Roundtrip flight Toronto - Chicago for $231
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CHICAGO, Illinois 🇺🇸

$231

Normal average price: $325 (or 32,500 simple points)

Roundtrip, all taxes/fees included

FROM: YTZ - Billy Bishop Toronto City Airport

TO: MDW - Chicago Midway International Airport

See all available dates

Normal average price: $325 (or 32,500 simple points)

Roundtrip, all taxes/fees included

FROM: YTZ - Billy Bishop Toronto City Airport

TO: MDW - Chicago Midway International Airport

IMPORTANT WARNING ABOUT THIS DEAL

  • Limited carry-on ⌄

    → At least one of the date combinations in this flight deal is with an airline that charge extra for to bring a standard carry-on on board. You will always be allowed a smaller personal item for free.

🔎 Pro tip: Always check if the flight price is the same on the airline's direct website before booking!

DATES

Deals expire quickly; act fast! Click here for more details.

May 19 → May 26 7d Tue - Tue
DNCPorter Airlines
$247
May 19 → May 26 7d  ·  Tue - Tue  ·  YTZ-MDW
DNC
Porter Airlines
$247 Details > 
May 19 → May 27 8d Tue - Wed
DNCPorter Airlines
$247
May 19 → May 27 8d  ·  Tue - Wed  ·  YTZ-MDW
DNC
Porter Airlines
$247 Details > 
May 19 → May 31 12d Tue - Sun
DNCPorter Airlines
$252
May 19 → May 31 12d  ·  Tue - Sun  ·  YTZ-MDW
DNC
Porter Airlines
$252 Details > 
May 19 → Jun 2 14d Tue - Tue
DNCPorter Airlines
$247
May 19 → Jun 2 14d  ·  Tue - Tue  ·  YTZ-MDW
DNC
Porter Airlines
$247 Details > 
May 21 → May 26 5d Thu - Tue
DNCPorter Airlines
$245
May 21 → May 26 5d  ·  Thu - Tue  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
May 21 → May 27 6d Thu - Wed
DNCPorter Airlines
$245
May 21 → May 27 6d  ·  Thu - Wed  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
May 21 → May 30 9d Thu - Sat
DNCPorter Airlines
$245
May 21 → May 30 9d  ·  Thu - Sat  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
May 21 → May 31 10d Thu - Sun
DNCPorter Airlines
$251
May 21 → May 31 10d  ·  Thu - Sun  ·  YTZ-MDW
DNC
Porter Airlines
$251 Details > 
May 21 → Jun 2 12d Thu - Tue
DNCPorter Airlines
$245
May 21 → Jun 2 12d  ·  Thu - Tue  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
May 21 → Jun 3 13d Thu - Wed
DNCPorter Airlines
$245
May 21 → Jun 3 13d  ·  Thu - Wed  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
May 23 → May 27 4d Sat - Wed
DNCPorter Airlines
$231
May 23 → May 27 4d  ·  Sat - Wed  ·  YTZ-MDW
DNC
Porter Airlines
$231 Details > 
May 23 → Jun 1 9d Sat - Mon
DNCPorter Airlines
$251
May 23 → Jun 1 9d  ·  Sat - Mon  ·  YTZ-MDW
DNC
Porter Airlines
$251 Details > 
May 26 → May 31 5d Tue - Sun
DNCPorter Airlines
$245
May 26 → May 31 5d  ·  Tue - Sun  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
May 26 → Jun 2 7d Tue - Tue
DNCPorter Airlines
$245
May 26 → Jun 2 7d  ·  Tue - Tue  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
May 26 → Jun 9 14d Tue - Tue
DNCPorter Airlines
$245
May 26 → Jun 9 14d  ·  Tue - Tue  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
May 27 → May 31 4d Wed - Sun
DNCPorter Airlines
$249
May 27 → May 31 4d  ·  Wed - Sun  ·  YTZ-MDW
DNC
Porter Airlines
$249 Details > 
May 27 → Jun 2 6d Wed - Tue
DNCPorter Airlines
$245
May 27 → Jun 2 6d  ·  Wed - Tue  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
May 27 → Jun 3 7d Wed - Wed
DNCPorter Airlines
$237
May 27 → Jun 3 7d  ·  Wed - Wed  ·  YTZ-MDW
DNC
Porter Airlines
$237 Details > 
May 27 → Jun 4 8d Wed - Thu
DNCPorter Airlines
$245
May 27 → Jun 4 8d  ·  Wed - Thu  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
May 27 → Jun 5 9d Wed - Fri
DNCPorter Airlines
$251
May 27 → Jun 5 9d  ·  Wed - Fri  ·  YTZ-MDW
DNC
Porter Airlines
$251 Details > 
May 27 → Jun 9 13d Wed - Tue
DNCPorter Airlines
$245
May 27 → Jun 9 13d  ·  Wed - Tue  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
May 27 → Jun 10 14d Wed - Wed
DNCPorter Airlines
$245
