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Cheap flights from Halifax to Chicago from C$ 256

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 20/5. 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
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
10:25 a.m. - 11:44 p.m.
MDW
-
YHZ
11h 19m
2 stops
C$ 465Porter Airlines
Thu, 28 May - Thu, 4 Jun
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.
YHZ
-
MDW
9h 35m
2 stops
Porter Airlines Logo
10:25 a.m. - 11:44 p.m.
MDW
-
YHZ
11h 19m
2 stops
C$ 473Porter Airlines
Thu, 28 May - Thu, 4 Jun
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.
YHZ
-
ORD
9h 35m
2 stops
Porter Airlines Logo
3:20 p.m. - 11:44 p.m.
ORD
-
YHZ
6h 24m
2 stops
C$ 478Porter Airlines
Wed, 2 Sep - Wed, 9 Sep
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.
YHZ
-
ORD
9h 35m
2 stops
Porter Airlines Logo
7:00 a.m. - 4:29 p.m.
ORD
-
YHZ
7h 29m
2 stops
C$ 481Porter Airlines
Fri, 18 Sep - Sat, 26 Sep
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
ORD
8h 35m
2 stops
Porter Airlines Logo
7:00 a.m. - 4:29 p.m.
ORD
-
YHZ
7h 29m
2 stops
C$ 485Porter Airlines
Sat, 19 Sep - Fri, 25 Sep
Multiple Airlines Logo
8:15 p.m. - 9:00 a.m.
YHZ
-
ORD
14h 45m
1 stop
Multiple Airlines Logo
9:55 a.m. - 9:17 p.m.
ORD
-
YHZ
9h 22m
1 stop
C$ 487Multiple Airlines
Wed, 10 Jun - Wed, 17 Jun
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.
YHZ
-
ORD
9h 35m
2 stops
Porter Airlines Logo
7:00 a.m. - 4:29 p.m.
ORD
-
YHZ
7h 29m
2 stops
C$ 496Porter Airlines
Fri, 18 Sep - Sat, 19 Sep
American Airlines Logo
6:20 a.m. - 12:43 p.m.
YHZ
-
ORD
8h 23m
1 stop
American Airlines Logo
2:47 p.m. - 11:02 p.m.
ORD
-
YHZ
6h 15m
1 stop
C$ 534American Airlines
Wed, 20 May - Tue, 2 Jun
Delta Logo
6:30 a.m. - 4:16 p.m.
YHZ
-
MDW
11h 46m
2 stops
Delta Logo
11:05 a.m. - 11:32 p.m.
MDW
-
YHZ
10h 27m
2 stops
C$ 564Delta
Wed, 10 Jun - Wed, 17 Jun
Multiple Airlines Logo
8:15 p.m. - 9:45 a.m.
YHZ
-
MDW
15h 30m
1 stop
Multiple Airlines Logo
3:20 p.m. - 9:25 p.m.
MDW
-
YHZ
28h 05m
1 stop
C$ 567Multiple Airlines
Thu, 28 May - Thu, 4 Jun

WestJet flights from Halifax to Chicago

Our best WestJet deals on Halifax to Chicago flight tickets
WestJet
20 Jun
YHZ3:30 p.m.Halifax Intl
7h 01m
1 stop
ORD8:31 p.m.Chicago O'Hare Intl
27 Jun
ORD11:15 a.m.Chicago O'Hare Intl
8h 30m
1 stop
YHZ9:45 p.m.Halifax Intl
C$ 545
WestJet
25 Aug
YHZ3:30 p.m.Halifax Intl
6h 54m
1 stop
ORD8:24 p.m.Chicago O'Hare Intl
29 Aug
ORD1:35 p.m.Chicago O'Hare Intl
6h 05m
1 stop
YHZ9:40 p.m.Halifax Intl
C$ 553
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$ 558

