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$197+ Cheap flights from Halifax (YHZ) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
1 adult, Economy
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Cheapflights Tip: The best prices from Halifax Intl to Chicago are usually found in January or February, booked 51 days in advance, depart on a Saturday or Tuesday and return on a Monday

Cheap flight deals from Halifax to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Halifax (YHZ) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated July 30, 2025.

Round-trip from

$357
(Delta)

One-way from

$197
(Kiwi.com)

Popular in

June

Cheapest in

January

Average price

$460

Good round-trip deal

$352 or less

Good one-way deal

$216 or less
From Halifax Intl to Chicago (CHI)
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One-way flight from Halifax Intl to Chicago (CHI)
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Highest demand for flights based on searches. 11% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in July 2025
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Price to beat on a round-trip flight from Halifax Intl to Chicago (CHI).
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Price to beat on a one-way flight from Halifax Intl to Chicago (CHI).
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Find flight deals from Halifax to Chicago

Cheapest flights from Halifax to Chicago
Explore the most affordable flight options available from Halifax to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 30, 2025.

This Delta deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/186:40 amYHZ - ORD
1 stop8h 25mDelta
Tue 9/2311:05 amORD - YHZ
2 stops10h 08mDelta
Deal found 7/29$357
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/278:20 amYHZ - MDW
1 stop10h 04mMultiple Airlines
Wed 9/39:35 amMDW - YHZ
1 stop11h 04mMultiple Airlines
Deal found 7/29$366
This Air Canada deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/45:45 amYHZ - ORD
1 stop6h 06mAir Canada
Thu 9/118:40 amORD - YHZ
1 stop5h 30mAir Canada
Deal found 7/29$381
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/136:30 amYHZ - ORD
2 stops17h 28mMultiple Airlines
Sat 9/206:30 amORD - YHZ
1 stop9h 06mMultiple Airlines
Deal found 7/29$384
This American Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/134:01 pmYHZ - ORD
1 stop22h 01mAmerican Airlines
Sat 9/208:20 amORD - YHZ
Nonstop3h 10mAmerican Airlines
Deal found 7/29$386
This Trip.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/278:20 amYHZ - MDW
1 stop10h 04mPorter Airlines
Wed 9/39:35 amMDW - YHZ
2 stops12h 05mPorter Airlines
Deal found 7/29$393
This FlightHub deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/198:30 amYHZ - ORD
2 stops12h 16mWestJet
Wed 9/247:55 amORD - YHZ
2 stops12h 44mWestJet
Deal found 7/29$470
This FlightHub deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/198:30 amYHZ - MDW
2 stops15h 06mWestJet
Wed 9/2412:43 pmMDW - YHZ
2 stops16h 30mWestJet
Deal found 7/29$503
This United Airlines deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:55 amYHZ - ORD
2 stops13h 40mUnited Airlines
Thu 1/11:37 pmORD - YHZ
1 stop8h 13mUnited Airlines
Deal found 7/29$540
This Delta deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/28:30 amYHZ - MDW
2 stops12h 10mDelta
Tue 8/510:30 amMDW - YHZ
2 stops10h 59mDelta
Deal found 7/30$840

Cheapflights Fare Finder

 
Customize your flight search to find flights from Halifax to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 30, 2025.
Use the filters below to find and compare flights from Halifax to Chicago that are best for you.

Fly from

Halifax

Fly to

Chicago

Route

Depart

Return

Price

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 9/18

6:40 am-1:05 pm

1 stop8h 25m

Chicago O'Hare Intl

Tue 9/23

11:05 am-11:13 pm

2 stops10h 08m

$357

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 8/27

8:20 am-4:24 pm

1 stop10h 04m

Chicago Midway

Wed 9/3

9:35 am-10:39 pm

1 stop11h 04m

$366

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 9/4

5:45 am-9:51 am

1 stop6h 06m

Chicago O'Hare Intl

Thu 9/11

8:40 am-4:10 pm

1 stop5h 30m

$381

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 9/13

6:30 am-9:58 pm

2 stops17h 28m

Chicago O'Hare Intl

Sat 9/20

6:30 am-5:36 pm

1 stop9h 06m

$384

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 9/13

4:01 pm-12:02 pm

1 stop22h 01m

Chicago O'Hare Intl

Sat 9/20

8:20 am-1:30 pm

Nonstop3h 10m

$386

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 8/27

8:20 am-4:24 pm

1 stop10h 04m

Chicago Midway

Wed 9/3

9:35 am-11:40 pm

2 stops12h 05m

$393

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 9/19

8:30 am-6:46 pm

2 stops12h 16m

Chicago O'Hare Intl

Wed 9/24

7:55 am-10:39 pm

2 stops12h 44m

$470

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 9/19

8:30 am-9:36 pm

2 stops15h 06m

Chicago Midway

Wed 9/24

12:43 pm-7:13 am

2 stops16h 30m

$503

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 12/25

11:55 am-11:35 pm

2 stops13h 40m

Chicago O'Hare Intl

Thu 1/1

1:37 pm-11:50 pm

1 stop8h 13m

$540

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 10/25

9:00 am-9:58 pm

1 stop14h 58m

$197

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/29

Showing 1-10 of 18 results
1
2

Best time to book a flight from Halifax to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Halifax with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Halifax to Chicago

How far ahead should I book a flight from Halifax to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Halifax to Chicago. Price data was last updated on July 25, 2025.

