Find cheap flights to Chicago

• Book at least 3 weeks before departure in order to get a below-average price.
• High season is considered to be February, March and April. The cheapest month to fly from Canada is June.
• Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.
• The highest number of flights to Chicago have Chicago O'Hare International Airport (ORD) as the arrival airport. The airport is located about 16 miles (27 km) northwest of Chicago. Most travellers prefer landing here because of the availability of a variety of transport options, which makes it easier for them to connect to various parts within and outside Chicago.
• You have better chances of getting cheaper flight deals when booking your flight to Chicago if you choose to book one that has Chicago Midway International Airport (MDW) as the arrival airport. This is because the flights that arrive at MDW have a lower demand among travellers flying to Chicago. Additionally, you will enjoy shorter queues at the security checkpoints and baggage claim area when you land at MDW as opposed to if you land at ORD.
• You will make one stop or travel nonstop to Chicago, depending on the airline you book. Spirit Airlines is one of the carriers that makes one stop when flying to Chicago, with the layover airport being Hartsfield–Jackson Atlanta International Airport (ATL). However, if you book Air Canada, JetBlue, or Porter Airlines, you will enjoy direct flights to Chicago.
• If you’re interested in flights to Chicago, there are three primary airports that you can fly into. While Chicago Midway International Airport is most convenient for travelers that will be staying in the city center, O'Hare International Airport services the highest number of flights. Chicago Rockford International Airport is a practical choice for individuals staying in the suburbs.
• For those that would like a direct flight to Chicago, there are several airlines that you can choose from. While American and Porter Airlines are known for having affordable flights and comfortable chairs, United Airlines provides travelers with above-average legroom.
• To unwind after a long day of traveling, stop by the yoga room in Chicago Midway International Airport. Located in Concourse C, this room provides travelers with complimentary mats and DVD footage of popular yoga positions. It is open 7 days a week from 6 AM to 10 PM.
• Traveling with your family? Chicago Midway International Airport has a large baby care room that contains a sink, a private nursing area and change tables, making it a convenient place to tend to your child after your flight has landed.
• If you would like to freshen up after a long day of traveling, purchase an access pass to either the Hilton Athletic Club, Airlines Admirals Club or United Club in O'Hare International Airport in order to access their private showers. Each of these locations provides complimentary towels and toiletries, so you will have everything you need.

• Which other cities does Chicago O'Hare International Airport (ORD) serve?

  Apart from serving Chicago, Chicago O'Hare International Airport also serves as the arrival airport for those travelling to Oak Park and Cicero. Therefore, booking a flight to Chicago is an opportunity to access these nearby cities conveniently. Car rentals at ORD provide the most convenient means of transport from the airport to Cicero and Oak Park.

• How convenient is it to travel to Chicago with kids?

  You will enjoy a variety of kid-friendly perks with a number of airlines that fly to Chicago, with JetBlue ranking the highest. If you book JetBlue, you and your kids are guaranteed to travel in a much more comfortable way, with the airline popular for its spacious seats and extra legroom in all the cabins. Additionally, parents enjoy extra baggage allowance and are allowed to board the plane first before other travellers.

• What hotels are near Rockford International Airport?

  The Red Roof Inn is a budget-friendly choice that is a 15-minute drive from Rockford International Airport and a 6-minute drive to the Magic Waters Waterpark. The Radisson Hotel & Conference Center is a modern choice that is a 20-minute drive from the airport and an 8-minute drive from the Midway Village Museum.

• What is the best way to travel from O'Hare International Airport to downtown Chicago?

  The easiest and quickest way to travel from O'Hare International Airport to downtown Chicago is by either renting a car or grabbing a taxi, as the drive only takes 25 to 30 minutes in good traffic. If you prefer a more affordable option, it is also possible to use public transportation, such as the local train, which takes approximately 45 minutes.

• Does O'Hare International Airport have a prayer room?

  O'Hare International Airport has a multi-faith chapel that is located inside of Terminal 1 on the Mezzanine level. Religious books, rosaries and prayer rugs are available for use, and the chapel is open to all travelers, no matter what their religious affiliation is. It is open 7 days a week during standard business hours.

• What shopping options are there at O'Hare International Airport?

