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Cheap flights from Halifax to Chicago from C$ 218

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Halifax to Chicago departing on 12/9. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Halifax to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
3:15 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 29m
2 stops
C$ 396Porter Airlines
Wed, 19 Aug - Wed, 26 Aug
Porter Airlines Logo
6:40 a.m. - 5:30 p.m.
YHZ
-
ORD
12h 50m
2 stops
Porter Airlines Logo
11:45 a.m. - 11:45 p.m.
ORD
-
YHZ
10h 00m
2 stops
C$ 396Porter Airlines
Thu, 12 Nov - Tue, 17 Nov
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
3:15 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 29m
2 stops
C$ 397Porter Airlines
Mon, 24 Aug - Thu, 27 Aug
Air Canada Logo
5:15 a.m. - 9:00 a.m.
YHZ
-
ORD
5h 45m
1 stop
Air Canada Logo
8:45 a.m. - 4:02 p.m.
ORD
-
YHZ
5h 17m
1 stop
C$ 399Air Canada
Mon, 12 Oct - Sun, 18 Oct
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
10:25 a.m. - 11:44 p.m.
MDW
-
YHZ
11h 19m
2 stops
C$ 402Porter Airlines
Wed, 12 Aug - Wed, 26 Aug
Air Canada Logo
5:45 a.m. - 10:17 a.m.
YHZ
-
ORD
6h 32m
1 stop
Air Canada Logo
8:45 a.m. - 4:02 p.m.
ORD
-
YHZ
5h 17m
1 stop
C$ 403Air Canada
Tue, 6 Oct - Thu, 22 Oct
Air Canada Logo
6:25 a.m. - 10:16 a.m.
YHZ
-
ORD
5h 51m
1 stop
Air Canada Logo
8:40 a.m. - 4:07 p.m.
ORD
-
YHZ
5h 27m
1 stop
C$ 404Air Canada
Wed, 12 Aug - Wed, 26 Aug
Air Canada Logo
7:15 a.m. - 1:19 p.m.
YHZ
-
ORD
8h 04m
2 stops
Air Canada Logo
8:45 a.m. - 4:02 p.m.
ORD
-
YHZ
5h 17m
1 stop
C$ 406Air Canada
Wed, 7 Oct - Thu, 22 Oct
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
2 stops
Porter Airlines Logo
3:15 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 29m
2 stops
C$ 407Porter Airlines
Mon, 24 Aug - Thu, 27 Aug
United Airlines Logo
12:40 p.m. - 5:00 p.m.
YHZ
-
ORD
6h 20m
1 stop
United Airlines Logo
3:55 p.m. - 11:55 p.m.
ORD
-
YHZ
6h 00m
1 stop
C$ 420United Airlines
Sat, 19 Sep - Tue, 22 Sep

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American Airlines flights from Halifax to Chicago

Our best American Airlines deals on Halifax to Chicago flight tickets
American Airlines
1 Sep
YHZ3:04 p.m.Halifax Intl
22h 08m
1 stop
ORD11:12 a.m.Chicago O'Hare Intl
7 Sep
ORD5:00 a.m.Chicago O'Hare Intl
6h 36m
1 stop
YHZ1:36 p.m.Halifax Intl
C$ 567
American Airlines
17 Jul
YHZ2:28 p.m.Halifax Intl
12h 01m
1 stop
ORD12:29 a.m.Chicago O'Hare Intl
19 Jul
ORD6:00 a.m.Chicago O'Hare Intl
6h 20m
1 stop
YHZ2:20 p.m.Halifax Intl
C$ 767

United Airlines flights from Halifax to Chicago

Our best United Airlines deals on Halifax to Chicago flight tickets
United Airlines
19 Sep
YHZ12:40 p.m.Halifax Intl
6h 20m
1 stop
ORD5:00 p.m.Chicago O'Hare Intl
22 Sep
ORD3:55 p.m.Chicago O'Hare Intl
6h 00m
1 stop
YHZ11:55 p.m.Halifax Intl
C$ 420
United Airlines
1 Sep
YHZ7:00 a.m.Halifax Intl
13h 39m
1 stop
ORD6:39 p.m.Chicago O'Hare Intl
9 Sep
ORD3:55 p.m.Chicago O'Hare Intl
6h 00m
1 stop
YHZ11:55 p.m.Halifax Intl
C$ 501
United Airlines
12 Nov
YHZ6:00 a.m.Halifax Intl
10h 21m
2 stops
ORD2:21 p.m.Chicago O'Hare Intl
17 Nov
ORD7:00 a.m.Chicago O'Hare Intl
6h 58m
1 stop
YHZ3:58 p.m.Halifax Intl
C$ 504

momondo 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, momondo users made 96,600 searches. Data last updated 16 July 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 - MDW

YHZMDW

Halifax Intl

Wed 19/8

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

1 stop8h 35m

Chicago Midway

Wed 26/8

3:15 p.m.-11:44 p.m.

2 stops6h 29m

C$ 396

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 12/11

6:40 a.m.-5:30 p.m.

