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Boston Logan International to Illinois Flight Information

Flights Arrive in Illinois
Flights Depart from Boston Logan International
Flight Price $105
Airlines United Airlines, American Airlines, JetBlue, Spirit Airlines, Delta, Sun Country Air, Major Airline, Frontier

Book cheap flights from Boston to Illinois (round-trip)

Airports
Origin
Boston
$105
only
$105
Destination
Decatur
$212
only
$212
Chicago
$105
only
$105
$219
only
$219
Sat, May 4
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 48m
Thu, May 9
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 14m
Trip: 6 days
6.8GoodShow reviews
Overall 6.8 Good
Based on 179 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
BOS
ORD
Good 6.0

Cons: Crew stop carry on bags when there was still lots of roon

BOS
ORD
Mediocre 2.0

Pros: Nothing

Cons: Long complicated and rude

BOS
ORD
Mediocre 2.0

Cons: Terrible flight!

BOS
ORD
Okay 5.3

Cons: Our plane was constantly moved around prior to boarding and it was 2 hours late.

BOS
ORD
Okay 4.6

Pros: Honestly, don’t care for this airline. There’s always some hiccups with boarding, ride staff, mediocre cabin, etc.

Cons: Why do they always want to check bags that are your everyday carryon items (large purse, medium backpac, etc.), but allow people to carryon their larger carry on suitcases filling up the overhead bins. Those are the people they should be making check their “carry-one.” And then be rude about it on top of that.

Wed, May 8
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 57m
Tue, May 14
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 18m
Trip: 7 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 82 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
DFW
SFO
Mediocre 2.0

Cons: Never made it

PVD
DCA
Okay 4.0

Cons: Delayed more than 2 hours

LGA
DFW
Okay 4.3

Pros: service was consistent

Cons: Plane was unusually hot

DFW
PDX
Okay 4.8

Pros: movies

Cons: the bumpiest, harrowing flight ever

LAX
LAS
Mediocre 2.4

Pros: Delayed

Tue, May 21
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 37m
Fri, May 31
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 17m
Trip: 11 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 70 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
BOS
ORD
Mediocre 2.0

Pros: When I got off the plane

Cons: it was late, the plane was dirty, the tv screens didn't work, and the seats were small.

BOS
ORD
Good 7.0

Pros: Easy boarding and flight

Cons: There’s nothing special about jet blue anymore.

JFK
KIN
Excellent 8.6

Pros: The crew was professional. The seat had great leg room. The flight and landing was very smooth.

BOS
ORD
Excellent 8.0

Pros: Great service and smooth flight. On time, all good things.

Cons: An individual who was very overweight sat next to me and took up half of my seat as well. I understand we all deserv to ride comfortably and my intent is not to shame them. That said, if someone can’t put the armrest down I think the airline should require them to purchase both seats as it’s very uncomfortable to be in the position of having no seat for the entire ride. I’m an average sized person so it was a challenge but even tiny people deserve the full seat they purchased. There really should be a rule or something.

JFK
BOS
Good 6.0

Pros: Good snacks, friendly flight attendants, efficient boarding

Cons: Flight was quiet delayed and there was no communication in the gate area about the reason for the delay until the end. Flight also kept saying it would take off at 2:22 and we weren’t even boarded at that point. Would have appreciated an updated departure time and clear and regular communication

Thu, May 2
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 46m
Thu, May 9
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 14m
Trip: 8 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 182 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
BOS
ORD
Mediocre 2.0

Cons: Cheap flight but they get you on bags. $55 for a carryon!!!, really?!!! If if your checked bag is over 40 lbs. You pay Ann extra $30. We paid $350 four the flight for 2 to boston round trip. We ended up paying $310 In extra luggage fees.

BOS
ORD
Mediocre 2.0

Cons: The customer service agent over the phone had told me "you are allowed one carry one and one checked bag." So I get to the flight desk and turns out I was allowed one checked bag, however I had to pay $52 for it. On top of that our flight was late and the workers at the boarding site was extremely rude. The overall experience was absolutely horrible.

BOS
ORD
Excellent 8.5

Pros: Boarding was fairly quick, but it was a smaller plane than many.

