Flights from Chicago to Key West (ORD to EYW)

Discover more affordable routes and cheaper dates from Chicago to Key West (ORD to EYW) within a date range.

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US$165

10:35am - 2:49pm
Mon Feb 10th 2025

3h 14m
Chicago (ORD) → Key West (EYW)

Direct

Mon Feb 10th 2025 United Airlines · UA 2070 Depart at 10:35am from Chicago (ORD) Fly for 3h 14m Arrive at 2:49pm in Key West (EYW)
US$188

8:45am - 6:55pm
Sun Feb 9th 2025

9h 10m
Chicago (ORD) → Key West (EYW)

1 Stop

Sun Feb 9th 2025 United Airlines · UA 743 Depart at 8:45am from Chicago (ORD) Fly for 3h 18m Arrive at 1:03pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 4h 47m

Sun Feb 9th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$188

8:45am - 6:55pm
Mon Feb 10th 2025

9h 10m
Chicago (ORD) → Key West (EYW)

1 Stop

Mon Feb 10th 2025 United Airlines · UA 743 Depart at 8:45am from Chicago (ORD) Fly for 3h 18m Arrive at 1:03pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 4h 47m

Mon Feb 10th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$188

7:00am - 6:55pm
Sun Feb 9th 2025

10h 55m
Chicago (ORD) → Key West (EYW)

1 Stop

Sun Feb 9th 2025 United Airlines · UA 1421 Depart at 7:00am from Chicago (ORD) Fly for 3h 14m Arrive at 11:14am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 6h 36m

Sun Feb 9th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$188

7:00am - 6:55pm
Mon Feb 10th 2025

10h 55m
Chicago (ORD) → Key West (EYW)

1 Stop

Mon Feb 10th 2025 United Airlines · UA 1421 Depart at 7:00am from Chicago (ORD) Fly for 3h 14m Arrive at 11:14am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 6h 36m

Mon Feb 10th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$188

6:25pm - 6:55pm
Sat Feb 8th 2025

23h 30m
Chicago (ORD) → Key West (EYW)

1 Stop

Sat Feb 8th 2025 United Airlines · UA 633 Depart at 6:25pm from Chicago (ORD) Fly for 3h 19m Arrive at 10:44pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 19h 6m

Sun Feb 9th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$188

6:25pm - 6:55pm
Sun Feb 9th 2025

23h 30m
Chicago (ORD) → Key West (EYW)

1 Stop

Sun Feb 9th 2025 United Airlines · UA 633 Depart at 6:25pm from Chicago (ORD) Fly for 3h 19m Arrive at 10:44pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 19h 6m

Mon Feb 10th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$188

6:25pm - 6:55pm
Mon Feb 10th 2025

23h 30m
Chicago (ORD) → Key West (EYW)

1 Stop

Mon Feb 10th 2025 United Airlines · UA 633 Depart at 6:25pm from Chicago (ORD) Fly for 3h 19m Arrive at 10:44pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 19h 6m

Tue Feb 11th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$212

7:35am - 4:01pm
Sat Feb 8th 2025

7h 26m
Chicago (ORD) → Key West (EYW)

1 Stop

Sat Feb 8th 2025 United Airlines · UA 2482 Depart at 7:35am from Chicago (ORD) Fly for 3h 3m Arrive at 10:38am in Houston (IAH)

Layover in Houston for 1h 31m

Sat Feb 8th 2025 United Airlines · UA 6200 Depart at 12:09pm from Houston (IAH) Fly for 2h 52m Arrive at 4:01pm in Key West (EYW)
US$220

8:45am - 6:55pm
Sat Feb 8th 2025

9h 10m
Chicago (ORD) → Key West (EYW)

1 Stop

Sat Feb 8th 2025 United Airlines · UA 743 Depart at 8:45am from Chicago (ORD) Fly for 3h 18m Arrive at 1:03pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 4h 47m

Sat Feb 8th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$220

7:00am - 6:55pm
Sat Feb 8th 2025

10h 55m
Chicago (ORD) → Key West (EYW)

