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Cheap flights from Chicago to anywhere

Fly from Chicago to anywhere in the world.

CHI — YYC
2 Mar — 9 Mar1
1 adult
Sat 2/3
Sat 9/3

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 26 February 2024.

Cheapest airline

Frontier
On average, Frontier currently has the cheapest one-way flight from Chicago.

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 26 February 2024. In the last 7 days, Cheapflights users made a total of 594,106 searches.
Thu 2/58:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 5/510:30 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 25/2C$ 296
Thu 6/65:55 p.m.ORD - YYC
Nonstop3h 27mWestJet
Mon 10/612:30 p.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 25/2C$ 300
Sat 8/65:55 p.m.ORD - YYC
Nonstop3h 27mWestJet
Fri 14/612:30 p.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 25/2C$ 301
Fri 29/311:55 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 31/310:30 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 25/2C$ 301
Sat 20/412:30 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 23/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 25/2C$ 303
Sat 30/312:30 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 4/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 24/2C$ 304
Sat 8/65:55 p.m.ORD - YYC
Nonstop3h 27mWestJet
Mon 10/612:30 p.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 25/2C$ 307
Tue 26/311:55 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 2/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 25/2C$ 311
Thu 21/311:25 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 24/310:45 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 25/2C$ 313

Last-minute flight deals from Chicago

Discover last-minute flight deals departing from Chicago. Take advantage of attractive deals offered by airlines for spontaneous travel. These deals are subject to availability and can provide significant savings for flexible travellers. Please note that the availability of last-minute deals can vary and may change quickly. Data last updated 26 February 2024 and based on user searches. In the last 7 days, Cheapflights users made a total of 594,106 searches.
Mon 4/34:35 p.m.ORD - YYC
1 stop8h 08mAir Canada
Sun 24/312:55 a.m.YYC - ORD
1 stop7h 07mAir Canada
Deal found 24/2C$ 402
Tue 5/311:55 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 26/39:30 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 25/2C$ 407
Mon 4/37:26 p.m.ORD - YYC
1 stop28h 44mMultiple Airlines
Tue 12/38:00 a.m.YYC - ORD
2 stops16h 20mMultiple Airlines
Deal found 24/2C$ 416
Tue 5/39:00 a.m.ORD - YYC
2 stops12h 59mDelta
Tue 12/36:25 a.m.YYC - ORD
1 stop10h 37mDelta
Deal found 24/2C$ 419
Tue 5/36:35 a.m.ORD - YYC
2 stops17h 35mMultiple Airlines
Wed 13/36:15 a.m.YYC - ORD
1 stop18h 16mMultiple Airlines
Deal found 24/2C$ 440
Tue 5/36:00 p.m.ORD - YYZ
1 stop15h 48mMultiple Airlines
Tue 26/37:00 a.m.YYZ - ORD
2 stops16h 12mMultiple Airlines
Deal found 25/2C$ 442
Tue 5/310:00 a.m.ORD - YYZ
Nonstop1h 33mAir Canada
Tue 26/36:35 p.m.YYZ - ORD
Nonstop2h 02mAir Canada
Deal found 25/2C$ 444
Tue 5/38:35 p.m.ORD - YYZ
2 stops25h 21mMultiple Airlines
Mon 11/31:00 p.m.YYZ - ORD
2 stops19h 21mMultiple Airlines
Deal found 25/2C$ 446
Tue 5/37:20 a.m.ORD - YYZ
1 stop6h 26mAir Canada
Fri 22/312:30 p.m.YYZ - ORD
Nonstop2h 02mAir Canada
Deal found 25/2C$ 451

Domestic airfare to nearby cities with cheap hotels

Discover domestic flight options from Chicago to cities with affordable hotel accommodations. Plan your travel to both enjoy budget-friendly flights and find affordable lodging in your chosen destination. Please note that the flight options are sourced from user searches. In the last 7 days, Cheapflights users made a total of 594,106 searches and data was last updated 26 February 2024.
Thu 9/56:40 a.m.ORD - DFW
Nonstop2h 28mSpirit Airlines
Wed 15/54:28 p.m.DFW - ORD
Nonstop2h 28mSpirit Airlines
Deal found 25/2C$ 77
Tue 12/310:47 p.m.ORD - MCO
1 stop9h 11mSpirit Airlines
Tue 19/310:00 p.m.MCO - ORD
1 stop10h 21mSpirit Airlines
Deal found 25/2C$ 92
Mon 15/410:23 a.m.ORD - FLL
Nonstop3h 06mSpirit Airlines
Thu 18/47:15 a.m.FLL - ORD
Nonstop3h 23mSpirit Airlines
Deal found 26/2C$ 93
Thu 9/56:40 a.m.ORD - DFW
Nonstop2h 28mSpirit Airlines
Wed 15/511:58 a.m.DFW - ORD
1 stop7h 08mSpirit Airlines
Deal found 25/2C$ 95
Mon 8/410:00 p.m.ORD - FLL
1 stop8h 20mSpirit Airlines
Thu 11/42:22 p.m.FLL - ORD
Nonstop3h 23mSpirit Airlines
Deal found 24/2C$ 97
Mon 22/410:00 p.m.ORD - FLL
1 stop8h 20mSpirit Airlines
Thu 25/44:31 p.m.FLL - ORD
1 stop5h 34mSpirit Airlines
Deal found 24/2C$ 99
Sat 16/37:37 p.m.ORD - FLL
Nonstop3h 11mSpirit Airlines
Wed 20/34:20 p.m.FLL - ORD
Nonstop3h 22mSpirit Airlines
Deal found 26/2C$ 101
Mon 8/410:00 p.m.ORD - FLL
1 stop10h 45mSpirit Airlines
Thu 11/44:31 p.m.FLL - ORD
1 stop5h 34mSpirit Airlines
Deal found 24/2C$ 103
Tue 12/36:46 a.m.ORD - DFW
Nonstop2h 30mSpirit Airlines
Sat 16/311:00 p.m.DFW - ORD
Nonstop2h 25mSpirit Airlines
Deal found 25/2C$ 103

