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Cheap flights from Halifax to Chicago from $180

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 10/6. 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.
Air Canada Logo
6:25 am - 10:15 amYHZ  Halifax Intl-ORD Chicago O'Hare Intl
5h 50m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
3:40 pm - 12:35 amORD  Chicago O'Hare Intl-YHZ Halifax Intl
6h 55m1 stop Montreal Pierre Elliott Trudeau Intl
$324Air Canada
Sat, Sep 19 - Sat, Sep 26
Porter Airlines Logo
7:00 am - 2:35 pmYHZ  Halifax Intl-MDW Chicago Midway
9h 35m2 stops Ottawa Toronto Island
Porter Airlines Logo
3:20 pm - 11:44 pmMDW  Chicago Midway-YHZ Halifax Intl
6h 24m2 stops Toronto Island Ottawa
$326Porter Airlines
Fri, Sep 25 - Mon, Oct 5
Air Canada Logo
6:05 am - 11:07 amYHZ  Halifax Intl-ORD Chicago O'Hare Intl
7h 02m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
7:05 am - 3:55 pmORD  Chicago O'Hare Intl-YHZ Halifax Intl
6h 50m1 stop Montreal Pierre Elliott Trudeau Intl
$327Air Canada
Wed, Nov 25 - Tue, Dec 1
Air Canada Logo
11:25 am - 2:52 pmYHZ  Halifax Intl-ORD Chicago O'Hare Intl
5h 27m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
7:05 am - 3:55 pmORD  Chicago O'Hare Intl-YHZ Halifax Intl
6h 50m1 stop Montreal Pierre Elliott Trudeau Intl
$327Air Canada
Tue, Nov 24 - Tue, Dec 1
Air Canada Logo
6:25 am - 10:15 amYHZ  Halifax Intl-ORD Chicago O'Hare Intl
5h 50m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
3:40 pm - 12:35 amORD  Chicago O'Hare Intl-YHZ Halifax Intl
6h 55m1 stop Montreal Pierre Elliott Trudeau Intl
$327Air Canada
Wed, Sep 16 - Wed, Sep 23
Air Canada Logo
6:25 am - 10:15 amYHZ  Halifax Intl-ORD Chicago O'Hare Intl
5h 50m1 stop Montreal Pierre Elliott Trudeau Intl
Air Canada Logo
8:45 am - 4:02 pmORD  Chicago O'Hare Intl-YHZ Halifax Intl
5h 17m1 stop Montreal Pierre Elliott Trudeau Intl
$328Air Canada
Sat, Sep 26 - Sat, Oct 3
Porter Airlines Logo
6:40 am - 5:30 pmYHZ  Halifax Intl-ORD Chicago O'Hare Intl
12h 50m2 stops Ottawa Toronto Island
Porter Airlines Logo
11:45 am - 11:45 pmORD  Chicago O'Hare Intl-YHZ Halifax Intl
10h 00m2 stops Toronto Island Ottawa
$329Porter Airlines
Wed, Nov 25 - Tue, Dec 1
Air Canada Logo
7:15 am - 1:11 pmYHZ  Halifax Intl-ORD Chicago O'Hare Intl
7h 56m2 stops Ottawa Toronto Island
Air Canada Logo
7:05 am - 3:55 pmORD  Chicago O'Hare Intl-YHZ Halifax Intl
6h 50m1 stop Montreal Pierre Elliott Trudeau Intl
$329Air Canada
Wed, Nov 25 - Tue, Dec 1
Air Canada Logo
1:45 pm - 8:21 pmYHZ  Halifax Intl-ORD Chicago O'Hare Intl
8h 36m2 stops Ottawa Toronto Island
Air Canada Logo
7:05 am - 3:55 pmORD  Chicago O'Hare Intl-YHZ Halifax Intl
6h 50m1 stop Montreal Pierre Elliott Trudeau Intl
$329Air Canada
Tue, Nov 24 - Tue, Dec 1
Porter Airlines Logo
6:40 am - 5:30 pmYHZ  Halifax Intl-ORD Chicago O'Hare Intl
12h 50m2 stops Ottawa Toronto Island
Porter Airlines Logo
11:45 am - 11:45 pmORD  Chicago O'Hare Intl-YHZ Halifax Intl
10h 00m2 stops Toronto Island Ottawa
$329Porter Airlines
Tue, Nov 24 - Tue, Dec 1

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Air Canada flights from Halifax to Chicago

Our best Air Canada deals on Halifax to Chicago flight tickets
Air Canada
Sep 19
YHZ6:25 amHalifax Intl
5h 50m
1 stop
ORD10:15 amChicago O'Hare Intl
Sep 26
ORD3:40 pmChicago O'Hare Intl
6h 55m
1 stop
YHZ12:35 amHalifax Intl
$324
Air Canada
Sep 16
YHZ6:25 amHalifax Intl
5h 50m
1 stop
ORD10:15 amChicago O'Hare Intl
Sep 23
ORD3:40 pmChicago O'Hare Intl
6h 55m
1 stop
YHZ12:35 amHalifax Intl
$327
Air Canada
Sep 26
YHZ6:25 amHalifax Intl
5h 50m
1 stop
ORD10:15 amChicago O'Hare Intl
Oct 3
ORD8:45 amChicago O'Hare Intl
5h 17m
1 stop
YHZ4:02 pmHalifax Intl
$328

