YHZ - CHI

C$ 230 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 27/5. 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
Travellers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
C$ 463
Porter Airlines
Thu 28/5Thu 4/6
YHZ - MDW • 1 stop
Cheapest direct flights
C$ 788
American Airlines
Sat 20/6Sat 27/6
YHZ - ORD • Direct
Advice from real travellers
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 airlines
Cheapest • from C$ 463 (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 53m
Direct flights
Direct flights
+1
+1
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 • 72% price drop
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

Thu, 28 May - Thu, 4 Jun
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$ 463Porter 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$ 472Porter 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
3:20 p.m. - 11:44 p.m.
ORD
-
YHZ
6h 24m
2 stops
C$ 477Porter Airlines
Wed, 10 Jun - Wed, 17 Jun
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$ 485Multiple Airlines
Mon, 8 Jun - Wed, 10 Jun
Delta Logo
6:30 a.m. - 5:04 p.m.
YHZ
-
ORD
12h 34m
2 stops
Delta Logo
8:08 a.m. - 11:32 p.m.
ORD
-
YHZ
13h 24m
2 stops
C$ 510Delta
Wed, 20 May - Tue, 2 Jun
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$ 533American Airlines
Sat, 20 Jun - Sat, 27 Jun
WestJet Logo
3:30 p.m. - 8:31 p.m.
YHZ
-
ORD
7h 01m
1 stop
WestJet Logo
11:15 a.m. - 9:45 p.m.
ORD
-
YHZ
8h 30m
1 stop
C$ 544WestJet
Tue, 25 Aug - Sat, 29 Aug
WestJet Logo
3:30 p.m. - 8:24 p.m.
YHZ
-
ORD
6h 54m
1 stop
WestJet Logo
1:35 p.m. - 9:40 p.m.
ORD
-
YHZ
6h 05m
1 stop
C$ 552WestJet
Wed, 10 Jun - Wed, 17 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$ 563Delta
Thu, 28 May - Thu, 4 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$ 566Multiple 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 May.

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$ 427 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$ 86 (return) on average. On the other hand, the most expensive months are January and February, where the average cost of round-trip tickets is C$ 653 and C$ 477 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.
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 seasonFebruary
Cheapest flightC$ 230
Best time to beat the crowds (21% less expensive on average)
Most popular time to fly (3% more expensive 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

  • How many flights are there between Halifax and Chicago per day?

    There is a maximum of 1 nonstop flight a day that takes off from Halifax and lands in Chicago, with an average flight time of 3h 53m. The most common departure time is 4:00 p.m. and most flights take off in the afternoon. Each week, there are 7 flights.

  • 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$ 230 for a one-way ticket and C$ 463 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.

  • 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$ 447 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$ 427 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$ 258 or less one-way and C$ 489 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

United Airlines,American Airlines

United Airlines,American 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

United Airlines,American Airlines

United Airlines,American 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 435 reviews
8.0Comfort
8.6Crew
7.0Entertainment
7.6Food
8.2Boarding
Airline reviews

I didn’t receive any help when they messed up and wasn’t honest and the supervisor did absolutely nothing to help me so I had to buy another ticket at $537

10.0 ExcellentAnonymous, Apr 2026
YHM - YHZ
Read more Porter Airlines reviews

I didn’t receive any help when they messed up and wasn’t honest and the supervisor did absolutely nothing to help me so I had to buy another ticket at $537

Even tho the flight was a bit delayed the team was apologetic. Everyone was friendly and efficient.

The Flight took off 2hrs late because there was no pilot showing up when the flight was ready to board.. Though the cabin crew was present and had prepared the plane, the FO turned around after 15 min and went away. A crew to fly the plane finally arrived over an hour later and we were able to board 1h30 min later than planned time... until everything was loaded, we left 2h late from the gate. This was a small plane, so don't expect any Entertainment... Wi-Fi access on board would work, but took an awful amount of time to figure out and get it work (I'm an IT person). Flying as VIPorter customer, I was expecting at least some warm meal, but everything served was just cold.. except the coffee maybe. Even in so-called VIPorter seats, space is cramped and trays are so tiny, you can barely setup your food. Flight caught up during the coast-to-coast crossing and was able to recoup about 45 min from the delay.. still arrived very late in Vancouver and had to wait a long time to get our registered bags. Let's see how the return flight will be in a few days..

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.

Due to a known technical error that Porter has not fixed in over a year, I was unable to check in the children on my reservation online and had to do it at the airport. Upon check in, there were no seats together, which was an issue as we had young children. The gate agent did manage to seat us together by moving other passengers, which was appreciated, but the other passengers were never informed, leading to confusion and delay upon boarding. The flight was over an hour late; no explanation or apology was ever issued. The bags on Porter take a long time to arrive--over half an hour at Hamilton on my inbound flight, and not much better on my return to Edmonton.

On my e-boarding pass it shows free wifi, yet the plane I was on didn’t have wifi. Please remove false advertising from your website and boarding passes

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

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.

Flight crew was super friendly and helpful. Food was frequent and honestly pretty good. Plenty of on-board entertainment. Economy seats are super cramped for such a long flight, but the crew allowed people to get up and stretch, and kids could wander with their parents, so we all made it work. Overall a very good experience.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

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

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

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

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

The flight I was supposed to be on was supposed to take off at 1:50 from State College. It was delayed over and over and over again until somehow I had to rebook on a flight that was supposed to have left State College at 8 am that morning but didn't end up taking off until almost 6 pm. Not only was this completely unacceptable, the "token from United" was a 15 dollar meal voucher that has to be used by today. I would personally like some miles added to my account for this inconvenience. I was in transit for 8 hours from the time I arrive at State College Aiport to when I got home. I was supposed to be home at 3 pm and I returned at 8 pm. Unacceptable. I have not been on an on Time united flight in nearly 5 years.

newer aircraft, ability to connect my headset via blue tooth for entertainment.

Very comfortable flight, snacks and drinks were good, good communication from crew. Could have used a little more information on timing of boarding for group 5

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

The window seat on the emergency row was too small. I had a different seat booked and they moved me. My seat remained open. It was very uncomfortable.

Experience was good, the wifi hook up is somewhat tough

Great flight, great landing, nice staff. Our seats were a little cramped.

I will not be flying with westjet again. I was uncomfortable in my seat. The position made my back hurt so bad. My wife was able to fit the seatbelt around her with out an extension but was unable to put the tray table down or fit in the seat for that matter. Our bag was smashed and I spent two hours trying to fill out the application for a damaged bag before I gave up. The 80 photos I took would not work and nothing telling me the format to upload them as.. I made the mistake of unpacking the bag before taking photos so no claim for me. Next trip to Canada I will have to use air Canada.

Overall good experience. The wait for baggage at our destination was quite long, but other than that everything was good as expected

Airplane is too small. Crew, especially the flight attendant who looked after our area, was not at all friendly and a touch authoratative. She may have been the most gruff flight attendant i've come across in 40 years of business travel

I selected "carry-on" for a round trip on Kayak, but my return flight on WestJet did not include a carry-on and they would not allow me to add one. My only option was to add a "checked bag" which I had to wait for on the luggage carousel after landing. Not a good experience.

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

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

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.

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

Information on your arrival and departure airports