YHZ - CHI

C$ 266 Find Cheap Flights from Halifax to Chicago – Compare and Save

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 7/10. 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.
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1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
C$ 462
Typical prices: C$ 272-C$ 290
Air Canada
Tue 8/9Tue 15/9
YHZ - ORD • 1 stop
Cheapest direct flights
C$ 657
American Airlines
Sat 29/8Sat 5/9
YHZ - ORD • Direct
Top airlines
Cheapest • from C$ 462 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct flights
Every day
You can fly direct with United Airlines and American Airlines. Average duration is 3h 47m
Direct flights
Direct flights
+1
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Direct flights
Direct flights
+1
Top routes
Cheapest
Most popular
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg C$ 445 (round-trip)
Shortest trip • 5h 25m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 53% price drop
Most popular
Good to know
Good to know
+1
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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, 8 Sep - Tue, 15 Sep
Air Canada Logo
6:25 a.m. - 10:15 a.m.
YHZ
-
ORD
5h 50m
1 stop
Air Canada Logo
8:45 a.m. - 4:02 p.m.
ORD
-
YHZ
5h 17m
1 stop
C$ 462Air Canada
Fri, 25 Sep - Tue, 6 Oct
Air Canada Logo
6:25 a.m. - 10:15 a.m.
YHZ
-
ORD
5h 50m
1 stop
Air Canada Logo
8:45 a.m. - 4:02 p.m.
ORD
-
YHZ
5h 17m
1 stop
C$ 480Air Canada
Sat, 19 Sep - Sat, 19 Sep
Air Canada Logo
6:25 a.m. - 10:15 a.m.
YHZ
-
ORD
5h 50m
1 stop
Air Canada Logo
3:40 p.m. - 12:35 a.m.
ORD
-
YHZ
6h 55m
1 stop
C$ 497Air Canada
Sat, 12 Sep - Sat, 12 Sep
Air Canada Logo
6:25 a.m. - 10:15 a.m.
YHZ
-
ORD
5h 50m
1 stop
Air Canada Logo
3:40 p.m. - 12:35 a.m.
ORD
-
YHZ
6h 55m
1 stop
C$ 499Air Canada
Tue, 13 Oct - Thu, 22 Oct
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.
YHZ
-
MDW
9h 35m
2 stops
Porter Airlines Logo
11:45 a.m. - 11:44 p.m.
MDW
-
YHZ
9h 59m
2 stops
C$ 504Porter Airlines
Fri, 25 Sep - Tue, 6 Oct
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.
YHZ
-
MDW
9h 35m
2 stops
Porter Airlines Logo
11:45 a.m. - 11:44 p.m.
MDW
-
YHZ
9h 59m
2 stops
C$ 506Porter Airlines
Fri, 25 Sep - Mon, 5 Oct
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.
YHZ
-
MDW
9h 35m
2 stops
Porter Airlines Logo
3:20 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 24m
2 stops
C$ 513Porter Airlines
Thu, 17 Sep - Mon, 21 Sep
Porter Airlines Logo
7:30 a.m. - 2:35 p.m.
YHZ
-
MDW
9h 05m
1 stop
Porter Airlines Logo
11:45 a.m. - 4:39 p.m.
MDW
-
YHZ
26h 54m
2 stops
C$ 521Porter Airlines
Sat, 29 Aug - Sat, 5 Sep
Air Canada Logo
1:35 p.m. - 8:41 p.m.
YHZ
-
ORD
9h 06m
2 stops
Air Canada Logo
8:40 a.m. - 6:16 p.m.
ORD
-
YHZ
7h 36m
1 stop
C$ 521Air Canada
Fri, 22 Jan - Tue, 26 Jan
United Airlines Logo
7:00 a.m. - 7:52 p.m.
YHZ
-
ORD
14h 52m
1 stop
United Airlines Logo
2:20 p.m. - 11:57 p.m.
ORD
-
YHZ
7h 37m
1 stop
C$ 533United 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 September.

Flight prices are below average for this route right now.

Flights to Chicago from Halifax usually cost between C$ 511 and C$ 672 in September.
The lowest price found in the past 5 days was C$ 462 on Air Canada (8 Sep–15 Sep).

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$ 498 on the route between Halifax (YHZ) and Chicago O'Hare Intl Airport (ORD). It is also the most popular route.

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$ 286 (return) on average. On the other hand, the most expensive months are January and May, where the average cost of round-trip tickets is C$ 972 and C$ 789 respectively.

