Cheap Flights from Halifax International to Chicago

Compare Halifax International to Chicago flight deals

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Flight deals from Halifax International to Chicago

Looking for a cheap last-minute deal or the best return flight from Halifax International Airport to Chicago? If you want to travel next month, return fares start from $620. Find the lowest prices on one-way and return tickets right here.

Chicago.$553 per passenger.Departing Sun, 1 Nov, returning Sun, 8 Nov.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Halifax International on Sun, 1 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with Porter Airlines, departs from Chicago O'Hare International on Sun, 8 Nov, arriving in Halifax International.Price includes taxes and charges.From $553, select.

Chicago.$553 per passenger.Departing Sat, 24 Oct, returning Sun, 8 Nov.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Halifax International on Sat, 24 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Porter Airlines, departs from Chicago O'Hare International on Sun, 8 Nov, arriving in Halifax International.Price includes taxes and charges.From $553, select.

Chicago.$595 per passenger.Departing Sat, 10 Oct, returning Sun, 11 Oct.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Halifax International on Sat, 10 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Sun, 11 Oct, arriving in Halifax International.Price includes taxes and charges.From $595, select.

Chicago.$596 per passenger.Departing Thu, 10 Sep, returning Wed, 30 Sep.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Halifax International on Thu, 10 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Porter Airlines, departs from Chicago O'Hare International on Wed, 30 Sep, arriving in Halifax International.Price includes taxes and charges.From $596, select.

Chicago.$620 per passenger.Departing Thu, 21 May, returning Tue, 26 May.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Halifax International on Thu, 21 May, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Tue, 26 May, arriving in Halifax International.Price includes taxes and charges.From $620, select.

Chicago.$707 per passenger.Departing Wed, 22 Jul, returning Tue, 28 Jul.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Halifax International on Wed, 22 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Tue, 28 Jul, arriving in Halifax International.Price includes taxes and charges.From $707, select.

Chicago.$711 per passenger.Departing Thu, 27 Aug, returning Thu, 3 Sep.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Halifax International on Thu, 27 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Thu, 3 Sep, arriving in Halifax International.Price includes taxes and charges.From $711, select.

Chicago.$724 per passenger.Departing Wed, 12 Aug, returning Sat, 15 Aug.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Halifax International on Wed, 12 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Sat, 15 Aug, arriving in Halifax International.Price includes taxes and charges.From $724, select.

Chicago.$724 per passenger.Departing Thu, 25 Jun, returning Mon, 29 Jun.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Halifax International on Thu, 25 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Mon, 29 Jun, arriving in Halifax International.Price includes taxes and charges.From $724, select.

Chicago.$795 per passenger.Departing Wed, 27 May, returning Mon, 1 Jun.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Halifax International on Wed, 27 May, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Mon, 1 Jun, arriving in Halifax International.Price includes taxes and charges.From $795, select.

Chicago.$833 per passenger.Departing Mon, 27 Jul, returning Sun, 2 Aug.Return flight with Porter Airlines.Outbound indirect flight with Porter Airlines, departs from Halifax International on Mon, 27 Jul, arriving in Chicago Midway.Inbound indirect flight with Porter Airlines, departs from Chicago Midway on Sun, 2 Aug, arriving in Halifax International.Price includes taxes and charges.From $833, select.

Chicago.$885 per passenger.Departing Wed, 17 Jun, returning Thu, 30 Jul.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Halifax International on Wed, 17 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Thu, 30 Jul, arriving in Halifax International.Price includes taxes and charges.From $885, select.

Chicago.$1,015 per passenger.Departing Fri, 29 May, returning Sun, 31 May.Return flight with United.Outbound direct flight with United departs from Halifax International on Fri, 29 May, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sun, 31 May, arriving in Halifax International.Price includes taxes and charges.From $1,015, select.

Chicago.$1,017 per passenger.Departing Wed, 1 Jul, returning Tue, 7 Jul.Return flight with United.Outbound direct flight with United departs from Halifax International on Wed, 1 Jul, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 7 Jul, arriving in Halifax International.Price includes taxes and charges.From $1,017, select.

Chicago.$1,034 per passenger.Departing Fri, 22 May, returning Sat, 6 Jun.Return flight with United.Outbound direct flight with United departs from Halifax International on Fri, 22 May, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Sat, 6 Jun, arriving in Halifax International.Price includes taxes and charges.From $1,034, select.

