Cheap flights from Toronto to Chicago from $224!

Roundtrip flight Toronto - Chicago for $224

Flytrippers Deals
Apr 5, 2026
Deals from Toronto

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CHICAGO, Illinois 🇺🇸

$224 (or 22,400 simple points)
	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

$224

(or 22,400 simple points)

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

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.

Jun 17 - Jun 26	9d	Wed - Fri	$224		Details >	$224 >
Jun 27 - Jul 22	25d	Sat - Wed	$233		Details >	$233 >
Jun 29 - Jul 15	16d	Mon - Wed	$224		Details >	$224 >
Jun 30 - Jul 7	7d	Tue - Tue	$224		Details >	$224 >
Jun 30 - Jul 14	14d	Tue - Tue	$233		Details >	$233 >
Or redeem points of the more simple type			22,400 points instead of $224		Learn more >
Or redeem points of the more simple type (22,400 points instead of $224)				Details >

Jul 1 - Jul 4	3d	Wed - Sat	$231		Details >	$231 >
Jul 6 - Jul 13	7d	Mon - Mon	$224		Details >	$224 >
Jul 7 - Jul 14	7d	Tue - Tue	$224		Details >	$224 >
Jul 7 - Jul 18	11d	Tue - Sat	$224		Details >	$224 >
Jul 7 - Jul 21	14d	Tue - Tue	$224		Details >	$224 >
Jul 8 - Jul 15	7d	Wed - Wed	$233		Details >	$233 >
Jul 8 - Jul 30	22d	Wed - Thu	$233		Details >	$233 >
Jul 9 - Jul 25	16d	Thu - Sat	$288		Details >	$288 >
Jul 14 - Jul 19	5d	Tue - Sun	$288		Details >	$288 >
Jul 14 - Jul 28	14d	Tue - Tue	$233		Details >	$233 >
Jul 14 - Aug 9	26d	Tue - Sun	$236		Details >	$236 >
Jul 15 - Jul 29	14d	Wed - Wed	$224		Details >	$224 >
Jul 16 - Aug 6	21d	Thu - Thu	$236		Details >	$236 >
Jul 18 - Jul 28	10d	Sat - Tue	$233		Details >	$233 >
Jul 20 - Jul 28	8d	Mon - Tue	$233		Details >	$233 >
Jul 20 - Jul 29	9d	Mon - Wed	$233		Details >	$233 >
Jul 21 - Aug 2	12d	Tue - Sun	$236		Details >	$236 >
Jul 21 - Aug 4	14d	Tue - Tue	$227		Details >	$227 >
Jul 21 - Aug 6	16d	Tue - Thu	$227		Details >	$227 >
Jul 21 - Aug 8	18d	Tue - Sat	$236		Details >	$236 >
Jul 21 - Aug 11	21d	Tue - Tue	$236		Details >	$236 >
Jul 21 - Aug 13	23d	Tue - Thu	$236		Details >	$236 >
Jul 22 - Jul 31	9d	Wed - Fri	$233		Details >	$233 >
Jul 22 - Aug 5	14d	Wed - Wed	$236		Details >	$236 >
Jul 22 - Aug 12	21d	Wed - Wed	$236		Details >	$236 >
Jul 22 - Aug 13	22d	Wed - Thu	$236		Details >	$236 >
Jul 22 - Aug 19	28d	Wed - Wed	$236		Details >	$236 >
Jul 25 - Jul 31	6d	Sat - Fri	$224		Details >	$224 >
Jul 26 - Aug 13	18d	Sun - Thu	$236		Details >	$236 >
Jul 27 - Aug 15	19d	Mon - Sat	$236		Details >	$236 >
Jul 28 - Aug 5	8d	Tue - Wed	$236		Details >	$236 >
Jul 28 - Aug 6	9d	Tue - Thu	$236		Details >	$236 >
Jul 28 - Aug 11	14d	Tue - Tue	$227		Details >	$227 >
Jul 28 - Aug 12	15d	Tue - Wed	$227		Details >	$227 >
Jul 28 - Aug 18	21d	Tue - Tue	$236		Details >	$236 >
Jul 29 - Aug 7	9d	Wed - Fri	$236		Details >	$236 >
Jul 29 - Aug 15	17d	Wed - Sat	$236		Details >	$236 >
Jul 29 - Aug 19	21d	Wed - Wed	$236		Details >	$236 >
Jul 29 - Aug 26	28d	Wed - Wed	$236		Details >	$236 >
Jul 31 - Aug 10	10d	Fri - Mon	$236		Details >	$236 >
Or redeem points of the more simple type			22,400 points instead of $224		Learn more >
Or redeem points of the more simple type (22,400 points instead of $224)				Details >

Aug 2 - Aug 28	26d	Sun - Fri	$239		Details >	$239 >
Aug 4 - Aug 6	2d	Tue - Thu	$230		Details >	$230 >
Aug 4 - Aug 13	9d	Tue - Thu	$239		Details >	$239 >
Aug 4 - Aug 17	13d	Tue - Mon	$239		Details >	$239 >
Aug 4 - Aug 25	21d	Tue - Tue	$230		Details >	$230 >
Aug 5 - Aug 10	5d	Wed - Mon	$239		Details >	$239 >
Aug 5 - Aug 16	11d	Wed - Sun	$239		Details >	$239 >
Aug 5 - Aug 26	21d	Wed - Wed	$239		Details >	$239 >
Aug 5 - Aug 27	22d	Wed - Thu	$239		Details >	$239 >
Aug 11 - Aug 14	3d	Tue - Fri	$239		Details >	$239 >
Aug 12 - Aug 24	12d	Wed - Mon	$239		Details >	$239 >
Aug 12 - Aug 27	15d	Wed - Thu	$230		Details >	$230 >
Aug 18 - Aug 28	10d	Tue - Fri	$230		Details >	$230 >
Aug 18 - Aug 29	11d	Tue - Sat	$239		Details >	$239 >
Aug 19 - Aug 27	8d	Wed - Thu	$230		Details >	$230 >
Aug 19 - Aug 29	10d	Wed - Sat	$230		Details >	$230 >
Aug 20 - Aug 31	11d	Thu - Mon	$230		Details >	$230 >
Or redeem points of the more simple type			23,000 points instead of $230		Learn more >
Or redeem points of the more simple type (23,000 points instead of $230)				Details >

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

Dates for weekend getaway

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

Self-transfer that implies a few pecularities

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Featured image:

Other images associated with this deal: Main page: Pixabay, Social media: Pixabay

Share this deal to help us help more people travel for less:

CHICAGO, Illinois 🇺🇸

IMPORTANT WARNING ABOUT THIS DEAL

DATES

Accommodation Options

Sign up for our free newsletter

Check out today's best deals from Toronto

Our latest travel content

Travel News

An airline will actually offer bunk beds on a plane

It’s back: The famous double-decker airplane seat concept is now “improved”

My experiences today: my flights in the world’s best business class (again) and my transit in Qatar (near Iran)

Travel Rewards

Last chance to attend the Points Travel Festival Toronto where I’m speaking (or our Flytrippers conference in Montreal)

Best redemptions of Marriott Bonvoy points

Introduction: How Marriott Bonvoy points work

Follow Flytrippers on Facebook

Follow Flytrippers on Twitter