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

WestJet is the most popular carrier 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 December 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.

$159 Cheap Flights from Halifax to Chicago in 2025/26

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 $243 to $412. The lowest price recently found on this route was $238.

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7:00 am - 3:20 pm

YHZ

MDW

10h 20m2 stops

11:00 am - 8:05 pm

MDW

YHZ

7h 05m1 stop

$238Porter Airlines

Tue, Apr 14 - Wed, Apr 15

7:00 am - 3:20 pm

YHZ

MDW

10h 20m2 stops

11:00 am - 8:05 pm

MDW

YHZ

7h 05m1 stop

$246Porter Airlines

Tue, Apr 14 - Wed, Apr 15

8:30 am - 3:20 pm

YHZ

MDW

8h 50m1 stop

11:00 am - 8:05 pm

MDW

YHZ

7h 05m1 stop

$274Porter Airlines

Tue, Apr 14 - Wed, Apr 15

8:30 am - 3:20 pm

YHZ

MDW

8h 50m1 stop

11:00 am - 8:05 pm

MDW

YHZ

7h 05m1 stop

$282Porter Airlines

Tue, Apr 14 - Wed, Apr 15

7:00 am - 3:20 pm

YHZ

MDW

10h 20m2 stops

11:00 am - 11:54 pm

MDW

YHZ

10h 54m2 stops

$295Porter Airlines

Tue, Apr 14 - Wed, Apr 15

8:25 am - 3:20 pm

YHZ

MDW

8h 55m2 stops

11:00 am - 8:05 pm

MDW

YHZ

7h 05m1 stop

$299Porter Airlines

Tue, Apr 14 - Wed, Apr 15

8:30 am - 3:20 pm

YHZ

MDW

8h 50m1 stop

11:00 am - 9:05 pm

MDW

YHZ

8h 05m2 stops

$324Porter Airlines

Thu, Apr 2 - Sun, Apr 5

8:45 am - 5:52 pm

YHZ

ORD

11h 07m1 stop

8:43 pm - 9:55 pm

ORD

YHZ

23h 12m2 stops

$339Multiple Airlines

Mon, Jan 12 - Thu, Jan 15

6:00 am - 4:57 pm

YHZ

ORD

12h 57m2 stops

5:35 pm - 1:41 am

ORD

YHZ

30h 06m2 stops

$394WestJet

Wed, Jan 21 - Sat, Jan 24

6:00 am - 9:41 am

YHZ

ORD

29h 41m2 stops

12:15 pm - 1:41 am

ORD

YHZ

11h 26m2 stops

$409WestJet

Tue, Jan 13 - Tue, Jan 20

WestJet flights from Halifax to Chicago

Our best WestJet deals on Halifax to Chicago flight tickets

WestJet

Jan 21

YHZ6:00 amHalifax Intl

12h 57m

2 stops

ORD4:57 pmChicago O'Hare Intl

Jan 24

ORD5:35 pmChicago O'Hare Intl

30h 06m

2 stops

YHZ1:41 amHalifax Intl

$394

Find similar

WestJet

Jan 13

YHZ6:00 amHalifax Intl

29h 41m

2 stops

ORD9:41 amChicago O'Hare Intl

Jan 20

ORD12:15 pmChicago O'Hare Intl

11h 26m

2 stops

YHZ1:41 amHalifax Intl

$409

Find similar

WestJet

Jan 17

YHZ6:00 amHalifax Intl

14h 58m

2 stops

ORD6:58 pmChicago O'Hare Intl

Jan 24

ORD10:35 amChicago O'Hare Intl

13h 06m

2 stops

YHZ1:41 amHalifax Intl

$419

Find similar

Air Canada flights from Halifax to Chicago

Our best Air Canada deals on Halifax to Chicago flight tickets

Air Canada

Mar 12

YHZ5:35 amHalifax Intl

7h 43m

1 stop

ORD11:18 amChicago O'Hare Intl

Mar 15

ORD3:35 pmChicago O'Hare Intl

6h 46m

1 stop

YHZ12:21 amHalifax Intl

$473

Find similar

Air Canada

Mar 12

YHZ6:55 amHalifax Intl

6h 23m

1 stop

ORD11:18 amChicago O'Hare Intl

Mar 15

ORD3:35 pmChicago O'Hare Intl

6h 46m

1 stop

YHZ12:21 amHalifax Intl

$474

Find similar

Air Canada

Apr 2

YHZ5:35 amHalifax Intl

9h 25m

2 stops

ORD1:00 pmChicago O'Hare Intl

Apr 5

ORD8:40 amChicago O'Hare Intl

5h 10m

1 stop

YHZ3:50 pmHalifax Intl

$485

Find similar

Fly from

Fly to

Route

Depart

Return

Price

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

7:00 am-3:20 pm

2 stops10h 20m

Chicago Midway

Wed 4/15

11:00 am-8:05 pm

1 stop7h 05m

$238

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

7:00 am-3:20 pm

2 stops10h 20m

Chicago Midway

Wed 4/15

11:00 am-8:05 pm

1 stop7h 05m

$246

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

8:30 am-3:20 pm

1 stop8h 50m

Chicago Midway

Wed 4/15

11:00 am-8:05 pm

1 stop7h 05m

$274

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

8:30 am-3:20 pm

1 stop8h 50m

Chicago Midway

Wed 4/15

11:00 am-8:05 pm

1 stop7h 05m

$282

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

7:00 am-3:20 pm

2 stops10h 20m

Chicago Midway

Wed 4/15

11:00 am-11:54 pm

2 stops10h 54m

$295

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 4/14

8:25 am-3:20 pm

2 stops8h 55m

Chicago Midway

Wed 4/15

11:00 am-8:05 pm

1 stop7h 05m

$299

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 4/2

8:30 am-3:20 pm

1 stop8h 50m

Chicago Midway

Sun 4/5

11:00 am-9:05 pm

2 stops8h 05m

$324

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Mon 1/12

8:45 am-5:52 pm

1 stop11h 07m

Chicago O'Hare Intl

Thu 1/15

8:43 pm-9:55 pm

2 stops23h 12m

$339

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 1/21

6:00 am-4:57 pm

2 stops12h 57m

Chicago O'Hare Intl

Sat 1/24

5:35 pm-1:41 am

2 stops30h 06m

$394

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 1/13

6:00 am-9:41 am

2 stops29h 41m

Chicago O'Hare Intl

Tue 1/20

12:15 pm-1:41 am

2 stops11h 26m

$409

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

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 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 $280.

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?

You could potentially save up to 44% 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 December 2025, prices for Halifax to Chicago flights are approximately 7% 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

Fastest flight time	7h 55m
Direct flights	Mon, Tue, Wed, Fri, Sat and Sun
Airports in Chicago	3 airports

The fastest flight from Halifax to Chicago takes 7h 55m

Direct flights go from Halifax to Chicago on Monday, Tuesday, Wednesday, Friday, Saturday and 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

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 7h 55m.
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 December 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 50.00% of all bookings. The subsequent popular model is Embraer 175 at 50.00%.
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 61% of the total bookings. Other popular airlines include United Airlines with 39%.

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 10,534 reviews		Search Air Canada flights

Merrillville

New Buffalo

Hammond

Benton Harbor

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

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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Sat 1/17

Sat 1/24

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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

Popular cities in the United States

Flights to New Yorkfrom $45

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Flights to San Franciscofrom $58

Flights to Las Vegasfrom $49

Flights to Washington, D.C.from $57

Flights to Bostonfrom $51

Flights to Atlantafrom $46

Flights to Dallasfrom $57

Flights to Seattlefrom $58

Flights to Denverfrom $53

Cheap flights from Halifax to Chicago from $159

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 6/16. 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

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WestJet flights from Halifax to Chicago

Our best WestJet 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

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 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 $280.

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?

You could potentially save up to 44% 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 December 2025, prices for Halifax to Chicago flights are approximately 7% cheaper when compared to flights at the same time last year.

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

WestJet is the most popular carrier 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

Fastest flight time

Direct flights

Airports in Chicago

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