May 27 → Jun 10 14d  ·  Wed - Wed  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
May 27 → Jun 11 15d Wed - Thu
DNCPorter Airlines
$245
May 27 → Jun 11 15d  ·  Wed - Thu  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
May 31 → Jun 8 8d Sun - Mon
DNCPorter Airlines
$245
May 31 → Jun 8 8d  ·  Sun - Mon  ·  YTZ-MDW
DNC
Porter Airlines
$245 Details > 
Or redeem points of the more simple type23,100 points instead of $231
Or redeem points of the more simple type (23,100 points instead of $231)
Jun 2 → Jun 16 14d Tue - Tue
DNCPorter Airlines
$251
Jun 2 → Jun 16 14d  ·  Tue - Tue  ·  YTZ-MDW
DNC
Porter Airlines
$251 Details > 
Jun 3 → Jun 17 14d Wed - Wed
DNCPorter Airlines
$251
Jun 3 → Jun 17 14d  ·  Wed - Wed  ·  YTZ-MDW
DNC
Porter Airlines
$251 Details > 
Jun 4 → Jun 14 10d Thu - Sun
DNCPorter Airlines
$251
Jun 4 → Jun 14 10d  ·  Thu - Sun  ·  YTZ-MDW
DNC
Porter Airlines
$251 Details > 
Jun 5 → Jun 19 14d Fri - Fri
DNCPorter Airlines
$251
Jun 5 → Jun 19 14d  ·  Fri - Fri  ·  YTZ-MDW
DNC
Porter Airlines
$251 Details > 
Jun 9 → Jun 23 14d Tue - Tue
DNCPorter Airlines
$251
Jun 9 → Jun 23 14d  ·  Tue - Tue  ·  YTZ-MDW
DNC
Porter Airlines
$251 Details > 
Jun 10 → Jun 24 14d Wed - Wed
DNCPorter Airlines
$251
Jun 10 → Jun 24 14d  ·  Wed - Wed  ·  YTZ-MDW
DNC
Porter Airlines
$251 Details > 
Jun 11 → Jun 21 10d Thu - Sun
DNCPorter Airlines
$251
Jun 11 → Jun 21 10d  ·  Thu - Sun  ·  YTZ-MDW
DNC
Porter Airlines
$251 Details > 
Jun 16 → Jul 7 21d Tue - Tue
DNCPorter Airlines
$261
Jun 16 → Jul 7 21d  ·  Tue - Tue  ·  YTZ-MDW
DNC
Porter Airlines
$261 Details > 
Jun 17 → Jul 8 21d Wed - Wed
DNCPorter Airlines
$261
Jun 17 → Jul 8 21d  ·  Wed - Wed  ·  YTZ-MDW
DNC
Porter Airlines
$261 Details > 
Jun 23 → Jul 7 14d Tue - Tue
DNCVPorter Airlines
$266
Jun 23 → Jul 7 14d  ·  Tue - Tue  ·  YTZ-MDW
DNCV
Porter Airlines
$266 Details > 
Jun 23 → Jul 14 21d Tue - Tue
DNCVPorter Airlines
$266
Jun 23 → Jul 14 21d  ·  Tue - Tue  ·  YTZ-MDW
DNCV
Porter Airlines
$266 Details > 
Jun 24 → Jul 8 14d Wed - Wed
DNCVPorter Airlines
$268
Jun 24 → Jul 8 14d  ·  Wed - Wed  ·  YTZ-MDW
DNCV
Porter Airlines
$268 Details > 
Jun 24 → Jul 15 21d Wed - Wed
DNCVPorter Airlines
$266
Jun 24 → Jul 15 21d  ·  Wed - Wed  ·  YTZ-MDW
DNCV
Porter Airlines
$266 Details > 
Jun 29 → Jul 8 9d Mon - Wed
DNCVPorter Airlines
$284
Jun 29 → Jul 8 9d  ·  Mon - Wed  ·  YTZ-MDW
DNCV
Porter Airlines
$284 Details > 
Jun 30 → Jul 21 21d Tue - Tue
DNCVPorter Airlines
$284
Jun 30 → Jul 21 21d  ·  Tue - Tue  ·  YTZ-MDW
DNCV
Porter Airlines
$284 Details > 
Or redeem points of the more simple type25,100 points instead of $251
Or redeem points of the more simple type (25,100 points instead of $251)
Jul 1 → Jul 22 21d Wed - Wed
DNCVPorter Airlines
$284
Jul 1 → Jul 22 21d  ·  Wed - Wed  ·  YTZ-MDW
DNCV
Porter Airlines
$284 Details > 
Jul 14 → Aug 4 21d Tue - Tue
DNCVPorter Airlines
$289
Jul 14 → Aug 4 21d  ·  Tue - Tue  ·  YTZ-MDW
DNCV
Porter Airlines
$289 Details > 
Jul 15 → Aug 5 21d Wed - Wed
DNCVPorter Airlines
$289
Jul 15 → Aug 5 21d  ·  Wed - Wed  ·  YTZ-MDW
DNCV
Porter Airlines
$289 Details > 
Or redeem points of the more simple type28,400 points instead of $284
Or redeem points of the more simple type (28,400 points instead of $284)

Might not be a deal, but at least find the lowest price for your specific dates

Check out our flight search tips and more tools here

DIR Non-stop flight

W Dates for weekend getaway

LD Very limited dates at this price

% Flight at an even more discounted price than usual!

Flytrippers logo in a flag Lowest price we have ever seen!

ULCC Involves at least 1 ultra low-cost carrier (ULCC)

No Suitcase Involves at least 1 airline without free regular carry-on bags

V Calendar Dates available during a popular vacation period

ST Self-transfer that implies a few pecularities

Porter Airlines Airline: Porter Airlines

Deals powered by Skyscanner, Momondo, Kiwi & Kayak

Accommodation Options



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