Cons: Given the fees for luggage in both directions, I'm not sure there would be much, if any, savings round trip compared to other airlines, and that's without any of free beverage/snack/entertainment.

BOS
ORD
Mediocre 2.0

Cons: My flight was cancelled less than 2 hours before the departure. I was told this at the airline counter. I took 7 o'clock AMTRAK to go Chicago and then took Blue line (45 minutes) to get to O'Hara airport. The girl at the counter did not explain why the airplane was cancelled. She offered a flight next day at the same time. My poster presentation was at 8:30AM next day. There was no alternative flight from Chicago to Boston. I just cannot believe this. I totally missed my conference presentation. BAD!

BOS
ORD
Mediocre 2.0

Pros: nothing, if the air line is cheap don't means attitude

Cons: Staff don't know how to talk to someone very expensive price for bags always canceling flight time.....

Sat, Jun 1
BOS
Boston Logan International
ORD
Chicago O'Hare International
5h 09m
Tue, Jun 4
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 27m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
PVR
ATL
Excellent 8.0

Cons: Boarding was a little confusing with seats not being assigned ahead of time

LGA
IND
Excellent 9.2

Pros: Our seats were assigned at the gate. Somehow we were given the comfort + seats. Very nice! Thank you!

SLC
MCI
Mediocre 2.0

Cons: Never made it because of my originating flight

MSY
ATL
Excellent 8.0

Cons: Leg room was lacking.

ATL
MSP
Excellent 10.0

Pros: My flight was missed due to immigration taking almost 3 hours to get through the line. Delta went out of their way to make sure that I was able to get to my destination on a later flight as comfortable as possible.

Cons: Maybe not traveling through Atlanta if there is immigration clearance involved. I was really slow.

Thu, May 23
BOS
Boston Logan International
ORD
Chicago O'Hare International
5h 50m
Sun, May 26
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 18m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 8,553 reviews
Overall
8.1
Boarding
8.2
Comfort
7.7
Crew
8.5
Entertainment
6.8
Food
7.1
SFO
MSP
Okay 5.0

Pros: Crew was pleasant and very nice!

Cons: 2 hour delay then 15th in line to take off and at the landing gate the bridge driver was 10 minutes late.

PHX
MSP
Excellent 10.0

Pros: Everything...thanks!

PHX
PDX
Excellent 10.0

Pros: The crew was really nice and the in flight entertainment was great

Cons: Wish there couldve been a complimentary in flight snack or something.

MSP
TPA
Excellent 10.0

Cons: The entertainment website appeared to be down

PHX
MSP
Good 6.6

Pros: The flight itself was great, but not sure why we were charged extra for our carry on bags and seat assignments.

Cons: We were charged extra (each way) for our carry on bags and seat assignments. If we would have booked directly with Sun Country we would not have had those fees. I don’t know if I’ll use this app to book tickets again.

Sun, Jun 2
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 48m
Thu, Jun 20
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 16m
Trip: 19 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 70 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
BOS
ORD
Excellent 8.0

Pros: The movies were okay. The crew was accommodating.

Cons: We spent 45 minutes on the tarmac, enough time to watch the baggage personnel throw our bags into his trolley with zero reason for him to do so. If you pack anything fragile... good luck.

BOS
ORD
Excellent 10.0

Pros: Quick security check. Flight was on time,

BOS
ORD
Mediocre 2.0

Cons: Six hours late, then there wasn’t enough fuel and had to wait for paperwork multiple times. Hands down the worst experience I have ever had. I will not be flying JetBlue again.

SEA
BOS
Good 6.3

Cons: Too hot. They need to turn off the blue light for a red eye...

MSP
BOS
Excellent 8.8

Pros: Crew informed us about the time delays and why we had to unload the plane .

Cons: Boston closed their airport due to high winds.

Tue, Jul 2
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 41m
Thu, Jul 4
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 19m
Trip: 3 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 82 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
DFW
LHR
Good 6.0

Pros: Not much.

Cons: The crew was either tired or not at it best; service was just ok. No smiles.

BOS
ORD
Mediocre 3.6

Cons: Delayed 3 hrs and then sat on runway upon arrival at ohare. I was forced to check my rollerboard even though I've fit it perfectly in the overhead compartment just yesterday on my previous flight (also American airline).

