$136 Find Cheap Flights from Canada to Chicago - Compare and Save

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 8/26. 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.
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Cheap Flights from Canada to Chicago

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Canada to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Canada to Chicago

Wed, Sep 9 - Wed, Sep 16
Air Canada Logo
4:00 pm - 8:12 pm
YYZ
-
ORD
5h 12m
1 stop
Air Canada Logo
9:55 am - 12:40 pm
ORD
-
YYZ
1h 45mnonstop
$205Air Canada
Mon, Sep 7 - Mon, Sep 14
Air Canada Logo
2:00 pm - 2:55 pm
YYZ
-
ORD
1h 55mnonstop
Air Canada Logo
11:05 am - 6:12 pm
ORD
-
YYZ
6h 07m
1 stop
$205Air Canada
Mon, Aug 31 - Mon, Sep 21
Porter Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
3:20 pm - 6:00 pm
MDW
-
YTZ
1h 40mnonstop
$206Porter Airlines
Tue, Aug 25 - Wed, Sep 9
Porter Airlines Logo
8:55 am - 9:45 am
YTZ
-
MDW
1h 50mnonstop
Porter Airlines Logo
11:45 am - 2:25 pm
MDW
-
YTZ
1h 40mnonstop
$207Porter Airlines
Fri, Sep 4 - Tue, Sep 8
United Airlines Logo
8:50 am - 9:53 am
YYZ
-
ORD
2h 03mnonstop
United Airlines Logo
9:18 pm - 11:59 pm
ORD
-
YYZ
1h 41mnonstop
$209United Airlines
Fri, Sep 4 - Wed, Sep 9
United Airlines Logo
11:00 am - 12:00 pm
YYZ
-
ORD
2h 00mnonstop
United Airlines Logo
12:59 pm - 3:46 pm
ORD
-
YYZ
1h 47mnonstop
$209United Airlines
Thu, Sep 24 - Sun, Sep 27
Multiple Airlines Logo
5:15 pm - 6:30 pm
YYZ
-
ORD
2h 15mnonstop
Multiple Airlines Logo
8:40 pm - 11:26 pm
ORD
-
YYZ
1h 46mnonstop
$209Multiple Airlines
Fri, Sep 11 - Sun, Sep 13
Multiple Airlines Logo
10:15 am - 11:21 am
YYZ
-
ORD
2h 06mnonstop
Multiple Airlines Logo
8:40 pm - 11:26 pm
ORD
-
YYZ
1h 46mnonstop
$209Multiple Airlines
Sat, Aug 29 - Mon, Aug 31
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$220WestJet
Sat, Aug 29 - Mon, Aug 31
WestJet Logo
12:00 pm - 4:40 pm
YYC
-
ORD
3h 40mnonstop
WestJet Logo
5:30 pm - 8:25 pm
ORD
-
YYC
3h 55mnonstop
$222WestJet
Booking Insights

KAYAK's insights & trends for flights to Chicago

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 round-trip prices found by users searching on KAYAK in the last 5 days.

In the last 5 days, the cheapest flight deal to Chicago was found on the route from Toronto, at $205 return. The most popular connection is from Montreal to Chicago and KAYAK users have found round-trip deals for as low as $269 in the last 5 days.

How much is a flight to Chicago?

The average and cheapest price for all round-trip flights to Chicago from each origin found by users searching on KAYAK in the last month.

A flight to Chicago costs $439 on average. The cheapest price found on KAYAK in the last 2 weeks cost $111 and departed from Toronto Island Airport. The most popular routes on KAYAK are Montreal to Chicago which costs $575 on average, and Toronto to Chicago, which costs $574 on average.

See prices from:

What is the cheapest day to fly to Chicago?

The average price of all round-trip 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 Friday where round-trip tickets can be as cheap as $461. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $659 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 round-trip 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 September, where tickets cost $279 on average for return flights. On the other hand, the most expensive months are July and June, where the average cost of tickets from Canada is $354 and $351 respectively. For one-way flights, the best month to travel is October with an average price of $200.

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

The average price for all round-trip 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 round-trip flights cost $390 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 $718.

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 $206 round-trip, from Toronto Pearson Intl Airport $360 round-trip, from Calgary $365 round-trip.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Chicago, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price, you should book around 4 weeks before departure, which saves you about 49% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks 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 Greater Rockford Airport (RFD), with an average flight price of $176.

