Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Halifax to Chicago from C$ 246

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 19/9. Fares are subject to change and may not be available on all flights or dates of travel.
YHZ — CHI
23 apr — 30 apr1
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 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 24 mars 2026.

ons 2/98:00 a.m.
YHZ
-
ORD
1 stop8h 35m
Porter Airlines
ons 9/911:45 a.m.
ORD
-
YHZ
2 stops9h 59m
Porter Airlines
Deal found 20/3C$ 428
tors 10/98:00 a.m.
YHZ
-
ORD
1 stop8h 35m
Porter Airlines
mån 14/93:20 p.m.
ORD
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 19/3C$ 429
fre 25/97:00 a.m.
YHZ
-
ORD
2 stops9h 35m
Porter Airlines
mån 5/103:20 p.m.
ORD
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 19/3C$ 440
mån 4/58:00 a.m.
YHZ
-
MDW
1 stop8h 35m
Porter Airlines
mån 11/53:20 p.m.
MDW
-
YHZ
2 stops6h 24m
Porter Airlines
Deal found 21/3C$ 494
fre 19/63:30 p.m.
YHZ
-
ORD
1 stop7h 01m
WestJet
mån 22/611:30 a.m.
ORD
-
YHZ
1 stop8h 15m
WestJet
Deal found 23/3C$ 509
lör 18/48:25 a.m.
YHZ
-
MDW
1 stop5h 45m
Porter Airlines
ons 22/411:00 a.m.
MDW
-
YHZ
1 stop7h 05m
Porter Airlines
Deal found 21/3C$ 510
tors 18/63:30 p.m.
YHZ
-
ORD
1 stop27h 06m
WestJet
tors 25/68:55 a.m.
ORD
-
YHZ
1 stop10h 50m
WestJet
Deal found 19/3C$ 513
ons 29/73:30 p.m.
YHZ
-
ORD
1 stop5h 11m
WestJet
mån 3/87:35 p.m.
ORD
-
YHZ
1 stop24h 10m
WestJet
Deal found 20/3C$ 526
tors 20/83:30 p.m.
YHZ
-
ORD
1 stop5h 11m
Multiple Airlines
tors 3/911:45 a.m.
ORD
-
YHZ
2 stops9h 59m
Multiple Airlines
Deal found 23/3C$ 541
ons 29/77:00 a.m.
YHZ
-
MDW
2 stops9h 35m
Porter Airlines
mån 3/810:25 a.m.
MDW
-
YHZ
2 stops11h 19m
Porter Airlines
Deal found 20/3C$ 548
fre 1/58:15 p.m.
YHZ
-
MDW
1 stop15h 30m
Multiple Airlines
mån 4/53:20 p.m.
MDW
-
YHZ
1 stop17h 25m
Multiple Airlines
Deal found 24/3C$ 565
fre 1/56:05 p.m.
YHZ
-
MDW
2 stops17h 40m
Porter Airlines
mån 4/53:20 p.m.
MDW
-
YHZ
1 stop19h 04m
Porter Airlines
Deal found 24/3C$ 576

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 24 mars 2026.

Round-trip from

C$ 428

One-way from

C$ 242

Popular in

January

Cheapest in

September

Average price

C$ 458

Good round-trip deal

C$ 549 or less

Good one-way deal

C$ 1,174 or less
Porter Airlines
  • Porter Airlines
  • 2/9-9/9
  • 3 total stops
  • 18h 34m total
  • Halifax to Chicago
Search Deals
Porter Airlines
  • Porter Airlines
  • 3/5
  • 1 total stop
  • 8h 35m total
  • Halifax to Chicago
Search Deals
Highest demand for flights based on searches. 2% potential increase in price (C$ 24 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease (C$ 45 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 24 mars 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

tors 18/6

3:30 p.m.-8:31 p.m.

1 stop7h 01m

Chicago O'Hare Intl

tors 25/6

7:01 a.m.-9:45 p.m.

1 stop12h 44m

C$ 510

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

ons 1/7

3:30 p.m.-8:24 p.m.

1 stop6h 54m

Chicago O'Hare Intl

lör 11/7

5:45 p.m.-9:45 p.m.

1 stop26h 00m

C$ 513

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

fre 1/5

8:15 p.m.-9:45 a.m.

1 stop15h 30m

Chicago Midway

mån 4/5

3:20 p.m.-10:45 a.m.

1 stop17h 25m

C$ 565

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

lör 18/4

8:25 a.m.-12:10 p.m.

1 stop5h 45m

Chicago Midway

ons 22/4

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

2 stops10h 54m

C$ 575

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

fre 1/5

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

2 stops9h 35m

Chicago Midway

mån 4/5

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

2 stops11h 17m

C$ 590

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

ons 22/4

6:55 a.m.-12:24 a.m.

1 stop19h 29m

Chicago O'Hare Intl

ons 29/4

5:05 a.m.-12:19 a.m.

3 stops17h 14m

C$ 649

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

mån 4/5

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

2 stops9h 35m

Chicago Midway

fre 8/5

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

2 stops11h 19m

C$ 652

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

ons 22/4

11:00 p.m.-10:15 a.m.

1 stop13h 15m

Chicago Midway

ons 29/4

11:00 a.m.-12:19 a.m.

1 stop11h 19m

C$ 659

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

mån 4/5

8:00 a.m.-9:40 a.m.

1 stop27h 40m

Chicago Midway

mån 11/5

3:20 p.m.-12:24 p.m.

1 stop19h 04m

C$ 668

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

mån 27/4

6:30 a.m.-12:43 p.m.

1 stop8h 13m

Chicago O'Hare Intl

fre 1/5

2:53 p.m.-11:57 p.m.

1 stop7h 04m

C$ 681

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/3

Showing 1-10 of 39 resultsSorted by cheapest first
1
2
3
4

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 13 March 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$ 134). Flying from Halifax to Chicago in March is currently the most expensive (average of C$ 773). 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 48% 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$ 488.

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 24 mars 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
427 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Crew

8.6

Food

7.6

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
427 reviews
Porter Airlines
8.0
Very good
427 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Crew

8.6

Food

7.6

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
9,471 reviews
Porter Airlines
8.0
Very good
427 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Crew

8.6

Food

7.6

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
3,300 reviews
Porter Airlines
8.0
Very good
427 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Crew

8.6

Food

7.6

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
10,837 reviews
Porter Airlines
8.0
Very good
427 reviews
Check prices

Boarding

8.2

Overall

8.0

Entertainment

7.0

Comfort

8.0

Crew

8.6

Food

7.6

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. 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$ 510, Porter Airlines can have you in Chicago from Halifax in 7h 01m. 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$ 224, 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 62% 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$ 939 for a flight from Halifax to Chicago. The cheapest flight overall is C$ 254 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at C$ 560.

  • 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$ 134). Flying from Halifax to Chicago in March is currently the most expensive (average of C$ 773). 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

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 24 mars 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapestC$ 224AverageC$ 224FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
Air CanadaCheapestC$ 283AverageC$ 639FlexibilityNo 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.

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.