DFW
SFO
Mediocre 2.0

Cons: Never made it

BOS
ORD
Okay 5.6

Pros: had onboard in seat entertainment. Mostly TV shows but not bad.

Cons: Center seat, group 3 boarding, poor seat spacing in coach.

SMF
DFW
Okay 5.0

Pros: Another customer allowed me to sit in the aisle seat rather than the assigned middle seat. That was much appreciated. And I enjoyed an movie during the flight. I like being able to choose what I want to watch and stream it on my own device.

Cons: It was really cold on the airplane. I kept my jacket on for the entire flight. I’m typically warm natured, so it was unusually cold.

Wed, May 29
BOS
Boston Logan International
DEC
Decatur Arpt
13h 09m
Thu, May 30
DEC
Decatur Arpt
BOS
Boston Logan International
16h 01m
Trip: 2 days
Overall 0.0 Poor
Based on 0 reviews
Wed, Jun 26
BOS
Boston Logan International
MDW
Chicago Midway
2h 40m
Sat, Jun 29
MDW
Chicago Midway
BOS
Boston Logan International
2h 15m
Trip: 4 days
Overall 0.0 Poor
Based on 0 reviews
Sat, May 11
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 46m
Tue, May 14
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 17m
Trip: 4 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 182 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
BOS
ORD
Good 7.3

Pros: Very friendly crew

Cons: Did not like being told to pay for bags, seats, etc. in addition to the ticket. Especially thought that paying to choose a seat was ridiculous. Refused to do that and got seats anyway. Pretty cheesy way for the airline to make money

BOS
ORD
Okay 4.6

Pros: The only good thing was the cheap airfare, but with all the other charges you end up paying the same amount for a better airline.

Cons: Steep prices for carry ons ($100 RT), no free bevs even water!

BOS
ORD
Good 7.3

Pros: on time

Cons: low comfort seats

BOS
ORD
Good 6.0

Pros: PRICE

Cons: BOSTON AIRPORT PROBLEM , LOUSY BOARDING AREA. ROOM FOR 150 PEOPLE BUT 300 WAITING. NOT SPIRITS FAULT.

BOS
ORD
Excellent 8.5

Cons: Flight was delayed lost an hour, which threw off my connecting plans.

Tue, Jun 11
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 37m
Fri, Jun 14
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 16m
Trip: 4 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 70 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
BOS
ORD
Excellent 8.0

Pros: The movies were okay. The crew was accommodating.

Cons: We spent 45 minutes on the tarmac, enough time to watch the baggage personnel throw our bags into his trolley with zero reason for him to do so. If you pack anything fragile... good luck.

SYR
JFK
Good 7.0

Cons: You need to teach those who make announcements how to properly speak and annunciate. They are terrible. They speak so fast that it is very very very difficult to understand.

BOS
ORD
Excellent 9.0

Pros: Captain was very funny and thoughtful. Crew were great.

Cons: Plane boarded and left about 30 min late and when we arrived gate wasn't available. Things out of their control but of course have an affect on the experience. Also the plane was very oldz

BOS
ORD
Good 7.3

Pros: Plenty of leg room in economy seats.

BOS
ORD
Mediocre 3.3

Cons: Flight over 3 hours late leaving. Flight attendants rude, and nothing comped for drinks or food to make up for it. Had to circle for 45 min due to weather. Sat on tarmac 30 mijn on other end.

Wed, Jul 3
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 41m
Thu, Jul 4
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 19m
Trip: 2 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 82 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
BOS
ORD
Excellent 8.0

Pros: Direct flight, sketchy weather but we arrived pretty close to “on time”

OGG
PHX
Okay 4.8

Pros: Crew was good.

Cons: The seat was tiny. It took forever. I hate you people.

BOS
ORD
Okay 4.0

Cons: Paid for extra legroom, got a seat that didn't recline :(

BOS
ORD
Excellent 10.0

Pros: Best landing I’ve experienced recently!

BOS
ORD
Good 6.6

Cons: Seat 20f It was very uncomfortable and freezing My legs were sore after the journey. Besides until 30 seconds before actual boarding time the members didn't inform about the delay. Everybody had formed lines and we see people getting out only then.

