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$109+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheapflights Tip: The best prices from Halifax Intl to Chicago are usually found in January or March, 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 September 11, 2025.

Round-trip from

$162
(Mytrip)

One-way from

$109
(Air Canada)

Popular in

July

Cheapest in

January

Average price

$405

Good round-trip deal

$207 or less

Good one-way deal

$587 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. 19% potential increase in price ($92 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 September 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 September 11, 2025.

This Mytrip deal was found by Cheapflights users on 9/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/236:10 amYHZ - MDW
2 stops12h 14mPorter Airlines
Tue 10/2811:00 amMDW - YHZ
2 stops6h 51mPorter Airlines
Deal found 9/11$162
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Sat 9/205:00 pmYHZ - ORD
Nonstop3h 48mUnited Airlines
Sat 9/274:05 pmORD - YHZ
1 stop5h 50mUnited Airlines
Deal found 9/10$167
This Air Canada deal was found by Cheapflights users on 9/10. 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.
Tue 9/235:45 amYHZ - ORD
1 stop6h 06mAir Canada
Tue 9/308:40 amORD - YHZ
1 stop5h 30mAir Canada
Deal found 9/10$168
This Air Canada deal was found by Cheapflights users on 9/10. 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.
Sat 10/255:30 pmYHZ - ORD
1 stop5h 58mAir Canada
Sat 11/17:15 amORD - YHZ
1 stop6h 42mAir Canada
Deal found 9/10$169
This American Airlines deal was found by Cheapflights users on 9/10. 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 9/204:01 pmYHZ - ORD
1 stop17h 41mAmerican Airlines
Sat 9/278:20 amORD - YHZ
Nonstop3h 10mAmerican Airlines
Deal found 9/10$173
This Air Canada deal was found by Cheapflights users on 9/10. 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.
Tue 9/235:45 amYHZ - ORD
1 stop6h 06mAir Canada
Sat 9/276:20 pmORD - YHZ
1 stop5h 29mAir Canada
Deal found 9/10$175
This Air Canada deal was found by Cheapflights users on 9/11. 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 10/235:45 amYHZ - ORD
1 stop6h 06mAir Canada
Tue 10/283:55 pmORD - YHZ
1 stop6h 11mAir Canada
Deal found 9/11$176
This United deal was found by Cheapflights users on 9/10. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/247:00 amYHZ - ORD
1 stop9h 55mMultiple Airlines
Tue 9/308:40 amORD - YHZ
1 stop5h 30mMultiple Airlines
Deal found 9/10$178
This American Airlines deal was found by Cheapflights users on 9/10. 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.
Thu 9/254:06 pmYHZ - ORD
1 stop9h 42mAmerican Airlines
Thu 10/28:20 pmORD - YHZ
1 stop15h 51mAmerican Airlines
Deal found 9/10$183
This Air Canada deal was found by Cheapflights users on 9/10. 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.
Sun 11/236:55 amYHZ - ORD
2 stops8h 06mAir Canada
Sun 11/303:55 pmORD - YHZ
1 stop6h 31mAir Canada
Deal found 9/10$186
This United Airlines deal was found by Cheapflights users on 9/10. 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.
Sat 9/205:00 pmYHZ - ORD
Nonstop3h 48mUnited Airlines
Wed 9/246:00 amORD - YHZ
1 stop6h 03mUnited Airlines
Deal found 9/10$188
This Delta deal was found by Cheapflights users on 9/10. 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.
Wed 9/246:40 amYHZ - MDW
2 stops12h 55mDelta
Tue 9/309:20 amMDW - YHZ
2 stops11h 53mDelta
Deal found 9/10$226

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 September 11, 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 - MDW

YHZMDW

Halifax Intl

Thu 10/23

6:10 am-4:24 pm

2 stops12h 14m

Chicago Midway

Tue 10/28

11:00 am-7:51 pm

2 stops6h 51m

$162

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 9/23

7:00 am-1:08 pm

1 stop8h 08m

Chicago O'Hare Intl

Wed 9/24

6:00 am-2:03 pm

1 stop6h 03m

$194

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 9/23

6:40 am-1:01 pm

2 stops8h 21m

Chicago O'Hare Intl

Tue 9/30

2:45 pm-11:13 pm

1 stop6h 28m

$225

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Mon 9/22

6:40 am-9:25 pm

2 stops16h 45m

Chicago O'Hare Intl

Tue 9/30

12:55 pm-11:13 pm

1 stop8h 18m

$225

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 9/24

6:40 am-5:35 pm

2 stops12h 55m

Chicago Midway

Tue 9/30

9:20 am-11:13 pm

2 stops11h 53m

$226

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 9/20

11:00 am-7:09 pm

2 stops10h 09m

Chicago O'Hare Intl

Wed 9/24

7:10 am-11:13 pm

2 stops14h 03m

$226

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Mon 9/22

7:00 am-9:56 pm

1 stop16h 56m

Chicago O'Hare Intl

Sat 9/27

7:10 am-10:03 pm

2 stops12h 53m

$245

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sun 9/21

6:40 am-6:46 pm

2 stops14h 06m

Chicago O'Hare Intl

Tue 9/30

11:05 am-11:13 pm

2 stops10h 08m

$253

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 9/20

11:00 am-7:09 pm

2 stops10h 09m

Chicago O'Hare Intl

Thu 9/25

7:20 am-11:13 pm

2 stops13h 53m

$253

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Mon 9/22

6:40 am-6:46 pm

2 stops14h 06m

Chicago O'Hare Intl

Sat 9/27

7:00 am-3:49 pm

1 stop6h 49m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 38 results
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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 August 29, 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 September 11, 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.

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 September 11, 2025.
Read reviews from past customers who have flown United Airlines and Air Canada 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.
United Airlines
7.4
Good
8,937 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
United Airlines
7.4
Good
8,937 reviews
United Airlines
7.4
Good
8,937 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!
Air Canada
7.1
Good
10,000 reviews
United Airlines
7.4
Good
8,937 reviews

Crew

8.1

Overall

7.4

Entertainment

7.1

Comfort

7.3

Food

6.6

Boarding

7.7

Reviews

1 / 20
2.0
Mediocre

Deb,Jan 2025

MKE - ORD

It was terrible! So much to say, but in a nutshell we used vouchers from United because our last trip with them was awful with many mishaps and errors made. Unfortunately, this trip was even worse!

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. 2 airlines 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.

  • How long is the flight from Halifax to Chicago?

    There are many flights that can get you from Halifax to Chicago in 8h 08m. Fly via Porter Airlines, United Airlines, or Delta to get the fastest option. Halifax and Chicago are separated by a distance of 1235 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

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

    Flying on American Airlines is currently your cheapest option to Chicago, with prices starting at $193. Another option worth looking into is Air Canada, starting at $202 round trip. You may be able to fly from Halifax to Chicago for 50% 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 $109 on Air Canada. Other airlines that offer cheap prices include Porter Airlines from $129 and Delta from $140 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: American Airlines (90%), Envoy Air (90%), SkyWest Airlines (67%).

  • What are the cheapest flights from Halifax to Chicago?

    On average you can expect to pay $698 for a flight from Halifax to Chicago. The cheapest flight overall is $206 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at $164.

  • 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
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Top 2 airlines flying from Halifax to Chicago

Discover the top 2 airlines 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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$193Average$193FlexibilityNo cancel feeOn-time71%
Air CanadaCheapest$202Average$480FlexibilityNo cancel feeOn-time67%

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