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What To Know Before You Go To Chicago


by Gertie Larson



Welcome to the vibrant city of Chicago! Known for its stunning architecture, diverse culture, and bustling city life, Chicago is a metropolis that has something for everyone. Whether you’re a food enthusiast, history buff, art lover, or simply looking for a memorable vacation destination, Chicago offers a plethora of attractions and experiences to explore.


Located in the heart of the Midwest, Chicago is the third-largest city in the United States, and it is often referred to as the “Windy City.” With its breathtaking skyline, iconic landmarks, and picturesque waterfront views, the city truly captures the spirit and energy of urban life.


Home to a rich and diverse history, Chicago has played a significant role in the development of American architecture, art, music, and culture. From the famous skyscrapers designed by renowned architects such as Frank Lloyd Wright and Ludwig Mies van der Rohe to the vibrant neighborhoods that showcase different ethnic communities, the city’s heritage is woven into its very fabric.


In this comprehensive guide, we will explore various aspects of Chicago to help you make the most of your visit. From practical tips on weather and transportation to recommendations for accommodations, dining, shopping, and must-see attractions, we’ll cover it all.


So get ready to immerse yourself in the dynamic energy of Chicago, where tradition meets innovation, history merges with modernity, and every corner tells a unique story. Whether you’re a first-time visitor or a seasoned traveler, Chicago promises an unforgettable experience that will leave you wanting more.


Overview of Chicago

Chicago, often called the “Windy City,” is a vibrant and dynamic metropolis located in the state of Illinois. With a population of over 2.7 million people, it is the third-most populous city in the United States.


Renowned for its stunning architecture, cultural diversity, and thriving arts scene, Chicago attracts millions of visitors each year. The city is situated on Lake Michigan, giving it a beautiful waterfront that adds to its charm.


One of the most notable aspects of Chicago is its iconic skyline, dominated by skyscrapers like the Willis Tower (formerly known as the Sears Tower) and the John Hancock Center. These towering structures have become symbols of the city and offer breathtaking views of the surrounding area.


Chicago is also famous for its deep-dish pizza, Chicago-style hot dogs, and an array of culinary delights. Food enthusiasts can indulge in a diverse range of cuisines, from classic American dishes to international flavors.


When it comes to the arts, Chicago is home to world-class museums, theaters, and galleries. The Art Institute of Chicago houses an extensive collection of artwork, including pieces by famous artists like Grant Wood and Vincent van Gogh. The city’s theater scene is thriving, with Broadway shows, musicals, and independent productions taking center stage.


Sports enthusiasts will find plenty to cheer for in Chicago, as the city is passionate about its professional sports teams. From baseball to basketball, football to hockey, Chicago sports fans are known for their unwavering support.


It’s worth noting that Chicago is a city of neighborhoods, each with its own unique character and charm. From the vibrant streets of Wicker Park to the historic architecture of Lincoln Park, exploring the different neighborhoods is a great way to experience the diversity of the city.


Chicago also hosts numerous festivals and events throughout the year, such as the Chicago Jazz Festival, Taste of Chicago, and Lollapalooza music festival. These events showcase the city’s vibrant cultural scene and provide opportunities for visitors to immerse themselves in the local culture.


In summary, Chicago offers a blend of history, culture, and entertainment that appeals to visitors from all walks of life. From its stunning skyline to its vibrant neighborhoods, the city has a unique energy that is sure to captivate anyone who visits.


Weather in Chicago

When planning your trip to Chicago, it is essential to consider the city’s weather patterns throughout the year. The weather in Chicago can vary greatly depending on the season, so it is important to pack accordingly and plan your activities accordingly.


Chicago experiences a humid continental climate, characterized by four distinct seasons: spring, summer, fall, and winter. Each season brings its own unique weather conditions, offering visitors a range of experiences throughout the year.


Spring (March to May) is a transitional season in Chicago, with temperatures gradually warming up after the cold winter months. However, it can still be quite chilly, especially in the early spring. Average temperatures range from the 40s to the 60s Fahrenheit (around 5 to 20 degrees Celsius). It is advisable to pack layers, as the weather can be unpredictable during this time.


Summer (June to August) is the peak tourist season in Chicago, as the city comes alive with festivals, outdoor activities, and a vibrant atmosphere. The summer months are generally warm and humid, with temperatures ranging from the 70s to the 90s Fahrenheit (around 20 to 35 degrees Celsius). It is advisable to pack lightweight and breathable clothing, as well as sunscreen to protect yourself from the sun.