Sat, May 4
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 48m
Wed, May 8
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 27m
Trip: 5 days
6.8GoodShow reviews
Overall 6.8 Good
Based on 179 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
BOS
ORD
Mediocre 2.0

Cons: Still at airport. 40 minute flight delayed 3.5 hours. Now I get home at 2 am.

BOS
ORD
Okay 4.6

Cons: Delayed over an hour

BOS
ORD
Mediocre 2.0

Pros: Refund was prompt

Cons: Flight was canceled

BOS
ORD
Mediocre 2.0

Cons: I had to fly to San Francisco bcs maintenance and delays bullshit

BOS
ORD
Mediocre 2.0

Pros: Nothing

Cons: Long complicated and rude

Tue, Jun 4
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 46m
Thu, Jun 20
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 16m
Trip: 17 days
5.5OkayShow reviews
Overall 5.5 Okay
Based on 182 reviews
Overall
5.8
Boarding
6.1
Comfort
5.4
Crew
6.5
Entertainment
4.6
Food
4.7
BOS
ORD
Mediocre 2.0

Pros: It went where I needed to go

Cons: There is almost nothing that would make me use this airline again. My flight wasn't even cheap, so that definitely didn't make up for the fact that I paid $50 both ways for my carry on bag, and one $30 seat fee so that I could request a window seat on a cross-country red eye. Water is not free on the plane, and still there were no seat back pockets, so the water bottle I bought (and didn't want in my bag w/ important documents) rolled around on the floor all night. I'm a small woman, and there was barely space for me to fit in the seat. Uncomfortable, expensive.

BOS
ORD
Good 6.6

Pros: Price, but know what to expect.

Cons: Spirit charges even for water.

BOS
ORD
Excellent 8.8

Pros: I liked the easy boarding process. The crew was very polite. It was an easy, smooth flight.

Cons: I am 5'3 and I only had a few inches between my knees and the back of the seat in front of me. Not super comfortable but my flight was only 2 hours so it was manageable.

BOS
ORD
Okay 4.0

Cons: Flight way overbooked. Got bumped (said "voluntary" to get the best of two poor offers of compensation).

BOS
ORD
Good 6.0

Pros: PRICE

Cons: BOSTON AIRPORT PROBLEM , LOUSY BOARDING AREA. ROOM FOR 150 PEOPLE BUT 300 WAITING. NOT SPIRITS FAULT.

Tue, Jun 18
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 54m
Thu, Jun 20
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 16m
Trip: 3 days
7.0GoodShow reviews
Overall 7.0 Good
Based on 70 reviews
Overall
8.2
Boarding
8.3
Comfort
8.3
Crew
8.6
Entertainment
7.9
Food
7.8
RDU
FLL
Okay 5.6

Cons: Delay of 1.5 hours. Plane showed up late and then was further delayed when they realized the toilet was plugged up. Ridiculous.

SAV
BOS
Okay 4.3

Pros: I hate delays

BOS
ORD
Mediocre 2.0

Cons: Late flight delayed

BOS
LAX
Excellent 10.0

Pros: The crew was very friendly and attentive. I enjoyed the variety of entertainment offered as well.

Cons: A few more food options would be nice.

BOS
ORD
Good 7.0

Pros: JetBlue booked me on next flight out: AA flight only an hour and a half after the one I missed

Cons: Had to check my fragile instrument even though there was room in a closet.

Sat, May 4
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 48m
Sun, May 5
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 14m
Trip: 2 days
6.8GoodShow reviews
Overall 6.8 Good
Based on 179 reviews
Overall
7.2
Boarding
7.4
Comfort
7.0
Crew
7.7
Entertainment
6.5
Food
6.5
BOS
ORD
Mediocre 2.0

Cons: I missed my flight to San Diego from a connecting flight by a few minutes. Now I have to sit in the airport for over three hours waiting for my next flight.. not to mention it's my bday. Thanks United.

BOS
ORD
Okay 5.6

Pros: Staff was great, friendly, and accommodating

Cons: Upgraded to first thinking i would be more comfortable and have a decent meal...wrong...seats were so blown out that my butt and back were in pain most of the flight. Caught food posioning from the rice pilaf. I dig that united offers inflight entertainment through your phone but its annoying that i have to hold up my phone i watch something but now I'm just nitpicking.

