Published on: February 2, 2025 Updated 2 times since publishing
- 🥇 ExpressVPN : It has servers in 20+ locations in the US, including Chicago. It works reliably with all top streaming platforms, including ESPN+, DirecTV Stream, and Hulu. And it comes with high-end privacy and security features to keep you safe online. Plus, it backs all subscriptions with a 30-day money-back guarantee for first-time users.
I researched and tested all the top VPNs on the market to find the best ones for Chicago. The providers on my list all have servers in Chicago and nearby states. They’re also compatible with lots of sports streaming services that broadcast local sports teams, like ESPN+ and DirecTV Stream, as well as other top platforms, like Netflix and Amazon Prime.
My favorite VPN is ExpressVPN because it has super-fast speeds for streaming in high quality without interruptions, includes top-notch security features, offers a large US server network, and provides user-friendly apps for all of the popular operating systems. Editor's Note: ExpressVPN and this site are in the same ownership group.
Quick Summary of the Best VPNs for Chicago
Editor's Note: Intego ONE, Private Internet Access, CyberGhost and ExpressVPN are owned by Kape Technologies, our parent company.
🥇1. ExpressVPN — Best Overall VPN for Chicago
Basic 12-Months plan: $3.99 / month
1-month plan: $12.99 / month
ExpressVPN is my favorite VPN for Chicago. It has servers in the city as well as 20+ other US locations. It also has servers in 105 countries worldwide, so you have plenty of options for changing your location. It has blazing-fast speeds and prevents ISP speed throttling by hiding your online activities.
It’s the #1 VPN for streaming in Chicago in 2026. It works with 100+ streaming apps, including platforms that carry live games for the Chicago Bears, Cubs, White Sox, Bulls, and Blackhawks, such as ESPN+, DirecTV, NFL+, Hulu, and Fubo. It’s also compatible with other popular streaming services, like Netflix, Amazon Prime, Disney+, and Hulu.
I really like that ExpressVPN has apps for Android TV, Fire TV, and Apple TV, so you can watch on your large screen TV and includes a smart DNS tool — this lets you use the VPN on devices without native VPN support, like gaming consoles and other smart TVs. Additionally, ExpressVPN is one of the only VPNs on the market with a dedicated router app, which makes setting the VPN up on your router much simpler and allows you to connect all of the devices in your household to the VPN.
This VPN offers a ton of value with all of its extra features. For example, it has a split-tunneling feature, which lets you choose which app traffic you want to route through the VPN tunnel and which you want to use your regular internet connection. I use this feature to stream content securely with the VPN while using other apps that require my actual geolocation, like food delivery services. It also comes with a great ad, tracker, and malware blocker, called Advanced Protection.
Bottom Line:
ExpressVPN is the best VPN for Chicago. It has servers in the city and 20+ other US locations, prevents ISP speed throttling, and works with a ton of streaming services, including most streaming services that air local sports. Additionally, ExpressVPN makes it easy to stream content on the big screen and comes with a lot of extra features.
Read the full ExpressVPN review
🥈2. Private Internet Access — Lots of US Servers + Top VPN Ad Blocker
6-month plan: $7.50 / month
1-month plan: $11.95 / month
Private Internet Access (PIA) has impressive server coverage across the US, with servers in all 50 states — it’s server location in Illinois is Chicago. It also has servers in 50 countries across the globe.
PIA supports streaming on 2 optimized streaming servers — with one on each coast. It works well with Chicago sports streaming platforms, like Hulu, Fubo, ESPN+, and DirecTV. It also has apps for Android TV and Fire TV and comes with a smart DNS tool.
That said, it doesn’t have a dedicated router app like ExpressVPN, so if your streaming device doesn’t support VPNs, you’ll have to manually configure the VPN on your router. Luckily, PIA can be set up on popular router models and offers easy-to-follow guides on its website.
This provider has the #1 VPN ad blocker in 2026, MACE. In my tests, it prevented all ads from loading on local Chicago news sites and social media sites. It also successfully blocked phishing pages and malware-infected sites that I tried to visit. Additionally, I’m a big fan of its tracker blocking function. Most VPN ad blockers check trackers against a list before stopping them. PIA goes one step further, rerouting tracking requests to a different device.
PIA’s split-tunneling feature is very flexible, too. While most VPN only exclude apps, PIA’s tool also lets you exclude websites from the VPN tunnel.
Bottom Line:
Private Internet Access has servers in all 50 US states as well as Chicago. It supports streaming on Hulu, Fubo, ESPN+, and DirecTV, has apps for Android TV and Fire TV, as well as a smart DNS tool. Additionally, it comes with the #1 VPN ad blocker on the market and a very flexible split-tunneling tool.
Read the full Private Internet Access review
Editor's Note: Private Internet Access and this site are in the same ownership group.
🥉3. CyberGhost VPN — Streaming-Optimized Servers + Automation Tools
6-month plan: $6.99 / month
1-month plan: $12.99 / month
CyberGhost VPN is great for streaming in Chicago. It conveniently has dedicated streaming servers for ESPN+, Hulu, NFL+, and YouTube TV, as well as many other popular US streaming services, like Netflix, Amazon Prime, Disney+, and Max. The great thing about these servers is that CyberGhost staff check them regularly to make sure that they work with the platforms they’re optimized for.
This provider has a set of automation tools that make using a VPN a breeze. With Smart Rules, you can set it up so that after you launch the CyberGhost app, it automatically connects to a server. You can also have CyberGhost open a specific app for you after it connects or have CyberGhost auto-connect when it detects that you’re on an unsecured Wi-Fi network.
CyberGhost comes with a smart DNS tool, an ad blocker, and split-tunneling. However, its smart DNS tool only works with Netflix and Hulu — ExpressVPN’s smart DNS tool works with most popular US streaming services, and split-tunneling is only available on Android (Windows has a similar tool called Exceptions).
Bottom Line:
CyberGhost VPN has streaming servers for watching live Chicago sports games as well as other popular platforms in the US. It also has a great set of automation tools to streamline the process of using a VPN.
Read the full CyberGhost VPN review
Editor's Note: CyberGhost and this site are in the same ownership group.
4. NordVPN — Advanced Security Features for Staying Safe Online
Plus 24-month plan: $3.59 / month
Complete 24-month plan: $3.99 / month
Prime 24-month plan: $6.99 / month
NordVPN includes some unique advanced security features — it has a customizable kill switch that can be set to shut down only selected apps if the VPN connection drops or prevent you from going online unless you’re connected to the VPN. It’s also the only VPN on this list that comes with a malware scanner. File Protection scans everything you download for malicious code and uploads suspicious files to the cloud for further inspection.
This provider is pretty decent for streaming. It works with 10+ popular US streaming platforms, including Netflix, Amazon Prime, Disney+, Hulu, and Max, and has a smart DNS tool. But ExpressVPN is the better choice for streaming in Chicago because it works with more streaming sites.
Bottom Line:
NordVPN helps keep you safe online with advanced security features, like a customizable kill switch and a malware scanner. It’s also compatible with many popular US streaming platforms and has a smart DNS tool.
5. Surfshark — Good for Bypassing Network Restrictions
One 24-month plan: $2.49 / month
One+ 24-month plan: $4.19 / month
Surfshark is an excellent choice for bypassing network restrictions in Chicago. Its NoBorders feature turns on automatically when it detects a restrictive network (such as school or workplace networks) and provides you with a list of servers that will let you access blocked websites, like streaming or betting sites.
It also works with 50+ streaming services, including US sports streaming platforms, like ESPN+, Hulu, YouTube TV, and DirecTV, includes a smart DNS tool. Android users get a cool feature called Override GPS Location, which makes the GPS data on your phone match the location of the VPN server you’re connected to — this way, sites and apps don’t know your true location.
Bottom Line:
Surfshark is a great VPN for Chicago that can help you access blocked sites on your school or workplace network with its NoBorders feature. It also works with many US sports streaming platforms, has a smart DNS tool, and helps hide your real location on Android devices by overriding the GPS location on your phone.
Read the full Surfshark review
Quick Comparison Table
Editor's Note: Intego ONE, Private Internet Access, CyberGhost and ExpressVPN are owned by Kape Technologies, our parent company.
Testing Methodology: Comparison & Ranking Criteria
To create this list of the best VPNs in 2026 for Chicago, I followed our proven testing methodology. Every VPN on my list has servers in Chicago and works with streaming services that broadcast Chicago sports games. I also checked each provider’s speeds, security, ease of use, and more. For a detailed breakdown of how I ranked and compared the VPNs on my list, see below:
- I chose VPNs with large server networks. Every VPN on my list has servers in Chicago and many other cities and states.
- I looked for VPNs with good streaming support. I looked specifically for VPNs that support good sports streaming services, like ESPN+, DirecTV, NFL+, YouTube TV, Hulu, and Fubo, which carry games from the Bears, Cubs, White Sox, Bulls, and/or Blackhawks.
- I tested every provider’s speeds. Using any VPN will slow your connection speeds slightly due to the encryption process. But all of the VPNs I recommend maintain lightning-fast speeds for smooth browsing and streaming.
- I evaluated each VPN’s security features. I only picked VPNs that include industry-standard security features to stop your ISP or the US government from spying on you. These features include bank-grade 256-bit AES encryption, a strict no-logs policy (the provider doesn’t track your online activities), and a kill switch to prevent accidental data leaks.
- I selected VPNs that offer good overall value. The VPNs on my list all have affordable plans and allow multiple simultaneous connections. They also come with great extra features, like an ad blocker and split-tunneling. Plus, they all back subscriptions with a money-back guarantee.
Top Brands That Didn’t Make the Cut
- PrivateVPN. It’s a minimalistic VPN, which makes it easy to use but doesn’t have many extra features. For example, it lacks split-tunneling and an ad blocker.
- Norton Secure VPN. Norton Secure VPN is secure and good for streaming. However, it automatically connects you to the closest server based on your location. So, you can’t choose a specific city or US state to connect to.
- IPVanish. It’s a decent VPN for torrenting in the US — it’s one of the few that has SOCKS5 proxy servers in the country. However, it wasn’t as fast as the other VPNs on my list.
Frequently Asked Questions
Are VPNs legal in Illinois?
Yes, as many in the US use a VPN to protect their data and privacy. While all of the VPNs I recommend have strict no-logs policies, meaning that they don’t track your online activities, this doesn’t make it OK to engage in illegal activities, such as copyright infringement. Neither I nor anyone else here at SafetyDetectives condone the use of a VPN to break the law.
Does ExpressVPN have servers in Chicago?
Yes, ExpressVPN has servers in Chicago, so you can get a Chicago IP address and make it look like you’re located in the city. ExpressVPN also has servers in 20+ other locations in the US, so you have plenty of connection options.
Is there a good free VPN for Chicago?
Maybe, but generally, free VPNs aren’t very good, especially if you plan on streaming. Most free VPNs don’t support streaming and restrict your server options, so they likely won’t even have servers in Chicago. They also tend to be slower and cap how much data you can use per month/day. The worst-case scenario is some free VPNs have weak security that leaves you vulnerable to snoops and hackers. For all of these reasons, I recommend getting an affordable paid VPN instead.
Can I change my location to Chicago using a VPN?
Yes! It’s one of the easiest and most reliable ways to change your location. Here’s how to do it:
- Subscribe to a good VPN that offers a server location in Chicago. I prefer ExpressVPN because of its blazing-fast speeds and great streaming support.
- Download and install the VPN. You can find the app on the VPN’s official website or your device’s app store.
- Connect to a server in Chicago. That’s it! You now have a Chicago IP address.
Editor's Note: ExpressVPN and this site are in the same ownership group.