To ensure you get the cheapest price possible for a flight from Halifax to Chicago, you should look to book at least 50 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

What is the cheapest month to book a flight from Halifax to Chicago?

Currently, August is the cheapest month in which you can book a flight from Halifax to Chicago (average of $245). Flying from Halifax to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from YHZ to CHI?

Find hourly flight availability from Halifax to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 30, 2025.

One of the essential ways to save on airfare from Halifax to Chicago is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight at noon could potentially save you up to 7% on airfare.

How much does it cost to fly round-trip from Halifax to Chicago?

What’s the top layover airport for flights from Halifax to Chicago?

Share of 1-stop round-trip flights from Halifax to Chicago chosen by Cheapflights users in the past 12 months, using the same layover each way.

Toronto (YYZ) – chosen by Cheapflights users on 94% of 1-stop itineraries from Halifax to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Halifax to Chicago?

Average round-trip fare for 1-stop flights from Halifax to Chicago, chosen by Cheapflights users in the past 12 months, with the same layover each way.

Toronto (YYZ) is the most affordable 1-stop option, with an average round-trip price of $283.

What’s the fastest layover option from Halifax to Chicago?

Shortest average travel time for 1-stop one-way flights from Halifax to Chicago, based on itineraries clicked by Cheapflights users over the past 12 months, grouped by layover airport.

Flights via Montreal (YUL) have the shortest average one-way travel time for 1-stop routes: 5h 25m.

Which airport typically offers the quickest layover for flights from Halifax to Chicago?

Average layover duration for 1-stop one-way flights from Halifax to Chicago, chosen by Cheapflights users in the last 12 months, grouped by stopover airport.

Flights via Montreal (YUL) offer the fastest connection on this route, with an average layover time of 2h 04m.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated July 30, 2025.
Read reviews from past customers who have flown Porter Airlines, Delta, and United Airlines from Halifax to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
318 reviews

Food

7.6

Boarding

8.2

Comfort

8.0

Crew

8.7

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Porter Airlines
8.0
Very good
318 reviews
Porter Airlines
8.0
Very good
318 reviews

Food

7.6

Boarding

8.2

Comfort

8.0

Crew

8.7

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
Delta
8.0
Very good
7,980 reviews
Porter Airlines
8.0
Very good
318 reviews

Food

7.6

Boarding

8.2

Comfort

8.0

Crew

8.7

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
United Airlines
7.4
Good
8,896 reviews
Porter Airlines
8.0
Very good
318 reviews

Food

7.6

Boarding

8.2

Comfort

8.0

Crew

8.7

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
318 reviews

Food

7.6

Boarding

8.2

Comfort

8.0

Crew

8.7

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience
WestJet
7.2
Good
2,975 reviews
Porter Airlines
8.0
Very good
318 reviews

Food

7.6

Boarding

8.2

Comfort

8.0

Crew

8.7

Overall

8.0

Entertainment

7.0

Reviews

1 / 20
8.0
Excellent

Anonymous,Jul 2025

LIS - YYZ

Everything was on time and easy. Crew were nice on flights and helpful. International flight, so long and typically uncomfortable but not more than most. Food and drink service were below average but you get what you pay for. Overall, good experience

Related info for your journey

Find useful and relevant information for your journey from Halifax to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Halifax to Chicago?

    Halifax Intl (YHZ), located 16.7 mi from the city center, is the airport you fly out of when you book flights from Halifax to Chicago. 1 airline have flights from Halifax Intl to Chicago on a regular basis. Booking flights from Halifax Intl to Chicago should not be difficult; the airport handles an average of 0 outbound flights to Chicago per day.

  • What are the cheapest airlines flying from Halifax to Chicago round-trip?

    Flying on Delta is currently your cheapest option to Chicago, with prices starting at $357. Additional round-trip tickets that might be worth considering are offered by Air Canada and American Airlines, with the lowest prices starting at $381 and $386, respectively. You may be able to fly from Halifax to Chicago for 7% less than the average price by searching for these airlines.

  • What are the cheapest airlines to fly from Halifax to Chicago one-way?

    One-way options have recently been found by users for as low as $215 on Air Canada. Other airlines that offer cheap prices include Delta from $217 and WestJet from $243 one-way.

  • What are the most reliable airlines from Halifax to Chicago?

    Looking for the most reliable airlines to get you to your destination on time? Our data shows these are most likely to get you from Halifax to Chicago on time: SkyWest Airlines (100%), American Airlines (100%), Air Canada (100%).

  • What are the cheapest flights from Halifax to Chicago?

    On average you can expect to pay $284 for a flight from Halifax to Chicago. The cheapest flight overall is $208 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at $357.

  • Can I find deals for flights from Halifax to Chicago that include hotel bookings?

    Yes. In addition to deals on Halifax to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Halifax to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Halifax to Chicago.

  • Can I find deals for business class flights from Halifax to Chicago?

    Yes. Cheapflights offers flight deals from Halifax to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Halifax to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Halifax to Chicago (average of $245). Flying from Halifax to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Valparaiso
Chesterton

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Top airline flying from Halifax to Chicago

Discover the top airline that operate flights from Halifax to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$255Average$481FlexibilityNo cancel feeOn-time67%

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