Boasting famous professional sports teams like the Bulls and the Blackhawks, Chicago is one of the highest-profile sports cities in the United States.

It therefore comes as no surprise that sports betting is a massive deal in the city. Chicago operates under Illinois sports betting laws, which legalized wagering across the state in June 2019.

The first sportsbook app in the state went live in June 2020, and since then, Illinois has gone from strength to strength, becoming one of the hottest beds for online sports betting in the United States.

Chicago is by far the most populous city in Illinois, with over 2.6 million residents (the next best is Aurora with under 200,000 residents), and has therefore been the chief contributor to the sports betting numbers in Chicago.

If you are new to Chicago and want to join in the fun, you have landed on the right article. Here, we rank the best five legal online sportsbooks available to Chicago players. We considered quite a few factors in compiling this list, with the major metrics being the overall quality of the sportsbook, ease of use of the app, and the betting promotions available on the site.

1. Betrivers


Call it home court advantage and you may not be too far from the truth!

Betrivers is owned by Chicago-based Rush Street Interactive, and have made the most of local knowledge to position themselves as the go-to brand for Chicago players.

Betrivers were the first operator to launch a sportsbook app in the state, going live in June 2020, and have retained the loyalty of the locals ever since.

Having said all of that, to put Betrivers success in Chicago solely down to home advantage would be doing them a disservice.

This is genuinely one of the finest sportsbooks anywhere in the United States, as evidenced by their numbers in other states. Like all great sportsbooks, they have got all the major American sports covered, offering great markets and odds for NFL, NHL, NBA and MLB games.

And if you are into more international sports like tennis and soccer, betrivers take care of business pretty well as well.

Betrivers have distinguished themselves as one of the best sites for sportsbook bonuses in Chicago, with their trademark promotions being Betrivers parlay insurance and the bet and get offers. They are right up there amongst sportsbooks with best bonuses anywhere in Illinois.

2. FanDuel


Fanduel is the premier sports betting app in the United States and one of the top dogs in Chicago.

Having already gone live in five US states, Fanduel added Illinois to their list in August 2020, as sporting activities slowly returned following the coronavirus pandemic.

However, it wasn’t until March 2022 when Illinois finally ended its in-person registration requirement that Fanduel really blew up in Chicago.

With customers able to sign up on their mobile apps, and no longer needing to travel miles to open a betting account, Fanduel’s numbers grew exponentially.

They arrived in Chicago with a big reputation, and have gone on to enhance their fame in the few years they have been in the city.

With its nice blue and white theme, the Fanduel app is aesthetically-pleasing and very user-friendly. It is arguably the most intuitive betting app in Chicago.

Beyond the surface beauty, Fanduel also carries plenty of substance. The sportsbook stands tall amongst its rivals, while they are no slouches in the betting features department.

In fact, one of Fanduel’s strongest selling points has been their same game parlays, which gives bettors the chance to combine multiple betting options from just one game, thus improving the odds available on that single game.

3. Caesars


It took a long time, but the Caesars sportsbook app was finally available to Chicago players in March 2022 after the state of Illinois opened its doors to mobile betting registration.

Prior to joining the online betting party, Caesars were already established as one of Illinois’ top entertainment companies, and the sportsbook app only solidified that status.

Caesars have consistently offered some of the biggest sign up bonuses in Chicago, rarely dipping below the $1000 mark.

They have also become very famous for their Caesars Rewards program, arguably the best betting loyalty program in Chicago, fending off similar programs from Draftkings, BetMGM and home boys, Betrivers.

4. BetMGM


BetMGM shares very similar characteristics with Caesars. Both had already made their names in the entertainment and hospitality industries prior to their venture into sports betting, and both launched their Illinois sportsbook app in March 2022.

BetMGM also excels with their new customer bonus offer, with up to $1500 on the table as at the time of writing. That is by far the biggest sign up bonus in Chicago.

They have a great referral bonus package for their older customers who may want to bring new players to the sportsbook, as well as a top-class Rewards program.

As far as the actual betting goes, the sportsbook is pretty standard, with games from US and international sports, as well as features like cash out, odds boosts and same game parlays.

5. Draftkings


Draftkings went live with their online betting app in Illinois in August 2020, but their initial progress in Chicago was curtailed by the in-person sign up requirement which was in-place in Illinois at the time.

However, once that condition was taken down by the state government in March 2022, the sportsbook very quickly became one of the top options for Chicago players.

The draftkings sportsbook is an efficient betting app that does everything very well. There isn’t one feature that particularly screams out, but there isn’t any obvious weakness either. That is always a sign of a great betting app.

Draftkings is already one of the best bonus sites in Chicago, but they take it up a notch when major sporting events come around. They often have the best promotions for big occasions like the Super Bowl, NBA Finals and the World Series. So if you want to get the most from these big events, opening a Draftkings account is very much in order!