Which layover airport has the shortest connection time from Halifax to Chicago?

Toronto (YYZ) has the shortest average layover time for this route: 2h 09m.

Which airport is the most popular layover for flights between Halifax and Chicago?

Toronto (YYZ) was the most common stop: 86% of momondo users choosing one-stop flights on this route connected there.

Which airlines fly to Chicago?

Air Canada, United Airlines and Porter Airlines are the top three most popular airlines that fly to Chicago from Halifax according to our data. Air Canada is the first choice among our users, with 61% of people opting to fly with this airline when travelling to Chicago. Keep in mind that there are 3 different airlines that fly to Chicago on a routine basis, so you have a few additional options to choose from.

How many flights depart from Halifax to Chicago on average per week?

As of June 2026, there are 14 flights per week flying from Halifax to Chicago. The most common day of the week flights depart is Mon, with 14% of flights taking off on this day.

What is the cheapest airline that flies from Halifax Intl to Chicago?

Delta and Porter Airlines are the most popular carriers operating from Halifax Intl to Chicago

How many flights depart from Halifax to Chicago on average per day?

2 flights are operational daily from Halifax to Chicago as of June 2026. The most popular departure time for this route is 4:00p.m., with 100% of flights per day taking off in the afternoon.

Which layover airport offers the lowest fares from Halifax to Chicago?

Flights via Montreal (YUL) offer the lowest average round-trip price of C$ 269.

Which layover airport has the shortest travel time from Halifax to Chicago?

Flights connecting via Toronto (YYZ) have the shortest average one-way travel time: 6h 05m.

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?

The number of operators available for flights from Halifax Intl Airport to Chicago is 3 as of June 2026.

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.

C$ 256 Cheap Flights from Halifax to Chicago in 2026

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Not ready to book? to track prices.

Search flight deals

Find the cheapest flights from Halifax to Chicago

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

Enter your travel dates to find the best prices.

2:28 p.m. - 11:30 p.m.

YHZ

ORD

11h 02m

1 stop

7:59 p.m. - 2:32 p.m.

ORD

YHZ

16h 33m

1 stop

C$ 511American Airlines

Wed, 29 Jul - Fri, 31 Jul

2:28 p.m. - 11:30 p.m.

YHZ

ORD

11h 02m

1 stop

8:55 p.m. - 3:28 p.m.

ORD

YHZ

16h 33m

1 stop

C$ 513American Airlines

Thu, 9 Jul - Sat, 11 Jul

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

YHZ

MDW

9h 35m

2 stops

3:20 p.m. - 11:44 p.m.

MDW

YHZ

6h 24m

2 stops

C$ 515Porter Airlines

Wed, 1 Jul - Wed, 8 Jul

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

YHZ

ORD

8h 55m

2 stops

11:00 a.m. - 11:49 p.m.

ORD

YHZ

10h 49m

2 stops

C$ 520Porter Airlines

Tue, 10 Nov - Sun, 15 Nov

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

YHZ

MDW

8h 35m

1 stop

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

MDW

YHZ

11h 19m

2 stops

C$ 522Porter Airlines

Wed, 1 Jul - Wed, 8 Jul

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

YHZ

ORD

10h 20m

2 stops

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

ORD

YHZ

7h 10m

1 stop

C$ 522Porter Airlines

Tue, 10 Nov - Sun, 15 Nov

6:30 a.m. - 4:24 p.m.

YHZ

ORD

11h 54m

2 stops

6:00 a.m. - 2:04 p.m.

ORD

YHZ

6h 04m

1 stop

C$ 552Delta

Thu, 3 Sep - Thu, 10 Sep

11:00 p.m. - 9:35 a.m.

YHZ

MDW

12h 35m

1 stop

10:15 a.m. - 12:24 p.m.

MDW

YHZ

24h 09m

1 stop

C$ 556Multiple Airlines

Sat, 13 Jun - Tue, 16 Jun

11:00 p.m. - 9:35 a.m.

YHZ

MDW

12h 35m

1 stop

10:15 a.m. - 2:10 p.m.

MDW

YHZ

25h 55m

1 stop

C$ 563Multiple Airlines

Sat, 13 Jun - Mon, 15 Jun

3:30 p.m. - 8:27 p.m.

YHZ

ORD

6h 57m

1 stop

11:22 a.m. - 9:40 p.m.

ORD

YHZ

8h 18m

1 stop

C$ 585WestJet

Tue, 25 Aug - Sat, 29 Aug

WestJet flights from Halifax to Chicago

Our best WestJet deals on Halifax to Chicago flight tickets

WestJet

25 Aug

YHZ3:30 p.m.Halifax Intl

6h 57m

1 stop

ORD8:27 p.m.Chicago O'Hare Intl

29 Aug

ORD11:22 a.m.Chicago O'Hare Intl

8h 18m

1 stop

YHZ9:40 p.m.Halifax Intl

C$ 585

WestJet

25 Aug

YHZ3:30 p.m.Halifax Intl

23h 43m

1 stop

ORD1:13 p.m.Chicago O'Hare Intl

29 Aug

ORD11:22 a.m.Chicago O'Hare Intl

8h 18m

1 stop

YHZ9:40 p.m.Halifax Intl

C$ 627

WestJet

19 Jun

YHZ3:30 p.m.Halifax Intl

7h 01m

1 stop

ORD8:31 p.m.Chicago O'Hare Intl

22 Jun

ORD7:01 a.m.Chicago O'Hare Intl

12h 39m

1 stop

YHZ9:40 p.m.Halifax Intl

C$ 628

Delta flights from Halifax to Chicago

Our best Delta deals on Halifax to Chicago flight tickets

Delta

3 Sep

YHZ6:30 a.m.Halifax Intl

11h 54m

2 stops

ORD4:24 p.m.Chicago O'Hare Intl

10 Sep

ORD6:00 a.m.Chicago O'Hare Intl

6h 04m

1 stop

YHZ2:04 p.m.Halifax Intl

C$ 552

Delta

9 Sep

YHZ3:30 p.m.Halifax Intl

6h 54m

1 stop

ORD8:24 p.m.Chicago O'Hare Intl

12 Sep

ORD11:30 a.m.Chicago O'Hare Intl

8h 15m

1 stop

YHZ9:45 p.m.Halifax Intl

C$ 594

Delta

9 Sep

YHZ3:30 p.m.Halifax Intl

6h 54m

1 stop

ORD8:24 p.m.Chicago O'Hare Intl

12 Sep

ORD11:30 a.m.Chicago O'Hare Intl

8h 15m

1 stop

YHZ9:45 p.m.Halifax Intl

C$ 637

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 29/7

2:28 p.m.-11:30 p.m.

1 stop11h 02m

Chicago O'Hare Intl

Fri 31/7

7:59 p.m.-2:32 p.m.

1 stop16h 33m

C$ 511

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 9/7

2:28 p.m.-11:30 p.m.

1 stop11h 02m

Chicago O'Hare Intl

Sat 11/7

8:55 p.m.-3:28 p.m.

1 stop16h 33m

C$ 513

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 1/7

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

2 stops9h 35m

Chicago Midway

Wed 8/7

3:20 p.m.-11:44 p.m.

2 stops6h 24m

C$ 515

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 10/11

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

2 stops8h 55m

Chicago O'Hare Intl

Sun 15/11

11:00 a.m.-11:49 p.m.

2 stops10h 49m

C$ 520

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 1/7

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

1 stop8h 35m

Chicago Midway

Wed 8/7

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

2 stops11h 19m

C$ 522

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 10/11

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

2 stops10h 20m

Chicago O'Hare Intl

Sun 15/11

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

1 stop7h 10m

C$ 522

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 3/9

6:30 a.m.-4:24 p.m.

2 stops11h 54m

Chicago O'Hare Intl

Thu 10/9

6:00 a.m.-2:04 p.m.

1 stop6h 04m

C$ 552

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 13/6

11:00 p.m.-9:35 a.m.

1 stop12h 35m

Chicago Midway

Tue 16/6

10:15 a.m.-12:24 p.m.

1 stop24h 09m

C$ 556

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Sat 13/6

11:00 p.m.-9:35 a.m.

1 stop12h 35m

Chicago Midway

Mon 15/6

10:15 a.m.-2:10 p.m.

1 stop25h 55m

C$ 563

Quickest round-trip

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Tue 25/8

3:30 p.m.-8:27 p.m.

1 stop6h 57m

Chicago O'Hare Intl

Sat 29/8

11:22 a.m.-9:40 p.m.

1 stop8h 18m

C$ 585

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

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

Prices

Airlines

Layovers

Other information

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 December is another great option to travel to Chicago, with average flight prices from Halifax averaging around C$ 201.

