Is Porter Airlines cheaper than other airlines flying to Chicago?

Porter Airlines is the cheapest airline flying to Chicago with an average return price of C$ 204. Flights to Chicago with WestJet cost C$ 287 on average, while United Airlines cost C$ 456.

Which other airlines fly to Chicago?

Along with Porter Airlines, you can also fly to Chicago with WestJet, United Airlines, Air Canada, Air Canada and United Airlines.

How much is a flight to Chicago with Porter Airlines?

On average, Porter Airlines flights to Chicago cost C$ 204 for a round-trip.

Which airport do Porter Airlines flights to Chicago fly into?

Porter Airlines flights to Chicago will fly into either Chicago O'Hare Airport, Chicago Midway Airport and Chicago Greater Rockford.

Porter Airlines flights to Chicago (CHI) from C$ 138

Flights Deals

Cheap Porter Airlines Flight Deals to Chicago

Here are some of the best deals found on KAYAK recently from Porter Airlines 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.

Round-trip

One-way

Last minute

Direct

Recent round-trip Porter Airlines flight deals to Chicago

Thu, 12 Jun - Mon, 16 Jun

7:55 a.m. - 8:45 a.m.YTZ-MDW

1h 50mdirect

5:50 p.m. - 8:32 p.m.MDW-YTZ

1h 42mdirect

C$ 222Porter Airlines

Find Deal

Thu, 29 May - Sun, 1 Jun

3:35 p.m. - 4:24 p.m.YTZ-MDW

1h 49mdirect

5:50 p.m. - 8:32 p.m.MDW-YTZ

1h 42mdirect

C$ 226Porter Airlines

Find Deal

Thu, 29 May - Sun, 1 Jun

3:35 p.m. - 4:24 p.m.YTZ-MDW

1h 49mdirect

9:40 a.m. - 12:22 p.m.MDW-YTZ

1h 42mdirect

C$ 235Porter Airlines

Find Deal

Mon, 9 Jun - Thu, 12 Jun

4:05 p.m. - 4:54 p.m.YTZ-MDW

1h 49mdirect

9:40 a.m. - 12:20 p.m.MDW-YTZ

1h 40mdirect

C$ 236Porter Airlines

Find Deal

Fri, 20 Jun - Fri, 27 Jun

4:05 p.m. - 4:54 p.m.YTZ-MDW

1h 49mdirect

9:40 a.m. - 12:20 p.m.MDW-YTZ

1h 40mdirect

C$ 237Porter Airlines

Find Deal

Thu, 5 Jun - Thu, 12 Jun

7:55 a.m. - 8:45 a.m.YTZ-MDW

1h 50mdirect

9:40 a.m. - 12:20 p.m.MDW-YTZ

1h 40mdirect

C$ 239Porter Airlines

Find Deal

Thu, 29 May - Sun, 8 Jun

3:35 p.m. - 4:24 p.m.YTZ-MDW

1h 49mdirect

9:40 a.m. - 12:22 p.m.MDW-YTZ

1h 42mdirect

C$ 240Porter Airlines

Find Deal

Thu, 29 May - Mon, 2 Jun

3:35 p.m. - 4:24 p.m.YTZ-MDW

1h 49mdirect

9:40 a.m. - 12:20 p.m.MDW-YTZ

1h 40mdirect

C$ 242Porter Airlines

Find Deal

Wed, 28 May - Wed, 4 Jun

7:30 a.m. - 8:19 a.m.YTZ-MDW

1h 49mdirect

9:15 a.m. - 11:57 a.m.MDW-YTZ

1h 42mdirect

C$ 243Porter Airlines

Find Deal

Wed, 25 Jun - Wed, 2 Jul

7:55 a.m. - 8:45 a.m.YTZ-MDW

1h 50mdirect

9:40 a.m. - 12:22 p.m.MDW-YTZ

1h 42mdirect

C$ 244Porter Airlines

Find Deal

Useful Info

Low season	January
High season	August
Cheapest flight	C$ 138
Average price round-trip	C$ 282
Good deal round-trip	C$ 246

Best time to beat the crowds but there is an average 7% increase in price.

Most popular time to fly and prices are also 1% lower on average.

Flight from Toronto Island to Chicago Midway Airport

(avg. price over the last 2 weeks)

or less

When to book flights with Porter Airlines to Chicago

Average price per month

Flight prices as travel date approaches

Is Porter Airlines cheaper than other airlines flying to Chicago?
Porter Airlines is the cheapest airline flying to Chicago with an average return price of C$ 204. Flights to Chicago with WestJet cost C$ 287 on average, while United Airlines cost C$ 456.
Which other airlines fly to Chicago?
Along with Porter Airlines, you can also fly to Chicago with WestJet, United Airlines, Air Canada, Air Canada and United Airlines.
How much is a flight to Chicago with Porter Airlines?
On average, Porter Airlines flights to Chicago cost C$ 204 for a round-trip.
Which airport do Porter Airlines flights to Chicago fly into?
Porter Airlines flights to Chicago will fly into either Chicago O'Hare Airport, Chicago Midway Airport and Chicago Greater Rockford.

The cheapest flight to Chicago with Porter Airlines found on KAYAK in the last 2 weeks departed from Toronto Island Airport and cost C$ 184.

8.0

Very goodBased on 285 verified guest reviews

7.6Food

8.1Comfort

8.2Boarding

8.8Crew

7.0Entertainment

10.0 Wonderful

Anonymous, Apr 2025

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

10.0 Wonderful

Diane, Apr 2025

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

8.0 Very good

Jendan, Mar 2025

Overall very good... staff were friendly and helpful. boarding was good for the most part, but a little hard to get our carry-on bags on there.... I think people should be directed to keep their coats and small bags with them until all the carry-ons are loaded, and then, if there is space, they can put their small bags and coats up top.. makes it much easier to put baggage up. i loved the internet feature, but the entertainment was not there unless you have your own Netflix or similar platform. My chair did not recline, which was very annoying, and the arms won't go up near the isle, which makes it tough to get in and out of the seat.

8.0 Very good

Louise, Mar 2025

Staff were excellant. Only snacks served. Some turbulence so we were offered Free beer or wine.

8.0 Very good

Gregory, Feb 2025

Late on board ing Late deboarding

4.0 Mediocre

Jason, Feb 2025

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.

10.0 Wonderful

Ian, Jan 2025

Excellent overall - comfortable and great service.

10.0 Wonderful

Ian, Jan 2025

On time, great service, and overall excellent flight.

10.0 Wonderful

Kevin, Jan 2025

Efficient and comfortable

10.0 Wonderful

Anonymous, Jan 2025

Better than Air Canada, more space, friendly

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Find cheap Porter Airlines flights to Chicago from C$ 138

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Cheap Porter Airlines Flight Deals to Chicago

Recent round-trip Porter Airlines flight deals to Chicago

Recent one-way Porter Airlines flight deals to Chicago

Recent last minute Porter Airlines flight deals to Chicago

Recent direct Porter Airlines flight deals to Chicago

Good to know

When to book flights with Porter Airlines to Chicago

FAQs for flying to Chicago with Porter Airlines

Is Porter Airlines cheaper than other airlines flying to Chicago?

Which other airlines fly to Chicago?

How much is a flight to Chicago with Porter Airlines?

Which airport do Porter Airlines flights to Chicago fly into?

Top tips for your flights to Chicago with Porter Airlines

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