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Find Cheap Flights from Chicago

Where can I fly from Chicago?Prices from CHI, departing Sat 12/6 and returning Sat 12/13
Booking Insights

KAYAK's insights & trends for flights from Chicago

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

Which are the most popular places to fly to from Chicago?

The domestic destinations KAYAK users have most searched for when searching for flights from Chicago.
Based on KAYAK flight searches, the most popular place to fly from Chicago is New York (17% of total searches). The next most popular destinations are Dallas (6%) and Las Vegas Harry Reid Intl (5%).

What are the most popular international flights out of Chicago?

The international destinations KAYAK users have most searched for when searching for flights from Chicago.
There are many international destinations you can fly to from Chicago. The most popular international destinations among KAYAK users are Punta Cana, Tokyo and London.

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

The most popular countries KAYAK users have searched for from Chicago along with the average round-trip price for the route clicked by KAYAK users in the last 2 weeks.
Based on KAYAK flight searches, the most popular country to fly to from Chicago is Mexico (18% of total searches). The next most popular destinations are Turkey (11%) and United Arab Emirates (9%).

Which cities can I fly to direct from Chicago?

There are loads of places you can fly direct to from Chicago. The most popular destinations for direct flights among KAYAK users are Jacksonville, Los Angeles, Honolulu, Fayetteville and St. Louis. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Charlotte at $206, while the most expensive was Honolulu, at $394.

Which international cities can I fly to direct from Chicago?

There are many international destinations you can fly to non-stop from Chicago. The most popular international destinations from KAYAK users are Oranjestad, Puerto Vallarta, Guadalajara, Morelia and Guatemala City. On average, the cheapest of these destinations on KAYAK over the last 2 weeks for a return flight was Guatemala City at $186, while the most expensive was Oranjestad, at $751.

What is the longest direct flight from Chicago?

The longest direct flight you can take from Chicago is to Taipei City Taiwan Taoyuan Intl Airport, with a duration of 15h 55m. The next longest is Hong Kong at 15h 50m, followed by a flight to New Delhi at 15h 50m.

What are the cheapest places to fly to from Chicago?

The cheapest destination for a flight from Chicago found on KAYAK in the last two weeks was Miami and cost $29. The next cheapest destinations were New York at $29 and Houston at $29.

Good to know

Low seasonSeptember
Cheapest flight$44
Best time to beat the crowds with an average 18% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Chicago O'Hare Airport to Orlando