Non-stop flights from Chicago

Discover airlines that offer direct flights from Chicago to various destinations. Avoid layovers and travel efficiently with direct flight options, saving you time and providing a more convenient travel experience. Please note that the direct flight options are based on data from 26 February 2024 and based on user searches. In the last 7 days, Cheapflights users made a total of 594,106 searches.
Thu 2/58:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 5/510:30 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 25/2C$ 296
Thu 6/65:55 p.m.ORD - YYC
Nonstop3h 27mWestJet
Mon 10/612:30 p.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 25/2C$ 300
Sat 8/65:55 p.m.ORD - YYC
Nonstop3h 27mWestJet
Fri 14/612:30 p.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 25/2C$ 301
Fri 29/311:55 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 31/310:30 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 25/2C$ 301
Sat 20/412:30 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 23/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 25/2C$ 303
Sat 30/312:30 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Thu 4/43:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 24/2C$ 304
Sat 8/65:55 p.m.ORD - YYC
Nonstop3h 27mWestJet
Mon 10/612:30 p.m.YYC - ORD
Nonstop3h 35mWestJet
Deal found 25/2C$ 307
Tue 26/311:55 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Tue 2/49:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 25/2C$ 311
Thu 21/311:25 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Sun 24/310:45 a.m.YTZ - MDW
Nonstop1h 50mPorter Airlines
Deal found 25/2C$ 313

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 26 February 2024. In the last 7 days, Cheapflights users made a total of 594,106 searches

Fly to

Any airport

Budget

C$ 296 - C$ 313

Route

Depart

Return

Price

Chicago MidwayToronto Island

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 2/5

Nonstop1h 42m

Toronto Island

Sun 5/5

Nonstop1h 47m

C$ 296

Chicago O'Hare IntlCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Thu 6/6

Nonstop3h 27m

Calgary

Mon 10/6

Nonstop3h 35m

C$ 300

Chicago O'Hare IntlCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 8/6

Nonstop3h 27m

Calgary

Fri 14/6

Nonstop3h 35m

C$ 301

Chicago MidwayToronto Island

MDW - YTZ

MDWYTZ

Chicago Midway

Fri 29/3

Nonstop1h 42m

Toronto Island

Sun 31/3

Nonstop1h 47m

C$ 301

Chicago MidwayToronto Island

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 20/4

Nonstop1h 42m

Toronto Island

Tue 23/4

Nonstop1h 47m

C$ 303

Chicago MidwayToronto Island

MDW - YTZ

MDWYTZ

Chicago Midway

Sat 30/3

Nonstop1h 42m

Toronto Island

Thu 4/4

Nonstop1h 47m

C$ 304

Chicago O'Hare IntlCalgary

ORD - YYC

ORDYYC

Chicago O'Hare Intl

Sat 8/6

Nonstop3h 27m

Calgary

Mon 10/6

Nonstop3h 35m

C$ 307

Chicago MidwayToronto Island

MDW - YTZ

MDWYTZ

Chicago Midway

Tue 26/3

Nonstop1h 42m

Toronto Island

Tue 2/4

Nonstop1h 47m

C$ 311

Chicago MidwayToronto Island

MDW - YTZ

MDWYTZ

Chicago Midway

Thu 21/3

Nonstop1h 42m

Toronto Island

Sun 24/3

Nonstop1h 50m

C$ 313

Flights are sorted by cheapest first

Deals found on 25/2

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. Price data was last updated on 28 January 2024.
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 88 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Search Deals

When is the cheapest time to fly from Chicago?

Use this chart to determine the cheapest time to fly round-trip from Chicago. Price data was last updated on 25 February 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Those who are seeking the cheapest fare on flights departing from Chicago would be wise to consider leaving during Sunday evenings when prices are typically at their lowest. When considering other options, price-conscious travelers should avoid Sunday mornings when fares are usually the most expensive.
Search Deals

Average price of flights from Chicago by month

Plan your trip from Chicago by taking into account the cheapest months to travel. The average price of a one-way flight from Chicago is currently C$ 101 while a round-trip flight costs C$ 304. Price data was last updated on 18 February 2024.

