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Cheap flights from Halifax to Chicago from C$ 251

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 6/10. 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

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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.
Air Canada Logo
6:25 a.m. - 10:15 a.m.YHZ  Halifax Intl-ORD Chicago O'Hare Intl
5h 50m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
3:40 p.m. - 12:35 a.m.ORD  Chicago O'Hare Intl-YHZ Halifax Intl
6h 55m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 434Air Canada
Wed, 16 Sep - Wed, 23 Sep
Air Canada Logo
6:25 a.m. - 10:15 a.m.YHZ  Halifax Intl-ORD Chicago O'Hare Intl
5h 50m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
3:40 p.m. - 12:35 a.m.ORD  Chicago O'Hare Intl-YHZ Halifax Intl
6h 55m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 436Air Canada
Wed, 16 Sep - Wed, 30 Sep
Air Canada Logo
6:25 a.m. - 10:15 a.m.YHZ  Halifax Intl-ORD Chicago O'Hare Intl
5h 50m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
11:05 a.m. - 7:10 p.m.ORD  Chicago O'Hare Intl-YHZ Halifax Intl
6h 05m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 436Air Canada
Tue, 22 Sep - Wed, 30 Sep
Air Canada Logo
6:25 a.m. - 10:15 a.m.YHZ  Halifax Intl-ORD Chicago O'Hare Intl
5h 50m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
3:40 p.m. - 12:35 a.m.ORD  Chicago O'Hare Intl-YHZ Halifax Intl
6h 55m1 stop Montreal Pierre Elliott Trudeau Intl
C$ 439Air Canada
Fri, 25 Sep - Tue, 29 Sep
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.YHZ  Halifax Intl-MDW Chicago Midway
9h 35m2 stops Ottawa Toronto Island
Porter Airlines Logo
11:45 a.m. - 11:44 p.m.MDW  Chicago Midway-YHZ Halifax Intl
9h 59m2 stops Toronto Island Ottawa
C$ 450Porter Airlines
Fri, 25 Sep - Tue, 6 Oct
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.YHZ  Halifax Intl-MDW Chicago Midway
9h 35m2 stops Ottawa Toronto Island
Porter Airlines Logo
11:45 a.m. - 11:44 p.m.MDW  Chicago Midway-YHZ Halifax Intl
9h 59m2 stops Toronto Island Ottawa
C$ 462Porter Airlines
Tue, 29 Sep - Sat, 3 Oct
Multiple Airlines Logo
11:45 a.m. - 11:00 a.m.YHZ  Halifax Intl-MDW Chicago Midway
25h 15m1 stop Toronto Pearson Intl
Multiple Airlines Logo
3:20 p.m. - 10:45 a.m.MDW  Chicago Midway-YHZ Halifax Intl
17h 25m1 stop Toronto Island
C$ 464Multiple Airlines
Sat, 19 Sep - Sat, 26 Sep
United Airlines Logo
7:00 a.m. - 12:59 p.m.YHZ  Halifax Intl-ORD Chicago O'Hare Intl
7h 59m1 stop Newark
United Airlines Logo
5:00 a.m. - 2:03 p.m.ORD  Chicago O'Hare Intl-YHZ Halifax Intl
7h 03m1 stop Newark
C$ 530United Airlines
Thu, 10 Sep - Mon, 14 Sep
United Airlines Logo
7:00 a.m. - 12:08 p.m.YHZ  Halifax Intl-ORD Chicago O'Hare Intl
7h 08m1 stop Newark
United Airlines Logo
9:35 p.m. - 2:03 p.m.ORD  Chicago O'Hare Intl-YHZ Halifax Intl
14h 28m1 stop Newark
C$ 537United Airlines
Wed, 16 Sep - Fri, 18 Sep
United Airlines Logo
2:50 p.m. - 10:28 p.m.YHZ  Halifax Intl-ORD Chicago O'Hare Intl
9h 38m1 stop Newark
United Airlines Logo
12:40 p.m. - 12:49 a.m.ORD  Chicago O'Hare Intl-YHZ Halifax Intl
10h 09m2 stops Washington, D.C. Reagan-National Toronto Pearson Intl
C$ 619United Airlines
Fri, 25 Sep - Tue, 29 Sep

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United Airlines flights from Halifax to Chicago

Our best United Airlines deals on Halifax to Chicago flight tickets
United Airlines
16 Sep
YHZ7:00 a.m.Halifax Intl
7h 08m
1 stop
ORD12:08 p.m.Chicago O'Hare Intl
18 Sep
ORD9:35 p.m.Chicago O'Hare Intl
14h 28m
1 stop
YHZ2:03 p.m.Halifax Intl
C$ 537
United Airlines
25 Aug
YHZ6:00 a.m.Halifax Intl
10h 30m
2 stops
ORD2:30 p.m.Chicago O'Hare Intl
29 Aug
ORD3:00 p.m.Chicago O'Hare Intl
7h 59m
2 stops
YHZ12:59 a.m.Halifax Intl
C$ 747
United Airlines
14 Aug
YHZ2:50 p.m.Halifax Intl
8h 10m
1 stop
ORD9:00 p.m.Chicago O'Hare Intl
16 Aug
ORD6:00 a.m.Chicago O'Hare Intl
15h 55m
1 stop
YHZ11:55 p.m.Halifax Intl
C$ 777

