Best Chicago Apps

245+ iOS apps curated and reviewed

4.3 avg rating
20 free apps
Updated November 2026

Looking for free chicago apps? 20 of our 245+ tracked titles are free to download — no subscription, no trial. The rest are premium picks worth paying for.

Compare top Chicago Apps (November 2026)

#AppPriceRatingAdsIn-App PurchasesUpdated
1ParkChicago®ParkChicago®Free4.7★ (15K)NoNoNov 2026
2VentraVentraFree1.9★ (3.5K)NoNoNov 2026
3Transit Stop: CTA Tracker.Transit Stop: CTA Tracker.Free4.6★ (33K)YesYesNov 2026
4CHI311CHI311Free2.5★ (245)NoNoNov 2026
5My CityPASSMy CityPASSFree4.9★ (25K)NoNoNov 2026
6Chicago Public LibraryChicago Public LibraryFree3.5★ (64)NoNoOct 2026
7Chicago Bears Official AppChicago Bears Official AppFree4.8★ (113K)NoNoNov 2026
8Chicago TribuneChicago TribuneFree4.4★ (19K)YesYesNov 2026

Top Picks for Chicago

ParkChicago®#1

ParkChicago® by Chicago Parking Meters, LLC

The official parking app!
Editor's Choice
✈️ Travel
4.7😞(15K ratings)
Free
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Manage your entire parking experience directly from your smartphone. Pay for, extend, and track your parking sessions with ease, eliminating the need for physical meters or coins. Receive helpful notifications and access your parking history.

What We Love

  • 🚀 Convenient and easy to use
  • 🔒 Secure payment processing
  • ⏱️ Helpful time reminders
  • 📱 Ability to manage parking from phone

Room to Improve

  • 💰 Excessive fees and minimum balance requirements
  • 🐛 Buggy and unreliable app performance
  • 🔄 Forced account reloading
  • ⚠️ Lack of transparency and customer support
1.9😞(3.5K ratings)
Free
#99in Travel
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Manage your public transit fares and tickets for Chicago's CTA, Metra, and Pace services. Load value, buy Metra mobile tickets, and access real-time arrival information all in one place. Add your Ventra Card to your iPhone for seamless travel.

What We Love

  • 🚀 Easy to use
  • 🚀 Convenient for transit
  • 🚀 Helpful for visitors
  • 🚀 Reliable payment processing

Room to Improve

  • 🐛 Frequent crashes and bugs
  • 🐛 Inaccurate arrival/departure times
  • 🐛 Confusing user interface
  • 🐛 Unreliable login and account management
  • 🐛 Payment issues and declined transactions
  • 🐛 Lack of customer support
Transit Stop: CTA Tracker.#3

Transit Stop: CTA Tracker. by Kramer Concepts, LLC

Chicago Bus & Train Tracker
Worth Considering
🗺️ Navigation
4.6😊(33K ratings)
FreeAdsIn-App Purchases
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This app helps you track Chicago's public transit. Get real-time bus and train arrival information, view stops on a map, and save your frequently used locations for quick access. It's designed to make your commute smoother.

What We Love

  • 🚀 Accurate for trains and buses
  • 🚀 99% accuracy on time rate
  • 👍 Intuitive UI
  • 👍 Excellent paired with Apple Watch
  • 👍 Favorite transit app

Room to Improve

  • 🐛 Inaccurate arrival times
  • 🐛 Crashes on iPad
  • 🐛 Turns off audio when app is open
  • 🐛 Unreliable, with ghost buses and delayed updates
  • 👎 Poor user interface

More Chicago apps to explore

FAQ about Chicago

What are the best chicago apps for iPhone?
ParkChicago® tops our chicago apps ranking as of November 2026, with a 4.7-star average from 15K App Store ratings, and it's free to download.
Yes — 20 of the top chicago apps we rank are free to download, including ParkChicago® and Ventra.
ParkChicago® has no ads and has no in-app purchases, according to its App Store listing as of November 2026.
We track 245+ chicago apps on the iOS App Store as of November 2026, ranked by rating, recency, and analysis of real user reviews.

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