BOS
ORD
Good 7.3

Cons: I flew on JetBlue before this flight and legroom was much better. My knees are kind of bruised after the United flight. Otherwise the flight was fine.

BOS
ORD
Okay 4.6

Pros: Honestly, don’t care for this airline. There’s always some hiccups with boarding, ride staff, mediocre cabin, etc.

Cons: Why do they always want to check bags that are your everyday carryon items (large purse, medium backpac, etc.), but allow people to carryon their larger carry on suitcases filling up the overhead bins. Those are the people they should be making check their “carry-one.” And then be rude about it on top of that.

BOS
ORD
Excellent 9.6

Cons: Bereavement switched flights for me thanks

Sun, May 5
BOS
Boston Logan International
ORD
Chicago O'Hare International
2h 50m
Fri, May 10
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 27m
Trip: 6 days
7.2GoodShow reviews
Overall 7.2 Good
Based on 82 reviews
Overall
7.4
Boarding
7.5
Comfort
7.2
Crew
7.9
Entertainment
6.8
Food
6.7
BOS
ORD
Mediocre 2.0

Pros: Getting off the plane

Cons: The staff

TUS
ORD
Good 7.0

Pros: The flight was early.

Cons: More leg room needed.

BOS
ORD
Excellent 8.0

Pros: Direct flight, sketchy weather but we arrived pretty close to “on time”

BOS
ORD
Mediocre 3.6

Cons: Delayed 3 hrs and then sat on runway upon arrival at ohare. I was forced to check my rollerboard even though I've fit it perfectly in the overhead compartment just yesterday on my previous flight (also American airline).

BOS
ORD
Good 7.0

Pros: Easy check in at kiosk. On time flight. Helpful flight attendant.

Cons: Sat row 7. Very cramped shoulder room for three men.

Sat, Jun 22
BOS
Boston Logan International
ORD
Chicago O'Hare International
19h 19m
Sun, Jun 30
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 16m
Trip: 9 days
5.7OkayShow reviews
Overall 5.7 Okay
Based on 37,135 reviews
Overall
6.0
Boarding
6.4
Comfort
5.4
Crew
6.8
Entertainment
4.6
Food
4.7
DEN
SFO
Excellent 8.0

Pros: Friendliness of the SF counter agent.

Cons: Hidden charges! The quoted price did NOT include additional exhorbitant baggage charges, charges for in flight food and drinks, fixed seat backs. This was a classic case of bait and switch

CVG
LGA
Mediocre 3.5

Pros: Nothing

Cons: Flight was delayed by traffic control in NYC. Instead of just informing passengers why the flight was delayed, they just ignored the passengers and made people queue

SAN
DEN
Okay 5.5

Pros: Loved the price

Cons: That you must pay for all drinks including water

DEN
BZN
Excellent 8.4

Pros: Crew was fine, nothing special. Seat @ $28 extra should tilt. Legroom was decentl.

Cons: 1st row people should get on the plane first. Holding over head bins for them and msking row two folks put their bags 4 bins back is not cool.

SLC
DEN
Okay 5.6

Pros: The crew was very friendly and helpful!

Cons: If you want anything to eat or drink during the flight, you have to pay for it. It would be nice if those things were complementary, as they are with most airlines.

Fri, May 10
BOS
Boston Logan International
ORD
Chicago O'Hare International
4h 21m
Tue, May 14
ORD
Chicago O'Hare International
BOS
Boston Logan International
2h 18m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 22,994 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.7
Food
7.4
IAD
AMS
Excellent 9.0

Pros: Super comfortable seats. Lots of movie options.

Cons: Food was not very good

LAX
SEA
Good 6.0

Cons: Flight was delayed more than 4 hours. I switched flights to try to beat the 4 hour delay but was still delayed 4 hours. After verifying with delta t am members that my bags had been rechecked they had not

ATL
SXM
Excellent 10.0

Cons: Crazy rough, fast landing but not boring!!!

ATL
ICT
Excellent 10.0

Pros: Flight staff friendly and everything went smoothly.

Cons: Always wishing for roomier seats.

RDU
CLE
Mediocre 2.0

Pros: Very bad crew. Seats very uncomfortable

Cons: Crew could have been better

*
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