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$105 Find cheap flights from Canada to Chicago

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Chicago departing on 6/18. 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.
1 adult
0 bags
Thu 7/11
Thu 7/18

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These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
These are the airlines KAYAK users have selected most often from within our search results for flights to Chicago
In the last 7 days travelers have searched 44,212,782 times on KAYAK, and here is why:

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Flights to Chicago - Travel Insights & Trends

Get data-powered insights and trends for flights to Chicago to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest flight to Chicago?

These are the best prices found by users searching on KAYAK in the last 72 hours.
In the last 3 days, the cheapest flight deal to Chicago was found on the route from Calgary, at $105 one-way and $165 return. The most popular connection is from Toronto to Chicago and KAYAK users have found round-trip deals for as low as $232 in the last 3 days.

What is the cheapest day to fly to Chicago?

The average price of all flights to Chicago clicked on KAYAK for each day over the last 12 months.
Based on KAYAK data, the cheapest day to fly to Chicago is Wednesday where tickets can be as cheap as $366. On the other hand, the most expensive day to fly is Monday, where prices are $476 on average.

What is the cheapest month to fly to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.
The cheapest month for flights to Chicago is April, where tickets cost $303 on average for one-way flights. On the other hand, the most expensive months are November and October, where the average cost of tickets from Canada is $521 and $495 respectively. For return trips, the best month to travel is April with an average price of $239.

What is the cheapest time of day to fly to Chicago?

The average price for all flights to Chicago depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.
The cheapest time of day to fly to Chicago is generally at night, when flights cost $283 on average. The most expensive time of day to fly to Chicago is generally in the evening, which is peak travel time and where the average cost of a ticket is $319.

What is a good deal for flights to Chicago?

If you’re looking for cheap airfare to Chicago, 25% of our users found tickets to Chicago for the following prices or less: From Toronto Island Airport $132 one-way - $222 round-trip, from Toronto Pearson Intl Airport $166 one-way - $283 round-trip, from Vancouver Intl Airport $180 one-way - $268 round-trip.

How far in advance should I book a flight to Chicago?

To calculate daily average prices, KAYAK takes all prices for each day before departure over the last year for flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each month.
To get a below average price, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 37 days before departure.

Which is the cheapest airport to fly into in 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 $107.

Which airlines fly to Chicago?

Airlines flying the most to Chicago from Canada are United Airlines, American Airlines and Air Canada. See the amount of flights per week for popular airlines flying to Chicago.

Which airline offers the most flights to Chicago?

Of the 14 airlines that fly to Chicago, United Airlines offers the most flights, with around 4,937 per week, followed by American Airlines with 3,000 flights per week.

How many airports are there in Chicago?

There are 3 airports in Chicago: Chicago O'Hare Airport (ORD), Chicago Midway Airport (MDW) and Chicago Greater Rockford Airport (RFD). The busiest airport is Chicago O'Hare Airport (ORD), with 80% of all flights arriving there.

How long is the flight to Chicago?

The duration of your flight to Chicago depends on your departure and arrival airports. Obviously any flights that include a layover will also be longer. The most popular routes to Chicago on KAYAK are from Toronto, which takes 1h 53m, Montreal, which takes 2h 31m, Calgary, which takes 3h 25m, and Vancouver, which takes 4h 01m.

How many direct flights to Chicago are there each day?

There are around 1,630 direct flights from within Canada to Chicago every day. Most flights depart in the morning, with 6:00 am the most common departure time and 50% of flights departing in the morning.

How many direct flights to Chicago are there each week?

Each week there are around 11,406 direct flights from within Canada to Chicago. The most common day for departures is Friday, with 16% of flights taking off on this day.

How many long-haul flights are there to Chicago each week?

Each week, there are 28 medium-haul flights (3-6 hour flight duration) and 289 short-haul flights (up to 3 hour flight duration) to Chicago. There aren't any long-haul flights (6-12 hour flight duration).

How many cities have direct flights to Chicago?

From Canada, there are direct flights to Chicago from 7 cities. The city with the most direct flights is Toronto, with 150 direct flights each week.

Good to know

Low season

January

High season

May

Cheapest flight

$105
Best time to beat the crowds with an average 17% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Calgary to Chicago O'Hare Airport

FAQs - booking Chicago flights

  • 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.

  • What is the cheapest flight to Chicago?

    In the last 3 days, the cheapest flight deal to Chicago was found on the route from Calgary, at $105 one-way and $165 return. The most popular connection is from Toronto to Chicago and KAYAK users have found round-trip deals for as low as $232 in the last 3 days.

  • Which Chicago airport is closest to central Chicago?