  O'Hare International Airport has several duty-free stores located in Terminals 1, 2 and 3. In these stores, you can find a variety of electronics, clothing, liquor, cosmetics, food products and even local souvenirs. There are also several smaller shops that sell travel essentials, such as books, snacks, headphones and basic medicine.

• Which Chicago airport is closest to central Chicago?

  Chicago is served by 3 major airports. Chicago Midway Airport (14 km) is the closest to the centre of Chicago. Chicago O'Hare Airport is 26 km from the centre and Chicago Greater Rockford is 126 km away from the centre.

• Which airport is the cheapest to fly to Chicago?

  Prices will differ depending on the departure airport, but generally, the cheapest airport to fly to in Chicago is Chicago Midway Airport, with an average flight price of C$ 388.

• Which airlines have a flexible cancellation policy for flights to Chicago due to COVID-19?

  Air Canada, United Airlines and American Airlines have waived their change and cancellation fees on flights to Chicago. Confirm policies on booking site.

• How does KAYAK find such low prices on flights to Chicago?

  KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights to Chicago.

• How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket to Chicago?

  KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago is likely to change within 7 days, so travellers know whether to wait or book now.

• What is the Hacker Fare option on flights to Chicago?

  Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back with another airline.

• What is KAYAK's "flexible dates" feature and why should I care when looking for a flight to Chicago?

  Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Book Cheap Chicago Plane Tickets

