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Cheap flights from Halifax to Chicago from C$ 249

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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
13 Dec — 20 Dec1
1 adult
1 adult, Economy, 0 bags

Cheapflights Tip: The best prices from Halifax Intl to Chicago are usually found in September or January, booked 64 days in advance, depart on a Monday or Wednesday and return on a Wednesday

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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 13 November 2025.

Sat 13/127:00 a.m.YHZ - MDW
2 stops6h 50mPorter Airlines
Mon 15/1211:00 a.m.MDW - YHZ
1 stop7h 10mPorter Airlines
Deal found 11/11C$ 301
Fri 12/128:45 a.m.YHZ - ORD
1 stop15h 03mMultiple Airlines
Sun 14/122:36 p.m.ORD - YHZ
2 stops27h 36mMultiple Airlines
Deal found 10/11C$ 492
Sat 13/128:45 a.m.YHZ - ORD
1 stop15h 03mMultiple Airlines
Mon 15/125:00 a.m.ORD - YHZ
2 stops16h 54mMultiple Airlines
Deal found 11/11C$ 531
Fri 12/121:10 p.m.YHZ - ORD
1 stop8h 14mAmerican Airlines
Sun 14/122:55 p.m.ORD - YHZ
1 stop7h 27mAmerican Airlines
Deal found 10/11C$ 558
Wed 17/128:25 a.m.YHZ - ORD
2 stops26h 06mMultiple Airlines
Wed 7/15:29 p.m.ORD - YHZ
1 stop22h 09mMultiple Airlines
Deal found 11/11C$ 565
Sat 13/126:30 a.m.YHZ - ORD
1 stop8h 01mAmerican Airlines
Mon 15/122:55 p.m.ORD - YHZ
1 stop7h 27mAmerican Airlines
Deal found 11/11C$ 572
Sun 7/126:00 a.m.YHZ - ORD
2 stops16h 35mWestJet
Tue 9/127:00 a.m.ORD - YHZ
2 stops16h 42mWestJet
Deal found 10/11C$ 573
Sat 27/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Sat 3/111:00 a.m.MDW - YHZ
2 stops6h 51mPorter Airlines
Deal found 12/11C$ 642
Fri 26/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Fri 2/111:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 12/11C$ 668
Fri 19/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Wed 24/1211:00 a.m.MDW - YHZ
2 stops8h 29mPorter Airlines
Deal found 12/11C$ 693
Sat 27/128:25 a.m.YHZ - MDW
2 stops8h 55mPorter Airlines
Fri 2/111:00 a.m.MDW - YHZ
1 stop7h 05mPorter Airlines
Deal found 12/11C$ 702

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 13 November 2025.

Round-trip from

C$ 301

One-way from

C$ 249

Popular in

July

Cheapest in

September

Average price

C$ 507
Porter Airlines
  • Porter Airlines
  • 13/12-15/12
  • 3 total stops
  • 14h 00m total
  • Halifax to Chicago
Search Deals
11/12
  • 11/12
  • 1 total stop
  • 15h 03m total
  • Halifax to Chicago
Search Deals
Highest demand for flights based on searches. 22% potential increase in price (C$ 214 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease (C$ 25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
Search Deals

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 13 November 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

Sat 13/12

7:00 a.m.-11:50 a.m.

2 stops6h 50m

Chicago Midway

Mon 15/12

11:00 a.m.-8:10 p.m.

1 stop7h 10m

C$ 301

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 12/12

8:45 a.m.-12:09 a.m.

2 stops17h 24m

Chicago O'Hare Intl

Sun 14/12

1:52 p.m.-9:55 p.m.

3 stops30h 03m

C$ 532

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 13/12

8:45 a.m.-12:09 a.m.

2 stops17h 24m

Chicago O'Hare Intl

Mon 15/12

5:00 a.m.-11:54 p.m.

2 stops16h 54m

C$ 535

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 12/12

1:10 p.m.-7:24 p.m.

1 stop8h 14m

Chicago O'Hare Intl

Sun 14/12

2:55 p.m.-12:22 a.m.

