Chicago is a level you can unlock by spending money you've earned.
Collect SKATE Letters
Use the grey quarter-pipe in front of you to transfer right onto the upper ramp, fly off the end of it to get the S. Head down the road and make a left, go into the brown building through the middle door for the K. Cross the road and head up the slope on your right. Use the kickers on the other side of this plateau to grind the red rail on the building opposite to get the A. Make a right and follow the road, you'll see some steps with a quarter-pipe to the left of them. Use it to transfer left onto the ledge around the building and grind, it will lead you onto a wire, use an ollie or two to grind all the way up for the T. Drop back down to ground level. Find the planter with three trees in it, where the railtrack crosses above, Wallride the wall here for the E.
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Collect COMBO Letters
Grind the wall for the C, ollie into a Manual and ride across to the steps. Grind up the right side of the steps for the O, use ollies to maintain a good speed. Manual over to the red railing and grind that, jump into a grind on the curved wall to get the M. Get into another Manual and swerve right, hop the barrier for the B and continue on in a Manual. Head up the right side of the ramp and grind to the left for the last O.
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Deliver The Pizzas
Follow the red arrow to pick up each pizza box. For the first one the quickest way is to use the kicker to get up onto the railtrack above, and follow it to the pizza. This will give you plenty of time for the rest, which are pretty straightforward.
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The Bridge Challenge
Simple enough, jump over the bridge and while you're in the air do the tricks listed on screen.
Step 1: First up is a Triple Heelflip.
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Grind 5 Fire Hydrants
The first hydrant is just up ahead on the left hand side of the road, ollie and grind on it. Follow the road under the bridge and make a right, go under the next bridge and the second hydrant is on the left hand side. Carry on going, the third hydrant is in the lay-by next to the yellow bus. Turn right and carry on down the road, just before the intersect there's another hydrant on the left side. Turn right again, follow the road a short while and the last hydrant is on the right. Skitch on a car if you're low on time.
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Put Bugs On 5 Mafiosos
Turn around 180 as you start and head up onto the roof with the Helipad, use the wooden kicker to get onto the opposite roof. The first mafia guy is on this roof, ollie and do any flip trick over him (for example a Kickflip). Drop onto the ground below and head left up the sloped walkway, the second mafioso is here. Head forward to the road and make a right, make a right around the building, the next mafioso is standing outside the door here. Carry on following the road until you see the weird red metal sculpture, the fourth mafioso is here by the building's door. Turn the corner and follow the road, turn right and go under the bridge. On the left hand side here there's a building with green lion statues, the last mafioso is standing up by the entrance.
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Pro COMBO Letters
Head into the little enclosed area and turn left, the C is hovering over the half-pipe on this side. Land in a Revert to a Manual and ollie through (hold up while you ollie) the opposite side to grind the blue awning where the O is. Hop to the left a little and land in a Manual, grind the steps around and Manual over to the next set of steps. Grind up the right hand wall for the M. Manual over to the quarter-pipe against the wall, use it to launch right and grind to the B. Jump down into a grind on the lower wall where the O is and land it.
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Nail The Tricks They Yell Out
Go back and forth on the ramp doing the tricks listed. There will be one or two lip tricks in there but this is easy.
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Knock Over 10 Ballplayers In One Combo
Don't know what all these ball players are doing on the waterfront. Use the railing to grind on and knock them down, when you run out of rail jump down and Manual. Use the quarter-pipe to get air and land in a Revert to a Manual. Grind the rail the other way and you're done.
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Do A 100,000 Point Combo On The Ledge
Get into a Manual and tap in a load of flatland tricks while holding your balance. If you're having trouble you should set up some manual tricks that are specials.
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900 Off Bridge To Ferry's Top Deck
Fill up your special bar before attempting this, use some flatland tricks to do it quickest. Head up the bridge and near the top jump to the right. During the long drop down do a 900. You have to land on the ferry's top deck for it to count.
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Distract The Guards
There are 4 black cars lined up on the road, grind each one. You have to be reasonably quick about it.
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