Chicago.$1,060 per passenger.Departing Mon, 8 Jun, returning Tue, 16 Jun.Return flight with United.Outbound direct flight with United departs from Halifax International on Mon, 8 Jun, arriving in Chicago O'Hare International.Inbound direct flight with United departs from Chicago O'Hare International on Tue, 16 Jun, arriving in Halifax International.Price includes taxes and charges.From $1,060, select.

Find the cheapest month to fly from Halifax International to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Halifax International to Chicago flights are currently cheapest in November.

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Direct flights from Halifax International to Chicago

Alternative Halifax International to Chicago routes

Looking for the cheapest, fastest or easiest route from Halifax International to Chicago? You could fly into the following airports instead.

Halifax to Chicago: Flight information

The things to know before you go.

Cheapest flight found	$553
Cheapest month to fly	October
Average flight time	3 hrs, 47 mins
Most popular airline	Air Canada
Average flights per week	16

Finding cheap flights from Halifax International to Chicago: Frequently asked questions

How many airports are there in Chicago?

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.

How much are return flights from Halifax International to Chicago?

The best price we found for a return flight from Halifax International to Chicago is $553. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.

How long does it take to fly from Halifax International to Chicago?

3 hours and 47 minutes is the average flight time from Halifax International to Chicago.

Which airlines fly direct from Halifax International to Chicago?

Air Canada, United and SkyWest Airlines fly direct from Halifax International to Chicago.

How many flights are there a week from Halifax International to Chicago?

As of April 2026, there are 16 flights per week flying from Halifax International to Chicago.

When is the cheapest time to fly from Halifax International to Chicago?

The cheapest month to fly from Halifax International to Chicago is usually October.

Which is the cheapest airport to fly into in Chicago?

If you're flying from Halifax International Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $553.

Which upcoming date is cheapest to fly from Halifax International Airport to Chicago on?

After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Halifax International Airport to Chicago on Saturday, 24 October 2026.

Can I get a direct flight from Halifax International Airport to Chicago?

Yes – the average flight time is 3 hours and 47 minutes.

How can I get the best flight deal from Halifax International Airport to Chicago?

We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.

When is the best time to book flights to Chicago?

We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.

What’s the weather like in Chicago?

In April, the average temperature is usually around 8°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.

Which is the cheapest airline to fly from Halifax International Airport to Chicago with?

Currently, Porter Airlines and United offer the cheapest flight tickets to Chicago.

Travelling from Halifax Stanfield International Airport (YHZ) to Chicago: what you need to know

Book a direct flight from Halifax Stanfield International Airport to Chicago and you'll be travelling for around 3 hours 15 minutes.
Chicago is two hours behind Halifax, where Halifax Stanfield International Airport is located. Chicago observes the UTC-6 timezone.
The most popular route is from Halifax Stanfield International Airport (YHZ) to Chicago O'Hare International Airport (ORD). Choose from two services every week between these two airports. If you'd like to head off as soon as possible, the earliest flight from YHZ to ORD is the 14:15 American Airlines service. If you prefer to leave later in the day, the last departure is at 17:00 with United Airlines.
To avoid missing your YHZ to Chicago flight, leave enough time for things like baggage drop and finding your gate. Arriving two hours ahead of international departures and one hour before domestic flights is the general travel rule.
You can expect bigger queues in popular months like August. Arriving up to four hours in advance for an international flight and two hours for a domestic departure will give you plenty of time for security and boarding.
Direct Halifax Stanfield International Airport to Chicago tickets are available for booking. Chicago O'Hare International Airport (ORD) is where you'll step off the plane.
Book your ticket with United Airlines. This leading carrier operates direct flights from Halifax Stanfield International Airport to Chicago.
YHZ is about 27 kilometres from central Halifax. If you're catching a taxi, ride-sharing or driving from the centre, it'll take you 35 minutes or so to get there, depending on the traffic. If you're planning to take public transport, expect the journey time to be around 50 minutes.
Looking for a hotel near YHZ? If you're boarding an early flight from Halifax Stanfield International Airport to Chicago, these stays put the terminal practically at your doorstep:
Of the flights that depart from Halifax Stanfield International Airport, 67% touch down on time at their destination.

