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Cheap flights from Halifax to Chicago from C$ 255

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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
13 May — 20 May1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Halifax Intl to Chicago are usually found in September or December, booked 64 days in advance, depart on a Tuesday or Monday and return on a Monday

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 13 April 2026.

Tue 1/97:00 a.m.
YHZ
-
ORD
2 stops9h 35m
Porter Airlines
Sat 5/911:45 a.m.
ORD
-
YHZ
2 stops9h 59m
Porter Airlines
Deal found 11/4C$ 466
Sat 12/97:00 a.m.
YHZ
-
ORD
2 stops9h 35m
Porter Airlines
Mon 21/911:45 a.m.
ORD
-
YHZ
2 stops9h 59m
Porter Airlines
Deal found 11/4C$ 482
Thu 21/57:00 a.m.
YHZ
-
MDW
2 stops9h 35m
Porter Airlines
Wed 27/510:30 a.m.
MDW
-
YHZ
2 stops11h 17m
Porter Airlines
Deal found 12/4C$ 491
Thu 21/58:15 p.m.
YHZ
-
MDW
1 stop15h 30m
Multiple Airlines
Wed 27/53:20 p.m.
MDW
-
YHZ
2 stops6h 27m
Multiple Airlines
Deal found 12/4C$ 493
Tue 8/91:40 p.m.
YHZ
-
ORD
2 stops9h 55m
Porter Airlines
Thu 10/911:45 a.m.
ORD
-
YHZ
2 stops9h 59m
Porter Airlines
Deal found 11/4C$ 493
Wed 26/83:30 p.m.
YHZ
-
ORD
1 stop20h 54m
WestJet
Sun 30/811:30 a.m.
ORD
-
YHZ
1 stop8h 15m
WestJet
Deal found 8/4C$ 522
Wed 22/76:20 a.m.
YHZ
-
ORD
1 stop8h 24m
American Airlines
Tue 28/79:45 a.m.
ORD
-
YHZ
1 stop7h 57m
American Airlines
Deal found 9/4C$ 545
Thu 27/83:30 p.m.
YHZ
-
ORD
1 stop5h 11m
WestJet
Sun 30/87:35 p.m.
ORD
-
YHZ
1 stop24h 05m
WestJet
Deal found 8/4C$ 548
Fri 19/63:30 p.m.
YHZ
-
ORD
1 stop7h 01m
WestJet
Mon 22/67:01 a.m.
ORD
-
YHZ
1 stop12h 39m
WestJet
Deal found 9/4C$ 551
Thu 21/58:15 p.m.
YHZ
-
ORD
1 stop14h 45m
Multiple Airlines
Wed 27/59:55 a.m.
ORD
-
YHZ
1 stop11h 07m
Multiple Airlines
Deal found 8/4C$ 555
Sat 12/93:30 p.m.
YHZ
-
ORD
1 stop6h 54m
WestJet
Mon 21/97:35 p.m.
ORD
-
YHZ
1 stop24h 10m
WestJet
Deal found 11/4C$ 561
Wed 26/83:30 p.m.
YHZ
-
ORD
1 stop20h 54m
WestJet
Wed 2/911:30 a.m.
ORD
-
YHZ
1 stop8h 10m
WestJet
Deal found 8/4C$ 565

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 13 April 2026.

Round-trip from

C$ 466

One-way from

C$ 255

Popular in

January

Cheapest in

September

Average price

C$ 663

Good round-trip deal

C$ 495 or less

Good one-way deal

C$ 262 or less
Porter Airlines
  • Porter Airlines
  • 1/9-5/9
  • 4 total stops
  • 19h 34m total
  • Halifax to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 12/5
  • 2 total stops
  • 9h 35m total
  • Halifax to Chicago
Search Deals
High demand for flights, 0% potential price rise
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 44 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 13 April 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 - ORD

YHZORD

Halifax Intl

Thu 21/5

8:15 p.m.-9:00 a.m.

1 stop14h 45m

Chicago O'Hare Intl

Wed 27/5

9:55 a.m.-11:02 p.m.

1 stop11h 07m

C$ 555

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 21/5

7:00 a.m.-2:35 p.m.

2 stops9h 35m

Chicago Midway

Wed 27/5

10:30 a.m.-11:47 p.m.

2 stops11h 17m

C$ 601

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 27/8

8:00 a.m.-2:35 p.m.

2 stops8h 35m

Chicago Midway

Sun 30/8

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

2 stops6h 24m

C$ 637

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 25/8

8:00 a.m.-2:35 p.m.

2 stops8h 35m

Chicago Midway

Sat 29/8

10:25 a.m.-11:44 p.m.

2 stops11h 19m

C$ 670

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 26/8

7:45 a.m.-9:58 p.m.

2 stops16h 13m

Chicago O'Hare Intl

Sat 29/8

1:35 p.m.-9:40 p.m.

1 stop6h 05m

C$ 687

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 18/6

8:00 a.m.-2:35 p.m.

2 stops8h 35m

Chicago Midway

Thu 25/6

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

2 stops6h 24m

C$ 702

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 22/7

8:00 a.m.-2:35 p.m.

2 stops8h 35m

Chicago Midway

Tue 28/7

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

2 stops6h 24m

C$ 712

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 23/5

5:15 a.m.-2:47 p.m.

2 stops11h 32m

Chicago O'Hare Intl

Tue 26/5

7:25 a.m.-1:54 a.m.

2 stops16h 29m

C$ 724

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 26/8

6:00 a.m.-8:15 p.m.

2 stops16h 15m

Chicago O'Hare Intl

Wed 2/9

7:20 a.m.-12:39 a.m.

2 stops15h 19m

C$ 725

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 6/5

6:20 a.m.-12:43 p.m.

1 stop8h 23m

Chicago O'Hare Intl

Sat 9/5

2:50 p.m.-11:02 p.m.

1 stop6h 12m

C$ 738

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/4

Showing 1-10 of 29 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

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 10 April 2026.

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$ 132). Flying from Halifax to Chicago in April is currently the most expensive (average of C$ 861). 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.

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 49% 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$ 492.

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 11m.

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 13 April 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
434 reviews
Check prices

Entertainment

7.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Porter Airlines
8.0
Very good
434 reviews
Porter Airlines
8.0
Very good
434 reviews
Check prices

Entertainment

7.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
United Airlines
7.4
Good
9,578 reviews
Porter Airlines
8.0
Very good
434 reviews
Check prices

Entertainment

7.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
WestJet
7.2
Good
3,320 reviews
Porter Airlines
8.0
Very good
434 reviews
Check prices

Entertainment

7.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.
Air Canada
7.1
Good
10,918 reviews
Porter Airlines
8.0
Very good
434 reviews
Check prices

Entertainment

7.0

Overall

8.0

Food

7.6

Boarding

8.2

Crew

8.6

Comfort

8.0

Reviews

1 / 20
10.0
Excellent

John,Mar 2026

YYZ - PVR

I'm 6ft 4in. The seats don't have enough room. But was a good flight.

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. 3 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$ 601, Porter Airlines can have you in Chicago from Halifax in 9h 35m. The distance from Halifax to Chicago is about 1981 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$ 226, was found to be the cheapest airline from Halifax to Chicago.Alternate airlines to your destination round-trip include Air Canada and Porter Airlines. Users have found that United Airlines is 63% cheaper than the other options available to this destination.

  • What are the cheapest flights from Halifax to Chicago?

    On average you can expect to pay C$ 415 for a flight from Halifax to Chicago. The cheapest flight overall is C$ 256 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at C$ 466.

  • 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$ 132). Flying from Halifax to Chicago in April is currently the most expensive (average of C$ 861). 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 3 airlines flying from Halifax to Chicago

Discover the top 3 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 April 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 226AverageC$ 226FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 286AverageC$ 658FlexibilityNo cancel feeOn-time67%
Search Air Canada flights
Porter AirlinesCheapestC$ 508AverageC$ 668FlexibilityNo cancel feeOn-time52%
Search Porter Airlines flights

Fly with Cheapflights

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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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