Main game

Each episode featured winners of a second chance drawing (through an online website), who were flown to Las Vegas to participate in the show. Selected contestants, each from a different section of the audience, played a series of games that each offered a top prize of $100,000. Every contestant played a different game and kept half of his/her winnings, with the other half split equally among the drawing winners in his/her section. Eight different $100,000 games were played over the course of the series.

Episodes were originally taped at the Rio All Suite Hotel and Casino and featured five games per hour-long episode. The audience was split into five sections (battleship, boot, cat, dog, and wheelbarrow—all named after tokens in the classic U.S. version of Monopoly). Later, the taping location was moved to Bally's Events Center in Bally's Las Vegas and the episodes were reduced to 30 minutes featuring three games. The boot and cat audience sections were initially removed, but later restored.

Residents of states that did not sell lottery tickets during the period of the show's production were not eligible to participate in the program.

Additionally, during each episode, co-host Todd Newton chose a contestant to play a short game for up to $10,000. Two such games were played per episode in the first season, and one in the second. Contestants in these games kept their winnings for themselves, but were not eligible to play for the $1 million grand prize.

Go for a Million

At the end of each show, one contestant would be able to play "Go for a Million", giving up all previous winnings (including the portion shared with the audience section the contestant represented) for a chance to win up to $1 million in cash and additional prizes. Only the contestant who decided to give up the most money played this round, other contestants kept their winnings.

The contestant started at GO and attempted to make one full lap of the Monopoly board within five turns. Two dice were rolled on a shaker table referred to as the "Monopoly Rock-and-Roller". The contestant stopped it by pushing a button and moved clockwise according to the total shown. Rolling doubles awarded an extra roll. All colored properties awarded cash amounts, starting at $2,000 for Baltic Avenue (landing on Mediterranean Avenue was not possible due to being only one space away from GO) and increasing clockwise to $40,000 for Boardwalk. Other spaces awarded prizes or triggered mini-games that could award cash and prizes or penalize the contestant.

The game ended immediately and the contestant lost all cash and prizes if any of the following occurred:

• Landing directly on the "Go to Jail" space
• Rolling three consecutive doubles
• Drawing a "Go to Jail" card from Chance or Community Chest

Running out of turns without reaching GO or going to Jail, or landing on Luxury Tax in Season 2, split the final cash prize total with the audience section and allowed the contestant to keep all non-cash prizes. Passing GO augmented the cash total to $200,000, which was split with the section. Landing on GO exactly, either by dice roll or drawing an "Advance to GO" card from Chance or Community Chest, augmented the contestant's cash total to $1,000,000 and split the Audience Jackpot among the section. This jackpot was $200,000 for all but two episodes, in which it was $300,000. Winning the top prize also awarded the contestant a shiny, diamond-encrusted Mr. Monopoly top hat and a membership at the Monopoly Millionaires' Club. Four contestants had won this prize during the show's run.