Can I save money by flying with a layover from Halifax to Chicago?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at C$ 665 on average.

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.
Our travel experts
Stefanie Waldek

Stefanie Waldek

Expert on ORD

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.

Jody Robbins

Jody Robbins

Expert on YHZ

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.

Good to know

Low season

February

Cheapest flight

C$ 266
Best time to beat the crowds (17% less expensive on average)
Most popular time to fly and prices are also 28% 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 5 days, the lowest price for a flight from Halifax to Chicago was C$ 266 for a one-way ticket and C$ 462 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 airlines offer Wi-Fi service onboard planes from Halifax to Chicago?

    American Airlines, and WestJet offer inflight Wi-Fi service on the Halifax to Chicago flight route.

  • 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.

  • On which days can I fly direct from Halifax to Chicago?

    There are direct flights from Halifax to Chicago on a daily basis.

  • 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$ 485 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$ 441 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.

KAYAK’s top tips for finding a cheap flight from Halifax to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for C$ 326 or less one-way and C$ 698 or less round-trip.

Prefer to fly direct from Halifax to Chicago?

 
Direct data is based off flight results for the next 60 days. Find direct flights from all airlines flying direct from Halifax Intl to Chicago.
Find which airlines fly direct from Halifax Intl Airport to Chicago, which days they fly and book direct flights.

Direct departures

Halifax Intl to Chicago

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

United Airlines

United Airlines

See more nonstop flights

Direct returns

Chicago to Halifax Intl

Monday

United Airlines

United Airlines

Tuesday

United Airlines

United Airlines

Wednesday

United Airlines

United Airlines

Thursday

United Airlines

United Airlines

Friday

United Airlines

United Airlines

Saturday

American Airlines,United Airlines

American Airlines,United Airlines

Sunday

United Airlines

United Airlines

See more nonstop flights

Reviews of the top 4 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 448 reviews
8.0Comfort
8.2Boarding
8.6Crew
6.9Entertainment
7.5Food
Airline reviews

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

4.0 OkayJeff, Jul 2026
YYZ - SFO
Read more Porter Airlines reviews

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

I flew with Porter yesterday and overall had a positive experience. The flight was delayed, but the airline did a good job keeping passengers informed with frequent updates throughout the process. My biggest challenge was actually in Terminal 3, where the speaker system wasn’t very clear. It was often difficult to hear the announcements, which made it harder to follow updates at the gate. On board, the experience improved significantly. The aircraft felt very new and well maintained, and the seats were surprisingly comfortable for a short-haul flight. One of the flight attendants seemed a little disengaged, but the other was excellent—friendly, professional, and a pleasure to interact with. Despite the delay, the comfortable aircraft, clear communication from Porter, and positive onboard service made for a good overall experience.

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

The flight was fine see earlier note for the problem

I love the 2 seats per row. More room. The crew were excellent.

The staff is always great. Just the fact that our flight was the only one delayed from Halifax when all other carries were still flying. It happen a year ago out of Toronto as well. All others were flying but our flight got cancelled 1 hr before the time of departure.

Only packaged snacks were served. It was a flight at lunchtime and a hot meal would have been a great.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

I didn’t make my flight due to poor weather and I had an accident driving there. I tried to get my money back or even credit and nothing. I have an entire flight both to Florida and back that I paid for and no one will give me any money back. I know this isn’t just Porter and it’s 3rd party- however airlines should allow these companies to take money for things they don’t get. I’m so upset. Who can afford a full flight they never take?

Nothing , two weeks of dealing with booking glitches on porters side , as our main international carrier was fine ,we were assured. When we got to check in everything would be smooth , we were confirmed there would be no issues, guess what happened? After an hour and a half at check inn we were told there was technical glitch involving payment we may not be able to fly , which would have set off a catastrophic chain , the undue stress on my family was unbearable .

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

Reliable, nice crew, I fly often on that flight and I like it all.

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

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

Our flights got changed from United to Air Canada and our purchased seats did not get transferred so we had to pay for seats twice. I brought it up with Air Canada and they stated I had to go back and chase it with United. The united seats were $21 Canadian each and Air Canada were $56 each so we have paid $77 for each seat. Very unhappy

So far so good but food and entertainment are not available for this flight

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

Our itinerary included a 1 hour and 30 minute layover, which should have been sufficient under normal circumstances. However, our original flight was delayed. Before we even deplaned, we were instructed to collect our checked bags from baggage claim, clear immigration and customs, and then recheck our bags for the connecting flight. The airline knew—or should have known—that this was impossible. Checked baggage acceptance closes one hour before departure, meaning there was no realistic way for passengers from the delayed flight to recheck their bags in time. Despite this, the airline gave us misleading instructions instead of informing us that we would likely miss our connection. We completed immigration and customs in approximately 10 minutes, but our checked bags did not arrive at the carousel for more than 30 minutes. After collecting them, we had another 10-minute walk to the baggage drop area, only to find that no airline attendant was present. We then went to another airline counter, where an employee told us this had happened before and that there was nothing they could do because the baggage acceptance window had already closed. At that point, there were still 40 minutes remaining before our flight's departure, yet no one was willing to assist or offer a practical solution. When we asked to be rebooked, we were simply told to call the airline's 800 number ourselves. There was no accountability or customer support at the airport, leaving us stranded in a foreign country with no immediate assistance. After finally reaching an agent on the 800 number, we were rebooked on a flight for the following day. However, we were initially told that the airline would not provide any hotel accommodation and that we would have to arrange and pay for it ourselves. Only after making multiple calls and speaking with several different agents did one representative finally issue a hotel voucher. The entire experience was an exhausting and frustrating ordeal. What should have been a 20-hour journey ultimately became more than 30 hours due to the airline's poor planning, misleading instructions, lack of accountability, and inadequate customer service. The unnecessary delays, confusion, and absence of meaningful assistance caused significant physical exhaustion and severe mental stress. This experience fell far below the level of service passengers should reasonably expect.

Switching flights in Halifax was a nightmare. There was no agent waiting us when we disembarked to provide my mom with gate to gate assistance as we arranged. Our flight was delayed so our window to catch the other flight was very tight. The airport was poorly marked as to where to go. The plane was fairly crowded and space available was cramped.

Good flight. We were all boarded in good time for departure time but baggage loading had barely begun. So left late. No food just snacks and basic drinks for free (food also for purchase). No entertainment as again, unable to connect with wifi on WestJet despite being a rewards member.

I like the idea of a non-overnight flight to Europe.

The food was very good. I was nit expecting a meal on a red eye trip. I was pleasantly surprised! Plus we arrived a few minutes earlier than expected!

There was no food but a singular cookie for a flight that was over 5hours??? Yeah not fun I was starving and again super cramped plane and you guys need to get planes with screens too, WiFi is nice but common we need more

The plug in to charge our phones are all loose my block would not stay in!!

While I appreciated the food (it was unexpected), it was interruptive for sleeping. We paid extra for reserved seats, but when we checked in they gave us different seats. I had to call WestJet arounf 11:30pm the night before our flight to get this fixed. We were give seats in the emengency row to resolve the issue.

This flight was better than the first. Two of the flight attendants were wonderful at supporting m through nausea and vomiting through the flight. No tv, no food, very interesting. I’ve never paid for wifi (just the $3 chatting) until these 2 flights. This experience has changed my opinion on layovers. Idk if I’ll ever do one again

Entertainment was the only issue. I did not have app & not equipped to watch movie on my phone. Used to other carriers with access to a screen for viewing. Other than that, everything was fine.

Flight got delayed But satisfied with the pricing of tickets

Flight operated by PAL. We boarded, and one engine started. The crew found some problem that could not be fixed. The flight was canceled. This run from yhz-bos is very unreliable.

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

Other than flights being cancelled and 3.5 hours late causing missed connections it was ok.

My ticket did not exist when I got to the airport. I had to book another flight and was still charged by Kayak

taking our carryon and forcing us to check it through

no cookie/snack offered with beverage, poor leg room, shoulder room the best part about flight it left late arrived early

They were having “flow control “ issues in Boston per the overhead announcement by flight staff. So they boarded us, had us sit for several minutes l, then made their flow control delay announcement. Then pushed away and went and parked the plane with us on it, outlying of the way…. Were we darker for 1.5 more hours. 1625 departure became 1810, avoidably lengthening everyone’s trip, messing up connections and ground transportation for arrival. Poor.

Easy check in and boarding. Bags waiting for us when we got to baggage claim.

The way to the gate from the waiting area was a marathon, so pack light if you’re doing carryon. Overhead compartment is smaller than most on this plane. They seem to chronically run late due to their preceding leg.

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

Information on your arrival and departure airports