Recent round-trip flight deals

4/10Wed

directUnited Airlines

3h 24mYYC-ORD

11/10Wed

directUnited Airlines

3h 48mORD-YYC

C$ 336

Search

13/9Wed

1 stopUndisclosed Carrier

7h 44mYYC-ORD

20/9Wed

1 stopUndisclosed Carrier

8h 05mORD-YYC

C$ 339

Search

13/8Sun

directUndisclosed Carrier

1h 55mYYZ-ORD

15/8Tue

directUndisclosed Carrier

1h 39mORD-YYZ

C$ 342

Search

30/9Sat

1 stopUnited Airlines

12h 38mYYC-ORD

3/10Tue

directUnited Airlines

3h 48mORD-YYC

C$ 342

Search

4/10Wed

1 stopUnited Airlines

16h 36mYYC-ORD

11/10Wed

directUnited Airlines

3h 48mORD-YYC

C$ 343

Search

30/9Sat

2 stopsDelta

12h 19mYYC-ORD

3/10Tue

1 stopDelta

8h 44mORD-YYC

C$ 361

Search

28/6Wed

directUndisclosed Carrier

2h 38mYUL-ORD

3/7Mon

directUndisclosed Carrier

2h 10mORD-YUL

C$ 363

Search

11/10Wed

directAmerican Airlines

2h 00mYYZ-ORD

14/10Sat

directAmerican Airlines

1h 45mORD-YYZ

C$ 371

Search

21/6Wed

directPorter Airlines

1h 47mYTZ-MDW

28/6Wed

directPorter Airlines

1h 42mMDW-YTZ

C$ 379

Search

30/9Sat

1 stopDelta

9h 20mYYC-ORD

3/10Tue

1 stopDelta

8h 44mORD-YYC

C$ 379

Search

11/10Wed

directAmerican Airlines

2h 02mYYZ-ORD

14/10Sat

1 stopAmerican Airlines

8h 25mORD-YYZ

C$ 382

Search

20/6Tue

directPorter Airlines

1h 47mYTZ-MDW

20/6Tue

directPorter Airlines

1h 42mMDW-YTZ

C$ 384

Search

27/10Fri

1 stopDelta

5h 21mYUL-ORD

31/10Tue

1 stopDelta

6h 05mORD-YUL

C$ 385

Search

15/6Thu

directAir Canada

1h 50mYYZ-ORD

20/6Tue

directAir Canada

1h 43mORD-YYZ

C$ 396

Search

15/6Thu

directAir Canada

1h 50mYYZ-ORD

20/6Tue

1 stopAir Canada

5h 56mORD-YYZ

C$ 403

Search

16/10Mon

1 stopAeromexico

7h 52mYUL-MDW

21/10Sat

1 stopAeromexico

4h 55mMDW-YUL

C$ 431

Search

21/6Wed

1 stopMultiple Airlines

9h 35mYYZ-ORD

26/6Mon

1 stopMultiple Airlines

7h 30mORD-YYZ

C$ 435

Search

7/8Mon

1 stopWestJet

5h 52mYUL-ORD

11/8Fri

1 stopWestJet

11h 41mORD-YUL

C$ 514

Search

31/8Thu

1 stopFlair Airlines

9h 06mYVR-ORD

6/9Wed

1 stopFlair Airlines

19h 35mORD-YVR

C$ 546

Search

13/10Fri

1 stopAlaska Airlines

6h 15mYVR-ORD

17/10Tue

1 stopAlaska Airlines

6h 40mORD-YVR

C$ 568

Search

Show more results

Search by stops

Direct1 stop2+ stops

Search by airline

United AirlinesDeltaAmerican AirlinesPorter AirlinesAir CanadaAeromexicoWestJetFlair AirlinesAlaska Airlines

Search by price

C$ 340 or lessC$ 370 or lessC$ 380 or lessC$ 430 or lessC$ 570 or less

Recent one-way flight deals

19/8Sat

directAir Canada

1h 50mYYZ-ORD

C$ 99

Search

7/6Wed

1 stopMultiple Airlines

9h 46mYYZ-ORD

C$ 184

Search

14/6Wed

directPorter Airlines

1h 47mYTZ-MDW

C$ 187

Search

13/6Tue

directAir Canada

1h 50mYYZ-ORD

C$ 191

Search

17/6Sat

directPorter Airlines

1h 47mYTZ-MDW

C$ 192

Search

16/8Wed

directUndisclosed Carrier

3h 25mYYC-ORD

C$ 194

Search

17/6Sat

directPorter Airlines

1h 47mYTZ-MDW

C$ 195

Search

16/6Fri

directUndisclosed Carrier

1h 50mYYZ-ORD

C$ 206

Search

25/9Mon

directUnited Airlines

3h 23mYYC-ORD

C$ 209

Search

5/7Wed

directUnited Airlines

3h 24mYYC-ORD

C$ 211

Search

6/6Tue

1 stopMultiple Airlines

18h 20mYYZ-ORD

C$ 215

Search

25/9Mon

1 stopUnited Airlines

13h 41mYYC-ORD

C$ 215

Search

17/8Thu

directAir Canada

3h 25mYYC-ORD

C$ 218

Search

14/9Thu

1 stopWestJet

6h 13mYVR-ORD

C$ 220

Search

19/6Mon

1 stopUndisclosed Carrier

7h 35mYYC-ORD

C$ 220

Search

16/9Sat

directAmerican Airlines

1h 57mYYZ-ORD

C$ 230

Search

16/9Sat

1 stopDelta

5h 03mYYZ-MDW

C$ 239

Search

7/9Thu

1 stopWestJet

7h 13mYVR-ORD

C$ 240

Search

17/9Sun

1 stopAeromexico

7h 24mYYZ-MDW

C$ 295

Search

7/8Mon

1 stopJetBlue

11h 19mYVR-ORD

C$ 312

Search

Show more results

Search by stops

Direct1 stop2+ stops

Search by airline

Air CanadaPorter AirlinesUnited AirlinesWestJetAmerican AirlinesDeltaAeromexicoJetBlue

Search by price

C$ 190 or lessC$ 210 or lessC$ 220 or lessC$ 230 or lessC$ 310 or less

Recent domestic flight deals

7/11Tue

directDelta

2h 58mBOS-ORD

14/11Tue

directDelta

2h 32mORD-BOS

C$ 133

Search

26/6Mon

directSpirit Airlines

2h 32mDFW-ORD

3/7Mon

directSpirit Airlines

2h 28mORD-DFW

C$ 138

Search

23/8Wed

directJetBlue

2h 38mJFK-ORD

30/8Wed

directJetBlue

2h 16mORD-JFK

C$ 144

Search

2/9Sat

directUnited Airlines

2h 39mEWR-ORD

9/9Sat

directUnited Airlines

2h 14mORD-EWR

C$ 144

Search

13/9Wed

directDelta

2h 41mLGA-ORD

19/9Tue

directDelta

2h 13mORD-LGA

C$ 144

Search

Search by stops

Direct1 stop2+ stops

Search by airline

DeltaSpirit AirlinesJetBlueUnited Airlines

Search by price

C$ 130 or lessC$ 140 or less