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Cheap flights from Halifax to Chicago from C$ 151

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 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
16 Oct — 23 Oct1
1 adult
1 adult, Economy

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 Monday or Wednesday and return on a Wednesday

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 16 September 2025.

Round-trip from

C$ 242

One-way from

C$ 151

Popular in

October

Cheapest in

January

Average price

C$ 562

Good round-trip deal

C$ 652 or less

Good one-way deal

C$ 637 or less
Air Canada
  • Air Canada
  • 23/11-30/11
  • 2 total stops
  • 14h 14m total
  • Halifax to Chicago
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Air Canada
  • Air Canada
  • 11/11
  • 1 total stop
  • 7h 43m total
  • Halifax to Chicago
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Highest demand for flights based on searches. 6% potential increase in price (C$ 53 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease (C$ 23 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 16 September 2025.

Sun 23/115:35 a.m.YHZ - ORD
1 stop7h 43mAir Canada
Sun 30/113:55 p.m.ORD - YHZ
1 stop6h 31mAir Canada
Deal found 14/9C$ 242
Mon 10/117:00 a.m.YHZ - ORD
1 stop8h 01mAir Canada
Sat 29/1110:00 a.m.ORD - YHZ
1 stop5h 41mAir Canada
Deal found 13/9C$ 251
Thu 25/94:06 p.m.YHZ - ORD
1 stop9h 42mAmerican Airlines
Thu 2/107:00 a.m.ORD - YHZ
1 stop5h 11mAmerican Airlines
Deal found 14/9C$ 253
Sat 18/105:25 a.m.YHZ - ORD
1 stop5h 44mAir Canada
Tue 21/108:40 a.m.ORD - YHZ
1 stop5h 30mAir Canada
Deal found 15/9C$ 269
Wed 22/105:45 a.m.YHZ - ORD
1 stop6h 06mAir Canada
Wed 29/1010:00 a.m.ORD - YHZ
1 stop8h 10mAir Canada
Deal found 15/9C$ 285
Wed 22/109:15 a.m.YHZ - MDW
2 stops9h 09mPorter Airlines
Wed 29/1011:00 a.m.MDW - YHZ
2 stops10h 54mPorter Airlines
Deal found 15/9C$ 304
Thu 25/96:40 a.m.YHZ - ORD
2 stops11h 51mDelta
Thu 2/106:45 a.m.ORD - YHZ
2 stops14h 28mDelta
Deal found 14/9C$ 312
Sun 9/118:30 a.m.YHZ - MDW
1 stop8h 50mPorter Airlines
Thu 20/1111:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 15/9C$ 316
Sat 11/1012:05 p.m.YHZ - ORD
1 stop9h 19mAir Canada
Sat 25/103:35 p.m.ORD - YHZ
1 stop5h 03mAir Canada
Deal found 15/9C$ 319
Fri 31/106:55 a.m.YHZ - ORD
1 stop15h 05mAir Canada
Fri 7/113:55 p.m.ORD - YHZ
1 stop6h 31mAir Canada
Deal found 15/9C$ 326
Sat 11/105:00 p.m.YHZ - ORD
Nonstop3h 48mUnited Airlines
Sat 25/106:00 a.m.ORD - YHZ
1 stop6h 03mUnited Airlines
Deal found 15/9C$ 327
Sun 9/118:45 a.m.YHZ - ORD
1 stop6h 06mAir Canada
Thu 20/117:20 a.m.ORD - YHZ
1 stop5h 57mAir Canada
Deal found 15/9C$ 333

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 629,999 searches. Data last updated 16 September 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

Sun 23/11

5:35 a.m.-11:18 a.m.

1 stop7h 43m

Chicago O'Hare Intl

Sun 30/11

3:55 p.m.-12:26 a.m.

1 stop6h 31m

C$ 242

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 22/10

5:45 a.m.-9:51 a.m.

1 stop6h 06m

Chicago O'Hare Intl

Wed 29/10

10:00 a.m.-8:10 p.m.

1 stop8h 10m

C$ 285

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sun 9/11

8:30 a.m.-3:20 p.m.

1 stop8h 50m

Chicago Midway

Thu 20/11

11:00 a.m.-8:05 p.m.

1 stop7h 05m

C$ 316

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 22/10

9:15 a.m.-4:24 p.m.

2 stops9h 09m

Chicago Midway

Wed 29/10

11:00 a.m.-8:05 p.m.

1 stop7h 05m

C$ 325

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 31/10

6:55 a.m.-8:00 p.m.

1 stop15h 05m

Chicago O'Hare Intl

Fri 7/11

3:55 p.m.-12:26 a.m.

1 stop6h 31m

C$ 326

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 11/10

5:00 p.m.-6:48 p.m.

Nonstop3h 48m

Chicago O'Hare Intl

Sat 25/10

6:00 a.m.-2:03 p.m.

1 stop6h 03m

C$ 327

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sun 9/11

8:45 a.m.-12:51 p.m.

