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C$ 131+ 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 10/6. 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.
CHI — YYZ
24 Jun — 1 Jul1
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 25 May 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

Sat 13/6

10:15 a.m.-12:55 p.m.

Nonstop1h 40m

Toronto Island

Sun 14/6

8:45 a.m.-9:35 a.m.

Nonstop1h 50m

C$ 309

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 19/6

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

Nonstop1h 40m

Toronto Island

Sun 21/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 321

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Wed 24/6

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Wed 1/7

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 325

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 25/6

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

Nonstop1h 40m

Toronto Island

Mon 29/6

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

Nonstop1h 50m

C$ 329

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 20/6

10:25 a.m.-1:05 p.m.

Nonstop1h 40m

Toronto Island

Tue 23/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 368

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Wed 17/6

12:55 p.m.-3:46 p.m.

Nonstop1h 51m

Toronto Pearson Intl

Sun 21/6

7:00 a.m.-8:00 a.m.

Nonstop2h 00m

C$ 384

ChicagoToronto

ORD - YYZ

ORDYYZ

Chicago O'Hare Intl

Sat 13/6

5:55 p.m.-8:44 p.m.

Nonstop1h 49m

Toronto Pearson Intl

Sun 14/6

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

Nonstop2h 00m

C$ 384

ChicagoCalgary

MDW - YYC

MDWYYC

Chicago Midway

Wed 26/8

1:52 p.m.-8:35 p.m.

1 stop7h 43m

Calgary

Mon 31/8

6:35 a.m.-1:11 p.m.

1 stop5h 36m

C$ 398

ChicagoToronto

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 19/6

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

Nonstop1h 40m

Toronto Island

Sun 21/6

8:50 a.m.-9:40 a.m.

Nonstop1h 50m

C$ 409

ChicagoCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sun 18/10

8:40 a.m.-11:28 a.m.

Nonstop3h 48m

Calgary

Fri 23/10

12:30 p.m.-5:05 p.m.

Nonstop3h 35m

C$ 410

Flights are sorted by cheapest round-trip flights first.

Deals found on 21/5

Showing 1-10 of 60 resultsSorted by cheapest first
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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.

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

Currently, February is the cheapest month in which you can book a flight from Chicago (average of C$ 88). Flying from Chicago in March will prove the most costly (average of C$ 245). 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, Air Canada, American Airlines. These airlines depart to the following popular destinations: Toronto.

Etihad Airways
Etihad Airways
From C$ 990
Air India
Air India
From C$ 849
Emirates
Emirates
From C$ 889
United Airlines
United Airlines
From C$ 170

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: Detroit (1,404 flights per day), New York (1,233 flights per day) and Los Angeles (798 flights per day).

Toronto
Toronto
From C$ 131
Abu Dhabi Zayed Intl
Abu Dhabi Zayed Intl
From C$ 440
Calgary
Calgary
From C$ 188
New Delhi Indira Gandhi Intl
New Delhi Indira Gandhi Intl
From C$ 588

What is the cheapest place to fly to from Chicago?

The cheapest city to fly to from Chicago is Dallas/Fort Worth, with prices starting at C$ 65. Explore other affordable destinations below.

Dallas/Fort Worth
Dallas/Fort Worth
From C$ 65
New York
New York
From C$ 102
Toronto
Toronto
From C$ 131
Boston Logan Intl
Boston Logan Intl
From C$ 136

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

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 64 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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 23 May 2026.

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 Saturday mornings when fares are usually the most expensive.

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 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
9,747 reviews
Check prices

Crew

8.1

Overall

7.4

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Food

6.6

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.
United Airlines
7.4
Good
9,747 reviews
United Airlines
7.4
Good
9,747 reviews
Check prices

Crew

8.1

Overall

7.4

Entertainment

7.1

Boarding

7.7

Comfort

7.3

Food

6.6

Reviews

1 / 20
4.0
Okay

Dynasty,May 2026

LAX - EWR

The food wasn’t nice - Hosts were not that kind.

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 Dubai
Flights from O'Hare Intl to New Delhi
Flights from O'Hare Intl to Calgary

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 25 May 2026.

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

    This month, the top selected destinations from Chicago are Atlanta, Boston, Athens. 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$ 275. While Chicago O'Hare Intl airport is usually cheaper if your destination is Hamilton with prices starting at C$ 304. 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 Frontier, Spirit Airlines, and Air Canada to have the cheapest round-trip prices from Chicago. Some of the destinations and prices are as follows: Frontier flights from Chicago to Dallas/Fort Worth (C$ 61). Spirit Airlines flights from Chicago to Miami (C$ 100). Air Canada flights from Chicago to Vancouver 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 February; with March 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$ 275 round trip
    Travel from Chicago to Calgary from C$ 369 round trip
    Travel from Chicago to Montreal from C$ 421 round trip
    Travel from Chicago to Vancouver from C$ 492 round trip
    Travel from Chicago to Halifax from C$ 551 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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