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BBuy Before You Fly

Free travel game

Side Quest

Turn Chicago into an adventure.

Tell us where you are. Pick your kind of adventure. We'll give you something unexpected to do. No account. No app. Just go.

Start a side quest

Play anywhere · Complete quests · Earn points · Screenshot your wins · Challenge your friends

  1. Step 1

    Pick your place

    Tell us what city you're exploring.

  2. Step 2

    Get your quest

    Choose a category or let us surprise you.

  3. Step 3

    Complete + share

    Finish the challenge, earn points and screenshot your achievement.

Where are you right now?

No location access needed — just tell us the city.

What kind of side quest?

How far do you want to go?

Your side quest score today

0 points

0 all-time

100 points to Explorer

Scores are saved in this browser on this device only. No account, no email, nothing sent anywhere. Clearing your browser data clears your score.

Side quests written for Chicago

These challenges only work here. Play them in any order — the game will mix them with quests that work anywhere in United States.

Look Up Downtown

Local Culture · Easy · 100 points · 1 hr

Walk downtown Chicago looking only at the upper floors.

The catch: No shop windows.

Bonus +50: Find the oldest steel-frame building you can.

The Lakefront Mile

Outdoors · Easy · 100 points · 1 hr

Walk or ride a stretch of the Chicago lakefront path.

The catch: No leaving the path.

Bonus +50: Swim from a beach on the way.

Settle It Yourself

Food & Drink · Easy · 100 points · 1 hr

Try both Chicago pizza styles and pick a side properly.

The catch: You must try both.

Bonus +50: Ask a local which they actually eat.

Ride The L Loop

Explore · Easy · 100 points · 45 min

Ride the elevated Loop and watch the city at window height.

The catch: No underground sections.

Bonus +25: Get off in a neighbourhood you do not know.

Past The Loop

Hidden Gems · Adventure · 200 points · 2 hrs

Spend two hours in a Chicago neighbourhood away from downtown.

The catch: No returning downtown to eat.

Bonus +75: Find a bakery that predates you.

Lake To Neighbourhood

Must-Do · Epic · 500 points · 4 hrs

Cross Chicago from the lakefront to a far neighbourhood using transit and feet.

The catch: No taxis or ride-hailing.

Bonus +150: Return a different way.

Share your Side Quest

Chicago Side Quest

Send Chicago side quests to whoever you're travelling with. The link opens this city ready to play.

https://buybeforeyoufly.com/pt/side-quest/chicago

#BuyBeforeYouFly #SideQuestTravel #ChicagoSideQuest

What is a travel side quest?

A side quest is a small, self-contained challenge you can complete wherever you happen to be standing. Side Quest is a free browser-based travel game from Buy Before You Fly: you tell it which city you are exploring, choose the kind of adventure you are in the mood for, and it hands you something unexpected to do. Every quest is built from an objective, a constraint that makes it interesting, and an optional bonus — so instead of another list of the same twenty attractions, you get a reason to walk down a different street, order something you cannot pronounce, or look at one painting for twenty minutes.

There is nothing to install and nothing to sign up for. It works on the phone in your pocket, in the gap between a late checkout and an evening flight, or on a full free day in a city you have never visited.

How Side Quest works

  1. Pick your place. Search for the city you are exploring. No location permission and no precise GPS required.
  2. Choose a category. Food, museums, landmarks, exploring, photography, culture, outdoors or hidden gems — or let the dice decide.
  3. Get your quest. Each one comes with a mission, a catch and a bonus objective worth extra points.
  4. Earn points. Quick quests are worth 50 points and epic ones 500, with bonuses from 25 to 100 on top.
  5. Screenshot and share. Completing a quest turns it into an achievement card built to fit a phone screenshot.

Side Quest ideas for travelers

Food & Drink

Markets, bakeries, street food and the dish locals order without looking at the menu.

Museums

One room, one object, one story — museum challenges that beat drifting past everything.

Must-Do

The landmark experiences, with a twist that stops them feeling like a checklist.

Explore

Neighbourhood walks, wrong turns on purpose and streets guidebooks skip.

Photo Quest

Small photo missions that train you to notice details other travellers walk past.

Local Culture

Language, music, craft, ritual and everyday life where you happen to be standing.

Outdoors

Parks, water, viewpoints and green detours between the busy bits.

Hidden Gems

The small, quiet, odd and overlooked corners of a city.

Play Side Quest with friends

Side Quest has no accounts, no friend lists and no leaderboards to join — which is exactly what makes it easy to play together. Everyone opens the page on their own phone, plays the same city, and compares screenshots at dinner. Agree on a target before you split up: first to 500 points, most quests completed before sunset, or one epic quest each. Points are kept in your own browser, so the only scoreboard is the one you keep between you.

  • 100 — Explorer
  • 500 — Wanderer
  • 1,000 — Adventurer
  • 2,500 — Globetrotter
  • 5,000 — Side Quest Legend

Explore more with Buy Before You Fly

Side Quest is free and always will be. When you want the rest of the trip sorted, the same site covers it: