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Best Online Sports Betting Chicago 2025

Last Updated on April 15, 2025
Fact checked by: Jesse M Cox

Legal sports betting in Chicago is finally here and we’re going to show you the best sports betting sites Chicago has to offer. Take a look below to get started with safe and legal Chicago online sports betting!

It’s hard to believe that legal sports betting only came to Chicago as late as March 2020. But there is now an awesome number of sports betting sites Chicago sports fans can use. Time to pack your bags and discover the best sports betting sites Chicago has to offer!

Compare the Best Online Betting Sites in Chicago

Our Top Picks
Key Highlights
Bonus Type
Reset
Bet365
We recommend
4.9/5
  • Fantastic welcome bonus available
  • Niche sports like Gaelic and futsal
  • Market-leading betting odds
Bet365 Promo
Get $150 in Bonus Bets Win or Lose when you bet $5!
User Rating
4.4/5
Open Bet365
Bet now
Deposit Methods
Find out more on Bet365.
Withdrawal
0 – 10 Days
Apps
License
Illinois (US)
Award
EGR – Operator of the year (2017)
Subject to meeting qualifying criteria. Minimum wager $5. Minimum odds -500 or greater. $10 minimum deposit. Paid in Bonus Bets. Bonus Bets wager excluded from returns. New customers only. Available in app only. Max. prize, game restrictions, time limits and T&Cs apply.
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BetMGM
Hot Offer
4.5/5
  • Massive range of betting markets
  • Plenty of different wager choices
  • Live match tracker and data available
BetMGM Promo
Up To $1500 in Bonus Bets Paid Back if your First Bet Does Not Win
T&Cs and 18+ apply
User Rating
4.3/5
Copy
Bet now
Deposit Methods
Bank Transfer
Play+
PayPal
+
Withdrawal
0 – 3 Days
Apps
License
Illinois (US)
Award
GGA – Digital Operator of the Year (2023)
Show less
FanDuel
Hot Offer
4.4/5
  • Huge range of games to bet on; both real and fantasy!
  • Guides to help you responsibly bet
  • Competitive odds compared to other betting sites
FanDuel Promo
Bet $5 Get $250 in Bonus Bets IF YOU WIN
T&Cs and 18+ apply
User Rating
5.0/5
Open FanDuel
Bet now
Deposit Methods
Bank Transfer
Play+
PayPal
+
Withdrawal
1 – 10 Days
Apps
License
Illinois (US)
Award
Global Gaming Awards (2022)
Show less
Caesars
4.
4.3/5
  • – Top Tier Customer Service
  • – Quick Withdrawals
  • – Best Odds
Caesars Promo
Bet $1, Double Your Winnings Your Next 10 Bets
T&Cs and 18+ apply
User Rating
4.8/5
Copy
Bet now
Deposit Methods
Bank Transfer
Play+
PayPal
+
Withdrawal
0 – 5 Days
Apps
License
Illinois (US)
Show More
DraftKings
5.
4.2/5
  • Over 18 sports to choose from
  • Great live betting options
  • Available in many states
DraftKings Promo
Bet $5 and Get $150 in Bonus Bets Instantly!
User Rating
3.6/5
Open DraftKings
Bet now
Deposit Methods
Bank Transfer
Play+
PayPal
+
Withdrawal
0 – 5 Days
Apps
License
Illinois (US)
Award
EGR – Operator of the year (2023)
GAMBLING PROBLEM? CALL 1-800-GAMBLER, (800) 327-5050 or visit gamblinghelplinema.org (MA). Call 877-8-HOPENY/text HOPENY (467369) (NY).Please Gamble Responsibly. 888-789-7777/visit ccpg.org (CT), or visit www.mdgamblinghelp.org (MD). 21+ and present in most states. (18+ DC/KY/NH/WY). Void in ONT/OR/NH. Eligibility restrictions apply. On behalf of Boot Hill Casino & Resort (KS). 1 per new customer. $5+ first-time bet req. Max. $150 issued as non-withdrawable Bonus Bets that expire in 7 days (168 hours). Stake removed from payout. Terms: Promos | DraftKings Sportsbook. Ends 4/13/25 at 11:59 PM ET. Sponsored by DK
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Fanatics
6.
4.1/5
  • Backed by a major name in sports retail
  • Built for US betting fans
  • Likely to offer some fantastic promotions
Fanatics Promo
Bet $10 Get $50 Bonus Bets
T&Cs and 18+ apply
User Rating
4.3/5
Open Fanatics
Bet now
Deposit Methods
Bank Transfer
PayPal
Venmo
+
Apps
License
Illinois (US)
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Barstool
7.
  • Over 100 betting markets
  • Competitive odds
  • Generous bonuses
User Rating
3.8/5
Best Alternative
Bet365 Open Bet365
Deposit Methods
Bank Transfer
Play+
PayPal
+
Withdrawal
1 – 5 Days
Apps
License
Illinois (US)
Show More
ESPN Bet
8.
  • Multiple betting markets
  • Incredible offers for sportsbook lovers
  • Competitive odds across different markets
ESPN Bet Promo
T&Cs and 18+ apply
User Rating
3.0/5
Best Alternative
Bet365 Open Bet365
Deposit Methods
PayPal
Visa
Mastercard
+
Withdrawal
0 – 10 Days
Apps
License
Illinois (US)
Show More

