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Cheap flights from Halifax to Chicago from C$ 335

YHZ — CHI
5 Dec — 12 Dec1
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

Sat 21/116:05 a.m. -
1 stop7h 02m
Fri 27/113:40 p.m. -
1 stop6h 35m
Deal found 31/10C$ 588
Fri 25/125:10 a.m. -
1 stop8h 07m
Tue 5/14:30 p.m. -
1 stop7h 28m
Deal found 1/11C$ 628
Sat 26/125:00 a.m. -
1 stop6h 08m
Tue 5/110:05 a.m. -
1 stop5h 53m
Deal found 31/10C$ 630
Sat 26/125:00 a.m. -
1 stop6h 08m
Mon 4/14:30 p.m. -
1 stop7h 28m
Deal found 1/11C$ 634
Sat 21/116:30 a.m. -
2 stops13h 10m
Fri 27/1112:15 p.m. -
2 stops9h 35m
Deal found 1/11C$ 642
Wed 2/126:05 a.m. -
1 stop7h 02m
Mon 7/124:30 p.m. -
1 stop7h 28m
Deal found 31/10C$ 647
Tue 1/125:10 a.m. -
1 stop7h 57m
Mon 7/124:30 p.m. -
1 stop7h 28m
Deal found 1/11C$ 649
Wed 2/126:25 a.m. -
2 stops13h 15m
Mon 7/1212:15 p.m. -
2 stops9h 36m
Deal found 31/10C$ 659

Find flight deals from Halifax to Chicago

Round-trip from

C$ 588

One-way from

C$ 335

Popular in

November

Cheapest in

August

Average price

C$ 1,172

Good round-trip deal

C$ 818 or less
Air Canada
  • Air Canada
  • 21/11-27/11
  • 2 total stops
  • 13h 37m total
  • Halifax to Chicago
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7/12-31/12
  • 7/12-31/12
  • 3 total stops
  • 36h 03m total
  • Halifax to Chicago
Search Deals
Highest demand for flights based on searches. 16% potential increase in price (C$ 186 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease (C$ 64 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2026
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Price to beat on a round-trip flight from Halifax Intl to Chicago (CHI).
Search Deals

Cheapflights Fare Finder

 
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

Fri 20/11

5:00 a.m.-9:23 a.m.

1 stop6h 23m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 352

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 12/12

9:30 a.m.-7:20 a.m.

3 stops23h 50m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 353

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 20/3

7:15 a.m.-3:38 p.m.

2 stops10h 23m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 357

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Mon 16/11

7:15 a.m.-1:20 p.m.

2 stops8h 05m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 366

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Thu 17/12

9:25 a.m.-5:40 p.m.

2 stops10h 15m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 371

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Mon 16/11

6:30 a.m.-1:01 p.m.

1 stop8h 31m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 380

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sun 14/3

1:49 p.m.-11:58 p.m.

1 stop12h 09m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 383

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 12/12

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

1 stop7h 02m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 385
Quickest round-trip

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 19/12

5:00 a.m.-9:08 a.m.

1 stop6h 08m

Chicago O'Hare Intl

Wed 31/12

12:00 a.m.-2:00 a.m.

Nonstop0h 00m

C$ 387

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 21/11

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

1 stop7h 02m

Chicago O'Hare Intl

Fri 27/11

3:40 p.m.-12:15 a.m.

1 stop6h 35m

C$ 592

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/11

Showing 1-10 of 19 resultsSorted by cheapest first
1
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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

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, August is the cheapest month in which you can book a flight from Halifax to Chicago (average of C$ 515). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 964). 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?

Montreal (YUL) – chosen by Cheapflights users on 41% of one-stop itineraries from Halifax to Chicago on Cheapflights.

What’s the cheapest layover airport for flights from Halifax to Chicago?

Newark (EWR) is the most affordable 1-stop option, with an average round-trip price of C$ 464.

What’s the fastest layover option from Halifax to Chicago?

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?

Flights via Newark (EWR) offer the fastest connection on this route, with an average layover time of 1h 18m.

Reviews of airlines servicing Chicago

Read through reviews of airlines operating flights from Halifax to Chicago, such as Porter Airlines,WestJet, 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
467 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Porter Airlines
8.0
Very good
467 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
WestJet
7.2
Good
3,441 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.
Air Canada
7.1
Good
11,861 reviews
Porter Airlines
8.0
Very good
467 reviews
Check prices

Comfort

8.0

Entertainment

6.9

Food

7.6

Overall

8.0

Crew

8.6

Boarding

8.2

Reviews

1 / 20
8.0
Excellent

D,Sep 2026

YHM - YVR

The flight including check-in, checked baggage, boarding, flight and timing were great. My checked bag was delayed two days which was concerning. They did deliver it to my door though which was great.

Related info for your journey

  • 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. 1 airline has flights to Chicago from Halifax Intl on a regular basis.

  • How long is the flight from Halifax to Chicago?

    For as low as C$ 620, Air Canada can have you in Chicago from Halifax in 6h 28m. The distance from Halifax to Chicago is about 1988 km. This flight may include one or multiple stops.

  • What is the cheapest airline to fly from Halifax to Chicago round-trip?

    Air Canada, at C$ 270, was found to be the cheapest airline from Halifax to Chicago.. Users have found that Air Canada is 60% 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: Republic Airways (100%), American Airlines (80%), Qatar Airways (80%).

  • What are the cheapest flights from Halifax to Chicago?

    On average you can expect to pay C$ 1,322 for a flight from Halifax to Chicago. The cheapest flight overall is C$ 756 while the most popular route, (Halifax Intl - Chicago O'Hare Intl) is currently priced at C$ 620.

  • 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, August is the cheapest month in which you can book a flight from Halifax to Chicago (average of C$ 515). Flying from Halifax to Chicago in January is currently the most expensive (average of C$ 964). 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

Top airline flying from Halifax to Chicago

AirlineCheapestAverageFlexibilityOn-time
Air CanadaCheapestC$ 270AverageC$ 601FlexibilityNo cancel feeOn-time67%
Search Air Canada flights

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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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