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Home»Other»A Beginner’s Guide to Online Sports Betting on Chicago-Based Teams – Everything You Need to Know
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A Beginner’s Guide to Online Sports Betting on Chicago-Based Teams – Everything You Need to Know

Alex RileyBy Alex RileyJuly 10, 20255 Mins Read
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MLB: St. Louis Cardinals at Chicago Cubs
MLB: St. Louis Cardinals at Chicago Cubs Jul 6, 2025; Chicago, Illinois, USA; Chicago Cubs outfielder Seiya Suzuki (27) and Pete Crow-Armstrong (4) after the game against the St. Louis Cardinals at Wrigley Field. Mandatory Credit: Matt Marton-Imagn Images
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Sports betting. What to do, what do you? How should you jump into this portal if you don’t know where to begin? You’ve been hearing rumors that the market is getting bigger and you’re a huge fan of almost every Chicago-based team, from the Bears to the Bulls. But sports betting is a whole other kettle of fish and you’re not sure how to best approach it. 

Luckily for you, you’re about to be taken on what some would call an expert crash course in terms of what sports betting is, how it works and how you should look at it. So, without further ado, it’s time to knock your Chicago White Sox off.

Starting with the Basics of Online Sports Betting

Sports betting is pretty straightforward once you understand the key parts. At its core, you’re placing a wager on the outcome of a sporting event, pretty easy. Now, whilst it does sound simple enough, the more you learn, the more you realize just how many options there are.

Here are some of the most common types of bets:

  • Moneyline: This is the easiest one to grasp. You’re just betting on who you think will win the game.
  • Point spread: This levels the playing field a bit. One team is given an advantage or disadvantage in the form of points. You’re betting on whether a team will win by a certain margin or not.
  • Totals (Over/Under): This is about the total points scored in a game. You bet on whether the total score will be over or under a number set by the bookmaker.
  • Parlays: Multiple bets combined into one. The payout is higher but all parts of the parlay need to win for you to cash in.
  • Props: Short for proposition bets, these are wagers on individual player performances or other non-final outcome details during the game.

Learning how odds work is also key. In the US, odds are usually shown as positive or negative numbers. A -150 means you’d have to bet $150 to win $100, while a +200 means you’d win $200 on a $100 bet. Yes, sounds tricky to start but if you practice a lot, you’ll soon get the hang of it.

Finding a Safe and Reliable Platform

Before you get too deep into betting strategies, the most important step is choosing a trustworthy online platform. With so many options out there, picking a site that’s legal, secure and user-friendly matters a lot, especially when money is involved.

You need to look for an online sportsbook that has a valid license to operate in your state, has strong user reviews and reputation, features clear terms and conditions, an easy-to-use mobile app or website interface and offers secure payment options and fast withdrawals.

Since you’re betting on Chicago-based teams, make sure the platform you choose covers all the local games and sports you’re interested in. A good one will give you everything from NFL and NBA action to baseball and even college sports.

Focusing on Chicago Teams

It’s always more fun to bet on the teams you follow. For Chicago fans, you’ve got a great spread to choose from.

If you’re thinking about betting on the Chicago Bears, keep in mind how unpredictable the NFL can be. One week a team can look unbeatable and the next, they’re off their game. Watching trends, injuries and how a team plays at home versus on the road will help shape smarter bets.

Then there’s the Chicago White Sox. Baseball betting is a bit different; games happen daily and the starting pitcher has a huge impact on outcomes. It pays to know who’s on the mound and how they’ve been performing lately.

The Chicago Bulls bring a different rhythm altogether. In basketball, pace of play and player stats come into sharper focus. With so many games in a season, there’s more data to work with but it also means more chances to win or lose.

Tips for Betting Smart

Chicago Bears quarterback Caleb Williams (18) and quarterback Tyson Bagent (17) enter the field before the game against the Green Bay Packers at Soldier Field.
Chicago Bears quarterback Caleb Williams (18) and quarterback Tyson Bagent (17) enter the field before the game against the Green Bay Packers at Soldier Field. Mandatory Credit: Daniel Bartel-Imagn Images

It’s tempting to go all in when you start, especially when your favorite team is playing. But smart betting means pacing yourself and thinking things through.

Here are a few things to keep in mind:

  • Set a budget and stick to it. Decide how much you’re willing to lose before you start and don’t go past it.
  • Do your homework. Even five minutes of reading up on injuries, player stats or head-to-head matchups can give you an edge.
  • Stay up to date. News about trades, lineup changes and even coaching strategies can have a big impact on the odds.
  • Explore live betting. Once you’ve got a handle on pre-game betting, live bets, placed as the game is happening, can add a new layer of excitement.

Keep It Fun and Strategic

Sports betting can be fun, yes. Just remember to engage with sports betting with responsibility in mind. Never invest more than what you have readily available and don’t spend too much time on sites. You might have a passion for sports but this doesn’t mean you automatically need to have a passion for betting. They don’t need to go hand in hand if you do not want them to. You see, sports betting is meant to be a fun hobby and not anything more, so please keep it that way.

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BY Alex Riley

Alex Riley is a trending news writer for ChiCitySports.

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