Why you should check our comparison for Chicago online sports betting

Sports betting in Chicago is only getting started and the chances are that you won’t know which sportsbook is right for you. This is why we’ve set up an awesome comparison of the best sports betting sites Chicago has to offer. As a result, you can simply use this comparison to find a fully regulated sportsbook that can offer you seriously competitive odds.

You might be a casual fan of the Chicago Bears who’s looking to take their first football bet.  Or you might even be a hardcore Blackhawks fan who wants to put down a tasty parlay bet. Whatever you’re looking for, you’ll find it in our comparison of the best sports betting sites Chicago has at the moment.

Things to check for the safest online sports betting Chicago has to offer

As long as you’re located within the Illinois state borders and are over the age of 21, you should be able to enjoy sports betting without a problem. However, we still think that there are few things to be careful of. So here are the five main trust factors we look for in all of the best sports betting sites Chicago has to offer:

IGB regulation

Sports betting in Illinois is regulated by the Illinois Gaming Board. This means that if you want to enjoy online sports betting in Chicago, you should only use those sportsbooks who are regulated by the IGB. Such regulation ultimately means that the sportsbook will operate in coordination with the gambling laws of Illinois to give you a safe and fair way to play.

SSL encryption

You will have to provide a sportsbook with some fairly personal information when you sign up to their sites to enjoy sports betting in Chicago. As such, you’ll want to be able to trust that sportsbook with your data. We always check that the betting site has a minimum 128-bit encryption to keep your data safe.

Payment methods

You’ll have to make real money deposits to enjoy some Chicago online sports betting. This means that each sportsbook will have to feature reputable payment providers for making secure and efficient deposits and withdrawals. We look for payment brands like Visa, MasterCard, PayPal, PayNearMe and so on.

Customer support

All good sportsbooks will provide plenty of customer support so that you can enjoy some stress-free Chicago online sports betting. It should usually be something as simple as using live chat, email or telephone to get help from a sportsbook. If a sportsbook doesn’t offer any customer support, then it’s probably best worth avoiding.

Terms and conditions

You should see a page of terms and conditions at all of the best sports betting sites Chicago has to offer. This describes what you can and can’t do at the sportsbook and it should ensure that you get a fair way to play. The terms and conditions will also dictate everything from how you use bonuses to how you make withdrawals. Incredibly important for knowing where you stand with the sportsbook.