1 Stop

Sat Feb 8th 2025 United Airlines · UA 1421 Depart at 7:00am from Chicago (ORD) Fly for 3h 14m Arrive at 11:14am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 6h 36m

Sat Feb 8th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$220

7:00am - 6:55pm
Thu Feb 6th 2025

10h 55m
Chicago (ORD) → Key West (EYW)

1 Stop

Thu Feb 6th 2025 United Airlines · UA 1421 Depart at 7:00am from Chicago (ORD) Fly for 3h 14m Arrive at 11:14am in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 6h 36m

Thu Feb 6th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$240

3:53pm - 10:10am
Sat Feb 8th 2025

17h 17m
Chicago (ORD) → Key West (EYW)

2 Stops

Sat Feb 8th 2025 United Airlines · UA 2451 Depart at 3:53pm from Chicago (ORD) Fly for 1h 52m Arrive at 6:45pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 3h 32m

Sat Feb 8th 2025 United Airlines · UA 1066 Depart at 10:17pm from Washington, D.C. (IAD) Fly for 2h 28m Arrive at 12:45am in Orlando (MCO)

Layover in Orlando for 8h 0m

Sun Feb 9th 2025 United Airlines · UA 3075 Depart at 8:45am from Orlando (MCO) Fly for 1h 25m Arrive at 10:10am in Key West (EYW)
US$241

6:08pm - 10:10am
Sun Feb 9th 2025

15h 2m
Chicago (ORD) → Key West (EYW)

2 Stops

Sun Feb 9th 2025 United Airlines · UA 444 Depart at 6:08pm from Chicago (ORD) Fly for 1h 53m Arrive at 9:01pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 16m

Sun Feb 9th 2025 United Airlines · UA 1066 Depart at 10:17pm from Washington, D.C. (IAD) Fly for 2h 28m Arrive at 12:45am in Orlando (MCO)

Layover in Orlando for 8h 0m

Mon Feb 10th 2025 United Airlines · UA 3075 Depart at 8:45am from Orlando (MCO) Fly for 1h 25m Arrive at 10:10am in Key West (EYW)
US$241

3:51pm - 10:10am
Sun Feb 9th 2025

17h 19m
Chicago (ORD) → Key West (EYW)

2 Stops

Sun Feb 9th 2025 United Airlines · UA 2451 Depart at 3:51pm from Chicago (ORD) Fly for 1h 52m Arrive at 6:43pm in Washington, D.C. (IAD)

Layover in Washington, D.C. for 3h 34m

Sun Feb 9th 2025 United Airlines · UA 1066 Depart at 10:17pm from Washington, D.C. (IAD) Fly for 2h 28m Arrive at 12:45am in Orlando (MCO)

Layover in Orlando for 8h 0m

Mon Feb 10th 2025 United Airlines · UA 3075 Depart at 8:45am from Orlando (MCO) Fly for 1h 25m Arrive at 10:10am in Key West (EYW)
US$244

7:15am - 5:15pm
Sat Feb 8th 2025

9h 0m
Chicago (ORD) → Key West (EYW)

1 Stop

Sat Feb 8th 2025 United Airlines · UA 2326 Depart at 7:15am from Chicago (ORD) Fly for 2h 54m Arrive at 11:09am in Tampa (TPA)

Layover in Tampa for 4h 51m

Sat Feb 8th 2025 United Airlines · UA 3137 Depart at 4:00pm from Tampa (TPA) Fly for 1h 15m Arrive at 5:15pm in Key West (EYW)
US$244

7:15am - 5:15pm
Mon Feb 10th 2025

9h 0m
Chicago (ORD) → Key West (EYW)

1 Stop

Mon Feb 10th 2025 United Airlines · UA 2326 Depart at 7:15am from Chicago (ORD) Fly for 2h 54m Arrive at 11:09am in Tampa (TPA)

Layover in Tampa for 4h 51m

Mon Feb 10th 2025 United Airlines · UA 3137 Depart at 4:00pm from Tampa (TPA) Fly for 1h 15m Arrive at 5:15pm in Key West (EYW)
US$244

7:15am - 5:15pm
Sun Feb 9th 2025

9h 0m
Chicago (ORD) → Key West (EYW)

