What is the cheapest month to fly to Chicago?

Currently, January is the cheapest month in which you can book a flight to Chicago . Flying to Chicago in March will prove the most costly. There are multiple factors that influence the price of a flight so comparing airlines, departure airports and times can help keep costs down.

Can I find cheaper flights to Chicago if I am willing to have layovers?

Yes, flights with layovers are often cheaper than direct flights. Keep an eye out for flight deals to Chicago on Cheapflights that require 1 or 2 stops for potential cost savings.

What is the best airline to fly to Chicago?

Based on reviews from Cheapflights users, Delta is rated the highest out of the airlines that fly to Chicago.

What is the cheapest airport to fly to in Chicago?

Chicago Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost C$ 54, while round-trip flights cost around C$ 83.

How much is a round-trip flight to Chicago?

A round-trip flight to Chicago will typically cost around C$ 82, however they can be found for as little as C$ 60.

Where does the fastest flight to Chicago depart from?

For those looking to save time traveling to Chicago, Toronto offers the quickest one-way flight (1 hour 49 minutes).

Does Chicago O'Hare Intl have rental cars?

Yes. Those touching down at Chicago O'Hare Intl can take advantage of the rental car services offered upon their arrival.

Are there hotels close to Chicago O'Hare Intl?

Yes. Chicago O'Hare Intl has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl (0.0 km away from Chicago O'Hare Intl).

What is good to know if travelling to Chicago?

One of the biggest challenges for visitors to Chicago can be the weather. Fiercely hot in the summer, the city is bitterly cold and windy in the winter. In the winter, wear layers and don’t expose skin to the wind; in summer, be sure to drink plenty of water and use sunscreen.

C$ 155+ Flights to Chicago, Illinois

Flights to Chicago in 2025

Round-trip from	C$ 236
One-way from	C$ 155
Popular in	December
Cheapest in	April
Average price	C$ 356
Good round-trip deal	C$ 234 or less
Good one-way deal	C$ 163 or less

Porter Airlines
28/6-5/7
Nonstop
3h 30m total
Toronto to Chicago

Search Deals

Air Canada
19/6
1 total stop
4h 29m total
Toronto to Chicago

Search Deals

Highest demand for flights based on searches. 6% potential increase in price (C$ 36 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 1% potential price decrease (C$ 7 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in May 2025

Search Deals

Price to beat on a round-trip flight from Toronto to Chicago.

Search Deals

Price to beat on a one-way flight from Toronto to Chicago.

Search Deals

Find flight deals to Chicago

Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 14 May 2025.

Sat 28/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sat 5/79:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 14/5C$ 236