The best of the best sports betting sites Chicago has right now

FanDuel offers you a great way to get started in enjoying online sports betting in Chicago. You’ll probably know that FanDuel was one of the key reasons why fantasy sports betting was big news a few years ago. But we’ve found that FanDuel has emerged to become a seriously credible sportsbook in its own right.

The brand has its headquarters in Collinsville, IL but once you’ve signed up you can enjoy betting on a massive range of odds anywhere in the Prairie State. We found that FanDuel offers awesome football odds which is great news for all Bears fans, and you’ll find no shortage of bets for basketball, hockey, baseball, golf, soccer and more.

FanDuel’s got all of its regulation in place from the Illinois Gaming Board, and we were glad to see that it only accepts the safest payment methods like Visa, MasterCard, Discover, Play+ and PayPal. Plus with an awesome no sweat first bet bonus to get you started, there’s never been a better time to sign up at FanDuel.

Check out these top US betting sites

Bet365
1.
4.9/5
up to 100€ Bet Credits
MGA - Malta Gaming Authority
Bet now
T&Cs and 18+ apply
Betway
2.
4.8/5
100% up to $60
Skrill
Neteller
Paysafecard
MGA - Malta Gaming Authority
Bet now
T&Cs and 18+ apply
Unibet
3.
4.7/5
100% up to 40€
Skrill
Neteller
Paysafecard
MGA - Malta Gaming Authority
Bet now
T&Cs and 18+ apply
William Hill
4.
4.6/5
30€ Free Bet
Entropay
Skrill
Neteller
MGA - Malta Gaming Authority
Bet here
18+ #Ad Play Safe ww.begambleaware.org Full terms & conditions apply.
Bwin
5.
4.5/5
100% up to 100€ + 10€ Free Bet
PayPal
Skrill
Neteller
MGA - Malta Gaming Authority
Bet now
T&Cs and 18+ apply

How we test all of the sports betting sites Chicago has at the moment

We believe that sports betting should be fun and stress free. This is why we always take care to personally test each sportsbook we come across so that you can enjoy sports betting in the Windy City. Here are the key criteria we use for testing online sportsbooks in Chicago:

  • Bonuses: It’s always nice to get a welcome bonus when you sign up to a sportsbook. We’ll let you know what you get in terms of sign up offers at all good Chicago sportsbooks.
  • Site design: We have no time for badly designed sports betting sites. Our reviews will let you know exactly how easy it is to use a sportsbook’s betting website and apps.
  • Customer care: Our reviews will examine the best ways of getting in touch with a sportsbook. You’ll also see exactly how professional the customer service teams are.
  • Payment options: Each review will describe how you can make deposits at the sportsbook from Chicago. We’ll also outline what the process is for withdrawing your winnings.
  • Licensing and security: We’ll make sure that each Chicago sportsbook is regulated by the Illinois Gaming Board. You’ll also get to see how the sportsbook looks after your personal data.
  • Reward programs: Here you’ll see whether there is any kind of loyalty scheme in place at the sportsbook. Such reward programs can be a great way of getting bet credit.
  • Betting markets: You’ll learn how many different ways you can bet on football, hockey, basketball, baseball, soccer, tennis, boxing, MMA fighting, golf and any other sport.
  • Odds: We’ll carry out odds comparison tests between all sportsbooks operating in Chicago. Perfect for seeing who has the best odds for the Cubs, Bears, White Sox, Blackhawks and Bulls.
  • Live betting: All decent sportsbooks let you bet live on sport. Our reviews will highlight what kinds of live bets the sportsbook has and you’ll learn whether there’s any live streaming.
  • Betting limits: Nobody wants to find that their bets or winnings have limits, so our reviews will reveal which Chicago sportsbooks are more generous than most.

Finding you the perfect site for sports betting in Chicago

There’s never been a better time to get started in betting on sport in Chicago. After all, legal sports betting has just opened up and there are some awesome sportsbooks waiting to give you competitive odds for your favorite sport.