Delta flights from Halifax to Chicago

Our best Delta deals on Halifax to Chicago flight tickets
Delta
Sep 2
YHZ6:30 amHalifax Intl
8h 30m
1 stop
ORD1:00 pmChicago O'Hare Intl
Sep 9
ORD6:00 amChicago O'Hare Intl
5h 27m
1 stop
YHZ1:27 pmHalifax Intl
$375
Delta
Sep 16
YHZ3:30 pmHalifax Intl
10h 29m
2 stops
ORD11:59 pmChicago O'Hare Intl
Sep 23
ORD11:17 amChicago O'Hare Intl
7h 53m
1 stop
YHZ9:10 pmHalifax Intl
$396
Delta
Aug 28
YHZ1:33 pmHalifax Intl
8h 57m
2 stops
ORD8:30 pmChicago O'Hare Intl
Sep 1
ORD11:30 amChicago O'Hare Intl
9h 48m
1 stop
YHZ11:18 pmHalifax Intl
$399

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 832,500 searches. Data last updated August 7, 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

Sat 9/19

6:25 am-10:15 am

1 stop5h 50m

Chicago O'Hare Intl

Sat 9/26

3:40 pm-12:35 am

1 stop6h 55m

$324

HalifaxChicago

YHZ Halifax Intl - MDW Chicago Midway

YHZMDW

Halifax Intl

Fri 9/25

7:00 am-2:35 pm

2 stops9h 35m

Chicago Midway

Mon 10/5

3:20 pm-11:44 pm

2 stops6h 24m

$326

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Wed 11/25

6:05 am-11:07 am

1 stop7h 02m

Chicago O'Hare Intl

Tue 12/1

7:05 am-3:55 pm

1 stop6h 50m

$327

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Tue 11/24

11:25 am-2:52 pm

1 stop5h 27m

Chicago O'Hare Intl

Tue 12/1

7:05 am-3:55 pm

1 stop6h 50m

$327

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Wed 9/16

6:25 am-10:15 am

1 stop5h 50m

Chicago O'Hare Intl

Wed 9/23

3:40 pm-12:35 am

1 stop6h 55m

$327
Quickest round-trip

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Sat 9/26

6:25 am-10:15 am

1 stop5h 50m

Chicago O'Hare Intl

Sat 10/3

8:45 am-4:02 pm

1 stop5h 17m

$328

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Wed 11/25

6:40 am-5:30 pm

2 stops12h 50m

Chicago O'Hare Intl

Tue 12/1

11:45 am-11:45 pm

2 stops10h 00m

$329

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Wed 11/25

7:15 am-1:11 pm

2 stops7h 56m

Chicago O'Hare Intl

Tue 12/1

7:05 am-3:55 pm

1 stop6h 50m

$329

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Tue 11/24

1:45 pm-8:21 pm

2 stops8h 36m

Chicago O'Hare Intl

Tue 12/1

7:05 am-3:55 pm

1 stop6h 50m

$329

HalifaxChicago

YHZ Halifax Intl - ORD Chicago O'Hare Intl

YHZORD

Halifax Intl

Tue 11/24

6:40 am-5:30 pm

2 stops12h 50m

Chicago O'Hare Intl

Tue 12/1

11:45 am-11:45 pm

2 stops10h 00m

$329

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 typical for flights on this route.

Typical prices usually range from $313 to $413.
The lowest price recently found on this route was $324.

What is the cheapest month to fly to Chicago?

The month of September is, on average, the cheapest month to fly to Chicago from Halifax, with most prices found around $206. If you’re not able to fly to Chicago in September, then December is your next best option. Flight prices from Halifax to Chicago during December average around $288.

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 Wednesday when prices can be found for as low as $377. This is often the case because there is less demand to fly during this day of the week. When flying out on a Friday, the most expensive travel day of the week, you can expect to see flight prices from Halifax to Chicago for around $715.

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 45% 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

$291

Fastest flight time

3h 45m

Direct flights

Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Halifax in the past 72 hours is $291. The best round-trip flight deal from Halifax to Chicago found on momondo in the last 72 hours is $361.
The fastest flight from Halifax to Chicago takes 3h 45m
Direct flights go from Halifax to Chicago on 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?

    The distance between Halifax Intl and Chicago is about 1220.0 mi. A reasonable flight in good conditions will take 3h 45m.

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

    Prices for flights from Halifax Intl Airport to Chicago are updated 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?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check 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?

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
Air CanadaPriceFrom $182Free CancellationRating
7.1
11,434 reviews
Search Air Canada flights

  • Air Canada Flights From Halifax to Chicago

    Air Canada operates around 6 flights from Halifax to Chicago every week. The average price of these flights found in the last 72 hours has been $539, but momondo users have found Air Canada deals from Halifax to Chicago from as low as $182 round-trip. Air Canada has been scored 7.1/10 in 11,434 reviews.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

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

It is quick and easy to find Halifax to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Flights from Halifax to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

Once you have performed a search for Halifax to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Halifax and alert you when they change.

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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 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport