Boston vs Chicago

Boston and Chicago compared across the three travel tiers — budget, mid-range and luxury — for daily costs, hotels, food, things to do and the practical stuff that actually decides which one you should visit.

Boston

United States · North America

America's revolution started here, and the Freedom Trail walks you through it, past Paul Revere's house and the Old North Church. Beacon Hill's brick lanes, Harvard across the river, Fenway Park and a harbour full of lobster and oysters make it the most walkable big city in the United States.

Chicago

United States · North America

The city that invented the skyscraper still has the best skyline in America, best seen from a boat on the river. Lake Michigan gives it beaches, the Art Institute holds one of the world's great collections, and between deep-dish, Italian beef and the blues clubs it eats and plays better than almost anywhere.

Daily cost per tier (USD)

Tier	Boston	Chicago
Budget	$75–$130	$70–$120
Mid-range	$200–$360	$190–$340
Luxury	$550–$1200	$550–$1300

At a glance

	Boston	Chicago
Country	United States	United States
Currency	USD	USD
Language	English	English
Best months	May–June and September–October; October brings New England's autumn colour. Summer is warm and busy; winters are cold and snowy.	May–June and September–October. July and August are hot and full of festivals; January and February are brutally cold.
Climate	Humid continental: warm summers (26–28°C), cold snowy winters (-2 to 3°C) with nor'easter storms. Autumn is crisp and bright.	Continental with lake effect: hot, humid summers (27–29°C), very cold windy winters (-6 to 0°C, often far colder with wind chill). Spring and autumn are short.
Visa	Visa Waiver Program: most European, UK and Australian visitors need an approved ESTA before flying; others need a B1/B2 visa.	Visa Waiver Program: most European, UK and Australian visitors need an approved ESTA before flying; others need a B1/B2 visa.
Safety	One of the safest large US cities. The usual big-city care applies late at night around Downtown Crossing and on quiet stretches of the T.	The Loop, River North, the Magnificent Mile and the North Side neighbourhoods are safe for visitors. As in any big US city, stay alert on late-night trains and avoid unfamiliar areas of the South and West Sides after dark.
Tipping	Tipping is expected: 18–22% in restaurants, $1–2 a drink, 15–20% for taxis and rideshares.	Tipping is expected: 18–22% in restaurants, $1–2 a drink at bars, 15–20% for taxis and rideshares.
Metro	Yes	Yes