Did you know that placing bets on Chicago sports is now legal in the state of Illinois? That’s right, you can now legally bet money on the Bears, Blackhawks, Bulls, Cubs and White Sox with just a few clicks. The days of blowing up your bookie’s voicemail with your picks are over Chicago.

Back in June 2019, Illinois Governor J.B. Pritzker signed a massive gambling expansion. The expansion was included in a group of bills with $45 billion worth of construction (six new casinos) and an increase in taxes on gas and cigarettes. This paved the way for Rivers Casino Des Plaines, BetRivers Sportsbook, to accept the first legal sports bet in Illinois in March 2020.

Betting on Chicago sports has never been easier, or legal, and DraftKings Sportsbook is the best mobile app to do it!

DraftKings Sportsbook

The DraftKings Sportsbook has the best overall experience for betting according to its 10+ million registered users. They advertise as the “#1 Sports Betting App” and their promotions are silly. They offer deposit matches, risk-free bets and profit boosts. Imagine betting $1 to win $100, on a regular game with the updated line, that’s the type of stuff happening on DraftKings everyday.

Registering for Bets

  1. Go to the DraftKings Sportsbook website: nothing fancy here, click the link and get started.
  2. Claim your first promotion: currently a sign up bonus up to $1,000 and a $500 risk-free bet.
  3. Create an Account: name, email, password… you know the drill.
  4. Deposit Money: they’ve made this easy, simply put in a credit card or login to your bank.
  5. Make Your First Bet: check out the lines, look at the additional promotions offered, make your first bet.

That’s it. Winnings are instantly paid out when the game/bet is over and you can withdraw your money anytime. There are no hidden rules where you have to let your money sit on the system, you can put your money in or take it out whenever you want. This is one of the things that makes the DraftKings Sportsbook the best mobile app for Chicago sports betting.

Screenshots of the DraftKings Sportsbook App


    • Crazy Good Promotions
    • Very Secure
    • Easy to Use
    • No Hidden Rules/Fees
    • Cons

    • Crowded Interface At Times
    • Some Peak Time Slowness

Reviews of the DraftKings Sportsbook App

The DraftKings Sportsbook app currently has over 101,000 reviews on iTunes with a 4.8 rating. The primary complaint in the reviews is the customer service of DraftKings, you’d have to think that likely comes from having 10+ million registered users. In any case, the overall opinion of the fans is the DraftKings Sportsbook is awesome.

Chicago Bears on DraftKings Sportsbook App

During Week 1 of the NFL season the Chicago Bears were a 2.5 point underdog to the Detroit Lions. The over/under for the game was 42.5 and the Bears were +115 on the money line. While reviewing the DraftKings Sportsbook app, we placed a few bets on the Bears.

  • $25 on the money line (Bears win) with a 25% profit boost.
    • Win pays out $62.50
  • $1 on the money line (Bears win) with odds boost.
    • Win pays out $101! (huge promotion)
  • FREE bet on the point spread (Bears +2.5) with free bet.
    • Win pays out $21.75
  • $25 bet on the point spread (Bears +2.5)
    • Win pays out $46.75 (regular bet)
    • $51 bet on the Chicago Bears to win $232 … they played the Lions!

As you know, Anthony Miller caught the go-ahead touchdown late in the game after a red-hot fourth quarter from Mitch Trubisky. D’Andre Swift, Lions running back, helped us out by dropping the game-winning touchdown pass with less than 10 ticks to play. That’s all behind us now and we quadrupled our money with a $50 risk.

Deposits and Withdraws

The deposit process is pretty easy, and instantaneous. You can use a credit card, or you can use their interface to login to your bank and choose your account. The deposit minimum for the DraftKings Sportsbook is $5, and if you do deposit the five spot you earn the ability to earn up to $500 addition bonus funds in the form of site credits moving forward.

If a bank deposit or credit card isn’t your thing, there’s actually several ways to withdraw and deposit money using the DraftKings Sportsbook.

  1. Bank account
  2. Credit card
  3. Debit card
  4. Prepaid DraftKings card (Play+)
  5. PayPal
  6. Casino cage
  7. E-Check

DraftKings also features a worry-free payout. This basically means your money is secure no matter what happens to DraftKings the company. If you wake up one day and DraftKings has gone bankrupt, your money would be secured using the liability policies DraftKings has in place to protect it. You can rest assured your money will be safe and secure while it is inside of the DraftKings Sportsbook application.


DraftKings bonuses and promotions are the best in the business. They are currently offering a two-tiered bonus that can be worth up to $1,000!

Here’s how it works:

  • The matched first bet: This applies to first-time users when they make their first bet at DraftKings Sportsbook. Here’s an example: If your first bet is $250, you will get $250 in free bets instantly added to your DraftKings account in the form of bonus bets. The max DraftKings will match your first bet is $500.
  • The deposit bonus: It’s a 20% match worth up to $500. So if you deposit $100, you would earn a $20 bonus. To receive the max $500 bonus, you would have to deposit $2,500.
  • No promo code is needed to redeem this exclusive $1,000 sign-up bonus.

This doesn’t even include all the other games/promotions included inside of the app. These come in various different forms allowing you to win extra money, move the line a few points in your favor or make bets for FREE.

Getting Started

So … what do you think? Are you ready to make your first bet? To get started all you have to do is follow the registration steps above. There’s also some terminology you should be familiar with.

  • Spread: the amount of points a team is the favorite/underdog by.
    • Example: The Bears were a 2.5 underdog to the Lions, so the Bears get +2.5 points if you bet on them. If the Lions win by one point, the people betting on the Bears would win the bet.
  • Over/Under: the total amount of points expected for the game.
    • Example: The over/under for the Bears vs. Lions game was 42.5. The final score was 27-23, making the total 50. Those that bet the over would have won.
  • Money Line: a bet made on the team winning the game, regardless of the spread.
    • Example: The Bears were getting 2.5 points against the Lions, if you bet them to win the game straight up,  you would get the money line odds which were +115. This means you would get $1.15 for every $1.00 you bet on the Bears. 

The primary ways to bet are as follows.

  • Bet on the spread
  • Take the over, or under
  • Pick a team to win based on money line odds

That’s basically it.

Watching a game you’ve bet on makes the experience more fun and it creates another level of excitement. If you’ve ever thought about doing it, give the DraftKings Sportsbook a try. It’s perfect for new bettors, and they’ve got some awesome promotions you can take advantage of.

draftkings sportsbook promo