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C$ 96+ Cheap flights from Chicago

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/9. 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.
CHI — YYZ
3 Aug — 10 Aug1
1 adult

What to know about flights from Chicago

Discover essential information about flights departing from Chicago, including flight schedules, destinations, airlines operating at the Chicago airport, and any specific guidelines or requirements for travellers. Please note that the information is based on the most recent updates available. Data last updated 29 July 2025.

Cheapest airline

Air Canada

Good round-trip deal

C$ 108 or less

Good one-way deal

C$ 81 or less
On average, Air Canada currently has the cheapest one-way flight from Chicago (avg. price of C$ 498).
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Price to beat on a round-trip flight from Chicago.
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Price to beat on a one-way flight from Chicago.
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Cheapest flights from Chicago
Explore the most affordable flight options available from Chicago. Find the lowest fares based on data from user searches, with prices last updated on 29 July 2025.

Mon 15/95:30 p.m.ORD - YYC
Nonstop3h 49mWestJet
Wed 24/912:15 p.m.YYC - ORD
Nonstop3h 28mWestJet
Deal found 29/7C$ 214
Mon 15/93:50 p.m.ORD - YYC
1 stop8h 32mMultiple Airlines
Wed 24/912:15 p.m.YYC - ORD
Nonstop3h 28mMultiple Airlines
Deal found 29/7C$ 217
Mon 15/96:20 p.m.ORD - YYC
1 stop7h 52mAir Canada
Tue 23/91:10 a.m.YYC - ORD
1 stop7h 41mAir Canada
Deal found 29/7C$ 220
Sun 7/99:35 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Fri 12/97:50 a.m.YTZ - MDW
Nonstop1h 49mPorter Airlines
Deal found 29/7C$ 236
Mon 22/98:25 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Tue 23/912:30 a.m.YYZ - ORD
1 stop10h 21mAir Canada
Deal found 27/7C$ 244
Wed 10/95:20 p.m.MDW - YTZ
Nonstop1h 42mAir Transat
Fri 12/93:35 p.m.YTZ - MDW
Nonstop1h 49mAir Transat
Deal found 29/7C$ 252
Wed 3/96:00 a.m.ORD - YYZ
1 stop4h 44mUnited Airlines
Sat 6/93:00 p.m.YYZ - ORD
1 stop6h 11mUnited Airlines
Deal found 26/7C$ 252
Tue 14/108:47 a.m.ORD - YYC
Nonstop3h 51mUnited Airlines
Fri 17/1012:38 p.m.YYC - ORD
Nonstop3h 32mUnited Airlines
Deal found 29/7C$ 259
Wed 20/89:40 a.m.MDW - YTZ
Nonstop1h 40mMultiple Airlines
Sat 30/89:00 a.m.YTZ - MDW
Nonstop1h 50mMultiple Airlines
Deal found 27/7C$ 259
Wed 24/95:20 p.m.MDW - YUL
1 stop3h 55mPorter Airlines
Fri 26/91:10 p.m.YUL - MDW
1 stop4h 14mPorter Airlines
Deal found 28/7C$ 269
Thu 23/103:35 p.m.ORD - YTZ
1 stop4h 59mAir Canada
Sun 26/107:20 p.m.YTZ - ORD
2 stops16h 58mAir Canada
Deal found 27/7C$ 270
Wed 17/91:10 p.m.ORD - YUL
Nonstop2h 23mAmerican Airlines
Mon 22/95:15 p.m.YUL - ORD
Nonstop2h 35mAmerican Airlines
Deal found 29/7C$ 278

Find flights from Chicago within your budget

 
Find flights departing from Chicago that match your specified budget. Filter results by price range, allowing you to narrow down options and find flights that fit within your financial constraints. Please note that the search results are based on data from user searches, with fares last updated on 29 July 2025. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Pearson Intl

Route

Depart

Return

Price

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 15/9

5:30 p.m.-8:19 p.m.

Nonstop3h 49m

Calgary

Wed 24/9

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

C$ 214

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 15/9

3:50 p.m.-11:22 p.m.

1 stop8h 32m

Calgary

Wed 24/9

12:15 p.m.-4:43 p.m.

Nonstop3h 28m

C$ 217

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Mon 15/9

6:20 p.m.-1:12 a.m.

1 stop7h 52m

Calgary

Tue 23/9

1:10 a.m.-9:51 a.m.

1 stop7h 41m

C$ 220

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sun 7/9

9:35 a.m.-12:17 p.m.

Nonstop1h 42m

Toronto Island

Fri 12/9

7:50 a.m.-8:39 a.m.

Nonstop1h 49m

C$ 236

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Mon 22/9

8:25 p.m.-11:08 p.m.

Nonstop1h 43m

Toronto Pearson Intl

Tue 23/9

12:30 a.m.-9:51 a.m.

1 stop10h 21m

C$ 244

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 10/9

5:20 p.m.-8:02 p.m.

Nonstop1h 42m

Toronto Island

Fri 12/9

3:35 p.m.-4:24 p.m.

Nonstop1h 49m

C$ 252

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 3/9

6:00 a.m.-11:44 a.m.

1 stop4h 44m

Toronto Pearson Intl

Sat 6/9

3:00 p.m.-8:11 p.m.

1 stop6h 11m

C$ 252

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Tue 14/10

8:47 a.m.-11:38 a.m.

Nonstop3h 51m

Calgary

Fri 17/10

12:38 p.m.-5:10 p.m.

Nonstop3h 32m

C$ 259

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 20/8

9:40 a.m.-12:20 p.m.

Nonstop1h 40m

Toronto Island

Sat 30/8

9:00 a.m.-9:50 a.m.

Nonstop1h 50m

C$ 259

ChicagoMontreal

MDW - YUL

MDWYUL

Chicago Midway

Wed 24/9

5:20 p.m.-10:15 p.m.

1 stop3h 55m

Montreal Pierre Elliott Trudeau Intl

Fri 26/9

1:10 p.m.-4:24 p.m.

1 stop4h 14m

C$ 269

Flights are sorted by cheapest round-trip flights first.

Deals found on 28/7

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Best time to book a flight from Chicago

Have a flexible travel schedule? Discover the best time to fly from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Travel insights for flights from Chicago

Get recent, data-driven insights about flights from Chicago including ideal travel times, pricing trends, and more.

When is the best time to book a flight from Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Pearson Intl. Price data was last updated on 25 July 2025.

The price you pay for your flight from Chicago may vary depending on when you book. For the best chance of a lower fare, look to book 68 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Chicago?

Currently, March is the cheapest month in which you can book a flight from Chicago (average of C$ 145). Flying from Chicago in May will prove the most costly (average of C$ 224). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

When is the cheapest time to fly from Chicago?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Pearson Intl. Price data was last updated on 16 December 2024.

Those who are seeking the cheapest fare on flights departing from Chicago would be wise to consider leaving during Thursday afternoons when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Monday at noon when fares are usually the most expensive.

Which airlines fly from Chicago?

For flights departing from Chicago check dates and pricing for the following: Air Canada, United Airlines. These airlines depart to the following popular destinations: Toronto.

Etihad Airways
Etihad Airways
From C$ 640
Air India
Air India
From C$ 685
Air Canada
Air Canada
From C$ 147
United Airlines
United Airlines
From C$ 176

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: Detroit (1,340 flights per day), New York (1,148 flights per day) and Los Angeles (795 flights per day).

Toronto
Toronto
From C$ 63
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From C$ 389
Calgary
Calgary
From C$ 63
New Delhi Indira Gandhi Intl
New Delhi Indira Gandhi Intl
From C$ 386

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Orlando, with prices starting at C$ 71. Explore other affordable destinations below.

Orlando
Orlando
From C$ 51
Minneapolis St Paul
Minneapolis St Paul
From C$ 59
Calgary
Calgary
From C$ 63
Toronto
Toronto
From C$ 63

Airline reviews for flights from Chicago

Get insights into the airlines that provide service from Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing airline for your flight from Chicago. In the last 7 days, Cheapflights users made a total of 629,999 searches.
Check out reviews from past customers who have flown Delta,KLM, andUnited Airlines from Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,979 reviews
Check prices

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,979 reviews
Delta
8.0
Very good
7,979 reviews
Check prices

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
KLM
7.8
Good
1,383 reviews
Delta
8.0
Very good
7,979 reviews
Check prices

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,896 reviews
Delta
8.0
Very good
7,979 reviews
Check prices

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,979 reviews
Check prices

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
WestJet
7.2
Good
2,972 reviews
Delta
8.0
Very good
7,979 reviews
Check prices

Overall

8.0

Food

7.3

Entertainment

7.9

Boarding

8.2

Crew

8.5

Comfort

7.9

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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Popular international destinations from Chicago

The most popular international flight routes departing from Chicago we’ve come across at this time.
Flights from O'Hare Intl to Dubai
Flights from O'Hare Intl to New Delhi
Flights from O'Hare Intl to Calgary
Flights from O'Hare Intl to Hong Kong

Related info for your journey

Access useful and relevant information related to your journey from Chicago. This can include details such as airport transportation, visa requirements, travel insurance, luggage regulations, and any other information that can ensure a smooth and hassle-free travel experience. Please note that the information is based on general guidance and may need to be verified with official sources. Data last updated 29 July 2025.

  • What are the most popular destinations to fly to from Chicago?

    This month, the top selected destinations from Chicago are Boston, Athens, Atlanta. Throughout the year, Atlanta, Boston, Mumbai are some of the top choices made by users flying from Chicago.

  • Which is the cheapest airport to catch a flight from Chicago?

    The cheapest routes to Toronto can be found at Chicago Midway airport from C$ 169. While Chicago O'Hare Intl airport is usually cheaper if your destination is Québec City with prices starting at C$ 202. Reference our flight search to find the best deals in real time.

  • What are the cheapest airlines flying from Chicago to anywhere?

    According to our data, users have found Spirit Airlines, Frontier, and WestJet to have the cheapest round-trip prices from Chicago. Some of the destinations and prices are as follows: Spirit Airlines flights from Chicago to Fort Lauderdale (C$ 56). Frontier flights from Chicago to Nashville Intl (C$ 70). WestJet flights from Chicago to Calgary (C$ 93).

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently March; with May being the most expensive. Prices will vary depending on multiple factors such as booking in advance, airline and departure airports and times.

  • Where are the cheapest places to fly to from Chicago?

    Check out the cheapest flights from Chicago to embark to:
    Travel from Chicago to Toronto from C$ 169 round trip
    Travel from Chicago to Montreal from C$ 196 round trip
    Travel from Chicago to Calgary from C$ 237 round trip
    Travel from Chicago to Vancouver from C$ 320 round trip
    Travel from Chicago to Québec City from C$ 483 round trip

  • How does Cheapflights help users find flights from Chicago?

    Cheapflights helps you search for flights from Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

  • Why should you use Cheapflights to find cheap flight tickets from Chicago?

    By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Chicago.

  • Can Cheapflights find flights from Chicago with no change fees?

    Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago, users can toggle the no change fees filter when performing a flight search.

  • Can Cheapflights notify me if prices for flights from Chicago become cheaper?

    Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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How does Cheapflights help users find flights from Chicago?

Cheapflights helps you search for flights from Chicago via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Chicago?

By finding flights from multiple airlines and providers at completely no cost, Cheapflights helps millions of users like you annually find the best flights from Chicago.

Can Cheapflights find flights from Chicago with no change fees?

Cheapflights does show flights with no change fees to all users. To see these options for flights from Chicago, users can toggle the no change fees filter when performing a flight search.

Can Cheapflights notify me if prices for flights from Chicago become cheaper?

Of course! You can now track prices for flights from Chicago and get an alert from Cheapflights when they change. Click the bell icon next to the flight deals above and provide your email address to set up price alerts.

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