In writing this solve I'm assuming you know how to play ICOM adventures, if not get some documentation on them. I've tried to make this as clear and concise as possible and to win the game in as little moves as possible.
Bathroom: Get pants, operate pants, open bathroom door, exit thru door.
Bedroom: Get cigar ring, get train schedule,open hotel room door, exit thru door.
Corridor: Open double doors under casino sign, exit thru double doors.
Lobby: Take left exit to cashier's cage.
Cashier's Room: Open wallet, operate $10 bill on cashier, get chips, exit left to blackjack room.
Blackjack Room: Keep going left and examining each of the dealer's name tags, until you find Rudy Kowalski, operate newspaper clipping in your wallet of you and Rudy boxing on Rudy for easy winning, bet until Rudy is replaced, get chips, exit right until your at the Cashier's room.
Cashier's Room: Give chips to cashier, get paper money, exit right into lobby.
Lobby: Exit thru glass doors outside.
Casino Entryway: Exit right to Train Station.
Train Station Entryway: Enter Train Station.
Train Station: Exit right to baggage claim booth.
Baggage Claim Department: Examine departure sign until a train boarding for Chicago appears and what gate, exit left back into station.
Train Station: Exit to appropriate gate.
Platform: Enter train.
Train: Pay conductor $20.00, wait until train arrives in Chicago, exit train.
Platform: Enter Train Station.
Train Station: Operate quarter in wallet on newsstand clerk, get newspaper, exit train station.
Train Station Entryway: Enter taxi cab.
Taxi: Operate drivers license in wallet on cab driver, exit taxi.
Apartment Entryway: Enter apartment building.
Hall: Operate key to your apartment on door 1A, enter apartment.
Your Apartment: Get flashlight, open overcoat on wall, get $10 bill, open drawer on floor, get penknife, exit apartment.
Hall: Exit apartment building.
Apartment Entryway: Enter taxi.
Taxi: Operate newspaper clipping in wallet that says "ACE CLEARS NAME" on taxi driver, Exit Cab.
Joe's Bar Entrance: Enter alleyway behind joe's bar.
Alley: Go to fire escape.
Fire Escape: Open penknife, operate penknife on bunch of boards nailed to window, operate boards, enter window.
Siegle's Office: Open old telephone on wall, get key, exit thru window.
Fire Escape: Exit to stairs down.
Alley: Exit to further down the alleyway.
Back Alley: Operate penknife on door, open door, enter door.
Hall: Operate flashlight, open bar door, enter bar door.
Bar Room: Open wine cellar door, enter wine cellar door.
Wine Cellar: Operate wine bottle with no cob webs, enter secret passage.
Secret Room: Open round door, enter round door.
Casino: Operate unusually shaped key on right slot machine, open slot machine, get diary,get card, exit thru round door.
Secret Room: exit thru wine cellar.
Wine Cellar: Exit to bar room.
Bar Room: Exit to hall.
Hall: Exit to back alley.
Back Alley: Exit to alley
Alley: Exit to street.
Joe's Bar Entrance: Enter Taxi.
Taxi: Operate business card on taxi driver, exit cab.
Apartment Entryway: Operate penknife on basement apartment door, open door, enter door.
Sugar's Apartment: Open clothes wardrobe, get cop's uniform, open vacuum cleaner, operate penknife on vacuum cleaner bag, get letter, exit apartment.