Air Canada flights from Halifax to Chicago

Our best Air Canada deals on Halifax to Chicago flight tickets
Air Canada
16 Sep
YHZ6:25 a.m.Halifax Intl
5h 50m
1 stop
ORD10:15 a.m.Chicago O'Hare Intl
23 Sep
ORD3:40 p.m.Chicago O'Hare Intl
6h 55m
1 stop
YHZ12:35 a.m.Halifax Intl
C$ 434
Air Canada
16 Sep
YHZ6:25 a.m.Halifax Intl
5h 50m
1 stop
ORD10:15 a.m.Chicago O'Hare Intl
30 Sep
ORD3:40 p.m.Chicago O'Hare Intl
6h 55m
1 stop
YHZ12:35 a.m.Halifax Intl
C$ 436
Air Canada
16 Sep
YHZ6:25 a.m.Halifax Intl
5h 50m
1 stop
ORD10:15 a.m.Chicago O'Hare Intl
20 Sep
ORD3:40 p.m.Chicago O'Hare Intl
6h 55m
1 stop
YHZ12:35 a.m.Halifax Intl
C$ 439

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 August 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 Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Wed 16/9

6:25 a.m.-10:15 a.m.

1 stop5h 50m

Chicago O'Hare Intl

Wed 23/9

3:40 p.m.-12:35 a.m.

1 stop6h 55m

C$ 434

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Wed 16/9

6:25 a.m.-10:15 a.m.

1 stop5h 50m

Chicago O'Hare Intl

Wed 30/9

3:40 p.m.-12:35 a.m.

1 stop6h 55m

C$ 436
Quickest round-trip

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Tue 22/9

6:25 a.m.-10:15 a.m.

1 stop5h 50m

Chicago O'Hare Intl

Wed 30/9

11:05 a.m.-7:10 p.m.

1 stop6h 05m

C$ 436

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 25/9

6:25 a.m.-10:15 a.m.

1 stop5h 50m

Chicago O'Hare Intl

Tue 29/9

3:40 p.m.-12:35 a.m.

1 stop6h 55m

C$ 439

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Fri 25/9

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

2 stops9h 35m

Chicago Midway

Tue 6/10

11:45 a.m.-11:44 p.m.

2 stops9h 59m

C$ 450

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Tue 29/9

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

2 stops9h 35m

Chicago Midway

Sat 3/10

11:45 a.m.-11:44 p.m.

2 stops9h 59m

C$ 462

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Sat 19/9

11:45 a.m.-11:00 a.m.

1 stop25h 15m

Chicago Midway

Sat 26/9

3:20 p.m.-10:45 a.m.

1 stop17h 25m

C$ 464

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Thu 10/9

7:00 a.m.-12:59 p.m.

1 stop7h 59m

Chicago O'Hare Intl

Mon 14/9

5:00 a.m.-2:03 p.m.

1 stop7h 03m

C$ 530

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Wed 16/9

7:00 a.m.-12:08 p.m.

1 stop7h 08m

Chicago O'Hare Intl

Fri 18/9

9:35 p.m.-2:03 p.m.

1 stop14h 28m

C$ 537

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Fri 25/9

2:50 p.m.-10:28 p.m.

1 stop9h 38m

Chicago O'Hare Intl

Tue 29/9

12:40 p.m.-12:49 a.m.

2 stops10h 09m

C$ 619

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?

Prices are currently low for flights on this route.

Typical prices usually range from C$ 436 to C$ 570.
The lowest price recently found on this route was C$ 434.

What is the cheapest month to fly to Chicago?

The month of December is another great option to travel to Chicago, with average flight prices from Halifax averaging around C$ 402.

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 Sunday when prices can be found for as low as C$ 518. 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 Tuesday because tickets tend to average around C$ 884. 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$ 771. 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$ 1,735 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 58% 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 August 2026, prices for Halifax to Chicago flights are approximately 20% 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$ 323

Fastest flight time

3h 42m

Direct flights

Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Halifax in the past 72 hours is C$ 323. The best round-trip flight deal from Halifax to Chicago found on momondo in the last 72 hours is C$ 493.
The fastest flight from Halifax to Chicago takes 3h 42m
Direct flights go from Halifax to Chicago on Sunday. The only airline offering direct flights is United Airlines.
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 42m.

  • 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$ 228Free CancellationRating
7.4
10,104 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 269Free CancellationRating
7.1
11,462 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$ 228. Generally, United Airlines has 1 flight on this route every week with an average price of C$ 228. United Airlines is rated 7.4/10 by our users.

  • Air Canada Flights From Halifax to Chicago

    Air Canada (7.1/10 from 11,462 reviews) operates around 1 flight from Halifax to Chicago in any given week. The average Air Canada airfare for this route is around C$ 596, with deals from around C$ 269 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