Admittedly, things have taken a little while to get going with legal sports betting in Illinois, but there are now a decent number of online sportsbooks to choose from. You can simply take an overview of all of the sportsbooks who are regulated by the Illinois Gaming Board in our operator comparison. Each of these sportsbooks has been checked to make sure that they offer a legal, safe and fair betting service.

You can also check out our reviews to see how each Chicago betting site works. Our reviews will examine everything from the sportsbook’s betting odds to its customer care facilities. All of which should give you an easy way to see whether the sportsbook is right for you.

Going beyond Chicago online sports betting

We won’t just help you find the best sportsbook in Chicago. Our whole site is devoted to all aspects of online gambling. Whether you’re looking for the best NHL odds for the Blackhawks or want to see which sportsbook features free live streaming for that Bulls NBA game, you’ll find it here. Take a look below to see what else you can find on our site:

  • Odds comparison: We’ll make sure that you can easily find the sportsbook with the best odds for anything from that White Sox game to the next bout of Bears gridiron action.
  • Bookmaker awards: This is where we award each sportsbook for outstanding service in anything from NFL odds to their withdrawal speed.
  • Betting app: You’ll learn which sportsbooks have developed the most user-friendly betting apps. Perfect for enjoying a bet while out and about in the Windy City.
  • Sportsbook reviews: This is where we carefully examine what it’s like to really use each sportsbook. The only way you’re going to know whether it’s right for your betting needs.
  • Betting deals: Here’s where we rank and rate each betting bonus. It’s never been easier to find the ultimate sports betting promo in Chicago.
  • Tipster: Want to know if the Chicago Bulls are looking likely to win their next NBA game? Then you’ll need to see what our tipster has to say about basketball and any other major sport.
  • Betting in US states: Illinois isn’t the only state to have legal sports betting. Check out our state guides to see whether sports betting is available everywhere from Washington to Florida.
  • Betting strategies: Luck can only take you so far with your sports bets. Read our strategies guide to see which tactic can work best in helping you get more from your bets on the Cubs or Bulls.
  • Betting guide: We’ve prepared an awesome guide that can take the mystery out of sports betting. Perfect for seeing whether you should try a system bet or a multiple bet on that Bears game.
  • Payments: Here’s where we examine whether a card, ewallet, bank transfer or a payment method like PayNearMe could work best for you.

Which kind of Chicago sportsbook do our experts use?

We’re more than happy to share our experiences of using online sportsbooks in Chicago with you. Here are a few pointers that our experts have found when picking a suitable sportsbook in the Windy City:

Sport specialization

Most sportsbooks cover major sports like NHL, NBA, MLB and NFL. However, some sportsbooks can be sketchy in their coverage of other sports like horse racing. While horse racing betting is legal in Illinois, only a few sportsbooks will have racing odds. So read our reviews to avoid disappointment.

App availability

You can legally bet on sport anywhere within the Illinois state borders. This is why our experts are keen to see which sportsbooks have developed their own iOS or Android betting apps. Perfect for enjoying a sports bet anywhere in Chicago and all over the Prairie State.

Easy registration

Illinois sports betting had some fairly complicated rules to begin with. These demanded that you have to sign up to a physical outlet that was offering sports betting. Thankfully things have eased a little since then, but our experts still like those sportsbooks who don’t require customers jump through too many hoops to start betting.

Decent reputation

Our experts always do their research before they sign up to any online sportsbook. This is important as there are lots of rogue offshore sportsbooks out there. While you might not get in trouble for using an offshore site, these sites are operating illegally. All of which means that our experts do their homework and only use those sportsbooks that are regulated in Illinois.

Conclusion – Get ready to enjoy some awesome Chicago online sports betting

We’ve reached our destination! While legal sports betting in Chicago has only been around for a couple of years, it’s already gotten pretty exciting. This is because there are a growing number of operators who can give you a safe and easy way to bet on everything from the NBA and NFL to the NHL, MLB and beyond.