    There are 3 airports in Chicago. The closest airport to Chicago’s city center is Chicago Midway Airport (9 miles). Chicago O'Hare Airport and Chicago Greater Rockford are respectively 16 miles and 79 miles from the center of Chicago.

  • How much is a flight to Chicago?

    On average, a flight to Chicago costs $342. The cheapest price found on KAYAK in the last 2 weeks cost $124 and departed from Calgary Airport.

  • 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 travelers 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.

See more FAQs

Top tips for finding cheap flights to Chicago

  • Enter your preferred departure airport and travel dates into the search form above to unlock the latest Chicago flight deals.
  • 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.
See more tips

Prefer to fly non-stop to Chicago?

Find which airlines fly direct to Chicago, which days they fly and book direct flights.

Nonstop departures

Canada to Chicago

Monday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

See more direct flights

Nonstop returns

Chicago to Canada

Monday

ANA, Aer Lingus, Aeromexico, +81 more

ANA, Aer Lingus, +82 more

Tuesday

ANA, Aer Lingus, Aerolineas Argentinas, +80 more

ANA, Aer Lingus, +81 more

Wednesday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Thursday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Friday

ANA, Aer Lingus, Aerolineas Argentinas, +82 more

ANA, Aer Lingus, +83 more

Saturday

ANA, Aer Lingus, Aeromexico, +80 more

ANA, Aer Lingus, +81 more

Sunday

ANA, Aer Lingus, Aerolineas Argentinas, +81 more

ANA, Aer Lingus, +82 more

See more direct flights
See more direct flights

Top 5 airlines serving from Canada to Chicago

 
See real verified KAYAK customer reviews for airlines flying to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Canada to Chicago. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.5
Porter AirlinesOverall score based on 380 reviews
7.6Boarding
6.6Entertainment
7.4Food
7.5Comfort
8.2Crew
Airline reviews

Due to mechanical problems it was delayed causing problems the actual flight. Was fune

6.0 GoodAnonymous, Jun 2024YOW - BOS
Read more about Porter Airlines reviews

Due to mechanical problems it was delayed causing problems the actual flight. Was fune

Wish we had music during take off and landing like the last flight

First time with Porter and I can say this is best airline company in Canada. Great service, free WiFi, free snack and drinks (including beer and wine). Seats were super comfy on the Embraer jet and I appreciated the folding try table too. Staff were excellent both legs of the trip.

Tight transfer in Montreal. (15 min) However, we made it, as did my luggage.

The E195-E2 is a great aircraft! Leather seats, lots of legroom and SO quiet! The flight crew is terrific!

Check in was slow because of passenger ahead in Reserve line. Seats were somewhat uncomfortable.

First time with Porter. Amazing experience overall, will be my airline of choice in North America whenever possible. Liked the quality of food and how it was served but one suggestion- a hot meal on the longer flights, perhaps?

Delayed by 2.5 hours. This happened previously on my flight from YOW to YVR on Dec. 26.2023. This is a terrible airline. The reason was there was lack of ground crew. This is a known event. AVOID PORTER AIRLINES IF YOU CAN. There is a reason half the plane was empty.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10 Tips for people flying porter from Boston. The airline doesn’t have inflight entertainment No TV No WIFI. Bring your entertainment with you.

The airline arrival at the downtown airport is a big plus.. Food and beverage was excellent. Their non weather related cancellation is horrible. Overall I gave the airline 7 over 10

It was fine. I had a lot of trouble trying to buy a seat. The Westjet website charged me and then didn’t give me my seat. I ended up keeping the seat I was assigned and hope that the charges didn’t go through.. they didn’t. But this problem with the website (trying to purchase a seat at check in) has happened a few times before. But overall the flight was good.

Terrible! Delayed three times, landed at some corner of airport, walked in bitter cold night, took a bus, bad experience