1 Stop

Sun Feb 9th 2025 United Airlines · UA 2326 Depart at 7:15am from Chicago (ORD) Fly for 2h 54m Arrive at 11:09am in Tampa (TPA)

Layover in Tampa for 4h 51m

Sun Feb 9th 2025 United Airlines · UA 3137 Depart at 4:00pm from Tampa (TPA) Fly for 1h 15m Arrive at 5:15pm in Key West (EYW)
US$244

6:03pm - 9:15am
Sun Feb 9th 2025

14h 12m
Chicago (ORD) → Key West (EYW)

1 Stop

Sun Feb 9th 2025 United Airlines · UA 2075 Depart at 6:03pm from Chicago (ORD) Fly for 2h 52m Arrive at 9:55pm in Tampa (TPA)

Layover in Tampa for 10h 5m

Mon Feb 10th 2025 United Airlines · UA 3135 Depart at 8:00am from Tampa (TPA) Fly for 1h 15m Arrive at 9:15am in Key West (EYW)
US$244

6:03pm - 9:15am
Sat Feb 8th 2025

14h 12m
Chicago (ORD) → Key West (EYW)

1 Stop

Sat Feb 8th 2025 United Airlines · UA 2075 Depart at 6:03pm from Chicago (ORD) Fly for 2h 52m Arrive at 9:55pm in Tampa (TPA)

Layover in Tampa for 10h 5m

Sun Feb 9th 2025 United Airlines · UA 3135 Depart at 8:00am from Tampa (TPA) Fly for 1h 15m Arrive at 9:15am in Key West (EYW)
US$244

6:03pm - 9:15am
Mon Feb 10th 2025

14h 12m
Chicago (ORD) → Key West (EYW)

1 Stop

Mon Feb 10th 2025 United Airlines · UA 2075 Depart at 6:03pm from Chicago (ORD) Fly for 2h 52m Arrive at 9:55pm in Tampa (TPA)

Layover in Tampa for 10h 5m

Tue Feb 11th 2025 United Airlines · UA 3135 Depart at 8:00am from Tampa (TPA) Fly for 1h 15m Arrive at 9:15am in Key West (EYW)
US$244

2:10pm - 9:15am
Mon Feb 10th 2025

18h 5m
Chicago (ORD) → Key West (EYW)

1 Stop

Mon Feb 10th 2025 United Airlines · UA 1634 Depart at 2:10pm from Chicago (ORD) Fly for 2h 52m Arrive at 6:02pm in Tampa (TPA)

Layover in Tampa for 13h 58m

Tue Feb 11th 2025 United Airlines · UA 3135 Depart at 8:00am from Tampa (TPA) Fly for 1h 15m Arrive at 9:15am in Key West (EYW)
US$276

7:35am - 4:01pm
Mon Feb 10th 2025

7h 26m
Chicago (ORD) → Key West (EYW)

1 Stop

Mon Feb 10th 2025 United Airlines · UA 2482 Depart at 7:35am from Chicago (ORD) Fly for 3h 3m Arrive at 10:38am in Houston (IAH)

Layover in Houston for 1h 31m

Mon Feb 10th 2025 United Airlines · UA 6200 Depart at 12:09pm from Houston (IAH) Fly for 2h 52m Arrive at 4:01pm in Key West (EYW)
US$276

8:45am - 6:55pm
Thu Feb 6th 2025

9h 10m
Chicago (ORD) → Key West (EYW)

1 Stop

Thu Feb 6th 2025 United Airlines · UA 743 Depart at 8:45am from Chicago (ORD) Fly for 3h 18m Arrive at 1:03pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 4h 47m

Thu Feb 6th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$284

7:15am - 5:15pm
Thu Feb 6th 2025

9h 0m
Chicago (ORD) → Key West (EYW)

1 Stop

Thu Feb 6th 2025 United Airlines · UA 2326 Depart at 7:15am from Chicago (ORD) Fly for 2h 54m Arrive at 11:09am in Tampa (TPA)

Layover in Tampa for 4h 51m

Thu Feb 6th 2025 United Airlines · UA 3137 Depart at 4:00pm from Tampa (TPA) Fly for 1h 15m Arrive at 5:15pm in Key West (EYW)
US$287