Fri 15/86:35 p.m.YYZ - ORD

Nonstop1h 54mAir Canada

Mon 18/83:50 p.m.ORD - YYZ

Nonstop1h 45mAir Canada

Deal found 14/5C$ 240

Sat 16/83:25 p.m.YTZ - ORD

1 stop5h 51mAir Canada

Sun 17/88:40 a.m.ORD - YTZ

1 stop5h 06mAir Canada

Deal found 14/5C$ 254

Fri 29/89:00 a.m.YYZ - ORD

Nonstop1h 55mUnited Airlines

Fri 5/93:50 p.m.ORD - YYZ

Nonstop1h 43mUnited Airlines

Deal found 13/5C$ 266

Sun 13/78:15 a.m.YYZ - ORD

Nonstop1h 54mMultiple Airlines

Wed 16/73:35 p.m.ORD - YYZ

1 stop6h 44mMultiple Airlines

Deal found 12/5C$ 268

Sat 28/67:55 a.m.YTZ - MDW

Nonstop1h 50mAir Transat

Tue 1/79:40 a.m.MDW - YTZ

Nonstop1h 42mAir Transat

Deal found 14/5C$ 278

Fri 11/73:35 p.m.YTZ - MDW

Nonstop1h 49mMultiple Airlines

Sun 13/75:20 p.m.MDW - YTZ

Nonstop1h 42mMultiple Airlines

Deal found 14/5C$ 282

Fri 29/85:59 p.m.YYZ - ORD

1 stop5h 49mAmerican Airlines

Fri 5/99:45 a.m.ORD - YYZ

Nonstop1h 45mAmerican Airlines

Deal found 13/5C$ 293

Sat 4/1012:15 p.m.YYZ - MDW

1 stop7h 21mDelta

Wed 15/109:30 a.m.MDW - YYZ

1 stop6h 53mDelta

Deal found 13/5C$ 293

Wed 23/76:30 a.m.YYZ - MDW

1 stop6h 59mKLM

Tue 29/76:20 p.m.MDW - YYZ

1 stop3h 38mKLM

Deal found 14/5C$ 301

Mon 21/712:16 p.m.YYZ - ORD

1 stop6h 51mDelta

Fri 8/86:00 a.m.ORD - YYZ

1 stop4h 54mDelta

Deal found 14/5C$ 311

Thu 3/712:00 p.m.YTZ - ORD

2 stops33h 23mMultiple Airlines

Mon 7/78:40 a.m.ORD - YTZ

1 stop7h 06mMultiple Airlines

Deal found 13/5C$ 389

Best flights to Chicago
Discover carefully curated flight deals to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated 14 May 2025.

Sat 28/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sat 5/79:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 14/5C$ 236

Fri 15/86:35 p.m.YYZ - ORD

Nonstop1h 54mAir Canada

Mon 18/83:50 p.m.ORD - YYZ

Nonstop1h 45mAir Canada

Deal found 14/5C$ 240

Thu 17/77:00 a.m.YYZ - ORD

Nonstop1h 59mUnited Airlines

Sun 20/79:14 p.m.ORD - YYZ

Nonstop1h 44mUnited Airlines

Deal found 14/5C$ 259

Wed 23/77:00 a.m.YYZ - ORD

Nonstop1h 59mLufthansa

Tue 29/77:15 a.m.ORD - YYZ

1 stop5h 32mLufthansa

Deal found 14/5C$ 276

Sat 28/67:55 a.m.YTZ - MDW

Nonstop1h 50mAir Transat

Tue 1/79:40 a.m.MDW - YTZ

Nonstop1h 42mAir Transat

Deal found 14/5C$ 278

Fri 11/73:35 p.m.YTZ - MDW

Nonstop1h 49mMultiple Airlines

Sun 13/75:20 p.m.MDW - YTZ

Nonstop1h 42mMultiple Airlines

Deal found 14/5C$ 282

Sat 4/103:59 p.m.YYZ - MDW

1 stop3h 37mDelta

Wed 15/101:00 p.m.MDW - YYZ

1 stop3h 23mDelta

Deal found 14/5C$ 294

Thu 3/73:45 p.m.YYZ - ORD

1 stop9h 12mAmerican Airlines

Fri 11/78:45 p.m.ORD - YYZ

1 stop18h 49mAmerican Airlines

Deal found 14/5C$ 300

Wed 23/76:30 a.m.YYZ - MDW

1 stop6h 59mKLM

Tue 29/76:20 p.m.MDW - YYZ

1 stop3h 38mKLM

Deal found 14/5C$ 301

Fri 17/1012:15 p.m.YYZ - MDW

1 stop7h 21mWestJet

Mon 20/109:30 a.m.MDW - YYZ

1 stop6h 53mWestJet

Deal found 13/5C$ 404

Sat 16/83:25 p.m.YTZ - ORD

1 stop5h 51mAir Canada

Sun 17/88:40 a.m.ORD - YTZ

1 stop5h 06mAir Canada

Deal found 14/5C$ 254

Fri 6/67:47 p.m.YYZ - ORD

1 stop4h 43mMultiple Airlines

Sun 13/73:35 p.m.ORD - YYZ

1 stop6h 44mMultiple Airlines

Deal found 14/5C$ 294

Direct flights to Chicago
Explore direct flight options to Chicago based on user searches, and compare prices and availability for your desired travel dates. Data last updated 14 May 2025.