Delta flights from Halifax to Chicago

Our best Delta deals on Halifax to Chicago flight tickets
Delta
18 Jul
YHZ3:50 p.m.Halifax Intl
6h 07m
1 stop
ORD7:57 p.m.Chicago O'Hare Intl
21 Jul
ORD8:03 a.m.Chicago O'Hare Intl
13h 20m
2 stops
YHZ11:23 p.m.Halifax Intl
C$ 562
Delta
10 Jun
YHZ6:30 a.m.Halifax Intl
11h 46m
2 stops
MDW4:16 p.m.Chicago Midway
17 Jun
MDW11:05 a.m.Chicago Midway
10h 27m
2 stops
YHZ11:32 p.m.Halifax Intl
C$ 564
Delta
8 Jun
YHZ6:30 a.m.Halifax Intl
12h 04m
2 stops
ORD4:34 p.m.Chicago O'Hare Intl
10 Jun
ORD11:35 a.m.Chicago O'Hare Intl
9h 53m
1 stop
YHZ11:28 p.m.Halifax Intl
C$ 571

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 27 April 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 - MDW

YHZMDW

Halifax Intl

Thu 28/5

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

1 stop8h 35m

Chicago Midway

Thu 4/6

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

2 stops11h 19m

C$ 465

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 28/5

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

2 stops9h 35m

Chicago Midway

Thu 4/6

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

2 stops11h 19m

C$ 473

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 2/9

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

2 stops9h 35m

Chicago O'Hare Intl

Wed 9/9

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

2 stops6h 24m

C$ 478

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 18/9

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

2 stops9h 35m

Chicago O'Hare Intl

Sat 26/9

7:00 a.m.-4:29 p.m.

2 stops7h 29m

C$ 481

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Sat 19/9

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

2 stops8h 35m

Chicago O'Hare Intl

Fri 25/9

7:00 a.m.-4:29 p.m.

2 stops7h 29m

C$ 485

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 10/6

8:15 p.m.-9:00 a.m.

1 stop14h 45m

Chicago O'Hare Intl

Wed 17/6

9:55 a.m.-9:17 p.m.

1 stop9h 22m

C$ 487

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Fri 18/9

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

2 stops9h 35m

Chicago O'Hare Intl

Sat 19/9

7:00 a.m.-4:29 p.m.

2 stops7h 29m

C$ 496
Quickest round-trip

HalifaxChicago

YHZ - ORD

YHZORD

Halifax Intl

Wed 20/5

6:20 a.m.-12:43 p.m.

1 stop8h 23m

Chicago O'Hare Intl

Tue 2/6

2:47 p.m.-11:02 p.m.

1 stop6h 15m

C$ 534

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Wed 10/6

6:30 a.m.-4:16 p.m.

2 stops11h 46m

Chicago Midway

Wed 17/6

11:05 a.m.-11:32 p.m.

2 stops10h 27m

C$ 564

HalifaxChicago

YHZ - MDW

YHZMDW

Halifax Intl

Thu 28/5

8:15 p.m.-9:45 a.m.

1 stop15h 30m

Chicago Midway

Thu 4/6

3:20 p.m.-9:25 p.m.

1 stop28h 05m

C$ 567

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?

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$ 198.

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$ 547. 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$ 836. 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$ 700. 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$ 1,700 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 3 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 April 2026, prices for Halifax to Chicago flights are approximately 168% 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$ 259

Fastest flight time

3h 40m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Halifax in the past 72 hours is C$ 259. The best round-trip flight deal from Halifax to Chicago found on momondo in the last 72 hours is C$ 490.
The fastest flight from Halifax to Chicago takes 3h 40m
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 40m.

  • 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
9,668 reviews
Search United Airlines flights
Air CanadaPriceFrom C$ 282Free CancellationRating
7.1
10,974 reviews
Search Air Canada flights
Porter AirlinesPriceFrom C$ 462Free CancellationRating
8.0
435 reviews
Search Porter Airlines flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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.

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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