My wife and I had an uncomfortable experience with your WestJet ticket counter rep at the WestJet Priority Member ticket counter at YYC (Calgary) on May 15, 2024. I not knowing this individual’s exact name, however, in order to easily identify her, she was one (of only two at the time) ticket counter reps at your Priority members ticket counter check-in, upon our arrival around 12:15 p.m. She was a Caucasian woman with blonde hair, and wore spectacles, approximate age being probably somewhere in her 30’s or 40’s. Background: After arriving in to the West Jet terminal in Calgary (YYC), I asked a terminal employee where the West Jet check-in ticket counter was. He told me, “Column 16”. My wife and I continuing to walk through the terminal, we finally arrived at the Column 16 area, i.e. this woman’s ticket counter area, which we discovered later was the Priority Member ticket counter. However, I was simply going by the directions given to me by the previous employee, i.e. “Walk to column 16.” Standing in her line (my wife and I being the only people in her line at the time), I tried to get her attention, and I then gestured to her, motioning to her as if to ask her if I should then possibly leave the waiting line in order to then proceed to walk up to her ticket counter. She never really motioned me to come forward. I sort of had to figure this out on my own, as my wife and I then finally decided to walk forward to her station. From this point on, after I arrived at her ticket counter, never once did she ever look me in the eye. She was always looking at her computer screen, or down at the ground, as she and I occasionally exchanged conversation with one another in order for me to be able to acquire my boarding passes from her. Shortly after she began servicing us, she commented that her work section is for Priority members only. Fair enough. I did not realize this at the time. Wishing to be polite, I then mentioned to her that, if I should, I could then walk over to the regular West Jet check-in ticket counter in order to complete the check-in process. She remained quiet, never responding to this goodwill gesture of mine. She continued to work in order to print out my boarding passes, and then finally handed them to me, never at all the entire time looking at me. I told her, “Thank you.” Never once did she respond. My wife and I then walked away. Even my wife commented to me afterward that this woman absolutely never looked at us. I cannot say that this attendant was outright rude. However, she certainly was not at all warm, congenial, nor friendly. Additionally, … After getting on the plane, we then discovered that she had needlessly assigned us seats in the very last row of the plane, these being the seats adjacent to the restroom back wall, thus, unfortunately not at all reclinable. I think that the row number of this last row of seats was 30. [However, I am not sure.] How strangely awkward that we were assigned these uncomfortable row of seats when in fact the row immediately ahead of us, i.e. I think that was row 29, had two vacancies, which could have otherwise easily seated my wife and me. That is, my wife and I could have easily been assigned these more comfortable seats, which would be reclinable, and then row 30 could have otherwise had instead our two vacancies. After our flight departed, and the fasten seatbelt sign was turned off, my wife and I had hoped to “jump seats”, that is, to leave row 30 and instead sit in row 29 to utilize the reclinable seats. However, another couple apparently had the same idea as us. That is, these other two people, for whatever reason, decided to leave their previously assigned seats, and instead, seat themselves in row 29. Thus, my wife and I were stuck with these miserably cramped row 30 seats for the entire 3.5 hour flight. To reiterate, the WestJet rep we originally encountered, knowledgeable of the plane lay-out as it appeared on her computer screen, could have easily assigned us the more comfortable row 29 seats, instead of the non-reclinable row 30 seats.

It was very, very cold extremely uncomfortable almost unbearable I was sitting at the front of the cabin

Was the longest flight I have ever taken to Orlando. Not Westjet’s fault necessarily. There was a traffic issue in Orlando. We sat in the airplane for about 2 hrs before leaving Calgary on a 5 hour flight was just a little long to be stuck in the plane. Once we arrived in Orlando we were stuck in traffic on the ground for another 30min. I guess maybe the flight could be delayed so boarding would have been later so we wouldn’t have to have the discomfort of being on the plane so long.

Airport monitors did not give the gate for our flight returning Detroit to Vancouver Juice served from glass storage containers are a far more healthy alternative for people. And would also minimize the need for recycling plastic or aluminum containers

I wish that seats closer to the front of the plan were available, but when I booked the flight the seats were VERY expensive so I did not book seats at that time. The day before flying only seats at the back of the plane were available. It takes so long to board the plane and empty the plane on arrival due to SO many roller bags.

Good flight. No I’m seat entertainment. But my phone worked just fine on the west jet app.

I had planned to watch the Westjet entertainment for the entire flight however, because the seat mounted outlets in our row did not work.

Not a bad flight but our priority tagged luggage was the very last to come down the carousel.

It is a modern tragedy that any airline expects you to travel for 14 hours in such discomfort and that the only way to add comfort is exorbitant prices. I was in pain by the time we landed. Shameful.

After the morning frenzy of 35 min wait through CLT security at 4;30 AM, it was nice to have a smooth pleasant boarding experience. This 6:30 AM flight was not full. We were able to get seated swiftly and took off promptly. Nice touch they distributed the old fashioned headsets with 8 mm jacks. Snacks were decent and arrival was uneventful.

I had a great flight. Everything went smoothly and the flight arrived early.

The flight and boarding were easy peasy. I was traveling with my 4-year-old, so a smooth boarding experience was especially appreciated. My only piece of feedback is really about where our gate was in O'Hare. They've shoved four gates into a tiny corner of the B terminal and there isn't early enough room or seating for everyone. Not United's problem, but did dent the overall experience.

