CHI - SAN

$40 Find Cheap Flights from Chicago to San Diego

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to San Diego departing on 3/5. 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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These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Diego.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to San Diego.
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Cheap Flight Deals from Chicago to San Diego (CHI-SAN)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to San Diego 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.

Recent round-trip flight deals from Chicago to San Diego

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from Chicago to San Diego.
Discover the best prices and deals for you by selecting your travel dates.
Choose your dates
7:47 am - 4:44 pmORD-SAN
10h 57m1 stop
8:14 pm - 6:42 amSAN-ORD
8h 28m1 stop
$82Spirit Airlines
Find Deal
Wed, Mar 5 - Mon, Mar 10
7:47 am - 4:44 pmORD-SAN
10h 57m1 stop
5:39 pm - 6:42 amSAN-ORD
11h 03m1 stop
$90Spirit Airlines
Find Deal
Wed, Mar 5 - Tue, Mar 11
7:47 am - 4:44 pmORD-SAN
10h 57m1 stop
9:19 pm - 5:14 amSAN-ORD
5h 55m1 stop
Wed, Mar 5 - Mon, Mar 10
7:05 am - 11:48 amMDW-SAN
6h 43m1 stop
12:38 pm - 12:17 amSAN-MDW
9h 39m1 stop
$97Frontier
Find Deal
Wed, Mar 5 - Tue, Mar 11
6:50 am - 12:20 amORD-SAN
19h 30m1 stop
5:39 pm - 6:42 amSAN-ORD
11h 03m1 stop
Mon, Feb 24 - Wed, Mar 5
7:05 am - 11:48 amMDW-SAN
6h 43m1 stop
9:19 pm - 5:31 amSAN-MDW
6h 12m1 stop
$108Frontier
Find Deal
Wed, Mar 5 - Mon, Mar 10
9:20 am - 2:09 pmMDW-SAN
6h 49m1 stop
7:10 am - 6:20 pmSAN-MDW
9h 10m1 stop
$319Delta
Find Deal
Wed, Apr 23 - Tue, Apr 29
1:00 pm - 6:27 pmMDW-SAN
7h 27m1 stop
8:50 am - 6:04 pmSAN-MDW
7h 14m1 stop
$329Delta
Find Deal
Fri, May 9 - Tue, May 13
1:45 pm - 4:15 pmMDW-SAN
4h 30mnonstop
2:45 pm - 8:40 pmSAN-MDW
3h 55mnonstop
$341Southwest
Find Deal
Tue, Mar 11 - Tue, Mar 18
5:40 am - 10:00 amMDW-SAN
6h 20m1 stop
2:45 pm - 8:40 pmSAN-MDW
3h 55mnonstop
$351Southwest
Find Deal
Tue, Mar 11 - Tue, Mar 18

Flights from Chicago to San Diego - Travel Insights & Trends

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

Planning a trip from Chicago to San Diego? KAYAK’s data-powered insights will help you find cheap flights. Learn the best time to fly, how early to book your ticket, and other tips to secure great prices.

What is the cheapest Chicago to San Diego flight route?

The cheapest price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from Chicago to San Diego.
Our data shows that the cheapest route for a return flight from Chicago to San Diego cost $341 and was between Chicago O'Hare Intl Airport (ORD) and San Diego (SAN). On average, the best prices are found if you fly this route. The average price for a return flight for this route is $341.

What’s the cheapest day of the week to fly from Chicago to San Diego?

The average price of all round-trip flights from Chicago to San Diego clicked on KAYAK for each day over the last 12 months.
If you are looking for a flight deal from Chicago to San Diego, look for departures on Tuesdays and avoid leaving on a Sunday, as it's usually the priciest day. When flying back from San Diego, Thursday is the cheapest day to fly and Sunday is the most expensive.

What is the cheapest month to fly from Chicago to San Diego?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago to San Diego, 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 from Chicago to San Diego is April, where tickets cost $366 (return) on average. On the other hand, the most expensive months are March and December, where the average cost of round-trip tickets is $491 and $480 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Chicago to San Diego, 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 on the flight from Chicago to San Diego, you should book around 4 weeks before departure. For the absolute cheapest price, our data suggests you should book 25 weeks before departure.