1 stop7h 27m

C$ 558

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sun 7/12

8:20 p.m.-12:09 a.m.

2 stops29h 49m

Chicago O'Hare Intl

Tue 9/12

4:38 p.m.-8:12 p.m.

3 stops25h 34m

C$ 604

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sun 23/11

6:30 a.m.-12:27 p.m.

1 stop7h 57m

Chicago O'Hare Intl

Sun 30/11

3:00 p.m.-12:22 a.m.

1 stop7h 22m

C$ 633

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 27/12

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

2 stops8h 55m

Chicago Midway

Sat 3/1

11:00 a.m.-7:51 p.m.

2 stops6h 51m

C$ 642

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 17/12

6:55 a.m.-11:18 a.m.

1 stop6h 23m

Chicago O'Hare Intl

Wed 7/1

7:15 a.m.-3:47 p.m.

1 stop6h 32m

C$ 643

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 27/12

6:55 a.m.-11:18 a.m.

1 stop6h 23m

Chicago O'Hare Intl

Mon 29/12

3:35 p.m.-12:06 a.m.

1 stop6h 31m

C$ 643

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 26/12

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

2 stops8h 55m

Chicago Midway

Fri 2/1

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

1 stop7h 05m

C$ 668

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 28 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 7 November 2025.

To ensure you get the cheapest price possible for a flight from Halifax to Chicago, you should look to book at least 63 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, September is the cheapest month in which you can book a flight from Halifax to Chicago (average of C$ 140). Flying from Halifax to Chicago in August is currently the most expensive (average of C$ 618). 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 13 November 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 54% on your trip compared to booking a flight at noon.

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 43% 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$ 408.

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 13 November 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
8.0
Very good
389 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Porter Airlines
8.0
Very good
389 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
United Airlines
7.4
Good
9,015 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.
Air Canada
7.1
Good
10,444 reviews
Porter Airlines
8.0
Very good
389 reviews
Check prices

Crew

8.6

Overall

8.0

Entertainment

7.0

Boarding

8.2

Comfort

8.0

Food

7.6

Reviews

1 / 20
2.0
Mediocre

Kelly,Nov 2025

YVR - YUL

I recently flew with Porter Airlines on Flight PD372 on October 30th, and unfortunately, had a very disappointing experience. At the gate, one of their attendants gave me two boarding passes. I assumed these were for my itinerary from Vancouver to Montreal and back, but one of the boarding passes unexpectedly included a connecting flight to Toronto, which was never part of my booking or invoice. As a result of this error, my checked baggage was mistakenly routed to Toronto. When I contacted Porter’s customer service, I spoke to an agent who apologized on behalf of the attendant (employee number 13209961) and promised to have my luggage flown back to Montreal. However, shortly after, I was told there was nothing they could do except for me to travel to Toronto myself to pick up my bag. This is highly unreasonable and unfair, considering the issue was caused by their staff printing the wrong boarding pass. This entire situation caused me significant inconvenience and stress. I expected Porter to correct the mistake and deliver my luggage as originally planned, but instead, I was left with the burden of fixing an error that was not mine. I even have a photo of the staff badge of the employee who made the promise, yet the company still failed to honor it. I hope Porter Airlines reviews their internal communication and baggage handling procedures to prevent this from happening to other passengers. Customer care and responsibility fell short in this experience, and I am still waiting for a satisfactory resolution.

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$ 301, Porter Airlines can have you in Chicago from Halifax in 6h 50m. The distance from Halifax to Chicago is about 1981 km.

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

    United Airlines, at C$ 229, 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 56% 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 (80%), Envoy Air (80%), Air Canada (75%).

  • 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, September is the cheapest month in which you can book a flight from Halifax to Chicago (average of C$ 140). Flying from Halifax to Chicago in August is currently the most expensive (average of C$ 618). 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

Browse thousands of different options on Cheapflights for your next trip

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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 13 November 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 229AverageC$ 424FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 340AverageC$ 578FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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

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

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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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