Sat 28/67:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Sat 5/79:40 a.m.MDW - YTZ

Nonstop1h 40mPorter Airlines

Deal found 14/5C$ 236

Fri 15/86:35 p.m.YYZ - ORD

Nonstop1h 54mAir Canada

Mon 18/83:50 p.m.ORD - YYZ

Nonstop1h 45mAir Canada

Deal found 14/5C$ 240

Thu 17/77:00 a.m.YYZ - ORD

Nonstop1h 59mUnited Airlines

Sun 20/79:14 p.m.ORD - YYZ

Nonstop1h 44mUnited Airlines

Deal found 14/5C$ 259

Sat 16/84:30 p.m.YYZ - ORD

Nonstop1h 57mLufthansa

Tue 19/88:55 a.m.ORD - YYZ

Nonstop1h 54mLufthansa

Deal found 14/5C$ 275

Sat 28/67:55 a.m.YTZ - MDW

Nonstop1h 50mAir Transat

Tue 1/79:40 a.m.MDW - YTZ

Nonstop1h 42mAir Transat

Deal found 14/5C$ 278

Fri 11/73:35 p.m.YTZ - MDW

Nonstop1h 49mMultiple Airlines

Sun 13/75:20 p.m.MDW - YTZ

Nonstop1h 42mMultiple Airlines

Deal found 14/5C$ 282

Fri 20/612:00 p.m.YYZ - ORD

Nonstop1h 54mMultiple Airlines

Sun 22/68:25 p.m.ORD - YYZ

Nonstop1h 45mMultiple Airlines

Deal found 13/5C$ 308

Tue 17/66:29 p.m.YYZ - ORD

Nonstop2h 00mAmerican Airlines

Wed 18/68:28 p.m.ORD - YYZ

Nonstop2h 00mAmerican Airlines

Deal found 14/5C$ 324

Last-minute flights to Chicago
Discover last-minute flight deals to Chicago. Data last updated 14 May 2025 and is based on user searches.

Wed 21/53:50 p.m.YYZ - ORD

1 stop3h 47mWestJet

Tue 27/56:24 a.m.ORD - YYZ

2 stops10h 39mWestJet

Deal found 13/5C$ 598

Thu 22/512:30 p.m.YYZ - ORD

1 stop7h 50mDelta

Tue 27/52:45 p.m.ORD - YYZ

1 stop4h 59mDelta

Deal found 14/5C$ 566

Thu 22/58:50 a.m.YTZ - ORD

3 stops16h 15mMultiple Airlines

Mon 26/55:05 a.m.ORD - YTZ

2 stops26h 25mMultiple Airlines

Deal found 13/5C$ 671

Fri 23/53:50 p.m.YYZ - MDW

1 stop3h 55mDelta

Mon 26/59:16 a.m.MDW - YYZ

1 stop4h 44mDelta

Deal found 12/5C$ 450

Fri 23/512:30 p.m.YYZ - MDW

1 stop6h 15mWestJet

Sun 1/612:48 p.m.MDW - YYZ

1 stop10h 07mWestJet

Deal found 12/5C$ 572

Sat 24/57:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Wed 28/55:50 p.m.MDW - YTZ

