Chicago Travel Guides
Chicago spotlight
48 hours in Chicago - see the best of the Midwest in a weekend
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.
View full guideA Chicago city guide – high-rise buildings, shopping avenues and sandy beaches
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.
A Chicago travel guide – iconic architecture, deep-dish pizza and miles of shopping
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.
Nightlife & Entertainment in Chicago
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.
Family Friendly Attractions in Chicago
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.
Arts and Culture in Chicago
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.
Where to stay in Chicago – a neighborhood guide
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.
Where to shop in Chicago – places to go and what to buy
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.
Where to eat in Chicago – a food and dining guide
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.
What to see and do in Chicago – a guide to notable attractions and landmarks
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.
How to plan your holiday time
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.
Top 10 historic things to do in Chicago
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.
Top 10 food and drink things to do in 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.
Summer vacations 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.
Short getaways in Chicago – a 48-hour tour of shopping, sightseeing and deep dish pizza
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.
Where to stay in Chicago - a travel guide to Chicago's neighbourhoods
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.
Top 10 hotels in Chicago
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.
Chicago Travel Tips
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.
Search for Chicago hotels
Explore our travel guides
North America
Alberta Travel Guides
Arizona Travel Guides
British Columbia Travel Guides
California Travel Guides
- Santa Barbara Travel Guides
- Santa Cruz (and vicinity) Travel Guides
- Coronado Travel Guides
- San Diego Travel Guides
- Los Angeles Travel Guides
- Monterey Travel Guides
- Palm Springs Travel Guides
- Anaheim Travel Guides
- San Francisco Travel Guides
- San Jose Travel Guides
- Long Beach Travel Guides
- Yosemite National Park Travel Guides
- Santa Monica Travel Guides
Canada Travel Guides
Colorado Travel Guides
District of Columbia Travel Guides
Florida Travel Guides
Georgia Travel Guides
Hawaii Travel Guides
Illinois Travel Guides
Indiana Travel Guides
Kentucky Travel Guides
Louisiana Travel Guides
Maryland Travel Guides
Massachusetts Travel Guides
Michigan Travel Guides
Minnesota Travel Guides
Missouri Travel Guides
Montana Travel Guides
Nevada Travel Guides
New Jersey Travel Guides
New Mexico Travel Guides
New York Travel Guides
North Carolina Travel Guides
Nova Scotia Travel Guides
Ohio Travel Guides
Ontario Travel Guides
Oregon Travel Guides
Pennsylvania Travel Guides
Quebec Travel Guides
Rhode Island Travel Guides
South Carolina Travel Guides
Tennessee Travel Guides
Texas Travel Guides
Utah Travel Guides
Vermont Travel Guides
Virginia Travel Guides
Washington Travel Guides
Wisconsin Travel Guides
Wyoming Travel Guides
Europe
Austria Travel Guides
Belgium Travel Guides
Bulgaria Travel Guides
Croatia Travel Guides
Cyprus Travel Guides
Czech Republic Travel Guides
Denmark Travel Guides
Finland Travel Guides
France Travel Guides
Germany Travel Guides
Greece Travel Guides
Hungary Travel Guides
Iceland Travel Guides
Ireland Travel Guides
Italy Travel Guides
Malta Travel Guides
Monaco Travel Guides
Montenegro Travel Guides
Netherlands Travel Guides
Norway Travel Guides
Poland Travel Guides
Portugal Travel Guides
Russia Travel Guides
Serbia Travel Guides
Slovenia Travel Guides
Spain Travel Guides
Sweden Travel Guides
Switzerland Travel Guides
Turkey Travel Guides
United Kingdom Travel Guides
- Edinburgh Travel Guides
- Nottingham Travel Guides
- Oxford Travel Guides
- Scarborough Travel Guides
- Swansea Travel Guides
- Birmingham Travel Guides
- Norwich Travel Guides
- Bristol Travel Guides
- St Ives Travel Guides
- Brighton Travel Guides
- Chester Travel Guides
- Exeter Travel Guides
- Lancaster Travel Guides
- Leicester Travel Guides
- Lincoln Travel Guides
- Canterbury Travel Guides
- Sheffield Travel Guides
- Aberdeen Travel Guides
- Winchester Travel Guides
- Whitby Travel Guides
- Harrogate Travel Guides
- Glasgow Travel Guides
- Manchester Travel Guides
- Llandudno Travel Guides
- Liverpool Travel Guides
- Leeds Travel Guides
- Eastbourne Travel Guides
- Newquay Travel Guides
- Newcastle-upon-Tyne Travel Guides
- Bath Travel Guides
- Cheltenham Travel Guides
- Weston-super-Mare Travel Guides
- Belfast Travel Guides
- York Travel Guides
- Keswick Travel Guides
- Torquay Travel Guides
- Blackpool Travel Guides
- Bournemouth Travel Guides
- Plymouth Travel Guides
- Stratford-upon-Avon Travel Guides
- Cambridge Travel Guides
- Durham Travel Guides
- Inverness Travel Guides
- Windermere Travel Guides
- Cardiff Travel Guides
- London Travel Guides
Caribbean
Asia
Cambodia Travel Guides
China Travel Guides
Hong Kong SAR Travel Guides
India Travel Guides
- Alibaug Travel Guides
- Pune Travel Guides
- Mumbai Travel Guides
- Matheran Travel Guides
- Puri Travel Guides
- Goa Travel Guides
- Srinagar Travel Guides
- Shimla Travel Guides
- New Delhi Travel Guides
- Mahabaleshwar Travel Guides
- Munnar Travel Guides
- Pondicherry Travel Guides
- Nainital Travel Guides
- Manali Travel Guides
- Lonavala Travel Guides
- Jaipur Travel Guides
- Delhi Cantonment Travel Guides
- Ooty Travel Guides
- Kolkata Travel Guides
- Cochin Travel Guides
- Hyderabad Travel Guides
- Kodaikanal Travel Guides
- Mysore Travel Guides
- Agra Travel Guides
- Chennai Travel Guides
- Udaipur Travel Guides
- Bengaluru Travel Guides
Indonesia Travel Guides
Japan Travel Guides
Laos Travel Guides
Macau SAR Travel Guides
Malaysia Travel Guides
Philippines Travel Guides
Singapore Travel Guides
South Korea Travel Guides
Sri Lanka Travel Guides
Taiwan Travel Guides
Thailand Travel Guides
Vietnam Travel Guides
South America
Australia - New Zealand and the South Pacific
Australian Capital Territory Travel Guides
Fiji Travel Guides
French Polynesia Travel Guides
Guam Travel Guides
New South Wales Travel Guides
New Zealand Travel Guides
Northern Territory Travel Guides
Queensland Travel Guides
South Australia Travel Guides
Tasmania Travel Guides
Victoria Travel Guides
Western Australia Travel Guides