Fall (September to November) brings cooler temperatures and colorful foliage to Chicago. Average temperatures range from the 40s to the 60s Fahrenheit (around 5 to 20 degrees Celsius). This season offers a pleasant climate for exploring the city and enjoying outdoor activities. It is recommended to bring layers, as temperatures can fluctuate throughout the day.


Winter (December to February) in Chicago can be harsh, with cold temperatures, strong winds, and snowfall. Average temperatures range from the 20s to the 30s Fahrenheit (around -5 to 0 degrees Celsius). It is crucial to pack warm clothing, including winter jackets, hats, gloves, and boots, to stay comfortable during your visit. Be prepared for possible flight delays or transportation disruptions due to winter weather conditions.


Overall, it is important to check the weather forecast before your trip and pack accordingly. Regardless of the season, Chicago offers a wide range of indoor and outdoor activities to enjoy, so you can make the most of your visit regardless of the weather.


Transportation in Chicago

Getting around in Chicago is a convenient and efficient experience, thanks to the city’s well-developed transportation system. From public transportation options to rideshare services and biking infrastructure, there are various ways to navigate the city and explore its numerous attractions.


One of the most popular modes of transportation in Chicago is the “L” train system. Operated by the Chicago Transit Authority (CTA), the elevated train network connects the city and its suburbs, making it easy to access different neighborhoods and landmarks. The “L” system consists of different color-coded lines, such as the Red Line, Blue Line, and Brown Line, each serving different parts of the city.


In addition to the “L,” the CTA also operates an extensive bus network, providing convenient and affordable transportation throughout the city. Buses run on designated routes and offer a great way to reach destinations that may not be accessible by train.


For those who prefer a more flexible mode of transportation, rideshare services like Uber and Lyft are widely available in Chicago. Simply download the app and request a ride whenever and wherever you need to go. This option is particularly convenient for traveling with a group or during off-peak hours.


If you enjoy biking, Chicago offers a robust network of bike-friendly paths, lanes, and trails. Divvy, the city’s bike-sharing program, provides an easy and affordable way to rent bikes and explore the city on two wheels. With numerous bike stations located throughout the city, you can conveniently pick up and drop off bikes at your desired locations.


Driving in Chicago is an option, but it is worth noting that traffic congestion can be significant, especially during rush hours. Additionally, parking can be expensive, particularly in the downtown area. However, if you choose to drive, there are numerous parking garages and street parking options available throughout the city.


When it comes to getting to and from Chicago, the city is served by two major airports: O’Hare International Airport (ORD) and Midway International Airport (MDW). Both airports offer a variety of domestic and international flights, connecting Chicago to destinations around the world. From the airports, you can easily access downtown Chicago via public transportation or taxi services.


In summary, Chicago provides a range of transportation options to suit every traveler’s needs. Whether you prefer public transportation, rideshare services, biking, or driving, getting around the city is convenient and accessible. Consider your preferences, the distance to your desired destinations, and the time of day when choosing the best mode of transportation for your Chicago adventure.


Accommodations in Chicago

As a bustling metropolis with a thriving tourism industry, Chicago offers a wide range of accommodation options to suit every traveler’s preferences and budget. From luxurious hotels to budget-friendly hostels and cozy bed and breakfasts, there are plenty of choices when it comes to finding the perfect place to stay in the city.


Downtown Chicago is a popular area for tourists, as it provides easy access to major attractions, shopping districts, and dining options. The Magnificent Mile, a stretch of Michigan Avenue, offers high-end hotels with stunning views of the city skyline and proximity to renowned shopping destinations. Millennium Park and the Loop area also house many hotels, making them convenient choices for travelers who want to be in the heart of the action.


If you’re looking for a neighborhood with a more local feel, consider exploring areas like Lincoln Park, Lakeview, or Wicker Park. These neighborhoods offer a range of accommodation options, from boutique hotels to vacation rentals and bed and breakfasts. Staying in these areas allows you to experience the charm and character of Chicago’s diverse neighborhoods while still being within reach of downtown attractions.


For budget-conscious travelers or those looking for a more communal and social experience, hostels are a great option. Chicago has several hostels located throughout the city, offering affordable accommodations, shared communal spaces, and the opportunity to connect with fellow travelers.


