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$180+ 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 7/8. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
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 Friday 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 June 12, 2025.

Round-trip from

$289
(American Airlines)

One-way from

$180
(Mytrip)

Popular in

June

Cheapest in

January

Average price

$472

Good one-way deal

$175 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. 10% potential increase in price ($44 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 June 2025
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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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/182:15 pmYHZ - ORD
2 stops10h 37mAmerican Airlines
Sat 7/198:09 amORD - YHZ
Nonstop3h 05mAmerican Airlines
Deal found 6/11$289
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/311:00 pmYHZ - MDW
1 stop11h 45mMultiple Airlines
Tue 7/89:40 amMDW - YHZ
1 stop10h 35mMultiple Airlines
Deal found 6/10$362
This Delta deal was found by Cheapflights users on 6/10. 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 8/136:40 amYHZ - ORD
2 stops27h 24mDelta
Wed 8/207:15 amORD - YHZ
2 stops14h 13mDelta
Deal found 6/10$382
This Mytrip deal was found by Cheapflights users on 6/10. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/312:00 pmYHZ - ORD
2 stops34h 23mMultiple Airlines
Tue 7/87:49 pmORD - YHZ
2 stops25h 35mMultiple Airlines
Deal found 6/10$402
This Gotogate deal was found by Cheapflights users on 6/10. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/39:15 amYHZ - MDW
2 stops9h 09mPorter Airlines
Tue 7/89:40 amMDW - YHZ
2 stops11h 44mPorter Airlines
Deal found 6/10$403
This Air Canada deal was found by Cheapflights users on 6/10. 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.
Mon 8/185:45 amYHZ - ORD
1 stop6h 07mAir Canada
Tue 10/78:40 amORD - YHZ
1 stop5h 20mAir Canada
Deal found 6/10$424
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Mon 8/115:05 amYHZ - ORD
2 stops15h 36mUnited Airlines
Tue 8/196:00 amORD - YHZ
1 stop6h 03mUnited Airlines
Deal found 6/10$476
This FlightHub deal was found by Cheapflights users on 6/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/266:40 amYHZ - ORD
1 stop8h 29mWestJet
Sat 8/306:10 amORD - YHZ
2 stops23h 05mWestJet
Deal found 6/11$487
This oojo deal was found by Cheapflights users on 6/11. 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 oojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/108:05 pmYHZ - MDW
2 stops15h 46mWestJet
Tue 10/142:00 pmMDW - YHZ
2 stops15h 13mWestJet
Deal found 6/11$492

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 June 12, 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

Fri 7/18

2:15 pm-10:52 pm

2 stops10h 37m

Chicago O'Hare Intl

Sat 7/19

8:09 am-1:14 pm

Nonstop3h 05m

$289

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 7/3

11:00 pm-8:45 am

1 stop11h 45m

Chicago Midway

Tue 7/8

9:40 am-10:15 pm

1 stop10h 35m

$362

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 8/13

6:40 am-8:04 am

2 stops27h 24m

Chicago O'Hare Intl

Tue 8/19

7:15 am-11:28 pm

2 stops14h 13m

$382

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 7/3

12:00 pm-8:23 pm

2 stops34h 23m

Chicago O'Hare Intl

Tue 7/8

7:49 pm-11:24 pm

2 stops25h 35m

$402

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 7/3

9:15 am-4:24 pm

2 stops9h 09m

Chicago Midway

Tue 7/8

9:40 am-11:24 pm

2 stops11h 44m

$403

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Mon 8/18

5:45 am-9:52 am

1 stop6h 07m

Chicago O'Hare Intl

Tue 10/7

10:40 am-7:18 pm

1 stop6h 38m

$424

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Mon 8/11

5:05 am-6:41 pm

2 stops15h 36m

Chicago O'Hare Intl

Tue 8/19

6:00 am-2:03 pm

1 stop6h 03m

$476

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 8/26

6:40 am-1:09 pm

1 stop8h 29m

Chicago O'Hare Intl

Sat 8/30

6:10 am-7:15 am

2 stops23h 05m

$487

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 10/10

8:05 pm-9:51 am

2 stops15h 46m

Chicago Midway

Tue 10/14

2:00 pm-7:13 am

2 stops15h 13m

$492

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 7/8

11:00 pm-8:45 am

1 stop11h 45m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 18 results
1
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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 June 9, 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 June 12, 2025.

One of the essential ways to save on airfare from Halifax to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the afternoon could potentially save you up to 40% on airfare.

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Porter Airlines
8.0
Very good
288 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Porter Airlines
8.0
Very good
288 reviews
Porter Airlines
8.0
Very good
288 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
Delta
8.0
Very good
7,950 reviews
Porter Airlines
8.0
Very good
288 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
United Airlines
7.4
Good
8,790 reviews
Porter Airlines
8.0
Very good
288 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
American Airlines
7.2
Good
10,000 reviews
Porter Airlines
8.0
Very good
288 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!
WestJet
7.2
Good
2,868 reviews
Porter Airlines
8.0
Very good
288 reviews

Food

7.6

Boarding

8.2

Crew

8.7

Entertainment

7.0

Comfort

8.1

Overall

8.0

Reviews

1 / 20
4.0
Okay

Mary,Jun 2025

FLL - YYZ

Fort Lauderdale staff was not helpful at all to try to accommodate my husband and myself to sit together. Also very surprised to get charged USD53 for each of our checked luggage, as when we booked the tickets online, the website indicated that our first checked luggage will be charged CAD50!! Very misleading!!!

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 American Airlines is currently your cheapest option to Chicago, with prices starting at $289. Additional round-trip tickets that might be worth considering are offered by Delta and Porter Airlines, with the lowest prices starting at $382 and $403, respectively. You may be able to fly from Halifax to Chicago for 23% 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 $225 on Porter Airlines. Other airlines that offer cheap prices include Air Canada from $237 and American Airlines from $238 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%), Air Canada (100%), United Airlines (100%).

  • What are the cheapest flights from Halifax to Chicago?

    On average you can expect to pay $302 for a flight from Halifax to Chicago. The cheapest flight overall is $174 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at $394.

  • 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 Halifax?

Book flights to Halifax if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapest$255Average$506FlexibilityNo cancel feeOn-time67%

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