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Find cheap Porter Airlines flights to Chicago from C$ 182

1 adult
0 bags
Sa 1/6
Sa 8/6

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Good to know

Low season

January

High season

August

Cheapest flight

C$ 182

Average price round-trip

C$ 692
Best time to beat the crowds (16% less expensive on average)
Most popular time to fly and prices are also 5% lower on average.
Flight from Toronto Island to Chicago Midway Airport
(price for this month)

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 currently the only airline with deals flying to Chicago, with an average return price of C$ 250.

  • Which other airlines fly to Chicago?

    Along with Porter Airlines, you can also fly to Chicago with United Airlines.

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

    On average, Porter Airlines flights to Chicago cost C$ 154 for one-way and C$ 250 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$ 178 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$ 173.

Porter Airlines customer reviews

7.4
GoodBased on 435 verified guest reviews
7.5Comfort
8.2Crew
7.4Food
7.6Boarding
6.6Entertainment
Traveler rating:
Sort by:
A
8.0 Very good
Pros:Crew is very polite and helpful. The truffles are awesome!
Cons:Frequent delays
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
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
4.3 Mediocre
Pros:Lounge, flight, flight service
Cons:90 min late take off.
A
8.0 Very good
Pros:Excellent service
Cons:Delay
A
10.0 Wonderful
Pros:I flew many airlines in my life and Porter is one if the most human and attentive airline I experienced. Hopefully, will not grow to a greedy and bureaucratic corporations :)
S
10.0 Wonderful
Cons:Coming back through customs as an American citizen and a member of the United States Military, treated like another scumbag coming back to the US
Read more about Porter Airlines

Book Cheap flights with Porter Airlines to Chicago

Recent round-trip flight deals

23/5Do
directPorter Airlines
1h 47mYTZ-MDW
26/5So
directPorter Airlines
1h 42mMDW-YTZ
C$ 317
23/5Do
directPorter Airlines
1h 47mYTZ-MDW
28/5Di
directPorter Airlines
1h 42mMDW-YTZ
C$ 318
24/5Fr
directPorter Airlines
1h 47mYTZ-MDW
26/5So
directPorter Airlines
1h 42mMDW-YTZ
C$ 319
30/5Do
directPorter Airlines
1h 47mYTZ-MDW
8/6Sa
directPorter Airlines
1h 42mMDW-YTZ
C$ 321
23/5Do
directPorter Airlines
1h 47mYTZ-MDW
30/5Do
directPorter Airlines
1h 42mMDW-YTZ
C$ 322
30/5Do
directPorter Airlines
1h 47mYTZ-MDW
8/6Sa
directPorter Airlines
1h 42mMDW-YTZ
C$ 323
22/5Mi
directPorter Airlines
1h 47mYTZ-MDW
26/5So
directPorter Airlines
1h 42mMDW-YTZ
C$ 325
4/6Di
directPorter Airlines
1h 47mYTZ-MDW
7/6Fr
directPorter Airlines
1h 42mMDW-YTZ
C$ 326
29/5Mi
directPorter Airlines
1h 47mYTZ-MDW
1/6Sa
directPorter Airlines
1h 42mMDW-YTZ
C$ 330
24/5Fr
directPorter Airlines
1h 47mYTZ-MDW
31/5Fr
directPorter Airlines
1h 42mMDW-YTZ
C$ 332
23/5Do
directPorter Airlines
1h 47mYTZ-MDW
26/5So
directPorter Airlines
1h 42mMDW-YTZ
C$ 334
23/5Do
directPorter Airlines
1h 47mYTZ-MDW
26/5So
directPorter Airlines
1h 42mMDW-YTZ
C$ 336
25/5Sa
1 stopPorter Airlines
4h 52mYUL-MDW
1/6Sa
1 stopPorter Airlines
5h 15mMDW-YUL
C$ 339
23/5Do
directPorter Airlines
1h 47mYTZ-MDW
26/5So
directPorter Airlines
1h 42mMDW-YTZ
C$ 340
2/6So
directPorter Airlines
1h 47mYTZ-MDW
3/6Mo
directPorter Airlines
1h 42mMDW-YTZ
C$ 341
25/5Sa
1 stopPorter Airlines
4h 52mYUL-MDW
27/5Mo
1 stopPorter Airlines
4h 45mMDW-YUL
C$ 341
26/5So
1 stopPorter Airlines
6h 37mYUL-MDW
30/5Do
1 stopPorter Airlines
3h 55mMDW-YUL
C$ 343
30/5Do
directPorter Airlines
1h 47mYTZ-MDW
3/6Mo
directPorter Airlines
1h 42mMDW-YTZ
C$ 344
26/5So
1 stopPorter Airlines
6h 37mYUL-MDW
30/5Do
1 stopPorter Airlines
5h 55mMDW-YUL
C$ 344
22/6Sa
1 stopPorter Airlines
4h 52mYUL-MDW
26/6Mi
1 stopPorter Airlines
4h 45mMDW-YUL
C$ 345

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Recent one-way flight deals

23/5Do
directPorter Airlines
1h 47mYTZ-MDW
C$ 182
1/6Sa
directPorter Airlines
1h 47mYTZ-MDW
C$ 187
1/6Sa
directPorter Airlines
1h 47mYTZ-MDW
C$ 189
9/6So
directPorter Airlines
1h 47mYTZ-MDW
C$ 190
4/6Di
directPorter Airlines
1h 47mYTZ-MDW
C$ 191
9/6So
directPorter Airlines
1h 47mYTZ-MDW
C$ 193
1/6Sa
directPorter Airlines
1h 47mYTZ-MDW
C$ 194
9/6So
directPorter Airlines
1h 47mYTZ-MDW
C$ 195
31/5Fr
directPorter Airlines
1h 47mYTZ-MDW
C$ 204
22/5Mi
directPorter Airlines
1h 47mYTZ-MDW
C$ 205
1/6Sa
directPorter Airlines
1h 47mYTZ-MDW
C$ 206
23/5Do
1 stopPorter Airlines
4h 07mYUL-MDW
C$ 209
18/6Di
1 stopPorter Airlines
4h 27mYUL-MDW
C$ 215
28/5Di
1 stopPorter Airlines
4h 27mYUL-MDW
C$ 216
15/5Mi
directPorter Airlines
1h 47mYTZ-MDW
C$ 217
25/6Di
1 stopPorter Airlines
4h 02mYUL-MDW
C$ 217
5/6Mi
directPorter Airlines
1h 47mYTZ-MDW
C$ 220
3/6Mo
1 stopPorter Airlines
4h 02mYUL-MDW
C$ 220
27/5Mo
1 stopPorter Airlines
4h 07mYUL-MDW
C$ 222
11/6Di
1 stopPorter Airlines
4h 07mYUL-MDW
C$ 226

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Flights to Chicago - Porter Airlines

Return flight deals:

Chicago - Canada

Cabin classes:

C$ 995
First Class flights to Chicago
C$ 834
Business Class flights to Chicago
C$ 546
C$ 281

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