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Cheap flights from Halifax to Chicago from C$ 247

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 12/12. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
8:25 a.m. - 3:20 p.m.YHZ-MDW
8h 55m2 stops
Porter Airlines Logo
11:00 a.m. - 8:10 p.m.MDW-YHZ
7h 10m1 stop
C$ 365Porter Airlines
Find Deal
Mon, 8 Dec - Mon, 15 Dec
Porter Airlines Logo
8:25 a.m. - 3:20 p.m.YHZ-MDW
8h 55m2 stops
Porter Airlines Logo
11:00 a.m. - 9:20 p.m.MDW-YHZ
8h 20m2 stops
C$ 372Porter Airlines
Find Deal
Mon, 8 Dec - Mon, 15 Dec
Multiple Airlines Logo
10:40 p.m. - 11:50 a.m.YHZ-MDW
15h 10m1 stop
Multiple Airlines Logo
11:00 a.m. - 8:05 p.m.MDW-YHZ
7h 05m1 stop
C$ 497Multiple Airlines
Find Deal
Fri, 27 Feb - Mon, 2 Mar
WestJet Logo
6:10 p.m. - 1:35 p.m.YHZ-ORD
21h 25m1 stop
WestJet Logo
2:20 p.m. - 6:02 a.m.ORD-YHZ
13h 42m2 stops
C$ 515WestJet
Find Deal
Thu, 26 Feb - Mon, 2 Mar
American Airlines Logo
1:10 p.m. - 7:24 p.m.YHZ-ORD
8h 14m1 stop
American Airlines Logo
2:55 p.m. - 12:22 a.m.ORD-YHZ
7h 27m1 stop
C$ 548American Airlines
Find Deal
Mon, 8 Dec - Mon, 15 Dec
American Airlines Logo
6:30 a.m. - 12:30 p.m.YHZ-ORD
8h 00m1 stop
American Airlines Logo
3:37 p.m. - 12:22 a.m.ORD-YHZ
6h 45m1 stop
C$ 556American Airlines
Find Deal
Fri, 30 Jan - Sun, 1 Feb
Multiple Airlines Logo
6:00 a.m. - 8:01 p.m.YHZ-ORD
16h 01m2 stops
Multiple Airlines Logo
7:10 a.m. - 9:20 p.m.ORD-YHZ
12h 10m2 stops
C$ 562Multiple Airlines
Find Deal
Mon, 8 Dec - Mon, 15 Dec
WestJet Logo
6:00 a.m. - 1:18 p.m.YHZ-ORD
9h 18m2 stops
WestJet Logo
10:35 a.m. - 1:41 a.m.ORD-YHZ
13h 06m2 stops
C$ 574WestJet
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Thu, 29 Jan - Mon, 2 Feb
Air Canada Logo
11:20 a.m. - 2:55 p.m.YHZ-ORD
5h 35m1 stop
Air Canada Logo
3:35 p.m. - 12:06 a.m.ORD-YHZ
6h 31m1 stop
C$ 642Air Canada
Find Deal
Wed, 24 Dec - Wed, 31 Dec
Air Canada Logo
6:55 a.m. - 11:06 a.m.YHZ-ORD
6h 11m1 stop
Air Canada Logo
3:35 p.m. - 12:06 a.m.ORD-YHZ
6h 31m1 stop
C$ 643Air Canada
Find Deal
Thu, 29 Jan - Sun, 1 Feb

WestJet flights from Halifax to Chicago

Our best WestJet deals on Halifax to Chicago flight tickets
WestJet
26 Feb
YHZ6:10 p.m.Halifax Intl
21h 25m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
2 Mar
ORD2:20 p.m.Chicago O'Hare Intl
13h 42m
2 stops
YHZ6:02 a.m.Halifax Intl
C$ 515
Find similar
WestJet
29 Jan
YHZ6:00 a.m.Halifax Intl
9h 18m
2 stops
ORD1:18 p.m.Chicago O'Hare Intl
2 Feb
ORD10:35 a.m.Chicago O'Hare Intl
13h 06m
2 stops
YHZ1:41 a.m.Halifax Intl
C$ 574
Find similar
WestJet
29 Jan
YHZ6:00 a.m.Halifax Intl
12h 40m
2 stops
ORD4:40 p.m.Chicago O'Hare Intl
31 Jan
ORD1:58 p.m.Chicago O'Hare Intl
9h 43m
2 stops
YHZ1:41 a.m.Halifax Intl
C$ 577
Find similar

