Perched on the edge of enormous Lake Michigan, Chicago’s size and famous skyline mark it out as the undisputed “King of the Midwest”. The Windy City is full of iconic sights and its closely-packed and distinct neighborhoods mean a visitor can see a huge amount in a weekend. Here is our recommended itinerary for getting the full Chicago experience in 48 hours.
Sprawling skyscrapers, smoky jazz and sandy beaches, Chicago is a city that has it all. Whether you choose to explore the buzzing Loop District of Downtown Chicago, the immaculate shopping avenues of Chicago O’Hare or the sparkling beaches of Lake Michigan, you are bound to fall in love with one of the greatest cities in Northern America.
Take a Chicago vacation to find a potpourri of world-class museums, parks and beaches, rocking blues clubs and scenic streets. Book a Chicago hotel and discover the richness of this diverse city on Lake Michigan’s sandy shores.
Home of countless blues bars and jazz clubs, Chicago’s a buzzing place for a night out. Rock and pop acts can also be enjoyed at hipster-swathed dive bars, and of course you always laugh your socks off at groundbreaking improv comedy nights.
The cosmopolitan capital of the Midwest is an adventure playground for families of all ages. Whether your little ones like making furry zoo friends, exploring new worlds in hands-on museums, or would prefer to splash about in the lakeside shallows, Chicago has plenty of fun-filled spots for entertaining kids.
Whether you've a hankering for high art, rocking music, or laugh out loud comedy, Chicago’s cultural offerings have something to suit every taste. From its iconic skyscrapers to its gleaming art galleries and world-class museums, you won’t be short of things to do and see when in the Windy City.
The best places to stay are in the Loop District in downtown Chicago, where you’ll find most of the major sights and attractions. Chicago is a large city, however, and offers much more than just a bustling downtown district. For a spot of tranquillity and seclusion, you may prefer to stay within the lush scenery surrounding the Chicago O’Hare Airport.
As you’d expect from a great city like Chicago, visitors are spoilt by all the shopping options on offer. Swing by Michigan Avenue, where you’ll find Magnificent Mile and get a feel for frenetic pace of life. Beyond Magnificent Mile, venture to Downtown Chicago to shop in the heart of the city – the Loop District. Finally, finish up near north side of the city, where you will discover independent stores and bargain prices.
Chicago has a complete array of culinary delights, from exotic dishes from foreign continents to the famed homemade Chicago-style pizzas. There are areas that are mostly dedicated to specific cuisines and also more eclectic parts of town that offer a wide-range of gastronomy, as is the case in Uptown Chicago.
There is no shortage of things to see and do in Chicago, with world-famous attractions, museums, restaurants, and shops. A lot of Chicago’s sights are concentrated along the Chicago River and, being such a green city, the best way to explore these local landmarks is on foot or by bicycle.
Whether you want to pre-book transport tickets or devise a city break itinerary, make the most of your holidays with our top tips on how to plan your holiday time.
Book your Chicago hotel for hot dogs in one of baseball’s oldest parks, a river tour through a century of architecture, and authentic Chicago blues in a legendary club. Time travel to the past with this guide to the best of historic Chicago.
Meat-and-sauce-stuffed, deep-dish pizza. Creamy fettucini Alfredo. Or a prime, Chicago-cut steak. Please your palate in a different way every night in Chicago. Book a Chicago hotel and indulge in its hearty meat-and-potatoes pleasures with this guide to the top 10 food and drink things to do in Chicago.
A summer vacation in Chicago sizzles with sunny days spent strolling art-filled street fairs, cruises on the lake and alfresco dining under the city lights. Book a summer hotel in Chicago and visit when music fills the air and the sun shines on the Windy City.
You can get only a glimpse of the city on a short getaway in Chicago. With just a few nights in a Chicago hotel, follow our exciting itinerary and see the city’s best.
Choosing where to stay in Chicago is the key to a relaxing visit. Book the best Chicago hotel using this guide to the city’s main neighborhoods.
Stylish spa retreats, grand Victorian mansions and roomy tower suites with lake views – find the right hotel with this guide to the top 10 hotels in Chicago.
The cultural hub of the Midwest, Chicago’s a buzzing metropolis swathed in blues and soul, arty enclaves, and sports mania. It’s where you can eat deep pan pizza for breakfast, lunch, and dinner, and still have time to hang out on the shores of Lake Michigan. No matter when you visit, you’ll discover a city of museums, galleries, and some of the coolest live music venues in America.