10:50am - 6:55pm
Sat Feb 8th 2025

7h 5m
Chicago (ORD) → Key West (EYW)

1 Stop

Sat Feb 8th 2025 United Airlines · UA 1775 Depart at 10:50am from Chicago (ORD) Fly for 3h 14m Arrive at 3:04pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 46m

Sat Feb 8th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$292

8:50am - 6:55pm
Sat Feb 8th 2025

9h 5m
Chicago (ORD) → Key West (EYW)

2 Stops

Sat Feb 8th 2025 United Airlines · UA 2490 Depart at 8:50am from Chicago (ORD) Fly for 1h 58m Arrive at 11:48am in Washington, D.C. (IAD)

Layover in Washington, D.C. for 1h 24m

Sat Feb 8th 2025 United Airlines · UA 761 Depart at 1:12pm from Washington, D.C. (IAD) Fly for 2h 51m Arrive at 4:03pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 1h 47m

Sat Feb 8th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$292

6:00am - 5:15pm
Sat Feb 8th 2025

10h 15m
Chicago (ORD) → Key West (EYW)

2 Stops

Sat Feb 8th 2025 United Airlines · UA 2343 Depart at 6:00am from Chicago (ORD) Fly for 2h 11m Arrive at 9:11am in New York (EWR)

Layover in New York for 1h 34m

Sat Feb 8th 2025 United Airlines · UA 2074 Depart at 10:45am from New York (EWR) Fly for 3h 6m Arrive at 1:51pm in Tampa (TPA)

Layover in Tampa for 2h 9m

Sat Feb 8th 2025 United Airlines · UA 3137 Depart at 4:00pm from Tampa (TPA) Fly for 1h 15m Arrive at 5:15pm in Key West (EYW)
US$292

6:00am - 6:55pm
Sat Feb 8th 2025

11h 55m
Chicago (ORD) → Key West (EYW)

2 Stops

Sat Feb 8th 2025 United Airlines · UA 2343 Depart at 6:00am from Chicago (ORD) Fly for 2h 11m Arrive at 9:11am in New York (EWR)

Layover in New York for 3h 19m

Sat Feb 8th 2025 United Airlines · UA 477 Depart at 12:30pm from New York (EWR) Fly for 3h 13m Arrive at 3:43pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 7m

Sat Feb 8th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$319

10:35am - 2:49pm
Fri Feb 7th 2025

3h 14m
Chicago (ORD) → Key West (EYW)

Direct

Fri Feb 7th 2025 United Airlines · UA 2070 Depart at 10:35am from Chicago (ORD) Fly for 3h 14m Arrive at 2:49pm in Key West (EYW)
US$319

10:36am - 2:50pm
Sun Feb 9th 2025

3h 14m
Chicago (ORD) → Key West (EYW)

Direct

Sun Feb 9th 2025 United Airlines · UA 2070 Depart at 10:36am from Chicago (ORD) Fly for 3h 14m Arrive at 2:50pm in Key West (EYW)
US$327

10:50am - 6:55pm
Mon Feb 10th 2025

7h 5m
Chicago (ORD) → Key West (EYW)

1 Stop

Mon Feb 10th 2025 United Airlines · UA 1775 Depart at 10:50am from Chicago (ORD) Fly for 3h 14m Arrive at 3:04pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 46m

Mon Feb 10th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$327

10:50am - 6:55pm
Thu Feb 6th 2025

7h 5m
Chicago (ORD) → Key West (EYW)

1 Stop

Thu Feb 6th 2025 United Airlines · UA 1775 Depart at 10:50am from Chicago (ORD) Fly for 3h 14m Arrive at 3:04pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 46m

Thu Feb 6th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$327

7:35am - 4:01pm
Fri Feb 7th 2025

7h 26m
Chicago (ORD) → Key West (EYW)

1 Stop

Fri Feb 7th 2025 United Airlines · UA 2482 Depart at 7:35am from Chicago (ORD) Fly for 3h 3m Arrive at 10:38am in Houston (IAH)