2 stops12h 50m

Chicago O'Hare Intl

Tue 17/11

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

2 stops10h 00m

C$ 396

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 24/8

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

1 stop8h 35m

Chicago Midway

Thu 27/8

3:15 p.m.-11:44 p.m.

2 stops6h 29m

C$ 397
Quickest round-trip

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Mon 12/10

5:15 a.m.-9:00 a.m.

1 stop5h 45m

Chicago O'Hare Intl

Sun 18/10

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

1 stop5h 17m

C$ 399

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 12/8

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

1 stop8h 35m

Chicago Midway

Wed 26/8

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

2 stops11h 19m

C$ 402

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 6/10

5:45 a.m.-10:17 a.m.

1 stop6h 32m

Chicago O'Hare Intl

Thu 22/10

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

1 stop5h 17m

C$ 403

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 12/8

6:25 a.m.-10:16 a.m.

1 stop5h 51m

Chicago O'Hare Intl

Wed 26/8

8:40 a.m.-4:07 p.m.

1 stop5h 27m

C$ 404

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 7/10

7:15 a.m.-1:19 p.m.

2 stops8h 04m

Chicago O'Hare Intl

Thu 22/10

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

1 stop5h 17m

C$ 406

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 24/8

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

2 stops8h 35m

Chicago Midway

Thu 27/8

3:15 p.m.-11:44 p.m.

2 stops6h 29m

C$ 407

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 19/9

12:40 p.m.-5:00 p.m.

1 stop6h 20m

Chicago O'Hare Intl

Tue 22/9

3:55 p.m.-11:55 p.m.

1 stop6h 00m

C$ 420

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Halifax to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Halifax and Chicago?

What is the cheapest month to fly to Chicago?

The month of July is another great option to travel to Chicago, with average flight prices from Halifax averaging around C$ 132.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Monday when prices can be found for as low as C$ 619. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Saturday because tickets tend to average around C$ 1,024. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the afternoon is the cheapest time of day to fly from Halifax to Chicago when you can find flight prices for as low as C$ 797. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. At noon is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 1,211 per ticket.

What is the cheapest Halifax Intl to Chicago flight route?

Fly from Halifax Intl to Chicago O'Hare Intl for the best Halifax Intl - Chicago flight prices

What cabin class options are available on Halifax to Chicago flights?

There are 2 cabin classes available to choose from on Halifax to Chicago flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Halifax to Chicago flights?

You could potentially save up to 49% on your flight if you consider stops on a Halifax to Chicago flight.

How have Halifax to Chicago flight prices changed over time?

As of July 2026, prices for Halifax to Chicago flights are approximately 9% more expensive when compared to flights at the same time last year.

When to book flights from Halifax to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Halifax to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Halifax to Chicago (YHZ to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Halifax to Chicago

Best price found

C$ 290

Fastest flight time

3h 53m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Halifax in the past 72 hours is C$ 290. The best round-trip flight deal from Halifax to Chicago found on momondo in the last 72 hours is C$ 719.
The fastest flight from Halifax to Chicago takes 3h 53m
Direct flights go from Halifax to Chicago on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. There are no airlines offering direct flights.
There are 3 airports in Chicago. From Halifax there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

Frequently asked questions about flying from Halifax to Chicago

  • How far is Halifax Intl to Chicago by plane?

    Chicago is 1963.4 km away from Halifax Intl. A reasonable flight in good conditions will take 3h 53m.

  • When did momondo last update prices for flights from Halifax Intl Airport to Chicago?

    Prices for flights from Halifax Intl Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Halifax Intl Airport to Chicago?

  • How old do you have to be to fly from Halifax Intl Airport to Chicago?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Halifax Intl Airport to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Halifax to Chicago?

  • What is the most popular airline from Halifax to Chicago?

Best airlines flying from Halifax to Chicago

Compare and see reviews for airlines that fly from Halifax to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom C$ 229Free CancellationRating
7.4
9,993 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 290Free CancellationRating
7.1
11,347 reviews
Search Air Canada flights

  • United Airlines Flights From Halifax to Chicago

    The lowest priced United Airlines flight from Halifax to Chicago from the last 72 hours was C$ 229. Generally, United Airlines has 7 flights on this route every week with an average price of C$ 229. United Airlines is rated 7.4/10 by our users.

  • Air Canada Flights From Halifax to Chicago

    Air Canada (7.1/10 from 11,347 reviews) operates around 7 flights from Halifax to Chicago in any given week. The average Air Canada airfare for this route is around C$ 600, with deals from around C$ 290 rare but found on momondo. Referenced prices are for round-trip Halifax to Chicago flight searches in the last 72 hours.

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Munster
Valparaiso
Portage

Why use momondo?

Why should I use momondo to find a flight deal from Halifax to Chicago?

Finding the right flight to Chicago from Halifax is quick and easy when you have a range of options in front of you, from reputable agents and recognizable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Halifax to Chicago with flexible booking policies on momondo?

All flight searches from Halifax to Chicago on momondo can be filtered to show those which offer flexible booking policies.

How can momondo help me find flights from Halifax to Chicago?

momondo helps you find the best flight between Halifax and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Halifax to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Halifax are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport