YHZ - CHI

C$ 261 Find Cheap Flights from Halifax to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Halifax to Chicago departing on 12/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Halifax to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Halifax to Chicago, as well as popular online travel agencies
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Everything you should know

Cheapest round-trip
C$ 376
Porter Airlines
Tue 14/4Wed 15/4
YHZ - MDW • 1 stop
Cheapest one-way flights
C$ 261
Typical prices: C$ 445-C$ 535
Multiple Airlines
Mon 12/1
YHZ - ORD • 3 stops
Our travellers' advice
AI-powered summary based on content written by travel experts. AI can make mistakes.
Halifax Airport's shorter lines ease your journey start.
Use the CTA Blue Line from ORD to reach downtown fast.
Expert advice
Expert advice
Expert advice
Expert advice
Top routes
YHZ-ORD
Cheapest
YHZ-ORD
Most popular
Insights
Insights
Insights
Insights
When to travel
September
Cheapest • 30% price drop
December
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches hundreds of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Expert advice
Flight Deals

Cheap Flights from Halifax to Chicago (YHZ-CHI)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Halifax to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Halifax to Chicago

Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 376Porter Airlines
Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 11:54 p.m.
MDW
-
YHZ
10h 54m2 stops
C$ 418Porter Airlines
Thu, 2 Apr - Sun, 5 Apr
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 459Porter Airlines
Tue, 14 Apr - Wed, 15 Apr
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 461Porter Airlines
Wed, 18 Mar - Sat, 28 Mar
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
12:45 p.m. - 8:05 p.m.
MDW
-
YHZ
5h 20m1 stop
C$ 463Porter Airlines
Sat, 10 Jan - Sat, 17 Jan
Multiple Airlines Logo
6:30 a.m. - 12:25 p.m.
YHZ
-
ORD
7h 55m1 stop
Multiple Airlines Logo
7:15 a.m. - 1:41 a.m.
ORD
-
YHZ
16h 26m2 stops
C$ 483Multiple Airlines
Wed, 28 Jan - Wed, 4 Feb
Multiple Airlines Logo
8:20 p.m. - 10:10 a.m.
YHZ
-
MDW
15h 50m1 stop
Multiple Airlines Logo
1:20 p.m. - 5:31 p.m.
MDW
-
YHZ
26h 11m2 stops
C$ 495Multiple Airlines
Fri, 16 Jan - Mon, 19 Jan
Multiple Airlines Logo
10:40 p.m. - 11:50 a.m.
YHZ
-
MDW
15h 10m1 stop
Multiple Airlines Logo
11:00 a.m. - 8:10 p.m.
MDW
-
YHZ
7h 10m1 stop
C$ 517Multiple Airlines
Thu, 12 Mar - Sun, 15 Mar
Porter Airlines Logo
8:30 a.m. - 3:20 p.m.
YHZ
-
MDW
8h 50m1 stop
Porter Airlines Logo
11:00 a.m. - 8:05 p.m.
MDW
-
YHZ
7h 05m1 stop
C$ 521Porter Airlines
Wed, 28 Jan - Wed, 4 Feb
Multiple Airlines Logo
8:30 a.m. - 11:46 p.m.
YHZ
-
ORD
17h 16m3 stops
Multiple Airlines Logo
5:15 a.m. - 12:27 a.m.
ORD
-
YHZ
17h 12m3 stops
C$ 521Multiple Airlines
Booking Insights

KAYAK's insights & trends for Halifax to Chicago flights

Get data-powered insights and trends into flights from Halifax to Chicago to help you find the cheapest flights, the best time to fly and much more.

How much is a round-trip flight from Halifax to Chicago?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Halifax to Chicago departing in April.

What is the cheapest Halifax to Chicago flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest return flight from Halifax to Chicago costs C$ 225 on the route between Halifax (YHZ) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

What’s the cheapest day of the week to fly from Halifax to Chicago?

The average price of all round-trip flights from Halifax to Chicago clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Halifax to Chicago, look for departures on Tuesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Chicago, Saturday is the cheapest day to fly and Friday is the most expensive.

What is the cheapest month to fly from Halifax to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Halifax to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Halifax to Chicago is September, where tickets cost C$ 359 (return) on average. On the other hand, the most expensive months are July and August, where the average cost of round-trip tickets is C$ 695 and C$ 658 respectively.

Expert advice

Expert advice for your flight from Halifax to Chicago

 
AI-powered summary based on content written by travel experts. AI can make mistakes.
KAYAK teamed up with top travel experts to share the best tips for your journey.
Airports
YHZ

Halifax Airport's shorter lines and quick processing make it easy to navigate, ideal for a stress-free start to your trip.

ORD

Take the CTA Blue Line from ORD to downtown Chicago in about 45 minutes, avoiding traffic and saving money.

Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

Stefanie Waldek

Stefanie Waldek

Stefanie Waldek is a freelance space, travel, and design writer based in Saratoga Springs, NY. Her words have appeared in Space.com, Travel + Leisure, Condé Nast Traveler, Architectural Digest, and House Beautiful, among other publications. An expert in aviation and expedition cruising, Stefanie is frequently up in the air or on the sea, likely en route to Antarctica or the Arctic.

Read more
Jody Robbins

Jody Robbins

Expert on YHZ

Jody Robbins

Jody Robbins

Recognized as the Canadian Travel Media of the Year by the Tourism Industry Association of Canada (2024), Jody is an award-winning travel and lifestyles writer based in Calgary. She’s spent the last two decades racking up the air miles, living in Japan, England and managing a European sales channel for a not-so-glamorous audio-visual company.

Read more

Good to know

Low seasonJanuary
Cheapest flightC$ 261
Best time to beat the crowds (25% less expensive on average)
Most popular time to fly and prices are also 18% lower on average.
Flight from Halifax to Chicago O'Hare Airport

When to book flights from Halifax to Chicago

Are your dates flexible? Find out the best times to travel from Halifax to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Halifax to Chicago

  • What is the cheapest flight from Halifax to Chicago?

    In the last 3 days, the lowest price for a flight from Halifax to Chicago was C$ 261 for a one-way ticket and C$ 376 for a round-trip.

  • Which airports will I be using when flying from Halifax to Chicago?

    Halifax is served by only 1 airport and there are 2 airports in Chicago. You will leave Halifax from Halifax Intl and you will be arriving in Chicago at one of these airports: Chicago Midway or Chicago O'Hare Intl.

  • Which aircraft models fly most regularly from Halifax to Chicago?

    The Embraer 175 (Enhanced Winglets) is the aircraft model that flies most regularly on the Halifax to Chicago flight route.

  • Which airline alliances offer flights from Halifax to Chicago?

    Star Alliance is the only airline alliance operating flights between Halifax and Chicago.

  • Which is the best airline for flights from Halifax to Chicago, Porter Airlines or United Airlines?

    The two airlines most popular with KAYAK users for flights from Halifax to Chicago are Porter Airlines and United Airlines. With an average price for the route of C$ 450 and an overall rating of 8.0, Porter Airlines is the most popular choice. United Airlines is also a great choice for the route, with an average price of C$ 524 and an overall rating of 7.4.

  • How does KAYAK find such low prices on flights from Halifax to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Halifax to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Halifax to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Halifax is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Halifax to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Halifax with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Halifax to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Halifax up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines flying from Halifax to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Halifax to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Halifax to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
Porter AirlinesOverall score based on 397 reviews
8.0Comfort
7.0Entertainment
8.2Boarding
8.6Crew
7.6Food
Airline reviews

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

4.0 OkayAnonymous, Dec 2025
YTZ - YUL
Read more Porter Airlines reviews

3.5 hr delay for a 1 hr work flight. No information as to why the delay until 20 mins before boarding.

Organization and the adjusted times but the snacks could be of a bigger portion

I like it, but the food isn't good. They need to offer more simple things. This bowls that have so many things your don't know what your are eating. The milenials like it, no the rest. And last but not least, they allowed somebody have a huge dog, vey agressive and fidgety in the flight. That's horrible. No animals should be allowed inside the airplane, what about allergies, etc

Smaller plane. Food and bar service for free is amazing. Drinks were in glass not plastic cups.

Poor landing as we overshot the runway and had to re land the plane. Lost both of my luggage not found as of yet. Had to pay extra money for my luggage in USD, now great my luggage is gone. Will not fly with Porter again.

This flight to St. Johns was really good. Boarding was a breeze. We left spot on time. Seats were actually pretty good. Recliner further than I expected. Three more flights to go we will see if this is the status quo for Porter.👍

I was not happy with AirfareAssist, the agency that kayak advised me would be handling my booking. I was advised by porter airlines that I had been overcharged for the Basic express , a option that I had asked airfare assist to help arrange after I realized that the basic fare I had chosen with porter did not include a carryon. At each checkin porter advised I had been overcharged for this . They advised that money would be refunded to my credit card, however, this is not likely to happen as it is not my name and credit card that appeared on the porter invoice, but that of another individual/agent. When airfare assist was arranging the basic express with porter on my behalf, they asked me to confirm that I agreed to pay $263 USD for this. I did agree, as I was advised this was needed to proceed. When I checked the invoice on the porter website and saw that it was not my name and credit card on the invoice, I was advised that this was how airfareassist processed the payment. The Porter invoice indicated a billed amount of $126USD I will not use Kayak or their designated AirfareAssist again

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

The flight was fine see earlier note for the problem

All good the seats a little tight and no I pad screen

It was nice to have gotten up upgraded to first class with a meal on a three hour flight

Very bad! They kept delaying my flight and wouldn’t do anything about it

Door to door, the crew and staff were amazing. It was a stressful travel day with delays, but they were focused on customers and doing what they could to get us to our destinations.

United has come a long way, it’s been a fantastic experience traveling with them.

This flight leg was fantastic - super comfortable and a great selection of things to watch on the TV. Staff were excellent, really above and beyond.

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Excellent all round, first time flying United. App is very helpful.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

I would like to review the next flight from Toronto to Fort Myers as it was a disaster!!

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

Seats too small and too cramped, I have stomach cancer and I threw up after the flight . No advance boarding for disabled people. No aisle seats available for disabled people who have to use the washroom frequently. No space for cabin baggage for disabled people who have to carry bulky medications or equipment to use on the flight. Baggage rules and fees are ridiculous. I have been an aeroplan member for 30 years and I fly frequently, but from now on I will choose offshore carriers. .

taking our carryon and forcing us to check it through

Obviously the leg room...but I guess that's what business class would be ..expensive though.

I was very excited when we were to arrive 19 mins early . However that did not last long since there was no available gate and sat there waiting almost a hour.

Seats horribly uncomfortable. Air nozzles didn't work so very overheated.

Every person and every experience with Air Canada was excellent. All customer service was outstanding and done pleasantly. The notifications through their App were timely and informative. This airline shines. All other airlines should take training from them.

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Better than usual. We’ve flown air Canada for years at least once or twice a year and used it to bring our Canadian American son back and forth from USA and Canada and Europe and we have had MANY bad experiences with late flights, missed connections, boarding issues, for almost 10 years. Just lots of bad experiences. This one wasn’t bad at all. It’s simply what we expected. Even though the first flight this time was 45 min late in leaving due to a maintenance issue, that didn’t mess us up. But all else was fine so we were pleased.

Everything you need to know for your flight from Halifax to Chicago

Information on your arrival and departure airports