When choosing accommodations in Chicago, it’s important to consider factors such as location, amenities, and reviews. Many hotels offer amenities such as fitness centers, on-site dining options, and concierge services, while others may focus more on offering basic comforts at a lower price point. Consider your preferences and priorities when selecting the right accommodation for your stay.


It is advisable to book your accommodations well in advance, especially during peak travel seasons or when major events and conferences are taking place in the city. This ensures that you secure your desired accommodations and allows you to take advantage of any early booking discounts that may be available.


In summary, Chicago offers a wide range of accommodations, catering to different budgets and preferences. Whether you’re seeking luxury and convenience in downtown Chicago or a more local experience in the city’s vibrant neighborhoods, there’s a perfect place to stay for every traveler in the Windy City.


Top Attractions in Chicago

Chicago is a city brimming with iconic landmarks, cultural institutions, and world-class attractions. From architectural marvels to vibrant parks, there is something for everyone to enjoy. Here are some of the top attractions that should be on your list when visiting Chicago:

  1. The Art Institute of Chicago: Known for its extensive collection of artworks, including pieces by Monet, Picasso, and Van Gogh, the Art Institute is a must-visit for art enthusiasts.
  2. The Magnificent Mile: Located along Michigan Avenue, this upscale shopping district is home to high-end boutiques, department stores, and renowned restaurants. It’s also a great place for a leisurely stroll and to admire the city’s impressive architecture.
  3. Millennium Park: This iconic park is famous for attractions like Cloud Gate, also known as “The Bean,” and the Jay Pritzker Pavilion, where free concerts and events are held. It’s a perfect spot for picnics, people-watching, and soaking in the city’s atmosphere.
  4. Navy Pier: A beloved landmark on the shoreline of Lake Michigan, Navy Pier offers amusement rides, restaurants, shops, and stunning views of the city skyline. Don’t miss the Ferris wheel and the IMAX theater.
  5. Shedd Aquarium: One of the largest indoor aquariums in the world, the Shedd Aquarium is home to a wide variety of marine life. Explore exhibits featuring dolphins, penguins, and sharks, and be captivated by the wonders of the underwater world.
  6. Willis Tower Skydeck: For breathtaking views of the city, head to the Skydeck on the 103rd floor of Willis Tower. Step out onto The Ledge, a glass box extending from the skyscraper, and experience the thrill of standing 1,353 feet above the ground.
  7. Field Museum: Delve into natural history at the Field Museum, where you can explore exhibits on dinosaurs, ancient civilizations, and the wonders of the natural world. Make sure to see Sue, the largest and most complete Tyrannosaurus rex skeleton ever discovered.
  8. Chicago Riverwalk: Stroll along the Chicago Riverwalk, a picturesque promenade lined with restaurants, bars, and outdoor seating areas. Take a boat tour to learn about the city’s architectural gems from a unique perspective.

These are just a few of the many attractions that Chicago has to offer. Whether you’re interested in art, history, nature, or simply enjoying the city’s vibrant atmosphere, you’ll find plenty of memorable experiences waiting for you in the Windy City.


Dining and Nightlife in Chicago

When it comes to dining and nightlife, Chicago is a city that knows how to satisfy every palate and cater to a variety of interests. From fine dining establishments to street food vendors and bustling bars, the city offers a vibrant culinary and nightlife scene that is sure to delight visitors.


Chicago is famous for its deep-dish pizza, a must-try for any food enthusiast. Head to renowned pizzerias such as Lou Malnati’s, Giordano’s, or Pequod’s for a taste of this iconic dish. If you’re in the mood for classic American fare, try a Chicago-style hot dog topped with mustard, relish, onions, tomatoes, pickles, and sport peppers on a poppy seed bun.


The city boasts a diverse food scene, with a wide range of international cuisines to explore. From authentic Mexican taquerias in Pilsen to trendy sushi spots in River North and upscale Italian restaurants in the West Loop, you’ll find an array of options to satisfy your cravings.


For those interested in experiencing Chicago’s fine dining, the city offers numerous Michelin-starred restaurants. Alinea, Grace, and Oriole are just a few of the establishments pushing culinary boundaries and delivering exceptional dining experiences.


