YHZ - MDW

C$ 254 Find Cheap Flights from Halifax to Chicago Midway Airport

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 14/8. 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 Midway Airport

 
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$ 433
Porter Airlines
Thu 21/5Wed 27/5
YHZ - MDW • 2 stops
Cheapest one-way flights
C$ 254
Porter Airlines
Fri 14/8
YHZ - MDW • 2 stops
Top airlines
Cheapest • from C$ 433 (round-trip)
Best reviews • 8.0 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Direct flights
Not available
There are currently no direct flights between Halifax and Chicago. You’ll need at least 1 connection.
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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
Flight Deals

Cheap Flights from Halifax to Chicago (YHZ-MDW)

 
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, 21 May - Wed, 27 May
Porter Airlines Logo
7:00 a.m. - 2:35 p.m.
YHZ
-
MDW
9h 35m
2 stops
Porter Airlines Logo
10:30 a.m. - 11:47 p.m.
MDW
-
YHZ
11h 17m
2 stops
C$ 433Porter Airlines
Thu, 21 May - Wed, 27 May
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
10:30 a.m. - 11:47 p.m.
MDW
-
YHZ
11h 17m
2 stops
C$ 441Porter Airlines
Sat, 16 May - Sat, 30 May
Porter Airlines Logo
8:00 a.m. - 9:45 a.m.
YHZ
-
MDW
27h 45m
1 stop
Porter Airlines Logo
10:30 a.m. - 11:47 p.m.
MDW
-
YHZ
11h 17m
2 stops
C$ 497Porter Airlines
Mon, 18 May - Mon, 25 May
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
10:30 a.m. - 11:47 p.m.
MDW
-
YHZ
11h 17m
2 stops
C$ 516Porter Airlines
Thu, 21 May - Wed, 27 May
Porter Airlines Logo
6:20 a.m. - 2:35 p.m.
YHZ
-
MDW
10h 15m
1 stop
Porter Airlines Logo
10:30 a.m. - 11:02 p.m.
MDW
-
YHZ
10h 32m
1 stop
C$ 520Porter Airlines
Mon, 18 May - Mon, 25 May
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
2 stops
Porter Airlines Logo
10:30 a.m. - 11:47 p.m.
MDW
-
YHZ
11h 17m
2 stops
C$ 528Porter Airlines
Sun, 7 Jun - Tue, 16 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$ 539Porter Airlines
Fri, 8 May - Mon, 11 May
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
3:20 p.m. - 11:47 p.m.
MDW
-
YHZ
6h 27m
2 stops
C$ 546Porter Airlines
Wed, 17 Jun - Wed, 24 Jun
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
1 stop
Porter Airlines Logo
3:20 p.m. - 11:44 p.m.
MDW
-
YHZ
6h 24m
2 stops
C$ 560Porter Airlines
Fri, 8 May - Mon, 11 May
Porter Airlines Logo
8:00 a.m. - 2:35 p.m.
YHZ
-
MDW
8h 35m
2 stops
Porter Airlines Logo
3:20 p.m. - 11:47 p.m.
MDW
-
YHZ
6h 27m
2 stops
C$ 568Porter 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.

Which airlines provide the cheapest flights from Halifax to Chicago Midway Airport?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from Halifax to Chicago Midway Airport were found on Porter Airlines (C$ 433) and Delta (C$ 605).

Good to know

Cheapest flightC$ 254
Flight from Halifax to Chicago Midway 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 Halifax to Chicago Midway Airport flights

  • What is the cheapest flight from Halifax to Chicago Midway Airport?

    In the last 3 days, the lowest price for a flight from Halifax to Chicago Midway Airport was C$ 254 for a one-way ticket and C$ 433 for a round-trip.

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

    Halifax and Chicago Midway Airport are both served by 1 main airport. You will leave Halifax from Halifax Intl and will be arriving at Chicago Midway.

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

    We unfortunately don’t have that data for this specific route.

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

    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 Midway Airport.

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

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

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

    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 Midway Airport 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 Midway Airport?

    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 Midway Airport 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 airline 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
8.2Boarding
7.0Entertainment
7.6Food
8.0Comfort
8.6Crew
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.

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

Information on your arrival and departure airports