1 stop6h 06m

Chicago O'Hare Intl

Thu 20/11

7:20 a.m.-3:17 p.m.

1 stop5h 57m

C$ 333

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 18/10

5:25 a.m.-6:30 p.m.

2 stops15h 05m

Chicago O'Hare Intl

Tue 21/10

4:00 p.m.-11:55 p.m.

1 stop5h 55m

C$ 350

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 7/11

8:25 a.m.-3:20 p.m.

2 stops8h 55m

Chicago Midway

Tue 11/11

11:00 a.m.-8:05 p.m.

1 stop7h 05m

C$ 351

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 22/10

5:25 a.m.-9:55 a.m.

1 stop6h 30m

Chicago O'Hare Intl

Wed 29/10

7:15 a.m.-8:10 p.m.

2 stops10h 55m

C$ 362

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/9

Showing 1-10 of 35 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 12 September 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, January is the cheapest month in which you can book a flight from Halifax to Chicago (average of C$ 261). Flying from Halifax to Chicago in March is currently the most expensive (average of C$ 348). 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 16 September 2025.

A simple way to save on the total cost of your ticket is to fly from Halifax to Chicago in the morning. If you’re flexible enough to do this you can expect to save up to 56% on your trip compared to booking a flight at noon.

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

Montreal (YUL) – chosen by Cheapflights users on 38% of one-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.

Newark (EWR) is the most affordable 1-stop option, with an average round-trip price of C$ 403.

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 Toronto (YTZ) have the shortest average one-way travel time for 1-stop routes: 5h 30m.

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 Newark (EWR) offer the fastest connection on this route, with an average layover time of 1h 42m.

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 16 September 2025.
Read through reviews of airlines operating flights from Halifax to Chicago, such as Porter Airlines,United Airlines, andAir Canada. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
7.9
Good
363 reviews
Check prices

Crew

8.6

Overall

7.9

Entertainment

7.0

Boarding

8.1

Food

7.6

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Porter Airlines
7.9
Good
363 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Crew

8.6

Overall

7.9

Entertainment

7.0

Boarding

8.1

Food

7.6

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
United Airlines
7.4
Good
8,929 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Crew

8.6

Overall

7.9

Entertainment

7.0

Boarding

8.1

Food

7.6

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.
Air Canada
7.1
Good
10,000 reviews
Porter Airlines
7.9
Good
363 reviews
Check prices

Crew

8.6

Overall

7.9

Entertainment

7.0

Boarding

8.1

Food

7.6

Comfort

7.9

Reviews

1 / 20
2.0
Mediocre

Anonymous,Sep 2025

YYZ - OPO

Very disappointing, booked with Porter airlines and changed to Air Transit last minute. Old plane, cramped seating, even the aisle was the narrowest I’ve ever seen. Very uncomfortable flight. Full meal at 130 am and only a small piece of banana bread in the morning… should be opposite.

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?

    For a flight from Halifax to Chicago, you will be flying from Halifax Intl. Halifax Intl (YHZ) is just 26.9 km from the centre of the city. Halifax Intl is the only Halifax airport and it handles 0 outbound flights to Chicago per day. 2 airlines have flights to Chicago from Halifax Intl on a regular basis.

  • How long is the flight from Halifax to Chicago?

    For as low as C$ 242, Air Canada can have you in Chicago from Halifax in 7h 43m. The distance from Halifax to Chicago is about 1988 km. This flight may include one or multiple stops.

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

    United Airlines, at C$ 225, was found to be the cheapest airline from Halifax to Chicago. An alternate airline flying to your destination would be Air Canada. Users have found that United Airlines is 57% cheaper than the other options available to this destination.

  • 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 C$ 822 for a flight from Halifax to Chicago. The cheapest flight overall is C$ 233 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at C$ 257.

  • 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, January is the cheapest month in which you can book a flight from Halifax to Chicago (average of C$ 261). Flying from Halifax to Chicago in March is currently the most expensive (average of C$ 348). 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

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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 629,999 searches. Data last updated 16 September 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 225AverageC$ 418FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 392AverageC$ 580FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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How does Cheapflights help users find flights from Halifax to Chicago?

Cheapflights goes through 900+ travel sites to look for the best flight deals for flights from Halifax to Chicago. Too many options? Cheapflights also provides filters for things like airlines, price ranges, and number of stops to help you make a decision easily.

Why should you use Cheapflights to find cheap flight tickets from Halifax to Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights to Chicago from Halifax.

Can Cheapflights find flights from Halifax to Chicago with no change fees?

Need flexible booking options for your flight to Chicago from Halifax? Don’t worry, Cheapflights have you covered. Use our search filter to only show flights with no change fees.

Can Cheapflights notify me if prices for flights from Halifax to Chicago become cheaper?

Yes, Cheapflights offers price alerts on Halifax to Chicago flights so you can book your travel at the perfect time. Price Alerts can be enabled by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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