American Airlines flights from Halifax to Chicago

Our best American Airlines deals on Halifax to Chicago flight tickets
American Airlines
8 Dec
YHZ1:10 p.m.Halifax Intl
8h 14m
1 stop
ORD7:24 p.m.Chicago O'Hare Intl
15 Dec
ORD2:55 p.m.Chicago O'Hare Intl
7h 27m
1 stop
YHZ12:22 a.m.Halifax Intl
C$ 548
Find similar
American Airlines
30 Jan
YHZ6:30 a.m.Halifax Intl
8h 00m
1 stop
ORD12:30 p.m.Chicago O'Hare Intl
1 Feb
ORD3:37 p.m.Chicago O'Hare Intl
6h 45m
1 stop
YHZ12:22 a.m.Halifax Intl
C$ 556
Find similar
American Airlines
30 Jan
YHZ6:30 a.m.Halifax Intl
8h 00m
1 stop
ORD12:30 p.m.Chicago O'Hare Intl
1 Feb
ORD3:37 p.m.Chicago O'Hare Intl
6h 45m
1 stop
YHZ12:22 a.m.Halifax Intl
C$ 558
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 10 November 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

Mon 8/12

8:25 a.m.-3:20 p.m.

2 stops8h 55m

Chicago Midway

Mon 15/12

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

1 stop7h 10m

C$ 365

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 8/12

8:25 a.m.-3:20 p.m.

2 stops8h 55m

Chicago Midway

Mon 15/12

11:00 a.m.-9:20 p.m.

2 stops8h 20m

C$ 372

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Fri 27/2

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

1 stop15h 10m

Chicago Midway

Mon 2/3

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

1 stop7h 05m

C$ 497

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 26/2

6:10 p.m.-1:35 p.m.

1 stop21h 25m

Chicago O'Hare Intl

Mon 2/3

2:20 p.m.-6:02 a.m.

2 stops13h 42m

C$ 515

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Mon 8/12

1:10 p.m.-7:24 p.m.

1 stop8h 14m

Chicago O'Hare Intl

Mon 15/12

2:55 p.m.-12:22 a.m.

1 stop7h 27m

C$ 548

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 30/1

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

1 stop8h 00m

Chicago O'Hare Intl

Sun 1/2

3:37 p.m.-12:22 a.m.

1 stop6h 45m

C$ 556

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Mon 8/12

6:00 a.m.-8:01 p.m.

2 stops16h 01m

Chicago O'Hare Intl

Mon 15/12

7:10 a.m.-9:20 p.m.

2 stops12h 10m

C$ 562

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 29/1

6:00 a.m.-1:18 p.m.

2 stops9h 18m

Chicago O'Hare Intl

Mon 2/2

10:35 a.m.-1:41 a.m.

2 stops13h 06m

C$ 574

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 24/12

11:20 a.m.-2:55 p.m.

1 stop5h 35m

Chicago O'Hare Intl

Wed 31/12

3:35 p.m.-12:06 a.m.

1 stop6h 31m

C$ 642

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 29/1

6:55 a.m.-11:06 a.m.

1 stop6h 11m

Chicago O'Hare Intl

Sun 1/2

3:35 p.m.-12:06 a.m.

1 stop6h 31m

C$ 643

Flights are sorted by cheapest round-trip flights 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 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$ 378.

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$ 442. 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$ 1,268. 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$ 542. 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$ 1,211 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 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 November 2025, prices for Halifax to Chicago flights are approximately 57% 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

Direct flights

None
There are no direct flights from Halifax to Chicago. There are no popular flight routes from Halifax to Chicago.
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 5h 35m.

  • 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
9,012 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 341Free CancellationRating
7.1
10,437 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