Good to know

Low season

February

High season

March

Cheapest flight

$40
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 18% increase in price.
Flight from Chicago O'Hare Airport to San Diego

When to book flights from Chicago to San Diego

Are your dates flexible? Find out the best times to travel from Chicago to San Diego based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Chicago to San Diego

  • Is there free Wi-Fi at O'Hare International Airport?

    Unlimited free Wi-Fi is available at the O'Hare International Airport throughout all terminals. If you want to access the Wi-Fi, enable wireless connection on your device and connect to “_Free_ORD _Wi-Fi” or “Boingo Hotspot.”

  • Are there nonstop flights from Chicago to San Diego?

    For flights from Chicago to San Diego, there are several airlines that serve this route, including American Airlines and United Airlines. Both offer nonstop flights from the O'Hare International Airport to the San Diego International Airport. You can also find flights by Frontier, which flies through Denver International Airport (DEN), but it could take longer, so book through KAYAK to compare routes and find the best option.

  • Where’s the chapel at O'Hare International Airport?

    The O'Hare International Airport offers a chapel, a peaceful space in the busy airport you can use for prayers, liturgies, and worship. It’s equipped with prayer books, worship materials, rosaries, rugs, and Juma ablution facilities. The facility is in Terminal 2 Mezzanine level above Delta Air ticket counters next to USO.

  • Are there lactation rooms at San Diego Airport?

    Mothers can access three lactation rooms found in each terminal post-security. In Terminal 1 West, you can find the lactation rooms on the second level. The rooms in Terminal 1 East are near the security checkpoint, while in Terminal 2 West, they’re on the second level. Each of these rooms is equipped with electrical outlets, artwork, a handwashing station, soft lighting, comfortable seating, and a children’s seat.

  • Are there hotels near the San Diego International Airport?

    There are no hotels within the airport. The closest near the airport is the Sheraton Hotel & Marina, located at a 10min walking distance or 3min if you’re using the free hotel shuttle. The Hampton Inn & Suites is located about a mile away, a 5min drive from the terminal. You can also book the TownPlace Suites by Marriott, located at a 5min driving distance from the airport.

  • What is the cheapest flight from Chicago to San Diego?

    In the last 3 days, the lowest price for a flight from Chicago to San Diego was $40 for a one-way ticket and $82 for a round-trip.

  • Do I need a passport to fly between Chicago and San Diego?

    No, a passport isn't needed to fly from Chicago to San Diego. However, local authorities might ask for an official ID.

  • Which airports will I be using when flying from Chicago to San Diego?

    Chicago has 2 major airports: Chicago Midway and Chicago O'Hare Intl. San Diego is the only airport in San Diego. You’ll usually find the cheapest deals if you fly from Chicago O'Hare Airport.

  • Which airlines offer Wi-Fi service onboard planes from Chicago to San Diego?

    American Airlines, and Alaska Airlines offer inflight Wi-Fi service on the Chicago to San Diego flight route.

  • Which aircraft models fly most regularly from Chicago to San Diego?

    The Boeing 737-800 is the aircraft model that flies most regularly on the Chicago to San Diego flight route.

  • Which airline alliances offer flights from Chicago to San Diego?

    oneworld, and Star Alliance are the airline alliances operating flights between Chicago and San Diego, with oneworld being the most commonly used for this route.

  • On which days can I fly direct from Chicago to San Diego?

    There are nonstop flights from Chicago to San Diego on a daily basis.

  • Which is the best airline for flights from Chicago to San Diego, Southwest or Delta?

    The two airlines most popular with KAYAK users for flights from Chicago to San Diego are Southwest and Delta. With an average price for the route of $472 and an overall rating of 8.1, Southwest is the most popular choice. Delta is also a great choice for the route, with an average price of $332 and an overall rating of 8.0.

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

    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 to San Diego.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Diego 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 to San Diego?

    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 San Diego 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 to San Diego?

    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 San Diego from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

KAYAK’s top tips for finding a cheap flight from Chicago to San Diego

  • Looking for a cheap flight? 25% of our users found flights on this route for $271 or less one-way and $449 or less round-trip.
  • Located 14 miles from the Loop Business District, the O'Hare International Airport is the ideal airport if you’re traveling from Chicago to San Diego, California.
  • If you need shower facilities at the O'Hare International Airport, they’re available at Concourse C. You can also access the VIP lounge if you’re a VIP member and need these services.
  • For mothers with small children, the O'Hare International Airport offers a Mother’s Room to help mothers nurse, use a breast pump, and care for young children. The rooms are in each terminal.
  • The O'Hare International Airport offers free unlimited Wi-Fi. You can connect to the Wi-Fi by searching “_Free_ORD _Wi-Fi.” It comes with ads, but you can also use a premium high-speed option for a fee.
  • For flights from the O'Hare International Airport to San Diego, you can use the San Diego International Airport (SAN), located 3 miles from downtown San Diego.
  • When you arrive at San Diego International Airport, you can explore the dining options at Terminal 1, including Banker’s Hill Bar & Market. On Terminal 2, there are options like the Artisan Market and Starbucks at Gate 37.
  • To access cash, you can use ATMs throughout the San Diego International Airport. In Terminal 1, they’re past the checkpoint near Gate 1, in the lobby opposite the food court, near Gate 5, and near Gate 13. The ATMs are also available in Terminal 2.
  • There are courtesy phones at San Diego International Airport throughout the terminals, which offer complimentary local calls. For long-distance calls, you can purchase phone cards at most retail concessions.
See more tips

Prefer to fly direct from Chicago to San Diego?

Find which airlines fly direct from Chicago to San Diego Airport, which days they fly and book direct flights.

Direct departures

Chicago to San Diego

Monday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Tuesday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Wednesday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Thursday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Friday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Saturday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Sunday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

See more direct flights

Direct returns

San Diego to Chicago

Monday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Tuesday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Wednesday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Thursday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Friday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Saturday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

Sunday

Aer Lingus, Air Canada, Alaska Airlines, +16 more

Aer Lingus, Air Canada, +17 more

See more direct flights
See more direct flights

Top 5 airlines serving from Chicago to San Diego

 
See real verified KAYAK customer reviews for airlines flying from Chicago to San Diego. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to San Diego? 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.
8.1
SouthwestOverall score based on 4496 reviews
7.1Food
8.2Boarding
7.6Entertainment
8.1Comfort
8.7Crew
Airline reviews

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

10.0 ExcellentAnonymous, Dec 2024AUS - OAK
Read more Southwest reviews

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

One of the crew performed a hilarious skit to accompany the standard instructions. Passengers enjoyed it so much they applauded at the end!

Excellent experience. WiFi worked on this leg of My trip

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a hell hole of an airport. It is the new LaGuardia. Everything Cobbled together. Security gates closed. Terri directional signage

I will be flying again Southwest Airlines. Friendly crew, comfortable and affordable.

The plane arrived 25 minutes late, and the Wi-Fi was slower than it usually is.

Forget beverage, they didn't even have water for half the passangers?

Can not wait for seating change to reduce the amount of pre boards - it’s disheartening the abuse. And then then deplaning

The crew was nice. Boarding sucked. Instead of loading from the back to the front people just sat wherever and you had to wait for them to move to get to a seat. And the flight was 25 minutes delayed.

Our seats were all the way in back of the plane,

The seats on this flight were almost roomy enough to be the basic amount needed for human existence. I think my favorite part of this flight was it landed at an A gate, which was the most palatial part of Sea-Tac I've ever seen - a massive improvement from the S gates.

The seats on this flight were almost roomy enough to be the basic amount needed for human existence.

The flight attendants in First Class were mediocre at best. They did not take our tray away until we were about to land and only did so when I press the call button. The United person at the United Club was asked to get us our boarding pass since we missed the flight due in Chicago. She argued that we did not have seats on the flight given to us in Moline. Furthermore, she was adamant that we did not have a First Class ticket. After I spent much time with her trying to show we were correct, she reluctantly agreed. She was probably the most incompetent ticketing person I have ever met and I have traveled 3 million miles on United plus many additional miles with other carriers. United has definitely deteriorated in more than on way.

Short flight - no food understandable. Flight was delayed for over an hour. Overall, it was good.

We arrived early and finally made it to our gate almost an hour after.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Plane was was better than th YVR to ORD flight but was a fraction of the distance. Fly your better planes on longer distance flights.

Nothing wrong with the flight itself. But due to 2+ hrs waiting in immigration and the additional security checkup in O’hare, I nearly missed the flight.

They need to improve their boarding process. Group 1 and/or paying first class passengers shouldn't be in the middle of boarding process

The service and food needs to improve to catch up with other international flights

Most of the delay was due to weather which is not what was at issue here. One delay was due to a missing flashlight and in the end the flashlight was actually found on the plane. The entertainment system is very limited. Live TV options offer only a few channels that are not very appealing. Boarding and deplaning are always difficult. It just takes too much time to get on and off the plane. On the plus side, I missed my connecting flight, but was easily able to book a later flight from the app while enroute.

You were more on time than United. I'm so over united delays.

The meals were mediocre and the alcohol selection was poor. I enjoyed the selection of movies and other entertainment.

I chatted with the captain before the flight, and similarly during the welcome announcement, he warned of a turbulent flight that may impact the in-flight service. However, once at altitude, he announced that the weather changed and he immediately turned off the seatbelt sign. But it appeared the cabin crew had already decided to take off this flight. They remained seated and then just chatted in the galley. The flight was fully catered, but only first class received service.

My flight attendant was attentive! The elderly person next to me was flatulent and the flight attendant could see that I was in distress and brought me some face masks

My boarding pass wouldn't pull up in the app very easily and had to really dig through my email. That caused a delay in TSA..

I had a TERRIBLE experience with the AA crew. I believe it was disability-related. It’s unlikely I will fly AA again.

Baby cried a lot. Nothing anyone could do about it. Just part of flying.

The flight crew was fantastic! Which the seats had a small TV.

Loved staff help @ kiosk, staff on airplane. Commitment to punctuality. I sat in a "blocked" row, where the middle seat had no passenger & loved it! I appreciate not having to pay for water, which I've experienced even on international flights. Only negative was how dirty the bathroom was for a 4.5 hrs flight. But I don't think flight attendants monitor this.

- flight attendants not very friendly. - Paid for WiFi and plane didn’t have it working , never got a refund.

We got to fly on the new airplane. Much better as it’s roomier and cleaner than before. Most Importantly it’s much more comfortable. I still can’t move the seat back but the extra space made up for it. I didn’t taste the food or drinks because they charge for everything so I didn’t bother. I didn’t experience the entertainment because I downloaded my own movies on my phone. The crew was great. The flight itself was smooth . No complaints.

Your employees need to learn how to talk to people as creations of Yah. We are not their children nor are we lower than them.

I was comfortable because I upgraded. I would not have been comfortable in economy. It was a short flight so there was limited food service and no inflight entertainment.

I thought since I upgraded my seat I would get some perks. Free water, free snacks. Free carry on luggage.

It’s ridiculous to pay for carry-on luggage. I also wasn’t given an option to specify I have carry on bag at time of ticket purchase. I also could not specify I have carry on luggage at time of online check-in.

Delayed fight LAS to LAX. OK, fog in LA, not your fault. But all your staff, onboard in in lounge, speak so fast, enunciate so poorly and often have a accent that it is impossible to understanding anything they are saying.

The gate area was terrible at San Diego airport -way too crowded in a small space. Since my husband was driving to our destination, we did not have to take any luggage so my kids and I only had backpacks. Therefore everything was easy and smooth. And we didn’t have to pay up charges for everything and it was a short flight. I tried table was broken and it was a little cramped, but it was fine for what we needed. I probably would not fly spirit on a longer flight and if I had to take baggage.

Boarding procedure is horribly slow. You charge me to check a bag and would not let me carry it on. Charged me to simply select a seat. Charged me for water. Charged me for every little thing on top of paying for an expensive ticket. Your seats are terrible. So uncomfortable, they don’t recline. No WiFi, no way to charge my phone. No entertainment. I mean you Offer noting and you charge for everything. Why would anyone want to fly with you again?

Check in at Philadelphia international was absolutely terrible! I fly 2 to 3 times a month and avoid frontier at all cost and will never fly Frontier again! The night before travel, I tried checking in however, the app was giving me an error, so I went to the desktop, which instructed you that you need to use the app. The next day I presented at the check-in gate after trying at least a half dozen times prior to getting into the airport and continuing to getting the error in the app. I actually had rebooted my phone numerous times and reinstall the app just in case. My phone is only one generation older than the current model. It has no problems completing a frontier flight purchase or any other app issues. There was only three frontier employees working at check-in and a huge line while I was in line I continued to try and check in via the app. As I approach the desk, I was dreading dealing with the agent. He was extremely unprofessional, anti-semantic & very ignorant, and mean to the people in front of me, as well as the people who ended up being behind me. He literally told people “Man I don’t care bout y’all” in his native dialect! Maintaining my composure I approached and explained the situation. To which he replied, you’re gonna have to pay then! I don’t understand. It’s an issue with their app not allowing me to check in! Not my issue! He told me if I pay cash it would be $15, $25 if I pay credit card. I don’t understand a $10 difference for paying with a credit card? I am completely cashless so I continued to try using the app to avoid the $25 fee, Which I still don’t believe that I should be responsible for since it was Frontier’s technical issue!!! I continued to check in via the app a couple more times after he verified I was doing everything right he proceeded to continue to belittle the people behind me. Yelling at them saying I don’t care about you people! I cannot believe that this is the way that businesses would treat its customers! Unfortunately, the black mail with dreadlocks did not have a name tag all he had was a frontier sweater on! For the $25 fee that I ended up getting charged on my credit card. I should’ve just booked originally with Spirit or any other carrier! I have no problem paying fees that I should be responsible for, but when it’s due to a technical failure of a company, the customer should not be responsible for it! I cannot believe that it’s not frontier going out of business!

they delayed my flight which ended up, causing my layover flight to leave without me, resulting in me missing a flight and having to stay overnight in Houston international. I got no compensation other than a flight to my original location only a day later. i’ve never experienced such a unprofessional situation

Very easy with the app to board and staff skills

After waiting several minutes to be acknowledged by 3 employees on their phones, was told we had missed our flight because the doors were closed at that literal moment. Had they given any actual service or help while we were standing there we would have been on with time to spare. More than 10 people were turned away in this fashion claiming there was no way they could let us on the plane, even though it was still sitting connected to the terminal. After the desk agents let us know they didn't care about the situation we were forced to pay more than twice the price of our original tickets as no credits were given for the price of the "missed" flight. And the icing on the cake was after being treated poorly, fleeced for another few hundred dollars for new tickets? We waited on the next plane for 25 minutes passed the "doors closed" time, letting almost an extra dozen passengers on board. You're company has lazy, disinterested employees and your lack of any real help will ensure this was the first and last time we fly Frontier. Awful.

The plane was clean, the crew was friendly and helpful. It’s a low cost airline so there was no food, drinks or in flight entertainment but we didn’t expect any of these things. In the room for improvement department, they should install USB ports in seats to charge mobile devices.

I was surprised that all baggage, including carry on, were charged. Each additional bag went up in cost. Really disappointed in the additional costs.

Charges unexpected. For seat that didnt recline. Please reverse extra seat and carryon charge. Bad business that is a bait and switch.

I couldn’t check in because the app didn’t work. It took 3 Frontier employees at the counter to get me checked in. Flight left 3 hours after departure time

Stop changing gates at sfo. When you are elderly going back for it’s not fun.

There was no easy way to check in. I don't want to install an app to checkin. I will use alaska from now on because they have a web check in method that is easy.

Everything you need to know for your flight from Chicago to San Diego

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