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Find cheap Porter Airlines flights to Chicago from C$ 170

1 adult
0 bags
Sat 29/6
Sat 6/7

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Good to know

Low season

January

High season

May

Cheapest flight

C$ 170

Average price round-trip

C$ 368

Good deal round-trip

C$ 314

Good deal one-way

C$ 181
Best time to beat the crowds (18% less expensive on average)
Most popular time to fly and prices are also 3% lower on average.
Flight from Toronto Island to Chicago Midway Airport
(avg. price over the last 2 weeks)
or less
or less

When to book flights with Porter Airlines to Chicago

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago with Porter Airlines

  • 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$ 269. Flights to Chicago with Air Canada cost C$ 501 on average.

  • Which other airlines fly to Chicago?

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

  • How much is a flight to Chicago with Porter Airlines?

    On average, Porter Airlines flights to Chicago cost C$ 143 for one-way and C$ 269 return.

  • 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.

See more FAQs

Top tips for your flights to Chicago with Porter Airlines

  • Looking to fly from Canada to Chicago with Porter Airlines? 25% of our users found flights for the following prices or less: From Toronto Island Airport C$ 181 one-way, C$ 314 round-trip.
  • The cheapest flight to Chicago with Porter Airlines found on KAYAK in the last 2 weeks departed from Toronto Island Airport and cost C$ 176.

Porter Airlines customer reviews

7.4
GoodBased on 394 verified guest reviews
7.5Comfort
7.6Boarding
8.2Crew
7.4Food
6.6Entertainment

Traveler rating:
Sort by:
A
9.2 Wonderful
Pros:due to weather then mechanical difficulty, we were quite delayed in take off, but the boarding area was comfortable and the airline did everything they could make our connection possible and we though delayed landed in Sault Ste. Marie that day. Not ideal, but admirable.
A
10.0 Wonderful
Pros:Ease of boarding. Carry on luggage is handled by crew staff - makes boarding much easier as passengers aren't struggling to find space for the carry on bags. The bags are ready for pickup upon exiting the aircraft. Would highly recommend Porter and would use again.
Cons:Flight was approx. 10 minutes late, but the time was made up during the flight.
A
9.6 Wonderful
Pros:it was such a smooth flight
Cons:all good
A
4.3 Mediocre
Pros:Lounge, flight, flight service
Cons:90 min late take off.
A
8.0 Very good
Pros:Excellent service
Cons:Delay
J
2.0 Poor
Pros:Nothing
Cons:I arrived to the checkout desk line @ 1:20pm and there was no attendant available. The attendant from the adjacent airline attempted to help me as best she could but to no avail she was unable to reach anyone at gate. I finally was directed to the information desk @1:45pm in which case the receptionist tried his best to help me board the plane and was told the plane already left despite the fact the departure time was 2:30pm. After calling Porter Airlines I was emotional distraught and upset. Not only was it my birthday but the airline refused to assist in giving me some sort of discount or fair adjustment I also never checked in my hotel reservations losing more money. The porter associate was RUDE and refused to transfer me to his Supervisor. He told the supervisor left @3:30pm and won't be back until 8pm. After calling the airline again I was told the insurance I purchased with my flight was invalid.
A
4.8 Mediocre
Cons:Flight was very delayed. We got turned around in flight and then ultimately made it. No apologies from crew or porter.
A
10.0 Wonderful
Pros:My flight was delayed due to bad weather but they offered complimentary drink service at the airport and I really appreciated it. I would like to fly with Porter Airlines again.
J
6.3 Okay
Pros:The flight was on time - for once.
Cons:Nothing to not like. No food or entertainment to rate.
A
10.0 Wonderful
Pros:Loved everything

Book Cheap flights with Porter Airlines to Chicago

Recent round-trip flight deals

29/7Mon
directPorter Airlines
1h 47mYTZ-MDW
3/8Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 287
27/6Thu
directPorter Airlines
1h 47mYTZ-MDW
4/7Thu
directPorter Airlines
1h 42mMDW-YTZ
C$ 297
14/6Fri
directPorter Airlines
1h 47mYTZ-MDW
18/6Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 298
25/7Thu
directPorter Airlines
1h 47mYTZ-MDW
29/7Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 302
13/6Thu
directPorter Airlines
1h 47mYTZ-MDW
30/6Sun
directPorter Airlines
1h 42mMDW-YTZ
C$ 304
1/7Mon
directPorter Airlines
1h 47mYTZ-MDW
4/7Thu
directPorter Airlines
1h 42mMDW-YTZ
C$ 305
18/6Tue
directPorter Airlines
1h 47mYTZ-MDW
5/7Fri
directPorter Airlines
1h 42mMDW-YTZ
C$ 306
14/6Fri
directPorter Airlines
1h 47mYTZ-MDW
17/6Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 308
13/6Thu
directPorter Airlines
1h 47mYTZ-MDW
15/6Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 309
1/7Mon
directPorter Airlines
1h 47mYTZ-MDW
3/7Wed
directPorter Airlines
1h 42mMDW-YTZ
C$ 311
24/7Wed
directPorter Airlines
1h 47mYTZ-MDW
28/7Sun
directPorter Airlines
1h 42mMDW-YTZ
C$ 313
28/7Sun
directPorter Airlines
1h 47mYTZ-MDW
7/8Wed
directPorter Airlines
1h 42mMDW-YTZ
C$ 315
31/7Wed
directPorter Airlines
1h 47mYTZ-MDW
8/8Thu
directPorter Airlines
1h 42mMDW-YTZ
C$ 317
30/7Tue
1 stopPorter Airlines
6h 12mYUL-MDW
13/8Tue
1 stopPorter Airlines
4h 35mMDW-YUL
C$ 317
1/8Thu
directPorter Airlines
1h 47mYTZ-MDW
6/8Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 319
21/8Wed
1 stopPorter Airlines
6h 32mYUL-MDW
28/8Wed
1 stopPorter Airlines
4h 45mMDW-YUL
C$ 319
31/7Wed
directPorter Airlines
1h 47mYTZ-MDW
2/8Fri
directPorter Airlines
1h 42mMDW-YTZ
C$ 320
25/6Tue
directPorter Airlines
1h 47mYTZ-MDW
29/6Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 322
31/7Wed
directPorter Airlines
1h 47mYTZ-MDW
3/8Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 323
30/6Sun
1 stopPorter Airlines
4h 32mYUL-MDW
6/7Sat
1 stopPorter Airlines
5h 15mMDW-YUL
C$ 323

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Recent one-way flight deals

5/8Mon
directPorter Airlines
1h 47mYTZ-MDW
C$ 170
28/7Sun
directPorter Airlines
1h 47mYTZ-MDW
C$ 172
31/7Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 175
15/8Thu
directPorter Airlines
1h 47mYTZ-MDW
C$ 177
1/7Mon
directPorter Airlines
1h 47mYTZ-MDW
C$ 178
19/6Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 182
13/6Thu
directPorter Airlines
1h 47mYTZ-MDW
C$ 185
14/6Fri
directPorter Airlines
1h 47mYTZ-MDW
C$ 186
9/7Tue
directPorter Airlines
1h 47mYTZ-MDW
C$ 187
6/8Tue
directPorter Airlines
1h 47mYTZ-MDW
C$ 189
29/6Sat
directPorter Airlines
1h 47mYTZ-MDW
C$ 190
14/6Fri
directPorter Airlines
1h 47mYTZ-MDW
C$ 193
4/7Thu
directPorter Airlines
1h 47mYTZ-MDW
C$ 194
16/6Sun
directPorter Airlines
1h 47mYTZ-MDW
C$ 197
4/9Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 198
4/7Thu
1 stopPorter Airlines
5h 52mYUL-MDW
C$ 198
11/7Thu
1 stopPorter Airlines
6h 32mYUL-MDW
C$ 200
6/7Sat
directPorter Airlines
1h 47mYTZ-MDW
C$ 201
12/8Mon
directPorter Airlines
1h 47mYTZ-MDW
C$ 203
19/6Wed
1 stopPorter Airlines
4h 27mYUL-MDW
C$ 204

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Flights to Chicago - Porter Airlines

Return flight deals:

Chicago - Canada

Cabin classes:

C$ 1,010
C$ 1,089
C$ 602
C$ 265

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