Good to know

Low season

January

Cheapest flight

$136
Best time to beat the crowds but there is an average 12% increase in price.
Most popular time to fly and prices are also 1% lower on average.
Flight from Toronto Pearson Airport to Chicago O'Hare Airport

Flights from Canada to Chicago: the best tips from KAYAK users

Insights shared by verified travelers who flew the route from Canada to Chicago 
MMFlew with United Airlines
YVR
-
ORD
Jan 2026
Pay extra for Boarding Zone 2 to make sure your carry on, gets on the plane.
LisaFlew with United Airlines
YWG
-
ORD
Dec 2024
Turn on your data or the wifi in case gates change.
Verified travelerFlew with WestJet
YYC
-
ORD
Jun 2024
checkin luggage online as they jack up the price 100% at airport
Verified travelerFlew with United Airlines
YUL
-
ORD
Apr 2024
Come prepared with your own entertainment as the flight did not offer in flight entertainment
Verified travelerFlew with United Airlines
YYZ
-
ORD
Mar 2024
Carry-on baggage sizing for United US bound flights appears to be much smaller than for Canadian flights, which forced me to check my bag at the last minute. So check online ahead of time

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 5 days, the cheapest flight deal to Chicago was found on the route from Toronto, at $205 return. The most popular connection is from Montreal to Chicago and KAYAK users have found round-trip deals for as low as $269 in the last 5 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 $439. The cheapest price found on KAYAK in the last 2 weeks cost $111 and departed from Toronto Island 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.

Top tips for finding cheap flights to Chicago

  • Looking for a cheap flight? 25% of our users found flights on this route for $254 or less one-way and $388 or less round-trip.
  • 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.

Reviews of the 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.
8.0
Porter AirlinesOverall score based on 448 reviews
6.9Entertainment
7.5Food
8.0Comfort
8.2Boarding
8.6Crew
Airline reviews

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

4.0 OkayJeff, Jul 2026
YYZ - SFO
Read more Porter Airlines reviews

Look, I understand that Kayak doesn't know I cancelled my flight on Porter. So I didn't actually fly yesterday. My main disappointment is with Porter ticket fare policies, and maybe you can pass this on to them: At my employer's request, I had booked a full fare ticket with no change fees since my trip to Toronto would likely be extended. Indeed, when I went to change my flight home to a later date, I was told the Fare Difference would cost an additional $550. So much for no change fees lol! While I had the agent on the line, I hopped over to Kayak, searched for new flights on the date in question, and saw a one-way ticket that got me home for only $355. So I got reimbursed about $450for the unused half of my roundtrip and bought a new ticket for $355. What good is a full fare / no change fee ticket if they screw you with "fare difference" BS. I'm still flying home on Porter Airlines but they just lost a hundred bucks with their stupid shenanigans.

I flew with Porter yesterday and overall had a positive experience. The flight was delayed, but the airline did a good job keeping passengers informed with frequent updates throughout the process. My biggest challenge was actually in Terminal 3, where the speaker system wasn’t very clear. It was often difficult to hear the announcements, which made it harder to follow updates at the gate. On board, the experience improved significantly. The aircraft felt very new and well maintained, and the seats were surprisingly comfortable for a short-haul flight. One of the flight attendants seemed a little disengaged, but the other was excellent—friendly, professional, and a pleasure to interact with. Despite the delay, the comfortable aircraft, clear communication from Porter, and positive onboard service made for a good overall experience.

It was okay. Had a thing with the front desk, she had me repack my suitcases to have them be under the weight restrictions, but then the other one was overweight, she argued with me about it when there were tons of people in line. Wasn’t great.

Organization and the adjusted times but the snacks could be of a bigger portion

Our flight was delayed by a bit. I appreciated that we were kept informed on why periodically. Boarding was fine. I overheard one flight attendant sounding very rude to a passenger who was not paying attention to the safety demonstration. The snacks were minimal as it was a short flight. There was no entertainment. Overall the flight was good back to LGA.

All good the seats a little tight and no I pad screen

Just an evening before they canceled my ticket and offered me ticket costing 3 x times more than. I will not fall prey to these scams,Will never book through kayak now. Such a bad experience.

was okay except.. 1)the porter check in webpage doesn't let you print your boarding pass from home 2)that there was a 90 min cut off for checking in on the kiosk in general, and to print a boarding pass, even tho i checked in online already....