Nonstop1h 42mPorter Airlines

Deal found 14/5C$ 379

Sat 24/59:00 a.m.YYZ - ORD

Nonstop1h 59mAir Canada

Sat 31/57:04 a.m.ORD - YYZ

Nonstop1h 54mAir Canada

Deal found 14/5C$ 414

Sat 24/57:25 a.m.YTZ - ORD

1 stop4h 59mAir Canada

Sat 31/58:40 a.m.ORD - YTZ

1 stop5h 10mAir Canada

Deal found 14/5C$ 420

Sat 24/56:00 a.m.YYZ - ORD

1 stop5h 41mAmerican Airlines

Wed 28/56:00 a.m.ORD - YYZ

1 stop4h 55mAmerican Airlines

Deal found 14/5C$ 449

Sat 24/57:55 a.m.YYZ - ORD

1 stop24h 32mMultiple Airlines

Sat 31/512:45 p.m.ORD - YYZ

2 stops34h 07mMultiple Airlines

Deal found 14/5C$ 456

Sat 24/57:55 a.m.YTZ - MDW

Nonstop1h 50mAir Transat

Sun 25/55:50 p.m.MDW - YTZ

Nonstop1h 42mAir Transat

Deal found 14/5C$ 523

Sat 24/54:30 p.m.YYZ - ORD

1 stop4h 57mUnited Airlines

Sun 25/57:04 a.m.ORD - YYZ

Nonstop1h 54mUnited Airlines

Deal found 14/5C$ 527

One-way flights to Chicago
Search for one-way flight options to Chicago. Find affordable one-way fares based on user searches. Data last updated 14 May 2025.

Thu 19/65:40 a.m.YHM - ORD

1 stop4h 29mAir Canada

Deal found 14/5C$ 155

Tue 3/66:15 a.m.YYZ - ORD

1 stop4h 37mAir Canada

Deal found 14/5C$ 165

Tue 1/73:35 p.m.YTZ - MDW

Nonstop1h 49mAir Transat

Deal found 13/5C$ 165

Tue 27/57:55 a.m.YTZ - MDW

Nonstop1h 50mPorter Airlines

Deal found 13/5C$ 167

Mon 9/67:25 a.m.YTZ - ORD

1 stop4h 59mAir Canada

Deal found 14/5C$ 169

Sun 15/612:00 p.m.YYZ - ORD

Nonstop1h 55mUnited Airlines

Deal found 14/5C$ 170

Tue 17/66:30 a.m.YYZ - ORD

Nonstop1h 55mAmerican Airlines

Deal found 14/5C$ 179

Fri 13/67:00 a.m.YTZ - ORD

2 stops24h 37mMultiple Airlines

Deal found 14/5C$ 180

Fri 12/912:15 p.m.YYZ - MDW

1 stop7h 21mDelta

Deal found 14/5C$ 185

Thu 12/67:55 a.m.YYZ - ORD

1 stop23h 42mMultiple Airlines

Deal found 14/5C$ 192

Sat 31/57:15 a.m.YYZ - MDW

1 stop14h 02mMultiple Airlines

Deal found 14/5C$ 208

Wed 4/61:35 p.m.YTZ - MDW

1 stop6h 56mMultiple Airlines

Deal found 14/5C$ 219

Cheapflights Fare Finder

Use the filters below to find and compare flights to Chicago that are best for you.

Fly from

Route

Depart

Return

Price

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 28/6

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Sat 5/7

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

Nonstop1h 40m

C$ 236

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Fri 25/7

8:15 a.m.-9:09 a.m.

Nonstop1h 54m

Chicago O'Hare Intl

Sun 27/7

8:25 p.m.-11:10 p.m.

Nonstop1h 45m

C$ 244

TorontoChicago

YTZ - ORD

YTZORD

Toronto Island

Sat 16/8

3:25 p.m.-8:16 p.m.

1 stop5h 51m

Chicago O'Hare Intl

Sun 17/8

8:40 a.m.-2:46 p.m.

1 stop5h 06m

C$ 254

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Wed 23/7

7:00 a.m.-7:59 a.m.

Nonstop1h 59m

Chicago O'Hare Intl

Tue 29/7

10:40 a.m.-5:29 p.m.

1 stop5h 49m

C$ 266

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 12/6

11:00 a.m.-12:01 p.m.

Nonstop2h 01m

Chicago O'Hare Intl

Mon 16/6

9:14 p.m.-11:58 p.m.

Nonstop1h 44m

C$ 269

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Sat 28/6

7:55 a.m.-8:45 a.m.

