Sell out the Orlando Citrus Bowl on March 8th, sell 14,000 season tickets and meet certain sponsorship goals. This was the challenge Orlando City SC President and Founder Phil Rawlins made to the team's front office at the beginning of the season. The Reward? An all-expenses paid trip to Chicago to watch the Lions take on the Fire. The staff promptly delivered and this past weekend, so did Phil.

The Orlando City front office headed to Chicago 70 strong this past Friday.

The Orlando City front office is about to head to Chicago 70 deep. Follow our trip with #LionsInChicago pic.twitter.com/AYR56dwJZ1 — Orlando City SC (@OrlandoCitySC) September 18, 2015

Watch out Ferris, it's our day off! #LionsInChicago #FlyMCO #LifeInPurple #OrlandoCity #Orlando A photo posted by JR Flo-Rida (@johnrawlins) on Sep 18, 2015 at 11:15am PDT

#flymco #lionsinchicago BOARDED with @a_bloom9 @cveedubs CHICAGO BOUND! A photo posted by Pat Moran (@pahkandtremont) on Sep 18, 2015 at 12:10pm PDT

Don't get caught sleeping on the plane with 70 of your friends around.

No one is safe when it comes to the rainbow tongue... Even when you are sleeping. #LionsInChicago pic.twitter.com/MpER1PeLCw — Stuart Drew (@studrew1) September 18, 2015

We arrived in a rainy Chicago, so naturally everyone took to social media.

We thought we had escaped the rainy Florida weather. Not so much... #LionsInChicago pic.twitter.com/Lk6KwzKAJ9 — Orlando City SC (@OrlandoCitySC) September 18, 2015

#LionsInChicago .. or is this Orlando? Rain and lightning A photo posted by Kirk (@kirkci) on Sep 18, 2015 at 3:04pm PDT

Rainy Chicago. #lionsinchicago A photo posted by Ed Cahill (@edcahilliv) on Sep 18, 2015 at 3:37pm PDT

We think we see a Chicago skyline past the raindrops. #LionsInChicago pic.twitter.com/rGGO6o1q6q — Orlando City SC (@OrlandoCitySC) September 18, 2015

Stuck in rush hour traffic, the two Orlando City buses exchanged dueling photos.

Keep it Konsistent. #DoTheKaka #2ndBus #LionsInChicago A photo posted by Molly (@mhartman89) on Sep 18, 2015 at 4:07pm PDT

Next up, an open bar and a night out on the town.

Orlando takes Chi Town #allsmiles #lionsinchicago #earnedit A photo posted by Kelsey Lynn (@kckelseylynn) on Sep 18, 2015 at 8:12pm PDT

#lionsinchicago #purplepride #bffs #lionspride #lionsprideinchicago @prawlinsocsc @niksantz A photo posted by villemignon (@villemignon) on Sep 18, 2015 at 6:54pm PDT

#lionsinchicago #lionsatabar #lionsinchicagodrinkingatabar A photo posted by villemignon (@villemignon) on Sep 18, 2015 at 6:25pm PDT

Taking in the sites!! #LionsinChicago #chitown #trumptower #urfired A photo posted by Jessica Rae♊ (@jessierae0528) on Sep 19, 2015 at 2:13am PDT

Before the match on Saturday, the staff split up to explore the city

Nailed it. Turning Chicago purple. #LionsInChicago @orlandocitysc A video posted by @alimatt14 on Sep 19, 2015 at 8:45am PDT

Whoever got here before us... really solid work #LionsInChicago #NotAJolly A photo posted by @gramlessjames on Sep 19, 2015 at 9:30am PDT

Beautiful day for baseball in Chicago. Check Wrigley off the bucket list. #lionsinchicago #Cubs A photo posted by Ed Cahill (@edcahilliv) on Sep 19, 2015 at 10:53am PDT

#LionsInChicago #TheFriendlyConfines Historic Wrigley Field A video posted by @miami.harold on Sep 19, 2015 at 10:49am PDT

#lionsinchicago #ocscmagnet A photo posted by dubie22 (@dubie22) on Sep 19, 2015 at 11:18am PDT

Took a moment to be tourist #lionsinchicago A photo posted by Kelsey Lynn (@kckelseylynn) on Sep 19, 2015 at 2:32pm PDT

Always seeing something, never seeing nothing. Chicago you've been good to us, can't wait to come back! #lionsinchicago #thebean A photo posted by Mikey Alfano (@mikeyalfano) on Sep 20, 2015 at 6:37am PDT

Under da bean with the squad @eallsopp00 @stuartdrew @markthorphotos @markthorphotos @rafacabrera11 #lionsinchicago A photo posted by Matthew Stone (@the_mattstone) on Sep 20, 2015 at 7:32am PDT

#LionsInChicago A photo posted by Kirk (@kirkci) on Sep 19, 2015 at 10:02pm PDT

Best part of the trip so far, meeting Mr. #vanGogh! #LionsInChicago #OrlandoCity #soccer #photographer A photo posted by Mark Thor (@markthorphotos) on Sep 19, 2015 at 11:32am PDT

If you didn't get a selfie, it didn't happen #LionsInChicago #NotAJolly A photo posted by @gramlessjames on Sep 19, 2015 at 11:48am PDT

The staff then headed to dinner before grabbing a bus to the match.

FO on the march!!!! #PurpleArmy #LionsInChicago #DefyExpectations Thanks @prawlinsocsc for the snap! A photo posted by Orlando City SC (@orlandocitysc) on Sep 19, 2015 at 2:42pm PDT

Chicago fun with the colleagues! #LionsInChicago A photo posted by Meghan Burke (@megoburke) on Sep 19, 2015 at 5:06pm PDT

Hey Chicago, we hereee! #CHIvORL #LionsInChicago A video posted by Molly (@mhartman89) on Sep 19, 2015 at 5:26pm PDT

Love the fact that you can hear our supporters #LionsInChicago — Gisselle☀∞ (@GisselleG29) September 20, 2015

Game time!!! Go City!!!! #LionsinChicago #vamosorlando #makeitcount A photo posted by Jessica Rae♊ (@jessierae0528) on Sep 19, 2015 at 5:52pm PDT

When Orlando City beats Chicago Fire you have a happy CEO and front office staff. #LionsInChicago #makeitcount A video posted by Meghan Burke (@megoburke) on Sep 19, 2015 at 7:49pm PDT

Hey Orlando, we're coming home with 3 points. #LionsInChicago A photo posted by Molly (@mhartman89) on Sep 19, 2015 at 7:52pm PDT

The three points were the perfect ending to the trip. The staff jumped on a plane early Sunday morning to head back to Orlando.

What a weekend! Had a great time with the @OrlandoCitySC fam. We are blessed to be part of such an incredible organization. #LionsInChicago — Dennis Sprenkle (@DennisSprenkle) September 21, 2015

#lionsleavingchicago #lionsinchicago A photo posted by villemignon (@villemignon) on Sep 20, 2015 at 7:39am PDT

Back to Orlando! #lionsinchicago memorable weekend @orlandocitysc A photo posted by Diogo Kotscho (@dkotscho) on Sep 20, 2015 at 6:12pm PDT

Goodbye #Chicago, it's been fun! #3pts #LionsInChicago #OrlandoCity #soccer #photographer A photo posted by Mark Thor (@markthorphotos) on Sep 20, 2015 at 10:13am PDT