It was amazing although they did bump us up to the front which gave us more leg room and a meal. The service was great! The staff were friendly. :)

The flight was delayed by more than one hour. The terminal was consequently overcrowded and hot. We lost our car reservation and hit rush hour traffic in Boston, which added two hours stuck in traffic to our trip.

Prefer not to have an almost 3 hour delay with useless communication that wasn't accurate.

Starlink is great Crew was polite Business class didn’t get a welcome drink just water and snacks were ok

very average service no complimentary alcoholics drinks unlike other airlines such as Porter airlines No decent seats available during check-in time the day before

Reliable, nice crew, I fly often on that flight and I like it all.

Efficient all round, very good crew. Short flight so the food, of course, was just snacks

My flight was delayed about 1 1/2 hours in Chicago, but other then that it was a good flight.

So far so good but food and entertainment are not available for this flight

It was my first time with United Airlines and I would say it was very good experience and best of all the flights were on time. Will definitely fly with United Airlines next time.

lots of delays the crew were unclear about where to pick up my carry-on, which they took from me to check in on the plane.

They needed people to check a bag, they did check my bag and I had to wait 10 minutes after the flight to get it it wasn’t too bad

Our itinerary included a 1 hour and 30 minute layover, which should have been sufficient under normal circumstances. However, our original flight was delayed. Before we even deplaned, we were instructed to collect our checked bags from baggage claim, clear immigration and customs, and then recheck our bags for the connecting flight. The airline knew—or should have known—that this was impossible. Checked baggage acceptance closes one hour before departure, meaning there was no realistic way for passengers from the delayed flight to recheck their bags in time. Despite this, the airline gave us misleading instructions instead of informing us that we would likely miss our connection. We completed immigration and customs in approximately 10 minutes, but our checked bags did not arrive at the carousel for more than 30 minutes. After collecting them, we had another 10-minute walk to the baggage drop area, only to find that no airline attendant was present. We then went to another airline counter, where an employee told us this had happened before and that there was nothing they could do because the baggage acceptance window had already closed. At that point, there were still 40 minutes remaining before our flight's departure, yet no one was willing to assist or offer a practical solution. When we asked to be rebooked, we were simply told to call the airline's 800 number ourselves. There was no accountability or customer support at the airport, leaving us stranded in a foreign country with no immediate assistance. After finally reaching an agent on the 800 number, we were rebooked on a flight for the following day. However, we were initially told that the airline would not provide any hotel accommodation and that we would have to arrange and pay for it ourselves. Only after making multiple calls and speaking with several different agents did one representative finally issue a hotel voucher. The entire experience was an exhausting and frustrating ordeal. What should have been a 20-hour journey ultimately became more than 30 hours due to the airline's poor planning, misleading instructions, lack of accountability, and inadequate customer service. The unnecessary delays, confusion, and absence of meaningful assistance caused significant physical exhaustion and severe mental stress. This experience fell far below the level of service passengers should reasonably expect.

Despite travelling ultra basic for the first time due to such increased rates we both managed with one bag each. Even boarding last wasn’t SO bad.

I loved the fact it was on time and it was a smooth flight to my destination.

Service was okay except attendant over served alcohol to passenger and passenger got tipsy and made me uncomfortable

Could not make the flight. No one would help us at all

The agents at the Kelowna YLW airport were really grumpy. Same with oversized baggage person. Staff on the plane were great.

Flight was early. That’s the only positive I can share. I paid for wifi on the flight and it didn’t allow me to use any streaming services so it was a waste of $20. West Jet also lost my ski equipment on my way to a ski vacation. They told me it would be delivered to the hotel as soon as it arrived at the airport. It was never delivered. I had to pick it up at the airport on my way home. I am completely disgusted with my experience on west jet

The window seat on the emergency row was too small. I had a different seat booked and they moved me. My seat remained open. It was very uncomfortable.

Experience was good, the wifi hook up is somewhat tough

Great flight, great landing, nice staff. Our seats were a little cramped.

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

Take this flight regularly. Every single week same thing. Departure delayed. Make up some time in the air. Land at ORD and then wait for gate in "L" concourse Terminal 3 for 30-40 min-which yields a very delayed final arrival. Plus I get to taxi around and see every runway and drive over the bridge (IFKYK) over the expressway 2-4 times in most cases. Change the sched of incoming plane/work with FAA to improve traffic flow at ORD/change the timing of these flights. Whatever it takes. But do better.

