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CHICAGO — While many of you may have years of experience in the sports gambling field, chances are thousands more are curious to learn how it’s done and where to do it, now that it’s legal in Illinois.

There are several options to choose from, all with different looks and feels, promotions,  withdrawing options, and security features. We took a look at the top-four options and broke down the ins and outs of each.

The top-four sportsbook application in Illinois:


#1: DraftKings Illinois Sportsbook 

Look and Feel and Ease of Use

The reason you hear and see all of the advertisements surround DraftKings is because of its popularity. The reason for that popularity is due to its user-friendly options and a wide variety of betting options.

Once inside of the app and logged in, you will be greeted with promotional banners such as “who is going to win this game,” or “do you think they will cover the spread?” You can choose to click on those and place basic bets right away or go through the options on your own. Perhaps the greatest plus to DraftKings is their option to use a beginner’s guide, where they walk you step-by-step how to place all kinds of bets.

The second thing you’ll notice is the endless options of sports to bet on, not just the big four (NFL, MLB, NBA, NHL). You can place bets on everything from darts and motocross to the English Premier League.

Next is the ways you choose to bet on them.

Options include sportsbook pools, a way to gamble with a group of friends for a certain amount of money, live cash-out options, live in-game betting, and even an online casino.

Live cashout options can be nice for beginners because they allow you to withdraw your winnings or cut your losses before the contest being decided. In-game betting allows you to bet on current innings, drives, etc.

Specifically, you click on the matchup for in-game betting, select the moneyline or spread you wish to gamble on and click submit. It’s that easy.

If you’re interested in singular bets, they offer everything you’d expect:

  1. MoneyLine (who is favored and by how much)
  2. Spread (The Cubs will win this game by at least 4 runs)
  3. Total (over/under how many points in the contest)
  4. Alternate Routes (betting on a higher/lower spread to win more money)
  5. Futures (Picking the Bears to win the Super Bowl before week 1)
  6. Prop Bets  (I think Allen Robinson will score the game’s first Touchdown)

Deposit/Withdraw Options

To get started, DraftKings only requires a $5 initial deposit. From there, you can bet on any level, including bets under $1.

Deposit options include bank account, credit/debit cards, bank cards, PayPal, Draftkings card, casino cage, and E-Checks.

Once funded, you can begin to place bets. Once contests conclude, money is placed in your account promptly. There is no need to wait days to get money out, either. You are allowed to take out funds as you wish.


Right now, new users are being granted a bonus of $1000 that includes a risk-free bet and deposit match. What does that mean?

Once the money is in your account, you can wager put to $500 risk-free on your first bet within the first 30-days of signing up.  If you win the risk-free bet, there is a play through requirement, and you will have to wager your winnings from the free bet then.

The other $500 comes in the form of a deposit match. To get the $500 deposit match, you’ll have to play through 25 times ($12,500) to receive the entire deposit bonus.

So, if you deposit $500, you will get a $500 risk-free bet and another $500 deposited free into your bonus account for you to bet with.


Due to gambling only being legal in 18 U.S. states right now, DraftKings will not allow you to place sportsbook related bets if you are outside of one of those states.

How do they know where you are?

As soon as you log in to your account for the first time, you’ll be asked to download GeoComply, a player location application. You can use this on IOS and Android devices, and it is safe to download. Once it pinpoints your device’s location, you’ll either be allowed to continue, or you won’t.

As for your personal and confidential information, all of it is secured by SSL (secured socket layer).

According to the website’s recommendations, they say never share your password and keep your device’s anti-virus software up-to-date.

If you believe your account has been compromised, you can email support@draftkings.com with any questions or concerns.

Ratings from iTunes and Google Play

With nearly 120,000 ratings on the IOS App Store, DraftKings Sportsbook has a 4.8/5 star rating. The overwhelming majority shows five-star ratings.

#2: FanDuel Sportsbook Illinois 

Look and Feel and Ease of Use

Much like DraftKings, FanDuel is user friendly and simple to use. It may trail behind competitors when it comes to updates, but the interface is up-to-date and easy to follow.

Much like its competitors, you can bet on just about every major sport using any bet you chose.

  1. MoneyLine
  2. Spread
  3. Total
  4. Alternate Routes
  5. Futures
  6. Prop Bets

FanDuel also introduced the idea of a one-day fantasy back in 2009. Today, you can wager any fantasy-related competition on the interface. Whether it’s fantasy baseball, football, soccer, or whatever your choice is, there is a type of gameplay that will suit what you’re looking for.

Deposit and Withdraw Options

Deposit options are what you’d expect. Credit/Debit cards, PayPal, bank account information, FanDuel Gift Cards, E-Checks, and PayNearMe.

Withdrawing options include ACH (online) checks. Once you cash-out, it will take 3-5 days to show up in your bank account.

Requesting a physical check is an option. It will be mailed to you within 5-7 business days.

Paypal and FanDuel pre-paid cards also serve as ways to withdraw your winnings.


Right off the bat, as soon as you deposit any money, FanDuel gives you $20. No catch.

Like DraftKings, FanDuel is also offering a $1000 welcome bonus. However, the terms are a little different.

  • FanDuel offers you a $1000 risk-free bet, rather than $500. Besides, if you win your risk-free bet, there is no required play-through. In other words, you only have to wager your initial deposit and winnings one time to withdraw your money.

For example, if you deposit $200 to FanDuel, they will match and give you $200. All you have to do is wager $400 worth of bets to withdraw, whereas, in other sportsbooks, you have to play through several more times.

  • FanDuel also offers a Daily Odds boost. In other words, they offer basic bets with way higher payouts.

