h 03m

Chicago O'Hare Intl

Mon 12/29

3:04 pm-12:22 am

1 stop7h 18m

$413

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 12/26

5:35 am-11:18 am

1 stop7h 43m

Chicago O'Hare Intl

Fri 1/2

3:35 pm-12:06 am

1 stop6h 31m

$460

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 12/18

5:35 am-11:18 am

1 stop7h 43m

Chicago O'Hare Intl

Thu 12/25

7:05 am-3:47 pm

1 stop6h 42m

$462

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

Other information

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Halifax, with most prices found around $260. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Halifax to Chicago during January average around $267.

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 $247. This is often the case because there is less demand to fly during this day of the week. When flying out on a Saturday, the most expensive travel day of the week, you can expect to see flight prices from Halifax to Chicago for around $448.

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

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Halifax to Chicago during this time can be as low as $377. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $414.

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?

No. A direct flight is the cheapest option for a flight between Halifax to Chicago.

How have Halifax to Chicago flight prices changed over time?

As of November 2025, prices for Halifax to Chicago flights are approximately 45% 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

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?
The distance between Halifax Intl and Chicago is about 1220.0 mi. 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 are updated daily.
How many operators does momondo search for flights from Halifax Intl Airport to Chicago?
As of November 2025, there is 1 operator available to choose from for flights from Halifax Intl Airport to Chicago.
How old do you have to be to fly from Halifax Intl Airport to Chicago?
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.
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?
momondo data reveals that the most frequently booked plane model on the route from Halifax to Chicago is Embraer 175 (Enhanced Winglets), representing 80.00% of all bookings. The subsequent popular model is Embraer 175 at 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 100% of the total bookings.

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 $182	Free Cancellation	Rating 7.1 10,398 reviews		Search Air Canada flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Schererville

Valparaiso

Crown Point

Munster

Chesterton

Monticello

Porter

Griffith

Saint John

Why use momondo?

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

It is quick and easy to find Halifax to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Flights from Halifax to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Halifax to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Halifax and alert you when they 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.

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Wed 12/10

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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

Chicago Greater Rockford Airport

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Flights to Denverfrom $47

Cheap flights from Halifax to Chicago from $172

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 4/29. 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 and deals

Big names and 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

American Airlines flights from Halifax to Chicago

Our best American Airlines 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

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 September is, on average, the cheapest month to fly to Chicago from Halifax, with most prices found around $260. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Halifax to Chicago during January average around $267.

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?

Our most recent data shows that the best time of day to fly to Chicago is in the morning. Flights from Halifax to Chicago during this time can be as low as $377. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $414.

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?

No. A direct flight is the cheapest option for a flight between Halifax to Chicago.

How have Halifax to Chicago flight prices changed over time?

As of November 2025, prices for Halifax to Chicago flights are approximately 45% more expensive when compared to flights at the same time last year.

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

Delta, Porter Airlines, and American Airlines are the most popular carriers operating from Halifax Intl to Chicago

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

Traveling 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 78.5 mi from Chicago