However, we’ve also revealed how you can’t let your guard down when enjoying some Chicago online sports betting. But by sticking with any one of our shortlist of the best sports betting sites Chicago has to offer, you can be sure of enjoying a legal, safe and fair way to bet on sport. So sign up with one of our featured sportsbooks and enjoy the ultimate in online sports betting in Chicago!

Boost your bets with these top bonuses

Bet365
1.
4.9/5
up to 100€ Bet Credits
Wagering (WR): 1x Deposit, Min. Deposit: 5€
Open Bet365
Get bonus now
T&Cs and 18+ apply
Betway
2.
4.8/5
100% up to $60
Wagering (WR): 6x Bonus, Min. Deposit: $10
Open Betway
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T&Cs and 18+ apply
Unibet
3.
4.7/5
100% up to 40€
Min. Deposit: 1€
Open Unibet
Get bonus now
T&Cs and 18+ apply
William Hill
4.
4.6/5
30€ Free Bet
Wagering (WR): 1x Bonus
Copy
Get bonus here
18+ #Ad Play Safe ww.begambleaware.org Full terms & conditions apply.
Bwin
5.
4.5/5
100% up to 100€ + 10€ Free Bet
Wagering (WR): 3x (Bonus + Deposit), Min. Deposit: 10€
Open Bwin
Get bonus now
T&Cs and 18+ apply

Chicago online sports betting FAQ

Read our guide to sports betting in Chicago to see all of the legalities surrounding this activity. After all, the city’s sports betting laws had a pretty large overhaul recently, and the resulting picture is now very different to online sports betting in Texas. So check out our guide to see how old you have to be to legally bet and where you are allowed to bet from when you use Chicago sportsbooks.

📱Who has the best Chicago betting app?

It depends what you’re looking from in your betting app. After all, some apps might be better suited to Chicago Bears fans while others could be perfect for Blackhawks fans. So read our guide to the best sports betting sites Chicago has to offer to see which of these sites have developed their own betting apps. Perfect for seeing which operators give you a convenient way to enjoy betting on sports.

⭐What is the sports betting Illinois age?

You will know that online sports betting in US states like Illinois requires that all participants be of a certain minimum age. However, it’s worth noting that the minimum betting age can vary significantly between states. So be sure to check out our guide to Chicago online sports betting. This will reveal what the minimum betting age is in the Windy City and the whole of the Prairie State.

Sports betting in Chicago is still some ways behind Pennsylvania online sports betting, but the situation is quickly changing. So check out our guide to betting in Chicago and the whole of Illinois. This will reveal whether you can legally bet here and we’ll also look at what sort of things you should be looking for in all good online sportsbooks.

👀What are the Illinois sports betting locations?

Until recently, if you wanted to enjoy some Chicago online sports betting, you’d only be able to do so by registering in person at some specific physical locations. This was almost as restrictive as trying to use the best betting sites Arizona before that state opened up its online betting laws. Thankfully things have changed for the better, so read our guide to sports betting in Chicago to see how you can be much more free in how you use online sportsbooks.

Top Betting Sites
Top Betting Bonuses
Bet365
4.9/5
Betway
4.8/5
Unibet
4.7/5
William Hill
William Hill
William Hill Review
4.6/5
Bwin
4.5/5
Bet365
Bet365 Promo
up to 100€ Bet Credits
T&Cs apply
4.9/5
Betway
Betway Promo
100% up to $60
T&Cs apply
4.8/5
Unibet
Unibet Promo
100% up to 40€
T&Cs apply
4.7/5
William Hill
William Hill Promo
30€ Free Bet
T&Cs apply
4.6/5
18+ #Ad Play Safe ww.begambleaware.org Full terms & conditions apply.
Bwin
Bwin Promo
100% up to 100€
T&Cs apply
4.5/5
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