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Cheap flights from Halifax to Chicago from C$ 251

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 9/9. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
14 Sep — 21 Sep1
1 adult
1 adult, Economy, 0 bags

Cheap flight deals from Halifax to Chicago

Enter your travel dates to find the best prices.

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 15 August 2026.

Wed 16/96:25 a.m. -
1 stop5h 50m
Wed 30/93:40 p.m. -
1 stop6h 55m
Deal found 10/8C$ 435
Wed 16/96:25 a.m. -
1 stop5h 50m
Wed 23/93:40 p.m. -
1 stop6h 55m
Deal found 12/8C$ 444
Tue 29/97:00 a.m. -
2 stops9h 35m
Sat 3/1011:45 a.m. -
2 stops9h 59m
Deal found 10/8C$ 460
Sat 19/96:25 a.m. -
1 stop5h 50m
Sat 26/93:40 p.m. -
1 stop6h 55m
Deal found 13/8C$ 460
Sat 12/96:25 a.m. -
1 stop5h 50m
Sat 19/93:40 p.m. -
1 stop6h 55m
Deal found 10/8C$ 461
Wed 9/96:25 a.m. -
1 stop5h 50m
Sat 12/93:40 p.m. -
1 stop6h 55m
Deal found 10/8C$ 464
Sun 6/96:25 a.m. -
1 stop5h 54m
Tue 8/98:45 a.m. -
1 stop5h 17m
Deal found 13/8C$ 468
Sun 27/95:15 a.m. -
1 stop5h 45m
Sun 4/108:45 a.m. -
1 stop5h 17m
Deal found 13/8C$ 475
Tue 29/96:25 a.m. -
1 stop5h 50m
Sat 3/108:45 a.m. -
1 stop5h 17m
Deal found 10/8C$ 476
Fri 25/96:25 a.m. -
1 stop5h 50m
Fri 2/108:45 a.m. -
1 stop5h 17m
Deal found 10/8C$ 483
Fri 13/116:05 a.m. -
1 stop7h 02m
Mon 16/114:30 p.m. -
1 stop6h 18m
Deal found 12/8C$ 486
Thu 15/105:45 a.m. -
1 stop6h 32m
Fri 30/104:30 p.m. -
1 stop6h 18m
Deal found 13/8C$ 489

Find 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 15 August 2026.

Round-trip from

C$ 435

One-way from

C$ 251

Popular in

January

Cheapest in

December

Average price

C$ 476

Good round-trip deal

C$ 491 or less

Good one-way deal

C$ 322 or less
Air Canada
  • Air Canada
  • 16/9-30/9
  • 2 total stops
  • 12h 45m total
  • Halifax to Chicago
Search Deals
Air Canada
  • Air Canada
  • 9/9
  • 1 total stop
  • 5h 50m total
  • Halifax to Chicago
Search Deals
Highest demand for flights based on searches. 6% potential increase in price (C$ 53 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 49 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2026
Search Deals
Price to beat on a round-trip flight from Halifax Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Halifax Intl to Chicago (CHI).
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 15 August 2026.
Use the filters below to find and compare flights from Halifax to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Tue 29/9

6:25 a.m.-10:15 a.m.

1 stop5h 50m

Chicago O'Hare Intl

Sat 3/10

8:45 a.m.-4:02 p.m.

1 stop5h 17m

C$ 476

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Mon 14/9

11:00 p.m.-2:35 p.m.

1 stop17h 35m

Chicago Midway

Wed 16/9

11:45 a.m.-11:33 p.m.

2 stops9h 48m

C$ 524

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 12/9

12:40 p.m.-7:22 p.m.

1 stop8h 42m

Chicago O'Hare Intl

Sat 19/9

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

1 stop6h 03m

C$ 531

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Wed 16/9

7:00 a.m.-12:08 p.m.

1 stop7h 08m

Chicago O'Hare Intl

Fri 18/9

9:35 p.m.-2:03 p.m.

1 stop14h 28m

C$ 535

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Thu 24/9

7:05 a.m.-1:23 p.m.

1 stop8h 18m

Chicago O'Hare Intl

Sun 27/9

8:45 a.m.-4:02 p.m.

1 stop5h 17m

C$ 539

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Fri 25/9

7:25 a.m.-2:35 p.m.

2 stops9h 10m

Chicago Midway

Fri 2/10

3:20 p.m.-11:44 p.m.

2 stops6h 24m

C$ 564

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 13/11

6:05 a.m.-11:07 a.m.

1 stop7h 02m

Chicago O'Hare Intl

Mon 16/11

4:30 p.m.-12:48 a.m.

1 stop6h 18m

C$ 574

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 12/9

3:35 p.m.-10:00 p.m.

1 stop8h 25m

Chicago O'Hare Intl

Sat 19/9

8:14 a.m.-1:40 p.m.

Nonstop3h 26m

C$ 593

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Wed 16/9

3:30 p.m.-11:59 p.m.

2 stops10h 29m

Chicago O'Hare Intl

Wed 30/9

6:40 a.m.-9:10 p.m.

2 stops12h 30m

C$ 603
Quickest round-trip

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Sat 19/9

3:30 p.m.-6:22 p.m.

1 stop4h 52m

Chicago Midway

Sat 26/9

1:19 p.m.-9:10 p.m.

1 stop5h 51m

C$ 613

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/8

Showing 1-10 of 39 resultsSorted by cheapest first
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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

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$ 393). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 958). 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 15 August 2026.

When flying from Halifax to Chicago, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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

Airfare is typical for this route at the moment.
Halifax to Chicago flights typically cost between C$ 435 and C$ 568 in September.
The cheapest round-trip price found within the last 5 days was C$ 435 on Air Canada (16 Sep-30 Sep).

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.

Detroit (DTW) is the most affordable 1-stop option, with an average round-trip price of C$ 494.

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 Detroit (DTW) have the shortest average one-way travel time for 1-stop routes: 5h 07m.

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 Detroit (DTW) offer the fastest connection on this route, with an average layover time of 1h 27m.

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 15 August 2026.
Read through reviews of airlines operating flights from Halifax to Chicago, such as Porter Airlines,United Airlines, andWestJet. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Porter Airlines
8.0
Very good
456 reviews
Check prices

Food

7.5

Overall

8.0

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Porter Airlines
8.0
Very good
456 reviews
Porter Airlines
8.0
Very good
456 reviews
Check prices

Food

7.5

Overall

8.0

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
United Airlines
7.4
Good
10,110 reviews
Porter Airlines
8.0
Very good
456 reviews
Check prices

Food

7.5

Overall

8.0

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
WestJet
7.2
Good
3,433 reviews
Porter Airlines
8.0
Very good
456 reviews
Check prices

Food

7.5

Overall

8.0

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.
Air Canada
7.1
Good
11,479 reviews
Porter Airlines
8.0
Very good
456 reviews
Check prices

Food

7.5

Overall

8.0

Boarding

8.2

Entertainment

6.9

Comfort

8.0

Crew

8.6

Reviews

1 / 20
10.0
Excellent

Regan,Aug 2026

YYZ - YVR

My first flight with an all female flight crew who were the best ever.

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$ 476, Air Canada can have you in Chicago from Halifax in 5h 50m. 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$ 227, 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 61% 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 (86%), Qatar Airways (86%), Envoy Air (86%).

  • What are the cheapest flights from Halifax to Chicago?

    On average you can expect to pay C$ 659 for a flight from Halifax to Chicago. The cheapest flight overall is C$ 305 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at C$ 490.

  • 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$ 393). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 958). 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 15 August 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 227AverageC$ 227FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 268AverageC$ 593FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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