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$ 611. 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$ 954. 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$ 768. 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$ 1,722 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 4 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 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 June 2026, prices for Halifax to Chicago flights are approximately 55% 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$ 700
Fastest flight time	3h 53m
Direct flights	Every day
Airports in Chicago	3 airports

The best flight deal from Halifax to Chicago found on momondo in the last 72 hours is C$ 700

The fastest flight from Halifax to Chicago takes 3h 53m

Direct flights go from Halifax to Chicago every day.

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 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?
The number of operators available for flights from Halifax Intl Airport to Chicago is 3 as of June 2026.
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?
Based on momondo bookings for flights between Halifax and Chicago, the leading plane model is Embraer 175 (Enhanced Winglets), making up 72.73% of the total bookings. Other popular models include Embraer 175 with 27.27%.
What is the most popular airline from Halifax to Chicago?
Based on momondo bookings for flights between Halifax and Chicago, the leading airline is Air Canada, making up 48% of the total bookings. Other popular airlines include Porter Airlines with 24%, WestJet with 15%, and United Airlines with 14%.

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 Airlines	PriceFrom C$ 226	Free Cancellation	Rating 7.4 9,772 reviews	Search United Airlines flights
Air Canada	PriceFrom C$ 286	Free Cancellation	Rating 7.1 11,122 reviews	Search Air Canada flights
Porter Airlines	PriceFrom C$ 468	Free Cancellation	Rating 8.0 440 reviews	Search Porter Airlines 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$ 226. Generally, United Airlines has 7 flights on this route every week with an average price of C$ 226. United Airlines is rated 7.4/10 by our users.
Air Canada Flights From Halifax to Chicago
Air Canada (7.1/10 from 11,122 reviews) operates around 7 flights from Halifax to Chicago in any given week. The average Air Canada airfare for this route is around C$ 686, with deals from around C$ 286 rare but found on momondo. Referenced prices are for round-trip Halifax to Chicago flight searches in the last 72 hours.

Merrillville

Hammond

Munster

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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Start using Trips

Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

1 adult

Fri 3/7

Fri 10/7

Email me momondo's favourite deals

By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Nearby airports

Airlines

Cabin classes

Other United States destinations

Other flights from Halifax

Complete your trip

Feeling lucky

Fly into one of these airports located in Chicago

Chicago Midway Airport

Chicago O'Hare Intl Airport

Cheap flights from Halifax to Chicago from C$ 282

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 25/8. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

Big names, great deals

Big names, great deals

Filter for what you want

Filter for what you want

Trusted and free

Trusted and free

Price Alerts

Price Alerts

Find the cheapest flights from Halifax to Chicago

Cheap round-trip flights

Cheap one-way flights

Cheap last-minute flights

Cheap direct flights

WestJet flights from Halifax to Chicago

Our best WestJet deals on Halifax to Chicago flight tickets

Delta flights from Halifax to Chicago

Our best Delta deals on Halifax to Chicago flight tickets

momondo Fare Finder

Use the filters below to find and compare flights from Halifax to Chicago that are best for you.

See travel insights to Chicago from

How to get the cheapest flight ticket from Halifax to Chicago

What is the typical price of a round-trip flight between Halifax and Chicago?

What is the cheapest month to fly to Chicago?

What is the cheapest day to depart on your flight to Chicago?

What is the cheapest time of day to depart on your flight to Chicago?

What is the cheapest Halifax Intl to Chicago flight route?

What cabin class options are available on Halifax to Chicago flights?

Can stopping save me money on Halifax to Chicago flights?

How have Halifax to Chicago flight prices changed over time?

What is the cheapest airline that flies from Halifax Intl to Chicago?

Which airlines fly to Chicago?

Which airport is the most popular layover for flights between Halifax and Chicago?

Which layover airport offers the lowest fares from Halifax to Chicago?

Which layover airport has the shortest travel time from Halifax to Chicago?

Which layover airport has the shortest connection time from Halifax to Chicago?

How many flights depart from Halifax to Chicago on average per day?

How many flights depart from Halifax to Chicago on average per week?

When to book flights from Halifax to Chicago

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

Fastest flight time

Direct flights

Airports in Chicago

Frequently asked questions about flying 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

United Airlines Flights From Halifax to Chicago

Air Canada Flights From Halifax to Chicago

Travelling to a place near Chicago?

Why use momondo?

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

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

Fly your favourite airline to Chicago

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Chicago

List of cabin classes available on flights landing in Chicago. Availability may vary depending on flight origin and airline.

Popular Cities in the United States

Popular flights according to clicks in the last 7 days on momondo

Fly to other destinations from Halifax

According to popular flight searches on momondo this year

Complete your trip to Chicago

Explore popular destinations other users love

According to popular flight searches on momondo this year