Nonstop1h 50m

Chicago Midway

Tue 1/7

9:40 a.m.-12:22 p.m.

Nonstop1h 42m

C$ 278

TorontoChicago

YTZ - MDW

YTZMDW

Toronto Island

Fri 11/7

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

Nonstop1h 49m

Chicago Midway

Sun 13/7

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

Nonstop1h 42m

C$ 282

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Sat 4/10

12:15 p.m.-6:36 p.m.

1 stop7h 21m

Chicago Midway

Wed 15/10

9:30 a.m.-5:23 p.m.

1 stop6h 53m

C$ 293

TorontoChicago

YYZ - ORD

YYZORD

Toronto Pearson Intl

Thu 3/7

3:45 p.m.-11:57 p.m.

1 stop9h 12m

Chicago O'Hare Intl

Fri 11/7

8:45 p.m.-4:34 p.m.

1 stop18h 49m

C$ 300

TorontoChicago

YYZ - MDW

YYZMDW

Toronto Pearson Intl

Wed 23/7

6:30 a.m.-12:29 p.m.

1 stop6h 59m

Chicago Midway

Tue 29/7

6:20 p.m.-10:58 p.m.

1 stop3h 38m

C$ 301

Flights are sorted by cheapest round-trip flights first.

Deals found on 14/5

Showing 1-10 of 37 results

Best time to book a flight to Chicago

Have a flexible travel schedule? Discover the best time to fly to 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.

Cheapflights Insights

Everything you need to know about your flight to Chicago

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

To ensure you get the cheapest price possible for a flight to Chicago, you should look to book at least 76 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

How long is the flight to Chicago?

On average, a flight from Toronto to Chicago takes 5 hours 43 minutes. Flights to Chicago from other popular cities in Canada will vary in length. Below are a few examples of popular routes and their flight times.

When is the cheapest time to fly to Chicago?

Users looking for the lowest fares to Chicago should consider flying on Sunday mornings, when prices are typically cheapest. Budget-minded travellers will want to avoid Sunday at noon, when prices are usually at their highest.

Weekly flight availability to Chicago

The most flights from Toronto to Chicago are scheduled on a Monday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (59 on average).

What are the most popular airlines that fly to Chicago?

The most popular airlines flying from Toronto to Chicago are Air Canada, United Airlines and Porter Airlines.

What are the cheapest airlines that fly to Chicago?

The cheapest airlines flying from Toronto to Chicago are Porter Airlines, American Airlines and Air Canada.

Rainfall in Chicago by month

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 mm per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with Porter Airlines, Delta and KLM to Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Porter Airlines