Currently, January is the cheapest month in which you can book a flight from Chicago (average of C$ 261). Flying from Chicago in August will prove the most costly (average of C$ 437). There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

January

C$ 222

February

C$ 236

March

C$ 201

April

C$ 178

May

C$ 196

June

C$ 232

July

C$ 309

August

C$ 290

September

C$ 190

October

C$ 194

November

C$ 246

December

C$ 261

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 594,106 searches.
8.1
Very good
9,254 reviews

Boarding

8.2

Overall

8.1

Entertainment

7.4

Crew

8.6

Food

7.4

Comfort

7.9

Reviews

1 / 10

I paid for an aisle seat and found I was bumped to the middle seat. No entertainment at all, bathroom was so tiny, a woman had a hard time in there. Seems it was considered for men only. This was my first time on Alaska airlines. I don’t think I want to fly on Alaska Airlines again.

8.1
Very good
9,254 reviews
8.1
Very good
9,254 reviews

Boarding

8.2

Overall

8.1

Entertainment

7.4

Crew

8.6

Food

7.4

Comfort

7.9

Reviews

1 / 10

I paid for an aisle seat and found I was bumped to the middle seat. No entertainment at all, bathroom was so tiny, a woman had a hard time in there. Seems it was considered for men only. This was my first time on Alaska airlines. I don’t think I want to fly on Alaska Airlines again.

8.1
Very good
11,853 reviews
8.1
Very good
9,254 reviews

Boarding

8.2

Overall

8.1

Entertainment

7.4

Crew

8.6

Food

7.4

Comfort

7.9

Reviews

1 / 10

I paid for an aisle seat and found I was bumped to the middle seat. No entertainment at all, bathroom was so tiny, a woman had a hard time in there. Seems it was considered for men only. This was my first time on Alaska airlines. I don’t think I want to fly on Alaska Airlines again.

7.7
Good
2,901 reviews
8.1
Very good
9,254 reviews

Boarding

8.2

Overall

8.1

Entertainment

7.4

Crew

8.6

Food

7.4

Comfort

7.9

Reviews

1 / 10

I paid for an aisle seat and found I was bumped to the middle seat. No entertainment at all, bathroom was so tiny, a woman had a hard time in there. Seems it was considered for men only. This was my first time on Alaska airlines. I don’t think I want to fly on Alaska Airlines again.

7.6
Good
3,139 reviews
8.1
Very good
9,254 reviews

Boarding

8.2

Overall

8.1

Entertainment

7.4

Crew

8.6

Food

7.4

Comfort

7.9

Reviews

1 / 10

I paid for an aisle seat and found I was bumped to the middle seat. No entertainment at all, bathroom was so tiny, a woman had a hard time in there. Seems it was considered for men only. This was my first time on Alaska airlines. I don’t think I want to fly on Alaska Airlines again.

7.4
Good
491 reviews
8.1
Very good
9,254 reviews

Boarding

8.2

Overall

8.1

Entertainment

7.4

Crew

8.6

Food

7.4

Comfort

7.9

Reviews

1 / 10

I paid for an aisle seat and found I was bumped to the middle seat. No entertainment at all, bathroom was so tiny, a woman had a hard time in there. Seems it was considered for men only. This was my first time on Alaska airlines. I don’t think I want to fly on Alaska Airlines again.

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Popular international destinations from Chicago
The most popular international flight routes departing from Chicago we’ve come across at this time.

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 26 February 2024.

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$ 296. While Chicago O'Hare Intl airport is usually cheaper if your destination is Montreal with prices starting at C$ 312. 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, American Airlines, and Frontier to have the cheapest round-trip prices from Chicago. Some of the destinations and prices are as follows: Spirit Airlines flights from Chicago to Dallas/Fort Worth (C$ 93). American Airlines flights from Chicago to New Delhi Indira Gandhi Intl (C$ 107). Frontier flights from Chicago to Dallas/Fort Worth (C$ 116).

What is the shortest nonstop flight from Chicago?

Consider Milwaukee, Moline, and Kalamazoo if you prefer a quick journey with a short flight time. These locations are all within 108 km of Chicago

What is the farthest nonstop flight from Chicago?

If flights to distant destinations are more of your preference, check pricing for Taipei City, Auckland, and Hong Kong.

What are popular destinations to fly to from Chicago?

From Chicago you can expect to find greater availability for the following destinations: New York (1,877 flights per day), Detroit (922 flights per day) and Los Angeles (647 flights per day).

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$ 296 round trip
Travel from Chicago to Calgary from C$ 312 round trip
Travel from Chicago to Montreal from C$ 326 round trip
Travel from Chicago to Vancouver from C$ 334 round trip

Which airlines fly from Chicago?

For flights departing from Chicago check dates and pricing for the following: Alaska Airlines, Frontier, Volaris, WestJet, Spirit Airlines. These airlines depart to the following popular destinations: Mexico City, Dallas, Edmonton, Seattle.

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

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

What is the cheapest month to fly from Chicago?

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

When is the cheapest time to fly from Chicago?

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

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

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.

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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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