Chicago was named the world’s best city to live in in 2018, and it’s no surprise. Here’s why you should visit and what to see and do in the Windy City – and the secret is the food and drink scene that helped the Midwestern city take the top spot in the Time Out City Life Index in 2018.

Chicago’s is famed for being the world’s best city ‘for having fun and enjoying life’ in the Time Out City Life Index.

The Illinois city was followed by Porto, New York, Melbourne and London after 32 cities were scored across food, drink, culture, friendliness, affordability, happiness and liveability. A whopping 15,000 people were surveyed and Chicago was found to have the highest scores for food and drink, and above average for city pride and how residents feel about their neighbourhood.

Not sure the US is for you? Be inspired with the Wise Living guide to visiting Japan and off-the-beaten-track destinations.

What to see and do in Chicago

Here’s why Chicago is worth a visit in 2020, and what to see and do in Chicago when you arrive.

Where to eat in Chicago

Classic Chicago hotdog
A classic Chicago dog with fries and a beer.

It may surprise you, but Chicago even beat New York in the food stakes. It has a total of 25 Michelin-starred restaurants, including one with three stars, Alinea. The midwest city is best known for its heart-warming comfort food though. Chicago does hot dogs like no other, and both the deep-dish pizza and Italian beef sandwich originated here. Au Cheval is often cited as the home of the city’s best burger, and people have been known to queue for three hours for a table. Chicago is also strangely famous for its doughnut shops – try the buttermilk glazed at Doughnut Vault in West Loop or River North.

Where to drink in Chicago

A beer flight in Chicago
Beer flight at microbrewery in Chicago.

Al Capone used to drink at Green Mill Cocktail Lounge, for a special seven course cocktail tasting menu head to The Aviary, while Three Dots and a Dash is famous for its oversized tiki-style cocktails. The craft beer scene is huge here and is growing all the time. Revolution Brewing is the largest craft brewer with a cult following, while Goose Island Beer Co. and Half Acre Beer Company also come highly recommended.

The distinctive Chicago neighbourhoods

What to see and do in Chicago usually involves a trip to the Ukrainian Village.
What to see and do in Chicago usually involves a trip to the Ukrainian Village.

There are no less than 77 well-defined community areas in Chicago, which are often grouped into nine districts and the neighbourhoods are a vibrant part of what to see and do in Chicago. Some of the coolest for visitors are the Ukrainian Village on the West Side, where, you guessed it, was the centre of a big Ukrainian community – many Ukrainian delis, cheap bars and restaurants have been there for over 100 years. The area of Pilsen has a vibrant art scene; expect street art everywhere you look and a growing number of artists basing themselves in this largely Hispanic area. Avondale is the latest neighbourhood to go through gentrification, but is still relatively good value, and Boystown was the first officially recognised gay neighbourhood in the USA.

Architecture – what to see and do in Chicago

Wrigley Building and Tribune Tower on Michigan Avenue with Illinois flag on the foreground in Chicago
Wrigley Building and Tribune Tower on Michigan Avenue.

Chicago has a unique skyline thanks to its mixture of old and new architecture. The best way to experience it is on the Chicago Architectural Foundation boat tour, (£32.50) headed up by volunteers and you’ll float past notable skyscrapers like the Aon Centre, Willis Tower and the John Hancock Building, as well as the art deco old Post Office and world famous Wrigley Building. If you don’t mind heights, there’s a viewing platform at the top of the John Hancock Building (360 Chicago) where a moving platform literally tilts you out over Michigan Avenue from the 94th floor.

The best Chicago beaches

Lake Michigan Beach, Chicago
Lake Michigan Beach, Chicago.

It’s easy to forget that Chicago is blessed with beaches, but they’re right on the doorstep of the city centre. The eastern border of Lake Michigan is dotted with lakeside hangouts in the summer months. Oak Street Beach is about a mile and a half long, Illinois Beach State Park is good for active travellers, with nature trails along the shoreline, and for some peace and quiet, head to 31st Street Beach or 57th Street Beach in South Chicago.

Fancy further US adventures? Read the Wise Living guide to planning and travelling a Route 66 holiday.


Please enter your comment!
Please enter your name here

This site uses Akismet to reduce spam. Learn how your comment data is processed.