Flights from Chicago: the best tips from KAYAK users' own experiences

Insights shared by verified travelers who flew from Chicago to anywhere 
Verified travelerFlew with British AirwaysORD-LHRJun 2025
Get a wheel chair if you have difficulty walking
RogerFlew with Japan AirlinesORD-PITJun 2025
Make sure when you go from one airline to another that your bag is marked properly so they can get it on the right damn airplane. I did that and it still didn’t make it.
Verified travelerFlew with United AirlinesORD-LASMar 2025
If you can select your seats in advance please do
JoeFlew with IberiaORD-LHRApr 2025
Get there early. Nice airport options while you wait.
Verified travelerFlew with IberiaORD-LHRMay 2025
Get to the airport early so you’re relaxed. Con yourself into believing it’s bedtime and try to sleep so that you can keep going all day when you get there. If you can afford more comfy seats it might be worth it - though I always have the cheap ones so I can’t say for sure. Try very hard not to. sit in the middle. I’m small and the guy next to me played games all night and didn’t care that he continually ( with every move) jabbed me with his arm. This was my first flight with Cheap Flights and it was far less convenient than other times I’ve flown overseas.
AndreaFlew with United AirlinesORD-ATLMay 2025
Ask for stewards to assist and provide amenities or you won’t get them.
Verified travelerFlew with EVA AirORD-TPEFeb 2025
Coming from Chicago which is also a busy airport, I recommend checking in online prior to thetrip. Make sure luggages follow the required weight and go directly bag drop. You may also want for the attendants to print your boarding pass with the recent details on boarding gate number and zoning.
Verified travelerFlew with ANAORD-HNDJan 2025
Consider light carry-ons to give yourself stretch room for economy and quick onboarding and off boarding especially with connecting flights.
TFlew with Scandinavian AirlinesORD-CPHJan 2025
Don’t forget you can pinch and slide the headrest up and down for maximum sleeping comfort.
Verified travelerFlew with American AirlinesORD-TPADec 2024
I recommend having movies and songs downloaded on your device.
DarylFlew with Cathay PacificORD-HKGJan 2025
They are strict with carry on and they weigh it upon check in.
JanieFlew with SWISSORD-PHXFeb 2025
I think you should prebook food or bring your own food.
valerieFlew with Air CanadaORD-YULJan 2025
“Meal” usually means more than a light snack. I thought what they served was an appetizer not the total meal. So I’d eat before or bring food.
Verified travelerFlew with Spirit AirlinesORD-LASSep 2024
Make sure you get your seats booked at time of booking or at the least when you check in and make sure you check in at the earliest to have preferred seating.
MikeFlew with American AirlinesORD-LAXSep 2024
Arrive early, grab a bottle of soda before getting on the plane and open it in the terminal. If you wait until flying the pressure will decarbonize the drink.
Verified travelerFlew with SWISSORD-ZRHSep 2024
Bring a neck pillow and a heavy sweater bc it does get cold. I used the blanket for my legs. Also: get a seat in the aisle.
Verified travelerFlew with Alaska AirlinesORD-PDXSep 2024
Not many amenities at the terminal. I would suggest grabbing anything that catches your eye before you get all the way down. There weren't a lot of Alaska flights out of Chicago, and we were at the extreme end of the terminal.
Verified travelerFlew with Cathay PacificORD-HKGNov 2024
First flight to hkg but been to asia many times. Most airlines have frequent beverage service to combat the dehydration that comes with a long flight.
DevikaFlew with Etihad AirwaysORD-AUHSep 2024
I wish I had known how much walking I had to do to the transfer terminal from landing to transfer gate.
Verified travelerFlew with Porter AirlinesMDW-YTZSep 2024
Please start bags check-in at least 2.5 hour before flight and finish at 30 min before flight.
Verified travelerFlew with United AirlinesORD-FRASep 2024
Be prepared to wait in long line for boarder control. Allow enough time for your layover
mauriceFlew with IberiaORD-JFKSep 2024
You should arrive early, take a lighht snack and be prepared for delays.
RuthFlew with United AirlinesORD-AMSOct 2024
Facial recognition seemed to slow boarding down, not speed it up. Why don’t airlines board from the back to the front? That would certainly speed things up!
HeatherFlew with LufthansaORD-MKEAug 2024
Make sure there's enough time between connections to go through customs and recheck your luggage. They will not let you proceed so you can't even try to run and catch the flight if you want to.
WilliamFlew with EVA AirORD-TPEJul 2024
Wear compression socks or prepare for massive swelling of your feet and ankles.
MikeFlew with British AirwaysORD-FCOJun 2024
Make sure you check the plane type and economy seating space.
EstherFlew with Ethiopian AirORD-ADDAug 2024
Eat before boarding the food is smelly. Do not sit near a toilet
Verified travelerFlew with United AirlinesORD-PHXApr 2024
Use the find my gate feature on the flights phone app if available as the airport is a bit confusing
AyannaFlew with Spirit AirlinesORD-TPAMay 2024
Fly out of Midway airport instead of O'Hare because its smaller and easier to manage.
PaulFlew with Alaska AirlinesORD-SEAApr 2024
The flight is long, at over four hours. I would try to get a window or aisle seat to be more comfortable. I would check with other airlines that allow you to choose your seat even if you are in the economy section. I would bring your own food on the plane as the service was sometimes sketchy.
Verified travelerFlew with Alaska AirlinesORD-SEAApr 2024
If you miss your flight ask any alaska agent to how and where to rebook the flight.
FreddieFlew with IcelandairORD-KEFMay 2024
If you’re in business class board first to avoid queuing
UzomaFlew with American AirlinesORD-DCAJan 2024
ORD and DCA are nice airports with plenty of space. ORD is always busy so allow ample time to drive there, drop your bag, and go through security if you don't have TSA pre check.
RogerFlew with ANAORD-HNDFeb 2024
The extra leg room and been able to recline better is worth the extra money. I bidding on the premium and offered the least they would accept and got it.
AaronFlew with American AirlinesORD-LHRDec 2023
Find a flight where you are allowed to choose your seats before the day of boarding for anything international.
RyanFlew with EVA AirORD-TPEJan 2024
Bring things to make the seats more comfortable
Verified travelerFlew with United AirlinesORD-YOWJan 2024
I always expect issues with United but there doesn't seem to be another airline to use. Advice: Give yourself and extra day to get anywhere - don't be in a hurry to get home either.

FAQs for booking flights out of Chicago

  • Does Midway International Airport have an on-site hotel?

    While Midway International Airport does not have an on-site hotel, there are several hotels are nearby. For example, the Holiday Inn Express & Suites Chicago Midway Airport is less than 5 minutes from the airport and has a free shuttle, while the Hilton Garden Inn Chicago Midway Airport is a 3-minute drive from the airport.

  • What lounges are available in Chicago O’Hare International Airport?

    There are a few different lounges to choose from at Chicago O’Hare International Airport, including the American Airlines Admirals Club, which is in Concourses G, H, K, and L. There is also the United Club in Concourses B and C, as well as the Delta Sky Club in Terminal 2.

  • What options are there for traveling from the city center to Midway International Airport?

    If you choose to drive from Downtown Chicago to Midway International Airport, the trip will typically take you around 15 to 20 minutes in total. You can also opt to use public transportation instead, such as the Orange subway line, which will typically take you between 30 and 35 minutes. A one-way ticket will cost you approximately $2.50.

  • Does Chicago O’Hare International Airport offer any facilities for those traveling with pets?

    If you are flying out of Chicago O’Hare International Airport with a pet, keep in mind that there are several indoor and outdoor pet relief areas available. These are equipped with sitting areas, trash cans, and free plastic bags.

  • What are the names of Chicago’s airports?

    All flights from Chicago depart from one of Chicago O'Hare Intl Airport, Chicago Midway Airport or Chicago Greater Rockford Airport. Chicago O'Hare Intl Airport’s airport code is ORD. It can also be referred to as Chicago O'Hare, O'Hare Intl. Chicago Midway Airport’s airport code is MDW. It can also be referred to as Chicago Midway, Chicago Midway Intl, Midway, Midway Intl. Chicago Greater Rockford Airport’s airport code is RFD. It can also be referred to as Chicago Rockford Intl, Greater Rockford.

  • How does KAYAK find such low prices on flights from 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 from Chicago.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from 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 from 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 your destination with an airline and back to Chicago with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from 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 from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Top tips for finding a cheap flight out of Chicago

  • Looking for a cheap flight? 25% of our users found tickets from Chicago to the following destinations at these prices or less: Miami $137 one-way - $112 round-trip
  • There are two primary airports in Chicago, Chicago O’Hare International Airport (ORD) and Midway International Airport (MDW). While Chicago O’Hare International Airport can be found just under 15 miles north of the city center, Midway International Airport is approximately 8 miles south of Downtown Chicago.
  • Chicago O’Hare International Airport is a major hub for airlines such as American Airlines and United Airlines, so it’s not uncommon for these companies to operate flights departing from this airport. Likewise, Midway International Airport is a hub for Southwest Airlines, so you’ll see that this airline commonly services trips from here.
  • If you have extra time before your flight boards at Chicago O’Hare International Airport, you can fit in a workout at the Hilton Athletic Club. Located in Terminal 2, it is equipped with facilities such as a steam room, sauna, and lap pool. There is also a yoga room in Terminal 3 open to all passengers for free.
  • Midway International Airport offers a few different services for those flying with children, such as a baby care room in Concourse C designed to give parents a private area to nurse their little ones. There is also a designated security lane for families.
  • If you feel like treating yourself before a long day of traveling, head to one of the Terminal Getaway Spa locations in Terminals 3 and 5 of Chicago O’Hare International Airport. Here, you can receive a variety of massages, manicures, pedicures, and facials.

Reviews of the top 5 airlines serving from Chicago to Worldwide

 
Need help choosing which airline to fly with from Chicago to Worldwide? 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
SouthwestOverall score based on 4240 reviews
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

2.0 MediocreAnonymous, Nov 2025ORD - LAS
Read more Southwest reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

I will never book a flight through Cheap fare. They booked me from Portland Main . And would not give me a refund, so I bought 2 tickets one for 299. From Portland Main to ORD. Then I had to buy a ticket from Oregon PDX to ORD that was another 440. So Just so you know they even told me it was there fault but no refund. Bad bussniess. I did inform United but they said they couldn't help me due to the fact I booked through Cheap Tickets. Never again. And I'm spreding the word. I let everyone know at my 50th class reunion

The flight attendants were rude. Seemed like they didn’t want to be there. Except for one girl that was really nice. Seats are sooooo uncomfortable. They give you a piece of paper and a thin cushion for a pillow and blanket that does nothing. Airlines have gone way downhill, especially United international flights. Food was disguting. Definitely flying ANA next time.

Crew and customer service were excellent. This flight also had plenty of leg room and seat mounted screens for entertainment. A very pleasant flight all around!

It would have been better if the crew has supported my husband's reasons for needing to keep the space clear around his feet, rather than insisting that he put his knapsack in that space.

Subject: Formal Complaint: Discriminatory and Unprofessional Conduct – Request for Immediate Action & Compensation Dear [Airline Customer Relations Team], I am writing to file a formal complaint regarding my recent travel experience with [Airline], which was by far the worst I have ever encountered. What occurred was not only unprofessional, but in several instances discriminatory, unsafe, and unacceptable. On the first leg of my trip, I arrived only four minutes past check-in. Instead of making any attempt to resolve the matter, your representative flatly denied me boarding and made me wait while she attended to passengers who arrived after me. By the time a manager intervened, it was too late to board, costing me time, money, and unnecessary frustration. The second leg of my trip (Chicago–San Francisco) raised even more serious concerns. From the outset, it was apparent that the staff—particularly two attendants—prioritized Caucasian passengers while dismissing African American and minority passengers. • When a Caucasian passenger in the exit row refused to comply with federal safety requirements, I, as a first responder, immediately offered to switch seats and assume the responsibility. My offer was blatantly ignored, and instead, a Caucasian passenger seated further up was chosen. This was discriminatory and deeply insulting, especially as I was actively de-escalating the situation that could have delayed the flight further. • During a lengthy tarmac delay of over 90 minutes, passengers were given conflicting and unreasonable instructions that created unnecessary distress and tension. • Throughout the flight, a visibly intoxicated passenger directly in front of me was disruptive, rude to others, failed to comply with seatbelt and electronic device rules, and yet faced no enforcement from the crew. In stark contrast, I was singled out for repeated compliance checks even though I was following every rule. This unequal treatment was so obvious that multiple passengers around me spoke up in my defense. This pattern of behavior demonstrated a clear lack of professionalism, disregard for passenger safety, and discriminatory treatment. I expect far better from an airline of your stature. As a paying customer subjected to this unacceptable treatment, I am formally requesting: 1. A full investigation into the conduct of the staff on both flights. 2. A written apology acknowledging the discriminatory and unprofessional behavior I endured. 3. Appropriate compensation for the distress, inconvenience, and mishandling of my travel. If this matter is not addressed promptly and thoroughly, I will have no choice but to escalate my complaint further, including filing with the U.S. Department of Transportation and sharing my experience through other channels. I trust [Airline] will take this complaint seriously and provide a timely resolution.

Check in was quick and easy during early hours. Flight was on time, and customer services was a plus.

Once we got in the air the pilot made up some of the time of the delay. So that was really nice.

We had a layover from YVR to Denver. We bought 4 bottles of Absolut Vodka at the YVR Duty Free for $116.20, after going through security and American Customs Pre Clearance at YVR, Vancouver. When we landed in Denver, United put us behind the American Customs as well as TSA again for some reason. We were forced to go through American Customs and TSA again. TSA confiscated our rightfully owned Duty Free Absolut Vodka bottles. Because United incorrectly forced our flight behind American border and TSA again, we missed the connecting flight. After United put us on a later flight, we eventually arrived in Chicago very late, with hardly any sleep. I am looking for compensation from United for our incorrectly confiscated Absolut Vodka bottles worth $116.20, as well as compensation for incorrectly putting us behind American Customs and TSA again, causing us to miss our connecting flight, making us arrive extremely late in Chicago.

We loved the steward on the plane. He made the night enjoyable

The plane was late, when we did board the plane was as cold as a freezer. I was freezing the entire flight, no blankets. Lost miserable flight I’ve ever had.

My wife and I love to travel, so we fly a lot. We've already logged 381,075 miles and with practically every major airline. But this flight was very disappointing. It started off well, with no delays and a new plane. But when lunchtime approached, all that good impression was ruined. Instead of white tablecloths, we were offered small, dark placemats, which, as it turned out, were perfectly adequate for the food. All the food offered—and my wife and I only took fish, and the meat—was not just bad, it was downright disgusting and not heated enough. The same applies to the appetizers. This was the first time in many years of traveling that we've been offered such disgusting food.

Lost luggage stuck no clothes and no word after 2 days leaving on cruise no stuff or clothes

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

After a two hour delay, my flight was CANCELLED! No pilot available. Such BS.

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

I wish American Airlines would change the airline industry by loading the plane back to front instead of front to back. Planes would board so much more smoothly and quickly.

I have long legs, my foot was out in the aisle and when a flight attendant came walking by and I didn't notice, instead of saying "excuse me" or anything like that, she kicked my foot. Extremely rude

The Hawaiian lady that boarded me was rude and the one help me a the ticket counter was rude

My experience was terrible. They cancelled my flight twice. They kept delaying it and leading me on, acting like the flight was going to go when it never had a chance. I missed out on valuable family time because of spirit and I won’t be flying with them again.

Prices for bags are extremely expensive and if you go higher on weight, the charge is ridiculous.

The flight was cancelled at the last minute. Will never fly Spirit again. Without a doubt the worst airline around.

My flight was delayed several times and eventually cancelled. Then the re-booked flight for 8pm was delayed multiple times over, and eventually it would have forced me to be at the airport for 9 hours. I accepted a rebook for the following day, fortunately I was able to stay with my friend again in New York, but if I didn’t have him as a resource it would have been much more upsetting.

Horrible, delay after delay due to our plane needing fuel.

Rough landings but comfortable and affordable if you can pack light

the plane was not full so the flight attendant had me move to an empty row which made for a good flight. The software for logging on and booking and confirming the flight is much too cumbersome.

Always comes in handy when I want a quick weekend getaway.

For the price I could have taken a “name brand” airline. No drink no snack and constant emails trying to get addition money for EVERYTHING other airlines include in the price. It looks cheaper but it’s Judy bait and switch and emails non stop!

There was no one at the counter to assist with our check in. The app didn’t work, so I arrived at the airport with time to check in and I couldn’t because no employees were there. When I finally got someone on the phone, it was inside the 60min rule and they said I could no longer check in and they could sell me another ticket. We had to scramble and pay an additional $800 for tickets and THEN AFTER (about 60 min from my original convo with customer service and 10min after original departure time) I had boarded my new flight, there was email saying my original flight from Frontier was delayed and leaving 2hr 50min later, but I STILL wouldn’t have been able to check in. Which means customer service should have been able to see it and let me check in because I was well within my check in time. When I call Frontier, they hang up on me. So their app didn’t work and they employees left and they take zero responsibility or assistance with their “customer service”

Terrible. Flight cancelled with no reasoning and no flights to rebook. Employees were useless and did nothing to help. Did not even know where to retrieve luggage from the cancelled flight. Flyers beware.

No fault of Frontier staff: plane was very late, reached Orlando at 1 am, took a while to get luggage. Weather, gov financial shutdown impact on TSA, air controllers seemed to have multiple flights backed up. Frontier staff seemed to cope as gracefully as possible. It did reassure me that I and my new hip could adapt to travel challenges. Food/entertainment were irrelevant to my trip.

Terrible. The canceled my entire flight when I requested a refund for a trip frontier canceled trip one way.

Boarding was on time and plane departed as scheduled. There are obviously no amenities (food, drink, entertainment) on Frontier, but there also didn't seem to be any issues with luggage space either.

Inbound plane was on time and flight departed on time with no issues while boarding.

I knew going into this that Frontier, being a low cost carrier, would be pretty bare bones and charge for most extras but this was made up for by the fact that the airplane was a reasonably new Airbus, every employee was great and best of all, Everett Washington is an amazing airport - thanks Frontier for flying there!!!

i was unable to check in the flight. refund requested

It was well done. It was my first time flying with them and I was nervous b/c I have heard of many cancelled and/or delray flights. Everything went smoothly.

Just know that everything, and I mean everything is “ala cart”. 60$ just to put something in the overhead bin. I will never fly Frontier again nor do I recommend them to anyone else.

Everything you need to know for your flight from Chicago

Cabin class types available on flights from Chicago

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