It was good! Appreciated that it was very on schedule so it made the connecting flight less stressful

I was told we'd have a hot breakfast option in first class, so I chose not get a hot breakfast. It was a very strange meal, but the fresh fruit was very good quality. Service was excellent from ORD to ELP. No service from MBS to ORD, not even water. However, when flying American from FNT to ORD, which is a shorter flight, they at least pass out snacks and offer water.

We were delayed an hour leaving Munich (No fault of the crew). They kept us posted on the status so we knew what was going on, but as a result we missed our connection in Chicago and the communication on connecting flights was pretty poor as we disembarked. It was already stressful and some of that could have been reduced by better communications about where to find transfers, etc.

One problem, but a serious one - the plane is built with electric windows that tint dark to reduce light. Sitting next to the window is VERY UNCOMFORTABLE as it emits so much HEAT in the face when tinted.

The delays (5 hrs) were a comedy of errors, and the multiple safety issues encountered were very concerning.

Wifi wasn't working on one of the UA flights after boarding.

Good with British Airways - terrible with American Airlines! Stood at gate for “mechanical problem” - plane delayed. Had to check my personal belonging with 5 empty bins available in plane, desk staff rude!!! Toilet not working- asked “to use working toilet sparingly - it may overflow in cabin!”

Internet service was erratic. Crew service was poor and slow. My luggage on this non-stop flight was lost and not recovered

Left on time. Arrived early. Turbulence coming in and gate not open due to early arrival but expected.

The CX617 from HK to BKK was delayed more than 1.5 hours.

The plane was old and in new of a cleaning up and renovating on the interior. Seats and carpets were very worn and dirty looking. Cushioning on the seats was broken down and not as comfortable as newer jet seats. Food was a little below average but okay. Staff were friendly and hard working but did not pick up debris or food they spilled when collecting from the customers. But they were very helpful and professional.

This flight is frequently delayed. The connections seemingly are more frequently delayed. I’ve missed connections as a result twice on the same route to charlotte then Charleston. Final destination arrival has been the next day, twice in a row. No pilots, no crew. Too many excuses. Unfortunately, my days with American are over.

Entertainment was okay not because anything was wrong but it is a short flight so having no wifi is annoying but understandable. Crew was outstanding as usual

Those seats were way too narrow. I had the middle seat, one person was a very skinny person and we still couldn’t avoid touching each other anytime one of us moved. The other person was larger and we were basically sitting in each others lap the entire flight. There was zero entertainment. The flight was long enough to justify tvs, but no. Gotta sit there in your infant seat and twiddle your thumbs.

Flight was fine. It took an unusually long time to have baggage delivered to the carousel in ORD.

Average - flew with Jet Blue internal and it was far more comfortable and better food and entertainment. Notable difference

The flight was very turbulent. The who 3 hours we mostly needed seat belts. Plane is older and does not have tv screens so no entertainment.

Experienced flight cancelations and delays in 5 days. They seem pretty common to AC. Experienced with one of AC's check-in agents at the counter of a big liar. She lied and acted (yes like acting in a movie) that an early flight was fully booked and refused to rebook me, but my flight was delayed two hours so I could not make my connection. Later, I got help at the gate to switch the early flight (Big thanks to that agent). Ater boading, I found the early flight was only 2/3 full meaning there was almost one vacant seat in a 3-person seater, and multiple empty 3-seaters. AC is wired that it is filled with good and bad employees. BTW, AC employees seem never smile, or they don't know how.

Not much food/snacks. I had just tea and it was so bitter.

My husbands flight last night Vancouver/Sydney was 90 minutes late in leaving. My flight tonight Vancouver/Seattle was also late in departing.

My mother, 80years old, had arranged for wheelchair assist to and from the aircraft cabin and in the airport but, no one showed up for her to de-plane. Apart from Air Canada having a reputation of being late for every leg of its flight so nothing was new this time so this time they did worse by not assisting seniors. I guess our whole family is done with this airline

Flights delayed over 4 hours with no compensation. No agents at counters to assist with re-booking.

Seating for almost 3 hours in the plan before aircraft takeoff. Very exhausted .

The bathroom did not have hand soap. That is unacceptable.

The only problem I encountered was they changed the gate on me while I was sitting down but no one notified me, they had sent me an email and by coincidence I checked it and found out that they had changed my boarding terminal. No one notified me and when I had asked the lady she told me yes this is the spot while they had already changed to another gate/terminal

I was seated next to someone who was, to be polite, not a small person. I had to press myself against the wall as I had no personal space. Aside from that the crew was wonderful and they got me home safely, which is the most important part of my journey. I am very appreciative to your air crews for the job they have, which isn't easy, and appreciative of the fact that they are professional and courteous. The employees I encountered on my journey, with the few exceptions I mentioned in a previous review, are a credit to Air Canada.

Book cheap flights from Canada to Chicago

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Chicago found on KAYAK in the last 72 hours.
9/28Sat
nonstopWestJet
3h 39mYYC-ORD
10/5Sat
nonstopWestJet
3h 50mORD-YYC
$165
6/27Thu
nonstopWestJet
3h 27mYYC-ORD
7/4Thu
nonstopWestJet
3h 45mORD-YYC
$199
6/27Thu
nonstopPorter Airlines
1h 47mYTZ-MDW
6/30Sun
nonstopPorter Airlines
1h 42mMDW-YTZ
$221
8/12Mon
nonstopPorter Airlines
1h 47mYTZ-MDW
8/20Tue
nonstopPorter Airlines
1h 42mMDW-YTZ
$222
7/11Thu
nonstopAir Canada
1h 57mYYZ-ORD
7/11Thu
nonstopAir Canada
1h 43mORD-YYZ
$232
9/5Thu
nonstopUnited Airlines
1h 56mYYZ-ORD
9/9Mon
nonstopUnited Airlines
1h 32mORD-YYZ
$233
9/17Tue
nonstopUnited Airlines
1h 56mYYZ-ORD
9/17Tue
nonstopUnited Airlines
1h 48mORD-YYZ
$234
9/16Mon
nonstopAir Canada
1h 53mYYZ-ORD
9/21Sat
nonstopAir Canada
1h 32mORD-YYZ
$235
9/6Fri
nonstopAmerican Airlines
2h 36mYUL-ORD
9/8Sun
nonstopAmerican Airlines
2h 10mORD-YUL
$241
7/1Mon
nonstopAmerican Airlines
1h 55mYYZ-ORD
7/2Tue
nonstopAmerican Airlines
1h 35mORD-YYZ
$251

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Chicago found on KAYAK in the last 72 hours.
6/18Tue
nonstopWestJet
3h 27mYYC-ORD
$105
7/12Fri
nonstopWestJet
3h 27mYYC-ORD
$106
8/30Fri
1 stopAir Canada
7h 54mYYC-ORD
$124
7/3Wed
1 stopUnited Airlines
15h 05mYYC-ORD
$128
6/18Tue
1 stopUnited Airlines
15h 30mYYC-ORD
$130
7/18Thu
1 stopPorter Airlines
4h 27mYUL-MDW
$131
7/9Tue
1 stopAir Canada
7h 41mYYC-ORD
$134
7/3Wed
nonstopPorter Airlines
1h 47mYTZ-MDW
$134
9/16Mon
nonstopAmerican Airlines
2h 36mYUL-ORD
$148
7/1Mon
nonstopAmerican Airlines
1h 55mYYZ-ORD
$155

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Search by price

Last minute flights to Chicago

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Chicago that are departing in the next 10 days.
6/14Fri
multi-stopAlaska Airlines
7h 05mYVR-ORD
6/20Thu
multi-stopAlaska Airlines
8h 17mORD-YVR
$275
6/13Thu
multi-stop
8h 35mYVR-ORD
6/17Mon
multi-stop
8h 22mORD-YVR
$277
6/13Thu
nonstopAmerican Airlines
4h 13mYVR-ORD
6/17Mon
nonstopAmerican Airlines
4h 40mORD-YVR
$294
6/14Fri
nonstopAir Canada
4h 01mYVR-ORD
6/15Sat
multi-stopAir Canada
8h 50mORD-YVR
$295
6/13Thu
nonstopAmerican Airlines
4h 13mYVR-ORD
6/17Mon
multi-stopAmerican Airlines
9h 05mORD-YVR
$318
6/15Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
6/24Mon
nonstopPorter Airlines
1h 42mMDW-YTZ
$335
6/16Sun
nonstopAir Canada
1h 54mYYZ-ORD
6/18Tue
nonstopAir Canada
1h 48mORD-YYZ
$365
6/15Sat
nonstopPorter Airlines
1h 47mYTZ-MDW
6/22Sat
nonstopPorter Airlines
1h 42mMDW-YTZ
$379
6/16Sun
nonstopUnited Airlines
4h 02mYVR-ORD
6/25Tue
multi-stopUnited Airlines
6h 47mORD-YVR
$386
6/14Fri
nonstopUnited Airlines
2h 02mYYZ-ORD
6/17Mon
multi-stopUnited Airlines
11h 19mORD-YYZ
$496

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