How to find the cheapest flights from Halifax Stanfield International Airport (YHZ) to Chicago

$319 is the lowest price we've seen for a one-way Halifax Stanfield International Airport to Chicago flight. A return plane ticket right now is $553. Depending on the availability when you book, these fares can change.
Don't leave things to the last minute. You're more likely to land cheap flights from YHZ to Chicago if you book in advance. Airlines often offer some great early bird rates.
Finding cheap tickets from Halifax Stanfield International Airport to Chicago is easier if you're flexible with your travel dates. Try using the 'Whole month' search tool to get the lowest fares across each month and bag an epic deal.
Cut down on the time spent looking for cheap flights from YHZ to Chicago by creating a Price Alert. You'll receive an email or notification through the app when a special offer becomes available.
Find an affordable flight from Halifax Stanfield International Airport to Chicago with the help of our filters. Select your preferred duration, departure time and airlines, then sort the results by 'Cheapest' to see the best deals.

Airports in Chicago

Chicago O'Hare International Airport (ORD)

Chicago O'Hare International Airport (ORD) to the centre of Chicago takes about 30 minutes by car. The centre is roughly 27 kilometres away.
It'll take around 45 minutes to get there using public transport.
If you're coming in on a late flight from Halifax Stanfield International Airport to Chicago, nothing beats the convenience of staying close to the terminal. Grab your luggage from the carousel and then be showered and snoozing soon after at one of these accommodation options near ORD:
To get the lowest price, book your vehicle from Chicago O'Hare International Airport about four weeks in advance of your flight from YHZ to Chicago.
The address for ORD is 10000 West O'Hare.

Chicago Midway International Airport (MDW)

After your flight from Halifax Stanfield International Airport to Chicago has arrived, you can get to the city centre in around 25 minutes by car. Central Chicago is roughly 16 kilometres from Chicago Midway International Airport (MDW).
If you choose to travel on public transport, you'll get to the city centre in 30 minutes or so.
After stepping off your YHZ to Chicago flight, kick back at a hotel close to MDW. These are some great options that'll help you slip into relaxation mode:
Score the best price by booking your ride from MDW four weeks ahead of time. You can also expect to have a bigger selection of vehicles.
You can find Chicago Midway International Airport at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

Step off your flight from Halifax Stanfield International Airport to Chicago and head for your hotel or jump right into sightseeing. Central Chicago is around 145 kilometres from Chicago Rockford International Airport (RFD) and usually takes 1 hour 40 minutes to drive there.
If you're using public transport, the journey will take you around 2 hours.
If you don't want to make the trip to the centre, head for a hotel close to RFD. Make yourself comfortable at one of these options after your YHZ to Chicago flight:
Rental companies sometimes offer promotions on early bookings, so reserve your ride from RFD a few weeks ahead of your flight from Halifax Stanfield International Airport to Chicago. A little prep work can make a big difference in cost.
Chicago Rockford International Airport's street address is 2 Airport Cir.

Best time to go to Chicago

It's time to choose your dates for your flight from Halifax Stanfield International Airport to Chicago. July is the busiest month to visit Chicago. If you want a more peaceful vibe, go in January.
Book a Halifax Stanfield International Airport to Chicago plane ticket with a departure in July to experience the city during its warmest month. You can expect temperatures to range from 16ºC to 28ºC.
Search for cheap tickets from YHZ to Chicago in January if you want to travel in cooler conditions. Temperatures are at their lowest then, ranging between -12ºC and 3ºC on average.

More about Chicago

Once you've booked your flight from Halifax Stanfield International Airport to Chicago, choose a hotel that combines comfort with a great location. Make one of these accommodation options your base for exploring Chicago:
All great holidays should include some sightseeing. Art Institute of Chicago, Millennium Park and Willis Tower are attractions you won't want to skip in Chicago.

Explore more of the United States

Chicago will leave a lasting impression, but there are so many other corners of the United States waiting to be discovered. Around 451 kilometres southeast of Chicago, a visit to Columbus will fill your itinerary to the brim. Start with popular sights like Franklin Park Conservatory and Botanical Gardens, Whetstone Park / Park of Roses and Ohio Theatre.
If you want to check out another corner of the United States, consider Indianapolis, roughly 257 kilometres southeast of Chicago. Lucas Oil Stadium, Eiteljorg Museum and The Children's Museum of Indianapolis are among the biggest draws.