For example, if the odds of Cole Kmet scoring a Touchdown in a game was +120, normally that means a $10 wager nets you $12. FanDuel boosts the odds to +200, so your payout is then double what you wager. $10 is a $20 payout.

  • FanDuel also offers a friend referral bonus called the $25/$20.

All you do is send them the referral link, they bet at least $10, and they will receive $25, and you receive $20.

  • Perhaps the best promotion FanDuel offers are the “NFL Play until you Win Vouchers.”

This is an awesome feature. There is no buy-in necessary, but you can still win money. FanDuel creates 20-player tournaments competing to beat a certain score each week. Winners split the $50 in prize money, and losers are given another free voucher to play again next week.

You will continue to receive vouchers until you win—a very unique and awesome feature.


FanDuel Partners with HackerOne to keep all information safe. They also showcase a team of engineering experts that monitor the site for hackers and other red flags.

They also offer a live 24/7 customer service chat, email, and phone line for any questions or concerns.

To contact, click here.


On the IOS App Store, FanDuel has a 4.7-star rating from 77 thousand ratings. The overwhelming amount of ratings are five stars.

#3: William Hill Sportsbook 

William Hill Sportsbook Illinois
William Hill Sportsbook Illinois

Look and Feel and Ease of Use

Much like DraftKings, William Hill‘s variety of sports to bet out stands out right away. As soon as you enter the interface, it can be a little more challenging to navigate because of all the words and advertisements. With the advertisements comes a very professional and up-to-date look, however.

Users can use the dropdown menu at the top of the page to find what sport they would like to bet. From there, William Hill gives you more betting options than the previous two listed.

Right now, their interface allows you only to search specific bets through the sport. In other words, there is no way to reach types of wagers. This would be a nice touch in the future.

Deposit and Withdrawing Options

One thing is for sure about William Hill – you’ll definitely be able to find a payment method that works for you.

For Deposit and Withdrawing options:

  • Credit/Debit Cards
  • EntroPay
  • Banking Information
  • EWallet
  • Cash Vouchers
  • Prepaid Cards

On average, withdrawing money using any form above takes 3-5 days to process.


1: New Customer Promotion

William Hill offers new customers approximately $40 in free bets after a new customer wager at least $10 on their first bet. It also allows a new customer to receive a 300% bonus on the initial bet.

2: Two Clear Bonus

When betting on horse racing, if a horse wins by two lengths, a player will win a 15% bonus on top of their winnings. The best part is you don’t have to sign up for these. They are automatically used when betting on horse racing. The bonus is capped off at approximately 118 dollars.

3: Four means more

You’re allowed a chance to win a 25% bonus on your winnings if four goals or more are scored in select games. It must be a matched betting, both teams score or match result, and both teams score. The bonus is capped off at approximately 118 dollars.

4: Cash in My Bet

Here is a promotion that sets William Hill away from the other apps. This promotion allows a player to get a cash buyback option before or during a match. In other words, if you’re losing or feel like things are about to turn against you, you can cut your losses.

5: Super Sub Promotion

If you’re betting on soccer and your goal scorer gets hurt, for select matches, William Hill will allow a replacement player, so you still have a chance to hit on your bet. This is also unique to their app.


William Hill offers a 24/7 direct chat for any concerns or questions. This is the most efficient way to contact.

You can also email or call them. They have workers monitoring the inbox and phone lines seven days a week.


On the IOS app store, the William Hill Illinois Sportsbook app has a 1.6-star rating from 23 total reviews.

#4: PointsBet Sportsbook 

Look and Feel and Ease of Use

PointsBet is a great place to bet on Chicago sports. This interface gives advice and tips to its users to be confident in the bets you place.

Also, they offer creative lines to bet on and allow you to bet on tons of sports. Another thing you’ll notice with this interface is how many more prop betting options you have.

This app is user-friendly and offers a categorized menu to pick and chose the sports you’re looking to place bets on that day.

Options include sportsbook pools, a way to gamble with a group of friends for a certain amount of money, live cash-out options, live in-game betting, and an online casino.

Deposit and Withdrawing Options

For Deposit and Withdrawing options:

  • Credit/Debit Cards
  • PayPal
  • Banking Information
  • EWallet
  • Cash Vouchers
  • Prepaid Cards


1: Sign Up Bonus

Once you’ve signed up, PointsBet offers up to $200 in risk-free bets. The bonus is then split into two parts. $100 in refunds for the first fixed-odds bet, and a refund of up to $100 for the first Pointsbetting wager.

2: Referral Bonus

Every friend you refer to that deposits $50 into your account will net you and your friend $50 each. You can earn up to $2500 in referral bonuses each year.

3: Parlay Bonus

For any parlay with four or more legs, you receive up to a $25 refund if one fails.

4: Rewards Program

Every bet you place earns you points. Every 1,000 points earned is $10 added to your account.


128-bit SSL encrypts the website and every page. Geolocation is necessary to place bets.

Like all of the other options, PointsBet offers a 24/7 live chat and email service service@pointsbet.com.


PointsBet has a 4.6 rating on the IOS app store with 1,500 plus ratings.

Top Chicago Sports Betting Apps

Description: When it comes to Chicago sports betting, these four apps are your best options.

Currency: FREE

Operating System: iOS, Android

Application Category: Chicago Sports Betting

Author: Kevin Wells

  • DraftKings
  • FanDuel
  • William Hill
  • PointsBet


You really can’t go wrong with any of the top four Chicago sports betting apps, but due to their promotion with the Chicago Bears and the crazy offers they have, PointsBet is the recommended app.