The Chicago City Guides deal with what every visitor wants to know: which beef stand and which deep dish locals stand by, how to fit the lakefront museums into a short stay, where to hear real blues and how to keep warm when the wind comes off the lake. Every guide is a short, opinionated list with the reason to go, what to order or look for and one practical tip per place, and it opens in your browser as soon as the payment goes through.
About the Chicago City Guides
- 142 places
- 6 guides
- 9 languages
- Works offline
- Print or PDF
- Instant access
- Free updates
The six Chicago guides
Food guide
24 places
Italian beef at the counter, deep dish with a burnt cheese crust, old-school steakhouses and delis, West Loop kitchens worth booking and doughnuts with coffee.
Things to do guide
24 places
The lakefront museums grouped by day, two skyscraper decks, the Bean and the grand lobbies of the Loop, and warm glasshouses for freezing days.
Family guide
22 places
Museums for icy days, a free zoo, playgrounds and a skating ribbon, heated views from high up and food children will happily eat.
Nightlife guide
23 places
Serious cocktail bars, Belgian beer and long bourbon lists, blues and jazz rooms that play late, skyline views and food after last call.
Day trips guide
25 places
Quiet beaches and lake walks, Frank Lloyd Wright in Oak Park, the Indiana dunes and a day in Milwaukee, all by train.
Budget guide
24 places
Free museums and grand buildings, free skyline views, hot dogs, beef and tacos for little money and cheap evenings around town.
Why an interactive guide beats a list
Tick places off
Mark each place as done and watch your progress, so you always know what is left.
Your own notes
Write notes on any place and add your own finds. They stay on your phone.
One tap to Maps
Every place opens in Google Maps, and the day route puts your picks in a sensible order.
Open now, near me
Filter by what is open right now or what is closest to you.
Works offline
Open the guide once with a connection and it keeps working without data.
Print it or save as PDF
On a computer, print any guide or save it as a PDF to take with you.
Three places from the guides
Kasama
1001 N Winchester Ave, Ukrainian Village
A Filipino restaurant with a Michelin star that turns into a bakery by day. People line up for the ube cake, the pastries and the savoury breakfast sandwiches, so arrive early before the best ones run out. From the food guide.
Cloud Gate
201 E Randolph St, Millennium Park
Anish Kapoor’s mirror-polished steel sculpture, better known as the Bean, free to visit every day. Come before 8 am in winter and you get the skyline and the snow reflected in it almost alone. From the things to do guide.
The Green Mill Cocktail Lounge
4802 N Broadway, Uptown
A jazz club running since 1907, with a curved bar and a booth said to have belonged to Al Capone. Weekend sets go on late, and Sunday brings the well-known Uptown Poetry Slam. From the nightlife guide.
Finish the game, start the guide
World City Trail’s Chicago scavenger hunt, escape game and audio tour lead you through the historic centre. Once the game is over, the guides take you further: an Italian beef for lunch, the Riverwalk at dusk, a blues club that plays into the night or a free conservatory when the lake wind bites.
Questions about the Chicago guides
What is inside the Chicago City Guides?
Six guides covering 142 places: food, things to do, family, nightlife, lakefront and day trips, and budget. For every place you get why it is worth it, the neighbourhood, opening notes and a practical tip.
When do I receive the guides?
Straight after payment. The links appear on your order page and in your order email and open in the browser of any phone or laptop, with no app or sign-up.
Will the guides work offline in Chicago?
Yes. Load each guide once with a connection and it keeps working without one, including your ticks and notes. The links to the maps need data.
What languages are available?
English, German, French, Italian, Spanish, Dutch, Portuguese, Greek and Polish, and you can change the language inside the guide at any moment.
Can I buy only one Chicago guide?
Yes. One guide costs $5.99, two cost $10.99, four cost $18.99 and the full set of six costs $23.99. With a World City Trail game, the food guide is $4.99 and all six are $17.99.
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