8.0

Very good

286 reviews

Check prices

Reviews

1 / 18

10.0

Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

Porter Airlines

8.0

Very good

286 reviews

Porter Airlines

8.0

Very good

286 reviews

Check prices

Reviews

1 / 18

10.0

Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

Delta

8.0

Very good

7,946 reviews

Porter Airlines

8.0

Very good

286 reviews

Check prices

Reviews

1 / 18

10.0

Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

KLM

7.8

Good

1,343 reviews

Porter Airlines

8.0

Very good

286 reviews

Check prices

Reviews

1 / 18

10.0

Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

Air Transat

7.8

Good

387 reviews

Porter Airlines

8.0

Very good

286 reviews

Check prices

Reviews

1 / 18

10.0

Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

Aeromexico

7.5

Good

1,699 reviews

Porter Airlines

8.0

Very good

286 reviews

Check prices

Reviews

1 / 18

10.0

Excellent

Anonymous,Apr 2025

MCO - YHZ

A good flight and the crew was very nice. Thank you

FAQs about flying to Chicago

What is good to know if travelling to Chicago?
One of the biggest challenges for visitors to Chicago can be the weather. Fiercely hot in the summer, the city is bitterly cold and windy in the winter. In the winter, wear layers and don’t expose skin to the wind; in summer, be sure to drink plenty of water and use sunscreen.
Can I find cheaper flights to Chicago if I am willing to have layovers?
Yes, flights with layovers are often cheaper than direct flights. Keep an eye out for flight deals to Chicago on Cheapflights that require 1 or 2 stops for potential cost savings.
What is the best airline to fly to Chicago?
Based on reviews from Cheapflights users, Delta is rated the highest out of the airlines that fly to Chicago.
What is the cheapest airport to fly to in Chicago?
Chicago Midway is currently the cheapest airport to fly to in Chicago. One-way flights to Chicago Midway typically cost C$ 54, while round-trip flights cost around C$ 83.
How much is a round-trip flight to Chicago?
A round-trip flight to Chicago will typically cost around C$ 82, however they can be found for as little as C$ 60.
Where does the fastest flight to Chicago depart from?
For those looking to save time traveling to Chicago, Toronto offers the quickest one-way flight (1 hour 49 minutes).
Does Chicago O'Hare Intl have rental cars?
Yes. Those touching down at Chicago O'Hare Intl can take advantage of the rental car services offered upon their arrival.
Are there hotels close to Chicago O'Hare Intl?
Yes. Chicago O'Hare Intl has hotels nearby for those requiring accommodations. Hilton Chicago O'Hare Airport is the closest property to Chicago O'Hare Intl (0.0 km away from Chicago O'Hare Intl).

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

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How does Cheapflights help users find flights to Chicago?

Cheapflights makes it easy to find Chicago flights by helping our users search from 900+ travel sites for deals. We also provide you with filters for cabin, price, airline, airports, number of stops, and many more to narrow down that perfect flight.

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

It’s simple! Cheapflights, which is free to use for everyone, saves millions of users time and money every year by helping them find the cheapest and most suitable flights to Chicago.

Can Cheapflights find flights to Chicago with no change fees?

Yes, we can. To see specific flights to Chicago with no change fees, users can toggle flexible booking options after using the search form above to find flights.

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

Yes, Cheapflights offers price alerts on Chicago flights so you can book your flight when prices are ideal. Enable price alerts by clicking the bell icon next to the flight deals above and providing your email address where you want to receive the alerts.

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C$ 155+ Cheap flights to 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 19/6. Fares are subject to change and may not be available on all flights or dates of travel.

Flights to Chicago in 2025

Find the latest flights to Chicago in 2025, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 14 May 2025.

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Good round-trip deal

Good one-way deal

Find flight deals to Chicago

Cheapest flights to ChicagoExplore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 14 May 2025.

Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 14 May 2025.

Cheapflights Fare Finder

Locate flights to Chicago that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 629,999 searches and data was last updated on 14 May 2025.

Use the filters below to find and compare flights to Chicago that are best for you.

Best time to book a flight to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight to Chicago

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

Use this chart to determine the optimal time to book a round-trip flight from Toronto to Chicago. Price data was last updated on 9 May 2025.

How long is the flight to Chicago?

When is the cheapest time to fly to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Toronto to Chicago. Price data was last updated on 30 June 2024.

Weekly flight availability to Chicago

What are the most popular airlines that fly to Chicago?

What are the cheapest airlines that fly to Chicago?

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 14 May 2025.

Get a feel of what it's like to fly with Porter Airlines, Delta and KLM to Chicago by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

FAQs about flying to Chicago

What is good to know if travelling to Chicago?

Can I find cheaper flights to Chicago if I am willing to have layovers?

What is the best airline to fly to Chicago?

What is the cheapest airport to fly to in Chicago?

How much is a round-trip flight to Chicago?

Where does the fastest flight to Chicago depart from?

Does Chicago O'Hare Intl have rental cars?

Are there hotels close to Chicago O'Hare Intl?

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.

Find the best flight deals to Chicago

Some of the lowest fares we’ve come across for flights to Chicago.

Fly with Cheapflights

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Cheapest flights to Chicago
Explore the most affordable flight options available to Chicago. Find the lowest fares based on data from user searches, with prices last updated on 14 May 2025.