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C$ 109+ 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 26/5. 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 — YVR
10 May — 17 May1
1 adult
1 adult, Economy, 0 bags

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 10 April 2026. In the last 7 days, Cheapflights users made a total of 629,999 searches

Fly to

Route

Depart

Return

Price

Cheapest round-trip
Quickest round-trip

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 8/5

10:30 a.m.-1:10 p.m.

Nonstop1h 40m

Toronto Island

Sun 10/5

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 313

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 14/5

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Fri 15/5

8:55 a.m.-9:45 a.m.

Nonstop1h 50m

C$ 317

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 15/7

3:20 p.m.-6:00 p.m.

Nonstop1h 40m

Toronto Island

Mon 20/7

1:45 p.m.-2:35 p.m.

Nonstop1h 50m

C$ 318

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sun 3/5

9:20 p.m.-11:59 p.m.

Nonstop1h 39m

Toronto Pearson Intl

Wed 6/5

2:45 p.m.-3:43 p.m.

Nonstop1h 58m

C$ 321

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sun 7/6

9:15 p.m.-11:59 p.m.

Nonstop1h 44m

Toronto Pearson Intl

Sun 14/6

11:00 a.m.-12:00 p.m.

Nonstop2h 00m

C$ 321

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Thu 24/9

7:00 a.m.-9:40 a.m.

Nonstop1h 40m

Toronto Island

Mon 28/9

1:40 p.m.-2:35 p.m.

Nonstop1h 55m

C$ 325

ChicagoToronto

ORD - YTZ

ORDYTZ

Chicago O'Hare Intl

Fri 3/7

11:05 a.m.-5:51 p.m.

1 stop5h 46m

Toronto Island

Mon 6/7

7:20 p.m.-8:16 p.m.

Nonstop1h 56m

C$ 336

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 13/6

7:01 a.m.-3:19 p.m.

1 stop7h 18m

Toronto Pearson Intl

Wed 17/6

4:10 p.m.-8:31 p.m.

1 stop5h 21m

C$ 342

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Thu 7/5

7:00 a.m.-1:30 p.m.

1 stop5h 30m

Toronto Pearson Intl

Mon 11/5

4:04 p.m.-8:14 p.m.

1 stop5h 10m

C$ 342

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 23/5

9:25 a.m.-5:21 p.m.

1 stop6h 56m

Toronto Pearson Intl

Fri 29/5

2:20 p.m.-6:05 p.m.

1 stop4h 45m

C$ 342

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/4

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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 Vancouver Intl. Price data was last updated on 3 April 2026.

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 74 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, May is the cheapest month in which you can book a flight from Chicago (average of C$ 159). Flying from Chicago in August will prove the most costly (average of C$ 445). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Which airlines fly from Chicago?

For flights departing from Chicago check dates and pricing for the following: United Airlines. This airline departs to the following popular destinations: Vancouver.

Etihad Airways
Etihad Airways
From C$ 991
Air India
Air India
From C$ 850
United Airlines
United Airlines
From C$ 128
Emirates
Emirates
From C$ 889

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: Detroit (1,276 flights per day), New York (1,059 flights per day) and Los Angeles (680 flights per day).

Toronto
Toronto
From C$ 106
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From C$ 454
New York
New York
From C$ 95
Montreal
Montreal
From C$ 144

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Houston Hobby, with prices starting at C$ 23. Explore other affordable destinations below.

Houston Hobby
Houston Hobby
From C$ 23
Atlanta Hartsfield-Jackson
Atlanta Hartsfield-Jackson
From C$ 39
New York
New York
From C$ 95
Toronto
Toronto
From C$ 106

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 United Airlines and Air Canada from Chicago to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
United Airlines
7.4
Good
9,562 reviews
Check prices

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
United Airlines
7.4
Good
9,562 reviews
United Airlines
7.4
Good
9,562 reviews
Check prices

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family
Air Canada
7.1
Good
10,915 reviews
United Airlines
7.4
Good
9,562 reviews
Check prices

Entertainment

7.1

Comfort

7.3

Crew

8.1

Overall

7.4

Food

6.6

Boarding

7.7

Reviews

1 / 20
10.0
Excellent

Dane,Jan 2026

TYS - IAD

It was a short flight, so no time for amenities. Just glad everything was quick and easy from boarding to arriving at my destination with my family

Browse thousands of different options on Cheapflights for your next trip

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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 Calgary
Flights from O'Hare Intl to Halifax
Flights from O'Hare Intl to Edmonton
Flights from O'Hare Intl to New Delhi

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 10 April 2026.

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

    This month, the top selected destinations from Chicago are Atlanta, Boston, Austin. Throughout the year, Boston, Atlanta, Ahmedabad 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$ 256. While Chicago O'Hare Intl airport is usually cheaper if your destination is Halifax with prices starting at C$ 286. 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, United Airlines, and Air Canada to have the cheapest round-trip prices from Chicago. Some of the destinations and prices are as follows: Spirit Airlines flights from Chicago to Miami (C$ 100). United Airlines flights from Chicago to Tirana Rinas (C$ 108). Air Canada flights from Chicago to Montreal Pierre Elliott Trudeau Intl (C$ 135).

  • What is the cheapest month to fly from Chicago?

    At the present moment the cheapest month to fly from Chicago is currently May; with August 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 Montreal from C$ 256 round trip
    Travel from Chicago to Toronto from C$ 263 round trip
    Travel from Chicago to Calgary from C$ 335 round trip
    Travel from Chicago to Vancouver from C$ 429 round trip
    Travel from Chicago to Ottawa from C$ 451 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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