When it comes to Chicago natives, few closets will be seen without a Cubs t-shirt, or perhaps a Bulls jersey. The sports loyalty in the city runs insanely deep, probably because midwesterners are nice about everything beyond sports! Don’t mess with a Chicago team, because die hard fans will come running. So when it comes to moments that define the great Windy City, none are more memorable than the ones involving sports.
Let’s just be honest here, Michael Jordan’s entire run with the Chicago Bulls could be counted as a defining moment in Chicago history. Jordan is still regarded as one of, if not the, greatest basketball player of all-time. His performances in the 1991 and 1992 championship runs were unbelievable, as well as the game he played through the flu. But the defining moment would be Jordan’s last game, where he sunk once final shot to solidify his time in the NBA. He played with a few other teams along the way, but his time in Chi-town will always be most memorable.
Destinations Unlocked:Let our travel expert Stefano help you find your perfect Culture trip
Looking for an expert's perspective?Uncover my top 3 recommended places from each continent on the map.
1. GuatemalaAn express adventure for those with limited time off. Prepare yourself incredible experiences. You will hike a volcano, visit mayan temples and witness a ceremony and take in beautiful colonial Antigua.
2. BelizeA quick trip not too far away for those seeking a relaxing mini break. You will have plenty of free time to relax but also some awesome activities to experience the rainforest and the caribbean sea.
3. MexicoAn exciting mini trip exploring the lesser known colonial towns of central Mexico. This is hte perfect trip for someone with limited time off and still wants to turn on explorer mode and do something different.
1. EcuadorA remarkable 8 days adventure through the Andes and the Amazon rainforest. The best choice for adventure seekers wishing to visit the 2 most iconic areas of South America, in only 1 week and no flights.
2. PeruAn alternative itinerary to classic Peru, from Cusco to Arequipa. This itinerary is great combination of highlights Cusco and Machu Picchu with the lesser known Arequipa and Colca Canyon.
1. ItalyThe ultimate Italian experience from the vibrant streets of Naples to the breathtaking sceneries of the Amalfi Coast followed by Matera and down to Puglia with its golden beaches, intense flavours and fascinating destinations.
2. ScotlandEmbark on this great adventure starting from London all the way to Scotland with a true Scottish experience made of breathtaking sceneries, whisky tasting and ..lots of fun! Ideal for train lovers and explorers.
3. PortugalA wonderful train journey around Portugal, from the romantic city of Porto to the Douro Valley, to the beautiful Aveiro all the way to Lisbon and Sintra. The perfect trip to train, culinary and culture lovers.
1. South KoreaDiscover incredible temples, mountains and modern cities on this 10 day adventure. This trip is perfect for those seeking immersion in the cuisine, culture and natural wonders of South Korea.
2. ThailandFrom Bankgok to Angkor Wat to Ho Chi Minh City and everything in between - adventure through the heart of South-East Asia. Taste the delights, see history brought to life and unwind on a Mekong River cruise.
3. Sri LankaA fantastic adventure that showcases Sri Lanka's fantastic landscapes, wildlife and flavours. With 3 epic rail journeys, 3 UNESCO heritage sites and time to relax, this trip has loads to offer at a great price
1. MoroccoAn epic journey across Morocco: from Casablanca to Marrakech, through the blue city of Chefchaouen to the wonders of the desert and deep to the High Atlas Mountains - this trip has it all! Ideal for true explorers!
2. EgyptFrom Cairo to Aswan, this trip brings the land of the pharaohs to life. You'll visit the Pyramids, Valley of the Kings and Luxor Temple and cruise down the Nile in style. This is the perfect way to explore Egypt.
Sox Throwing the World Series
While most of these sports memories are positive, some are unfortunately not … as is the case with the White Sox throwing the World Series in 1919. A number of players on the team made a deal with some big shot gamblers that they would throw, or intentionally lose, the game against the Cincinnati Reds. To this day, the scandal is still the biggest in sports history … and Cubs fans will never let them forget it.
First Organized Automobile Race
Though many don’t know it, the first automobile race took place in Chicago! Sponsored by the Chicago Times-Herald in 1895, the race featured six cars and the course ran from downtown Chicago up to the northern suburb of Evanston. The race was originally considered publicity for the motorcycle, which was introduced two years previously. The race was won by Charles Duryea in his motorized wagon after finishing in seven hours and roughly 50 minutes. Today, the drive to Evanston takes all of an hour.
The Birth of Softball
It often seems like baseball is the city sport of Chicago, but in fact, softball was invented in the fair city. On Thanksgiving Day in 1887 alumni of the Farragut Boat Club were waiting for the results of the Harvard vs Yale football game. When Yale was announced as the winner, a Yale fan threw a boxing glove at a Harvard fan, who hit it with a stick. The rest of the group looked up in awe as one yelled out “Play Ball!” and the game of softball was born.
The Blackhawks are beloved in Chicago whether they win or lose – but it’s a lot better when they win. And after 49 years without a Stanley Cup “W,” in 2010 when Patrick Kane hit a buzzer beater into the net, fans wanted to rejoice. Problem was, the shot was so fast that even the refs didn’t catch it! Luckily they reviewed the tape and the shot did go in, inciting Blackhawks fans everywhere to go nuts.
Cubs Winning the World Series after 108 Years
For a long time, the Cubs were laughably bad at baseball. Not only were they not winning the World Series, they were arguably the worst team ever to hit a mound. But in 2016 that all changed. Putting the “Billy Goat” curse aside, the 2016 Cubs seemed to tear through their competition. When they made the World Series, the city went wild. When they won it? The city was practically burned to the ground by dedicated lifelong fans setting off fireworks or drinking like it was the end of the world. When it comes to true Chicago sports moments, this is it.
Volcanic Iceland Epic Trip
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Culture Trip launched in 2011 with a simple yet passionate mission: to inspire people to go beyond their boundaries and experience what makes a place, its people and its culture special and meaningful — and this is still in our DNA today. We are proud that, for more than a decade, millions like you have trusted our award-winning recommendations by people who deeply understand what makes certain places and communities so special.
Increasingly we believe the world needs more meaningful, real-life connections between curious travellers keen to explore the world in a more responsible way. That is why we have intensively curated a collection of premium small-group trips as an invitation to meet and connect with new, like-minded people for once-in-a-lifetime experiences in three categories: Culture Trips, Rail Trips and Private Trips. Our Trips are suitable for both solo travelers, couples and friends who want to explore the world together.
Culture Trips are deeply immersive 5 to 16 days itineraries, that combine authentic local experiences, exciting activities and 4-5* accommodation to look forward to at the end of each day. Our Rail Trips are our most planet-friendly itineraries that invite you to take the scenic route, relax whilst getting under the skin of a destination. Our Private Trips are fully tailored itineraries, curated by our Travel Experts specifically for you, your friends or your family.
We know that many of you worry about the environmental impact of travel and are looking for ways of expanding horizons in ways that do minimal harm - and may even bring benefits. We are committed to go as far as possible in curating our trips with care for the planet. That is why all of our trips are flightless in destination, fully carbon offset - and we have ambitious plans to be net zero in the very near future.