- flight was delayed several hours due to weather (understandable) - flight delayed further and we were told by attendants "we are not sure where the pilots are but they are on their way" as we have to find different pilots for the flight - announcements over the PA were somewhat unprofessional by the attendants, seems they need more training and were not reading off the script. They showed their young age and immaturity in their communications with the passengers. They were not clear and lacked professional communication language. - going from a hub to hub we were also parked at the tarmac at ohare for an additional hour and kept being told "few more minutes". Please just let the passengers know the real wait time instead of hiding the truth. We understand there is traffic and weather delays, but we just want transparency. There are several logistics of our lives that revolve around what the attendants and pilots are sharing with us but they are not being transparant.

Boarding and Delays The boarding process for my American Airlines flight from Copenhagen to Philadelphia was a bit tricky. We experienced a gate change that required a long walk to a new area of the airport. Additionally, boarding was not via a jet bridge; we had to take a shuttle bus to the plane and then carry our luggage up the stairs ourselves. Furthermore, the bag drop didn't open until about 12:20 PM, which was only three hours before our scheduled departure. This meant I couldn't drop my bag off early and had to wait outside of security in order to drop off my bag and use the kiosk. The bag drop self-service kiosks also didn't open until about 12:00 PM when an American Airlines employee unlocked them so that we could print out our boarding passes and bag tags, which further created a backlog. The flight was delayed by over an hour because we had to wait for one of the tires on the plane to be changed. Flight Attendant Professionalism On a positive note, the flight attendant was very professional when handling a passenger who was sitting in the wrong seat. Even though the passenger was persistent and reluctant to move, the flight attendant calmly ensured the assigned passenger could take their seat. Kudos to the flight attendant for keeping his calm and composure, not allowing the issue to escalate, and handling it well under pressure while a line of passengers waited in the aisle to board. In-Flight Service The in-flight service was also fast, prompt, and efficient, although service had to be suspended for the last two hours of the flight due to weather and turbulence, which was outside of the crew's control. Limited Flight Options Please note that American Airlines only operates one flight per day in and out of Copenhagen. This means there are limited options available if your flight is delayed or canceled, which is something to take into consideration when booking.

This may have been the hottest cabin temperatures I have experienced on any flight prior to take off lasting for approximately 30 minutes. I am not typically one to complain but I was genuinely worried about the health of several passengers on the flight due to the extreme temperatures including a small toddler.

I will never but. through kayak again. and American Airlines. I will never fly again on. They're both thieves.

The flight was on time and crew were nice, seats were tight and there was entertainment available

Worst flight ever. I was suppose to have a 3 1/2 hour layover in Chicago but got to the gate 4 minutes before boarding.

lounge was the highlight - seats weren't that comfortable - it was a full flight but no complaints

Incompetent crew at the boarding counter. Never flying AA again.

After 3 hours of delays, they ended up cancelling my flight. And although I could purchase one-way tickets to get to my destination, they would not offer me these flights as compensation for the cancelled flight, and I didn't end up making it home until 13 hours after I was originally supposed to arrive. It made for an extremely strenuous end to an otherwise good trip.

It's kindof ridiculous that your system is even asking me about this since my flight was canceled and I wasn't rescheduled.

Bad service as well. Another 3hr delayed flight from chicago to Charlotte.

Terrible. 3 missed flights and 24 hours delayed with lost bag and promised $100 compensation from United and absolutely nothing from them…

flight was delayed 6 hours for weather, then cancelled because of the crash in toronto, but none of the links to cancel or rebook my flights are working

Minimal food offered (crackers). Had to clean the seat with a wet wipe because of dried food.

They charge 5 dollars for plastic headphones for a flight of 1 hour! Seats are awful. Service is terrible.

Everything was seamless. I would have appreciated knowing there would not be any real food available for purchase in advance. Otherwise a great experience. Thank you!

I was mostly pleased. My greatest disappointment was with respect to the timely update to the estimated departure and arrival times. It was especially sad that the arrival time was not updated online once we were in flight so as to allow my wife to arrive on time to the airport. She was not happy.

I needed to catch a United flight. There wasn't enough signage or help on arrival to navigate the transfer.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Saint Joseph
Hammond
Portage
Lansing
Valparaiso
Munster
Schererville
Chesterton
Porter
Monticello
Saint John
Griffith

Everything you need to know for your flight to Chicago

Cabin class types available on flights to Chicago

Cabin classes available on flights to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.