Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Halifax to Chicago from C$ 212

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 2/6. 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

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

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

Trusted and free

Trusted and free

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

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

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 55m
2 stops
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m
1 stop
C$ 390Porter Airlines
Mon, 20 Apr - Tue, 21 Apr
Porter Airlines Logo
7:00 a.m. - 3:20 p.m.
YHZ
-
MDW
10h 20m
2 stops
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m
1 stop
C$ 407Porter Airlines
Mon, 20 Apr - Tue, 21 Apr
Porter Airlines Logo
11:30 a.m. - 4:50 p.m.
YHZ
-
MDW
7h 20m
2 stops
Porter Airlines Logo
10:25 a.m. - 11:34 p.m.
MDW
-
YHZ
11h 09m
2 stops
C$ 414Porter Airlines
Thu, 28 May - Fri, 5 Jun
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m
1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m
1 stop
C$ 435Porter Airlines
Mon, 20 Apr - Tue, 21 Apr
Porter Airlines Logo
8:25 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 55m
2 stops
Porter Airlines Logo
11:00 a.m. - 11:54 p.m.
MDW
-
YHZ
10h 54m
2 stops
C$ 474Porter Airlines
Mon, 20 Apr - Tue, 21 Apr
Multiple Airlines Logo
10:40 p.m. - 10:10 a.m.
YHZ
-
MDW
13h 30m
1 stop
Multiple Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m
1 stop
C$ 511Multiple Airlines
Mon, 23 Feb - Mon, 2 Mar
Multiple Airlines Logo
8:00 a.m. - 4:50 p.m.
YHZ
-
MDW
10h 50m
1 stop
Multiple Airlines Logo
5:35 p.m. - 4:24 p.m.
MDW
-
YHZ
20h 49m
2 stops
C$ 529Multiple Airlines
Thu, 28 May - Fri, 5 Jun
WestJet Logo
4:05 p.m. - 4:40 p.m.
YHZ
-
ORD
26h 35m
2 stops
WestJet Logo
5:30 p.m. - 8:10 a.m.
ORD
-
YHZ
12h 40m
1 stop
C$ 537WestJet
Fri, 22 May - Mon, 1 Jun
WestJet Logo
3:35 p.m. - 4:40 p.m.
YHZ
-
ORD
27h 05m
1 stop
WestJet Logo
5:30 p.m. - 8:10 a.m.
ORD
-
YHZ
12h 40m
1 stop
C$ 543WestJet
Fri, 22 May - Mon, 1 Jun
WestJet Logo
6:15 p.m. - 4:40 p.m.
YHZ
-
ORD
24h 25m
1 stop
WestJet Logo
5:30 p.m. - 10:45 a.m.
ORD
-
YHZ
15h 15m
2 stops
C$ 562WestJet
Thu, 28 May - Fri, 5 Jun

WestJet flights from Halifax to Chicago

Our best WestJet deals on Halifax to Chicago flight tickets
WestJet
22 May
YHZ4:05 p.m.Halifax Intl
26h 35m
2 stops
ORD4:40 p.m.Chicago O'Hare Intl
1 Jun
ORD5:30 p.m.Chicago O'Hare Intl
12h 40m
1 stop
YHZ8:10 a.m.Halifax Intl
C$ 537
WestJet
22 May
YHZ3:35 p.m.Halifax Intl
27h 05m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
1 Jun
ORD5:30 p.m.Chicago O'Hare Intl
12h 40m
1 stop
YHZ8:10 a.m.Halifax Intl
C$ 543
WestJet
28 May
YHZ6:15 p.m.Halifax Intl
24h 25m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
5 Jun
ORD5:30 p.m.Chicago O'Hare Intl
15h 15m
2 stops
YHZ10:45 a.m.Halifax Intl
C$ 562

Air Canada flights from Halifax to Chicago

Our best Air Canada deals on Halifax to Chicago flight tickets
Air Canada
20 Apr
YHZ9:00 a.m.Halifax Intl
10h 45m
2 stops
ORD5:45 p.m.Chicago O'Hare Intl
21 Apr
ORD7:55 a.m.Chicago O'Hare Intl
9h 50m
2 stops
YHZ7:45 p.m.Halifax Intl
C$ 677
Air Canada
12 Mar
YHZ5:35 a.m.Halifax Intl
7h 43m
1 stop
ORD11:18 a.m.Chicago O'Hare Intl
15 Mar
ORD7:15 a.m.Chicago O'Hare Intl
6h 32m
1 stop
YHZ3:47 p.m.Halifax Intl
C$ 683
Air Canada
1 Jul
YHZ9:00 a.m.Halifax Intl
6h 22m
1 stop
ORD1:22 p.m.Chicago O'Hare Intl
7 Jul
ORD8:45 a.m.Chicago O'Hare Intl
7h 31m
1 stop
YHZ6:16 p.m.Halifax Intl
C$ 697

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 28 January 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

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 20/4

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

2 stops8h 55m

Chicago Midway

Tue 21/4

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

1 stop7h 05m

C$ 390

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 20/4

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

2 stops10h 20m

Chicago Midway

Tue 21/4

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

1 stop7h 05m

C$ 407

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 28/5

11:30 a.m.-4:50 p.m.

2 stops7h 20m

Chicago Midway

Fri 5/6

10:25 a.m.-11:34 p.m.

2 stops11h 09m

C$ 414

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 20/4

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

1 stop8h 50m

Chicago Midway

Tue 21/4

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

1 stop7h 05m

C$ 435

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 20/4

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

2 stops8h 55m

Chicago Midway

Tue 21/4

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

2 stops10h 54m

C$ 474

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Mon 23/2

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

1 stop13h 30m

Chicago Midway

Mon 2/3

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

1 stop7h 05m

C$ 511

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 28/5

8:00 a.m.-4:50 p.m.

1 stop10h 50m

Chicago Midway

Fri 5/6

5:35 p.m.-4:24 p.m.

2 stops20h 49m

C$ 529

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 22/5

4:05 p.m.-4:40 p.m.

2 stops26h 35m

Chicago O'Hare Intl

Mon 1/6

5:30 p.m.-8:10 a.m.

1 stop12h 40m

C$ 537

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 22/5

3:35 p.m.-4:40 p.m.

1 stop27h 05m

Chicago O'Hare Intl

Mon 1/6

5:30 p.m.-8:10 a.m.

1 stop12h 40m

C$ 543

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Thu 28/5

6:15 p.m.-4:40 p.m.

1 stop24h 25m

Chicago O'Hare Intl

Fri 5/6

5:30 p.m.-10:45 a.m.

2 stops15h 15m

C$ 562

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 March is another great option to travel to Chicago, with average flight prices from Halifax averaging around C$ 407.

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 Friday when prices can be found for as low as C$ 642. 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$ 942. 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$ 836. 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$ 1,178 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 January 2026, prices for Halifax to Chicago flights are approximately 43% 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

Fastest flight time

3h 43m

Direct flights

Every day

Airports in Chicago

3 airports
The fastest flight from Halifax to Chicago takes 3h 43m
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

  • 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 43m.

  • 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$ 223Free CancellationRating
7.4
9,206 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 283Free CancellationRating
7.1
10,660 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.

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 27/2
Fri 6/3
By creating a price alert you accept our terms of use and privacy policy.

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