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Cheap flights from Halifax to Chicago from C$ 261

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 12/1. 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
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 376Porter Airlines
Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 11:54 p.m.
MDW
-
YHZ
10h 54m2 stops
C$ 418Porter Airlines
Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 459Porter Airlines
Thu, 2 Apr - Sun, 5 Apr
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 461Porter Airlines
Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
12:45 p.m. - 8:05 p.m.
MDW
-
YHZ
5h 20m1 stop
C$ 463Porter Airlines
Wed, 18 Mar - Sat, 28 Mar
Multiple Airlines Logo
6:30 a.m. - 12:25 p.m.
YHZ
-
ORD
7h 55m1 stop
Multiple Airlines Logo
7:15 a.m. - 1:41 a.m.
ORD
-
YHZ
16h 26m2 stops
C$ 483Multiple Airlines
Sat, 10 Jan - Sat, 17 Jan
Multiple Airlines Logo
8:20 p.m. - 10:10 a.m.
YHZ
-
MDW
15h 50m1 stop
Multiple Airlines Logo
1:20 p.m. - 5:31 p.m.
MDW
-
YHZ
26h 11m2 stops
C$ 495Multiple Airlines
Wed, 28 Jan - Wed, 4 Feb
Multiple Airlines Logo
10:40 p.m. - 11:50 a.m.
YHZ
-
MDW
15h 10m1 stop
Multiple Airlines Logo
11:00 a.m. - 8:10 p.m.
MDW
-
YHZ
7h 10m1 stop
C$ 517Multiple Airlines
Fri, 16 Jan - Mon, 19 Jan
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 521Porter Airlines
Thu, 12 Mar - Sun, 15 Mar
Multiple Airlines Logo
8:30 a.m. - 11:46 p.m.
YHZ
-
ORD
17h 16m3 stops
Multiple Airlines Logo
5:15 a.m. - 12:27 a.m.
ORD
-
YHZ
17h 12m3 stops
C$ 521Multiple Airlines
Wed, 28 Jan - Wed, 4 Feb

American Airlines flights from Halifax to Chicago

Our best American Airlines deals on Halifax to Chicago flight tickets
American Airlines
25 Dec
YHZ6:30 a.m.Halifax Intl
8h 03m
1 stop
ORD12:33 p.m.Chicago O'Hare Intl
29 Dec
ORD3:04 p.m.Chicago O'Hare Intl
7h 18m
1 stop
YHZ12:22 a.m.Halifax Intl
C$ 758
Find similar
American Airlines
26 Dec
YHZ1:10 p.m.Halifax Intl
8h 13m
1 stop
ORD7:23 p.m.Chicago O'Hare Intl
29 Dec
ORD3:04 p.m.Chicago O'Hare Intl
7h 18m
1 stop
YHZ12:22 a.m.Halifax Intl
C$ 878
Find similar
American Airlines
24 Dec
YHZ1:10 p.m.Halifax Intl
29h 37m
2 stops
ORD4:47 p.m.Chicago O'Hare Intl
27 Dec
ORD3:00 p.m.Chicago O'Hare Intl
7h 22m
1 stop
YHZ12:22 a.m.Halifax Intl
C$ 1,030
Find similar

Air Canada flights from Halifax to Chicago

Our best Air Canada deals on Halifax to Chicago flight tickets
Air Canada
2 Apr
YHZ7:00 a.m.Halifax Intl
10h 10m
1 stop
ORD3:10 p.m.Chicago O'Hare Intl
5 Apr
ORD8:40 a.m.Chicago O'Hare Intl
5h 10m
1 stop
YHZ3:50 p.m.Halifax Intl
C$ 648
Find similar
Air Canada
14 Apr
YHZ5:35 a.m.Halifax Intl
6h 33m
1 stop
ORD10:08 a.m.Chicago O'Hare Intl
15 Apr
ORD3:45 p.m.Chicago O'Hare Intl
6h 20m
1 stop
YHZ12:05 a.m.Halifax Intl
C$ 650
Find similar
Air Canada
14 Apr
YHZ11:20 a.m.Halifax Intl
5h 35m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
15 Apr
ORD8:40 a.m.Chicago O'Hare Intl
5h 10m
1 stop
YHZ3:50 p.m.Halifax Intl
C$ 652
Find similar

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 11 December 2025.
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

Tue 14/4

8:30 a.m.-3:20 p.m.

1 stop8h 50m

Chicago Midway

Wed 15/4

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

1 stop7h 05m

C$ 376

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 14/4

8:30 a.m.-3:20 p.m.

1 stop8h 50m

Chicago Midway

Wed 15/4

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

2 stops10h 54m

C$ 418

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 2/4

8:30 a.m.-3:20 p.m.

1 stop8h 50m

Chicago Midway

Sun 5/4

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

1 stop7h 05m

C$ 459

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Tue 14/4

8:30 a.m.-3:20 p.m.

1 stop8h 50m

Chicago Midway

Wed 15/4

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

1 stop7h 05m

C$ 461

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 18/3

8:30 a.m.-3:20 p.m.

1 stop8h 50m

Chicago Midway

Sat 28/3

12:45 p.m.-8:05 p.m.

1 stop5h 20m

C$ 463

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 10/1

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

1 stop7h 55m

Chicago O'Hare Intl

Sat 17/1

7:15 a.m.-1:41 a.m.

2 stops16h 26m

C$ 483

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 28/1

8:20 p.m.-10:10 a.m.

1 stop15h 50m

Chicago Midway

Wed 4/2

1:20 p.m.-5:31 p.m.

2 stops26h 11m

C$ 495

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 16/1

10:40 p.m.-11:50 a.m.

1 stop15h 10m

Chicago Midway

Mon 19/1

11:00 a.m.-8:10 p.m.

1 stop7h 10m

C$ 517

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 12/3

8:30 a.m.-3:20 p.m.

1 stop8h 50m

Chicago Midway

Sun 15/3

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

1 stop7h 05m

C$ 521

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 28/1

8:30 a.m.-11:46 p.m.

3 stops17h 16m

Chicago O'Hare Intl

Wed 4/2

5:15 a.m.-12:27 a.m.

3 stops17h 12m

C$ 521

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 January is another great option to travel to Chicago, with average flight prices from Halifax averaging around C$ 386.

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$ 434. 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 Friday because tickets tend to average around C$ 1,246. 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 morning is the cheapest time of day to fly from Halifax to Chicago when you can find flight prices for as low as C$ 532. Flying to Chicago in the morning 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$ 1,189 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 December 2025, prices for Halifax to Chicago flights are approximately 7% 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

Fastest flight time

7h 55m

Direct flights

Mon, Tue and Wed

Airports in Chicago

3 airports
The fastest flight from Halifax to Chicago takes 7h 55m
Direct flights go from Halifax to Chicago on Monday, Tuesday and Wednesday. 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 7h 55m.

  • 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$ 225Free CancellationRating
7.4
9,095 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 334Free CancellationRating
7.1
10,516 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