YTZ - CHI

Find cheap flights from Toronto Island to Chicago from C$ 191

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight departing on 28/6. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
Return
1 adult
Economy
0 bags
Wed 5/7
Wed 12/7

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Good to know

Low season

January

High season

August

Cheapest flight

C$ 191

Average price round-trip

C$ 352

Good deal round-trip

C$ 425

Good deal one-way

C$ 230
Best time to beat the crowds (16% less expensive on average)
Most popular time to fly (16% more expensive on average)
Flight from Toronto Island to Chicago
(avg. price over the last 2 weeks)
or less
or less

When to book flights from Toronto Island to Chicago

Estimated round-trip price
Average price per month
Flight prices as travel date approaches

Top tips for finding a cheap flight out of Toronto Island

  • The cheapest flight from Toronto Island to Chicago was found, on average, 88 days before departure.
  • Book at least 3 weeks before departure in order to get a below-average price.
  • High season is considered to be July, August and September. The cheapest month to fly is January.
  • Morning departure is around 126% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for booking Toronto Island to Chicago flights

Book cheap flights from Toronto Island to Chicago

Recent round-trip flight deals

18/6Sun
directPorter Airlines
1h 47mYTZ-MDW
20/6Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 309
28/6Wed
directPorter Airlines
1h 47mYTZ-MDW
3/7Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 352
29/6Thu
directPorter Airlines
1h 47mYTZ-MDW
1/7Sat
directPorter Airlines
1h 42mMDW-YTZ
C$ 354
29/6Thu
directPorter Airlines
1h 47mYTZ-MDW
3/7Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 358
5/7Wed
directPorter Airlines
1h 47mYTZ-MDW
7/7Fri
directPorter Airlines
1h 42mMDW-YTZ
C$ 373
26/7Wed
directPorter Airlines
1h 47mYTZ-MDW
2/8Wed
directPorter Airlines
1h 42mMDW-YTZ
C$ 377
1/7Sat
directPorter Airlines
1h 47mYTZ-MDW
4/7Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 381
29/6Thu
directPorter Airlines
1h 47mYTZ-MDW
3/7Mon
directPorter Airlines
1h 42mMDW-YTZ
C$ 391
28/6Wed
directPorter Airlines
1h 47mYTZ-MDW
4/7Tue
directPorter Airlines
1h 42mMDW-YTZ
C$ 397
1/7Sat
directPorter Airlines
1h 47mYTZ-MDW
7/7Fri
directPorter Airlines
1h 42mMDW-YTZ
C$ 409
11/10Wed
1 stopAir Canada
5h 23mYTZ-ORD
19/10Thu
1 stopAir Canada
4h 30mORD-YTZ
C$ 476
5/9Tue
1 stopAir Canada
5h 23mYTZ-ORD
9/9Sat
1 stopAir Canada
4h 34mORD-YTZ
C$ 502
12/7Wed
1 stopAir Canada
5h 18mYTZ-ORD
18/7Tue
1 stopAir Canada
4h 56mORD-YTZ
C$ 517
5/9Tue
1 stopAir Canada
5h 23mYTZ-ORD
11/9Mon
1 stopAir Canada
4h 34mORD-YTZ
C$ 525
26/7Wed
1 stopAir Canada
5h 18mYTZ-ORD
29/7Sat
1 stopAir Canada
4h 56mORD-YTZ
C$ 541
10/7Mon
1 stopAir Canada
13h 34mYTZ-ORD
18/7Tue
1 stopAir Canada
6h 56mORD-YTZ
C$ 554
6/9Wed
2 stopsMultiple Airlines
17h 11mYTZ-ORD
10/9Sun
2 stopsMultiple Airlines
12h 45mORD-YTZ
C$ 612
6/7Thu
2 stopsMultiple Airlines
37h 04mYTZ-ORD
9/7Sun
2 stopsMultiple Airlines
34h 55mORD-YTZ
C$ 730
24/6Sat
2 stopsMultiple Airlines
12h 00mYTZ-ORD
27/6Tue
2 stopsMultiple Airlines
24h 40mORD-YTZ
C$ 745
24/6Sat
3 stopsMultiple Airlines
19h 30mYTZ-ORD
27/6Tue
2 stopsMultiple Airlines
24h 40mORD-YTZ
C$ 746

Search by stops

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Recent one-way flight deals

28/6Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 191
28/6Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 197
28/6Wed
directPorter Airlines
1h 47mYTZ-MDW
C$ 208
3/7Mon
directPorter Airlines
1h 47mYTZ-MDW
C$ 209
29/10Sun
directPorter Airlines
1h 50mYTZ-MDW
C$ 213
10/7Mon
directPorter Airlines
1h 47mYTZ-MDW
C$ 220
20/6Tue
directPorter Airlines
1h 47mYTZ-MDW
C$ 230
3/7Mon
directPorter Airlines
1h 47mYTZ-MDW
C$ 238
12/7Wed
1 stopAir Canada
5h 18mYTZ-ORD
C$ 248
9/8Wed
1 stopAir Canada
5h 18mYTZ-ORD
C$ 258
21/6Wed
1 stopAir Canada
5h 18mYTZ-ORD
C$ 264
22/6Thu
2 stopsMultiple Airlines
18h 27mYTZ-ORD
C$ 270
13/9Wed
1 stopAir Canada
5h 23mYTZ-ORD
C$ 274
16/9Sat
1 stopAir Canada
5h 33mYTZ-ORD
C$ 276
27/6Tue
2 stopsMultiple Airlines
15h 10mYTZ-MDW
C$ 283
17/9Sun
1 stopAir Canada
5h 23mYTZ-ORD
C$ 286
10/9Sun
1 stopAir Canada
5h 23mYTZ-ORD
C$ 287
18/7Tue
2 stopsMultiple Airlines
10h 19mYTZ-ORD
C$ 289
18/9Mon
2 stopsMultiple Airlines
9h 39mYTZ-ORD
C$ 323
21/6Wed
2 stopsMultiple Airlines
15h 38mYTZ-MDW
C$ 346

Search by stops

Search by airline

Search by price

Toronto Island - Chicago Flights

Departure:

Toronto Island (YTZ)Canada

Return flight deals:

Chicago - Toronto Island

Cabin classes:

C$ 350

Browse origins: