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Cheap flights from Halifax to Chicago from C$ 201

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 23/5. 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

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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
10:25 a.m. - 11:44 p.m.
MDW
-
YHZ
11h 19m
2 stops
C$ 330Porter Airlines
Mon, 20 Jul - Mon, 27 Jul
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
2 stops
Porter Airlines Logo
10:25 a.m. - 11:44 p.m.
MDW
-
YHZ
11h 19m
2 stops
C$ 336Porter Airlines
Mon, 20 Jul - Mon, 27 Jul
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.
YHZ
-
MDW
9h 35m
2 stops
Porter Airlines Logo
10:25 a.m. - 11:44 p.m.
MDW
-
YHZ
11h 19m
2 stops
C$ 367Porter Airlines
Mon, 27 Jul - Mon, 31 Aug
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$ 387Porter Airlines
Mon, 27 Jul - Mon, 31 Aug
Multiple Airlines Logo
10:40 p.m. - 1:01 p.m.
YHZ
-
ORD
16h 21m
1 stop
Multiple Airlines Logo
9:50 a.m. - 7:35 p.m.
ORD
-
YHZ
7h 45m
1 stop
C$ 404Multiple Airlines
Mon, 23 Mar - Mon, 30 Mar
Porter Airlines Logo
7:00 a.m. - 3:20 p.m.
YHZ
-
MDW
10h 20m
2 stops
Porter Airlines Logo
12:45 p.m. - 11:54 p.m.
MDW
-
YHZ
9h 09m
2 stops
C$ 408Porter Airlines
Thu, 19 Mar - Sat, 28 Mar
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$ 409Porter Airlines
Fri, 19 Jun - Mon, 22 Jun
WestJet Logo
3:30 p.m. - 8:24 p.m.
YHZ
-
ORD
6h 54m
1 stop
WestJet Logo
8:55 a.m. - 9:45 p.m.
ORD
-
YHZ
10h 50m
1 stop
C$ 449WestJet
Fri, 19 Jun - Mon, 22 Jun
WestJet Logo
3:30 p.m. - 6:41 p.m.
YHZ
-
ORD
5h 11m
1 stop
WestJet Logo
8:55 a.m. - 9:45 p.m.
ORD
-
YHZ
10h 50m
1 stop
C$ 450WestJet
Fri, 19 Jun - Mon, 22 Jun
WestJet Logo
3:30 p.m. - 9:24 a.m.
YHZ
-
ORD
19h 54m
1 stop
WestJet Logo
1:35 p.m. - 9:45 p.m.
ORD
-
YHZ
6h 10m
1 stop
C$ 457WestJet
Thu, 18 Jun - Thu, 25 Jun

Air Canada flights from Halifax to Chicago

Our best Air Canada deals on Halifax to Chicago flight tickets
Air Canada
12 Apr
YHZ7:00 a.m.Halifax Intl
10h 15m
1 stop
ORD3:15 p.m.Chicago O'Hare Intl
19 Apr
ORD2:00 p.m.Chicago O'Hare Intl
8h 04m
1 stop
YHZ12:04 a.m.Halifax Intl
C$ 484
Air Canada
11 Mar
YHZ1:50 p.m.Halifax Intl
7h 55m
1 stop
ORD7:45 p.m.Chicago O'Hare Intl
15 Mar
ORD8:00 a.m.Chicago O'Hare Intl
14h 51m
1 stop
YHZ12:51 a.m.Halifax Intl
C$ 769
Air Canada
7 Mar
YHZ6:55 a.m.Halifax Intl
6h 23m
1 stop
ORD11:18 a.m.Chicago O'Hare Intl
16 Mar
ORD3:55 p.m.Chicago O'Hare Intl
6h 56m
1 stop
YHZ12:51 a.m.Halifax Intl
C$ 829

WestJet flights from Halifax to Chicago

Our best WestJet deals on Halifax to Chicago flight tickets
WestJet
19 Jun
YHZ3:30 p.m.Halifax Intl
6h 54m
1 stop
ORD8:24 p.m.Chicago O'Hare Intl
22 Jun
ORD8:55 a.m.Chicago O'Hare Intl
10h 50m
1 stop
YHZ9:45 p.m.Halifax Intl
C$ 449
WestJet
19 Jun
YHZ3:30 p.m.Halifax Intl
5h 11m
1 stop
ORD6:41 p.m.Chicago O'Hare Intl
22 Jun
ORD8:55 a.m.Chicago O'Hare Intl
10h 50m
1 stop
YHZ9:45 p.m.Halifax Intl
C$ 450
WestJet
18 Jun
YHZ3:30 p.m.Halifax Intl
19h 54m
1 stop
ORD9:24 a.m.Chicago O'Hare Intl
25 Jun
ORD1:35 p.m.Chicago O'Hare Intl
6h 10m
1 stop
YHZ9:45 p.m.Halifax Intl
C$ 457

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 27 February 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

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 20/7

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

1 stop8h 35m

Chicago Midway

Mon 27/7

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

2 stops11h 19m

C$ 330

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 20/7

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

2 stops8h 35m

Chicago Midway

Mon 27/7

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

2 stops11h 19m

C$ 336

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 27/7

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

2 stops9h 35m

Chicago Midway

Mon 31/8

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

2 stops11h 19m

C$ 367

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 27/7

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

1 stop8h 35m

Chicago Midway

Mon 31/8

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

2 stops11h 19m

C$ 387

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Mon 23/3

10:40 p.m.-1:01 p.m.

1 stop16h 21m

Chicago O'Hare Intl

Mon 30/3

9:50 a.m.-7:35 p.m.

1 stop7h 45m

C$ 404

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 19/3

7:00 a.m.-3:20 p.m.

2 stops10h 20m

Chicago Midway

Sat 28/3

12:45 p.m.-11:54 p.m.

2 stops9h 09m

C$ 408

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 19/6

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

1 stop8h 35m

Chicago Midway

Mon 22/6

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

2 stops11h 19m

C$ 409

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 19/6

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

1 stop6h 54m

Chicago O'Hare Intl

Mon 22/6

8:55 a.m.-9:45 p.m.

1 stop10h 50m

C$ 449

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 19/6

3:30 p.m.-6:41 p.m.

1 stop5h 11m

Chicago O'Hare Intl

Mon 22/6

8:55 a.m.-9:45 p.m.

1 stop10h 50m

C$ 450

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 18/6

3:30 p.m.-9:24 a.m.

1 stop19h 54m

Chicago O'Hare Intl

Thu 25/6

1:35 p.m.-9:45 p.m.

1 stop6h 10m

C$ 457

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 March is another great option to travel to Chicago, with average flight prices from Halifax averaging around C$ 408.

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 Friday when prices can be found for as low as C$ 643. 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$ 964. 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$ 828. 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$ 1,179 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 Intl to Chicago flights?

There are 3 cabin classes available to choose from on Halifax Intl 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 February 2026, prices for Halifax to Chicago flights are approximately 1% cheaper 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$ 1,170

Fastest flight time

3h 53m

Direct flights

Tue, Wed, 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$ 1,170. The best round-trip flight deal from Halifax to Chicago found on momondo in the last 72 hours is C$ 466.
The fastest flight from Halifax to Chicago takes 3h 53m
Direct flights go from Halifax to Chicago on Tuesday, Wednesday, 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

  • 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$ 223Free CancellationRating
7.4
9,349 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 283Free CancellationRating
7.1
10,749 reviews
Search Air Canada flights

Travelling to a place near Chicago?

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

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