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Cheap flights from Halifax to Chicago from C$ 235

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 18/2. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
28 Feb — 7 Mar1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Halifax Intl to Chicago are usually found in September or March, booked 64 days in advance, depart on a Monday or Tuesday 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 29 January 2026.

Mon 20/48:25 a.m.
YHZ
-
MDW
2 stops8h 55m
Porter Airlines
Tue 21/411:00 a.m.
MDW
-
YHZ
1 stop7h 05m
Porter Airlines
Deal found 26/1C$ 387
Thu 28/511:30 a.m.
YHZ
-
MDW
2 stops7h 20m
Porter Airlines
Fri 5/610:25 a.m.
MDW
-
YHZ
2 stops11h 09m
Porter Airlines
Deal found 26/1C$ 411
Thu 28/58:00 a.m.
YHZ
-
MDW
1 stop10h 50m
Multiple Airlines
Fri 5/65:35 p.m.
MDW
-
YHZ
2 stops20h 49m
Multiple Airlines
Deal found 26/1C$ 525
Fri 22/54:05 p.m.
YHZ
-
ORD
2 stops26h 35m
WestJet
Mon 1/65:30 p.m.
ORD
-
YHZ
1 stop12h 40m
WestJet
Deal found 28/1C$ 529
Fri 20/26:45 p.m.
YHZ
-
MDW
1 stop19h 10m
Porter Airlines
Thu 26/211:05 a.m.
MDW
-
YHZ
1 stop7h 05m
Porter Airlines
Deal found 28/1C$ 543
Thu 28/56:15 p.m.
YHZ
-
ORD
1 stop24h 25m
WestJet
Fri 5/65:30 p.m.
ORD
-
YHZ
2 stops15h 15m
WestJet
Deal found 26/1C$ 558
Fri 20/210:40 p.m.
YHZ
-
MDW
2 stops12h 14m
Multiple Airlines
Thu 26/211:05 a.m.
MDW
-
YHZ
1 stop7h 05m
Multiple Airlines
Deal found 28/1C$ 589
Wed 11/26:30 a.m.
YHZ
-
ORD
1 stop7h 55m
Porter Airlines
Wed 11/32:55 p.m.
ORD
-
YHZ
1 stop7h 27m
Porter Airlines
Deal found 27/1C$ 591
Mon 20/46:30 a.m.
YHZ
-
ORD
1 stop8h 24m
Porter Airlines
Tue 21/411:48 a.m.
ORD
-
YHZ
1 stop6h 24m
Porter Airlines
Deal found 28/1C$ 601
Fri 19/68:30 a.m.
YHZ
-
ORD
2 stops12h 11m
WestJet
Mon 22/67:35 p.m.
ORD
-
YHZ
2 stops16h 35m
WestJet
Deal found 28/1C$ 615
Wed 25/36:30 a.m.
YHZ
-
ORD
1 stop8h 05m
Porter Airlines
Mon 6/46:40 p.m.
ORD
-
YHZ
1 stop24h 57m
Porter Airlines
Deal found 28/1C$ 631

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 29 January 2026.

Round-trip from

C$ 387

One-way from

C$ 235

Popular in

January

Cheapest in

September

Average price

C$ 891
Porter Airlines
  • Porter Airlines
  • 20/4-21/4
  • 3 total stops
  • 16h 00m total
  • Halifax to Chicago
Search Deals
18/2
  • 18/2
  • 3 total stops
  • 40h 54m total
  • Halifax to Chicago
Search Deals
Highest demand for flights based on searches. 4% potential increase in price (C$ 34 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease (C$ 43 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
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 29 January 2026.
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

Mon 20/4

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

2 stops8h 55m

Chicago Midway

Tue 21/4

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

1 stop7h 05m

C$ 387

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 28/5

8:00 a.m.-4:50 p.m.

1 stop10h 50m

Chicago Midway

Fri 5/6

5:35 p.m.-4:24 p.m.

2 stops20h 49m

C$ 525

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 22/5

4:05 p.m.-4:40 p.m.

2 stops26h 35m

Chicago O'Hare Intl

Mon 1/6

5:30 p.m.-8:10 a.m.

1 stop12h 40m

C$ 534

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 28/5

6:15 p.m.-4:40 p.m.

1 stop24h 25m

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-8:10 a.m.

1 stop12h 40m

C$ 539

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 20/2

6:45 p.m.-11:55 a.m.

1 stop19h 10m

Chicago Midway

Thu 26/2

11:05 a.m.-8:10 p.m.

1 stop7h 05m

C$ 543

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 20/2

10:40 p.m.-8:54 a.m.

2 stops12h 14m

Chicago Midway

Thu 26/2

11:05 a.m.-8:10 p.m.

1 stop7h 05m

C$ 589

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 20/2

6:30 a.m.-12:35 p.m.

1 stop8h 05m

Chicago O'Hare Intl

Thu 26/2

1:22 p.m.-9:37 p.m.

1 stop6h 15m

C$ 591

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 11/2

6:30 a.m.-12:25 p.m.

1 stop7h 55m

Chicago O'Hare Intl

Wed 11/3

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

1 stop7h 27m

C$ 591

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Mon 20/4

6:30 a.m.-12:54 p.m.

1 stop8h 24m

Chicago O'Hare Intl

Tue 21/4

11:48 a.m.-8:12 p.m.

1 stop6h 24m

C$ 601

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 19/6

8:30 a.m.-6:41 p.m.

2 stops12h 11m

Chicago O'Hare Intl

Mon 22/6

8:55 a.m.-7:15 p.m.

2 stops8h 20m

C$ 623

Flights are sorted by cheapest round-trip flights first.

Deals found on 26/1

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 23 January 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$ 136). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 650). 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’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 53% 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$ 396.

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 Montreal (YUL) offer the fastest connection on this route, with an average layover time of 1h 38m.

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 29 January 2026.
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
412 reviews
Check prices

Overall

7.9

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

6.9

Food

7.5

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Porter Airlines
7.9
Good
412 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Overall

7.9

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

6.9

Food

7.5

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
United Airlines
7.4
Good
9,215 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Overall

7.9

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

6.9

Food

7.5

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out
Air Canada
7.1
Good
10,667 reviews
Porter Airlines
7.9
Good
412 reviews
Check prices

Overall

7.9

Crew

8.6

Comfort

7.9

Boarding

8.2

Entertainment

6.9

Food

7.5

Reviews

1 / 20
8.0
Excellent

Mohameed,Nov 2025

LAS - YYZ

It's good. Planes are new and fresh. WiFi is best and stands out

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$ 387, Porter Airlines can have you in Chicago from Halifax in 8h 55m. 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$ 222, 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 59% cheaper than the other options available to this destination.

  • 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$ 136). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 650). 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 29 January 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 222AverageC$ 258FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 281AverageC$ 569FlexibilityNo 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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