Layover in Houston for 1h 31m

Fri Feb 7th 2025 United Airlines · UA 6200 Depart at 12:09pm from Houston (IAH) Fly for 2h 52m Arrive at 4:01pm in Key West (EYW)
US$330

7:20am - 2:20pm
Sun Feb 9th 2025

6h 0m
Chicago (ORD) → Key West (EYW)

1 Stop

Sun Feb 9th 2025 United Airlines · UA 1768 Depart at 7:20am from Chicago (ORD) Fly for 2h 57m Arrive at 11:17am in Orlando (MCO)

Layover in Orlando for 1h 38m

Sun Feb 9th 2025 United Airlines · UA 3071 Depart at 12:55pm from Orlando (MCO) Fly for 1h 25m Arrive at 2:20pm in Key West (EYW)
US$330

7:20am - 2:20pm
Fri Feb 7th 2025

6h 0m
Chicago (ORD) → Key West (EYW)

1 Stop

Fri Feb 7th 2025 United Airlines · UA 1768 Depart at 7:20am from Chicago (ORD) Fly for 2h 57m Arrive at 11:17am in Orlando (MCO)

Layover in Orlando for 1h 38m

Fri Feb 7th 2025 United Airlines · UA 3071 Depart at 12:55pm from Orlando (MCO) Fly for 1h 25m Arrive at 2:20pm in Key West (EYW)
US$330

7:20am - 2:20pm
Sat Feb 8th 2025

6h 0m
Chicago (ORD) → Key West (EYW)

1 Stop

Sat Feb 8th 2025 United Airlines · UA 1768 Depart at 7:20am from Chicago (ORD) Fly for 2h 57m Arrive at 11:17am in Orlando (MCO)

Layover in Orlando for 1h 38m

Sat Feb 8th 2025 United Airlines · UA 3071 Depart at 12:55pm from Orlando (MCO) Fly for 1h 25m Arrive at 2:20pm in Key West (EYW)
US$330

10:50am - 6:55pm
Sun Feb 9th 2025

7h 5m
Chicago (ORD) → Key West (EYW)

1 Stop

Sun Feb 9th 2025 United Airlines · UA 1775 Depart at 10:50am from Chicago (ORD) Fly for 3h 14m Arrive at 3:04pm in Fort Lauderdale (FLL)

Layover in Fort Lauderdale for 2h 46m

Sun Feb 9th 2025 United Airlines · UA 3094 Depart at 5:50pm from Fort Lauderdale (FLL) Fly for 1h 5m Arrive at 6:55pm in Key West (EYW)
US$330

7:35am - 4:01pm
Sun Feb 9th 2025

7h 26m
Chicago (ORD) → Key West (EYW)

1 Stop

Sun Feb 9th 2025 United Airlines · UA 2482 Depart at 7:35am from Chicago (ORD) Fly for 3h 3m Arrive at 10:38am in Houston (IAH)

Layover in Houston for 1h 31m

Sun Feb 9th 2025 United Airlines · UA 6200 Depart at 12:09pm from Houston (IAH) Fly for 2h 52m Arrive at 4:01pm in Key West (EYW)
US$372

10:35am - 2:49pm
Thu Feb 6th 2025

3h 14m
Chicago (ORD) → Key West (EYW)

Direct

Thu Feb 6th 2025 United Airlines · UA 2070 Depart at 10:35am from Chicago (ORD) Fly for 3h 14m Arrive at 2:49pm in Key West (EYW)

Sarah Belizaire

@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

John Ford

@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

Roaming Sonaa

@roamingsonaa

For people wanting to maximize their trips, Flightlist is my newest travel hack for uncovering the coolest routes at irresistible prices. No stress, no annoying ads — just seamless flight booking with amazing functionality.

Andy Travels

@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

Travel With Bender

@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Wesley Mergard

@travel.with.wes

One useful tool I've found for evaluating different departure and return dates is called FlightList.io. You can quickly scan different travel date ranges, carriers and one way flight options to easily determine the cheapest flight combinations for your trip.

Flights from Chicago to Key West (ORD to EYW)

Sarah Belizaire

John Ford

Roaming Sonaa

Andy Travels

Travel With Bender

Wesley Mergard

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