After dinner, explore Chicago’s nightlife scene, which offers something for everyone. The city is known for its thriving craft cocktail bars, speakeasies, and mixology lounges. Head to The Aviary, Three Dots and a Dash, or The Violet Hour to enjoy meticulously crafted cocktails in stylish settings.


If you’re a fan of live music, Chicago’s music venues will not disappoint. From legendary blues clubs like Buddy Guy’s Legends and Kingston Mines to iconic jazz spots like The Green Mill and Andy’s Jazz Club, you can immerse yourself in the city’s rich musical heritage.


The comedy scene in Chicago is also thriving, with renowned improv theaters like The Second City and iO Chicago showcasing talented comedians and hilarious performances. Catch a show and be prepared to laugh the night away.


It’s worth noting that Chicago’s neighborhoods offer unique dining and nightlife experiences. Exploring areas like Wicker Park, Logan Square, and Lincoln Park will reward you with trendy bars, local breweries, and eclectic dining options.


When it comes to late-night eats, Chicago doesn’t disappoint. Whether you’re craving a classic Chicago-style Italian beef sandwich or want to satisfy your sweet tooth with a late-night visit to a 24-hour bakery, you’ll find plenty of options to satiate those post-nightlife cravings.


In summary, Chicago’s dining and nightlife scene is a vibrant tapestry of flavors, experiences, and entertainment. With a range of culinary options, from street food to fine dining, and a nightlife scene that caters to all tastes, the Windy City is sure to leave you with a memorable and satisfying experience.


Shopping in Chicago

When it comes to shopping, Chicago is a true paradise for both shopaholics and fashion enthusiasts. From luxury boutiques to outlet malls and unique local shops, the city offers a diverse range of shopping experiences that cater to every style and budget.


One of the most famous shopping destinations in Chicago is the Magnificent Mile, a section of Michigan Avenue known for its upscale retail stores and luxury brands. Here, you’ll find iconic department stores like Bloomingdale’s, Neiman Marcus, and Saks Fifth Avenue, as well as designer boutiques such as Gucci, Louis Vuitton, and Burberry.


If you’re looking for a more unique and eclectic shopping experience, head to Chicago’s diverse neighborhoods. Lincoln Park and Wicker Park are known for their independent boutiques and trendy shops, offering everything from vintage clothing to handmade jewelry and home decor.


For those seeking a bargain or looking to shop at popular brands with discounted prices, Chicago offers several outlet malls. Fashion Outlets of Chicago features a range of designer and mainstream brands like Nike, Coach, and Prada, offering significant savings on their products.


Chicago is also home to a thriving art scene, and you’ll find many galleries and shops selling local artwork and crafts. Explore areas like River North and West Loop to discover unique pieces to take home as a memento of your visit.


Foodies will delight in the Green City Market, a farmers market held in Lincoln Park. Here, you can browse and purchase fresh produce, artisanal foods, and handcrafted specialties from local vendors.


Don’t forget to explore Chicago’s specialty stores and unique shops. Visit Garrett Popcorn Shops for their famous gourmet popcorn, or stop by The Spice House to stock up on a wide range of spices and seasonings.


If you’re looking for a one-stop shopping experience, Water Tower Place is a seven-story shopping center located on the Magnificent Mile. It features a mix of retail stores, boutiques, and eateries, making it a convenient option for all your shopping needs.


When planning your shopping trip, it’s worth considering the timing. Chicago is known for its seasonal sales, particularly during major holidays like Black Friday and Christmas. Taking advantage of these sales can lead to significant savings on your purchases.


In summary, Chicago offers a diverse and vibrant shopping scene with something for everyone. Whether you’re looking for luxury brands, unique local finds, or great deals at outlet malls, the city’s retail landscape is sure to satisfy your shopping desires.


Safety Tips for Chicago

As with any major city, it is important to take certain precautions to ensure your safety and make the most of your visit to Chicago. By following these safety tips, you can have an enjoyable and worry-free experience in the city:

  • Stay aware of your surroundings: Be mindful of your surroundings and stay alert, especially in crowded areas or late at night. Avoid distractions like using your phone excessively, as it can make you an easy target for pickpockets.
  • Use reliable transportation: Stick to using reputable transportation services and avoid unlicensed taxis or ride-hailing services. If using public transportation, keep an eye on your belongings and be cautious of your surroundings.
  • Avoid displaying valuable items: Keep your valuable items out of sight to minimize the risk of theft. Avoid flaunting expensive jewelry, cameras, or electronic devices in public.
  • Stay in well-lit and populated areas: Stick to well-lit streets and populated areas, especially at night. Avoid walking alone in unfamiliar or deserted areas, and consider using well-known routes or transportation options.
  • Keep your belongings secure: Carry your belongings securely and keep your purse, bag, or backpack in sight and close to your body. Be cautious of your belongings in crowded places, and consider using a money belt or a secure travel bag to prevent theft.
  • Be cautious with ATMs: Use ATMs located in well-lit and populated areas, such as banks or shopping centers. Shield your PIN entry and be aware of your surroundings while conducting any financial transactions.
  • Know emergency numbers: Familiarize yourself with the local emergency contact numbers, including the police, fire department, and medical services. Keep these numbers handy in case of any emergencies.
  • Research safe neighborhoods: Before your visit, research and choose accommodation in safe neighborhoods. Opt for areas with good reviews regarding safety and convenience.
  • Follow local laws and regulations: Familiarize yourself with Chicago’s laws and regulations, including those related to alcohol consumption, drug use, and smoking. Respect the city’s rules to ensure a safe and enjoyable visit.
  • Seek local advice: If you’re unsure about the safety of a particular area or have any concerns, don’t hesitate to ask locals or hotel staff for advice. They can provide insights and recommendations based on their knowledge of the city.

While Chicago is generally a safe city, it is always important to take precautions to protect yourself and your belongings. By staying aware, being cautious, and following these safety tips, you can fully enjoy your time in the Windy City.


Cultural Etiquette in Chicago

As a diverse and multicultural city, Chicago embraces people from all walks of life and celebrates various cultures. When visiting Chicago, it is important to be mindful of cultural etiquette to respect and appreciate the diversity of the city. Here are some tips to help you navigate cultural etiquette in Chicago:

  • Respect cultural differences: Chicago is a melting pot of different cultures and traditions. Embrace the diversity and be respectful of different customs, beliefs, and practices you may encounter during your visit.
  • Greet people respectfully: When meeting someone for the first time, a firm handshake and a friendly smile are generally appropriate. However, be mindful of personal boundaries and respect individual preferences when it comes to personal space and physical contact.
  • Be mindful of language use: English is the primary language spoken in Chicago, but other languages and dialects are also spoken by different communities. If you encounter someone who speaks a different language, it is polite to ask if they are comfortable communicating in English or if they prefer their native language.
  • Dress appropriately for the occasion: Chicagoans tend to dress casually for everyday activities, but it’s a good idea to dress slightly more formally for certain events or upscale establishments. When visiting religious sites or cultural events, be mindful of any dress code requirements or guidelines.
  • Tipping and gratuities: Tipping is customary in Chicago, and it is customary to leave a gratuity for services received, such as in restaurants, bars, and for taxi drivers. Check the local tipping guidelines for specific industries to ensure you follow appropriate practices.
  • Respect personal space: Chicagoans tend to value their personal space, so it’s important to be mindful of keeping an appropriate distance from others, especially when in crowded places or on public transportation.
  • Respect cultural sites and customs: When visiting religious sites, museums, or cultural landmarks, follow any rules or guidelines provided. This may include removing your shoes, covering your shoulders or head, or refraining from photography in certain areas.
  • Ask for permission before taking photos: Before taking photos of individuals, especially in cultural or religious settings, it’s always polite to ask for their permission first. Be mindful of privacy and respect the wishes of the people you encounter.
  • Be patient and courteous: Chicagoans are generally known for their friendliness and hospitality, but like in any busy city, patience and courtesy go a long way. Practice good manners, such as saying “please” and “thank you,” and be considerate of others around you.

By being mindful of cultural etiquette and showing respect for different customs and traditions, you can create positive interactions and foster meaningful connections during your visit to Chicago. Embrace the diversity of the city and enjoy the rich cultural experiences it has to offer.



Chicago, with its stunning architecture, vibrant culture, and diverse neighborhoods, is a captivating city that showcases the best of the Midwest. From exploring iconic landmarks and immersing yourself in the city’s rich history to indulging in delicious cuisine and experiencing its lively nightlife, Chicago offers a plethora of experiences for every visitor.


By considering the weather patterns and planning your activities accordingly, you can make the most of your time in the Windy City. Whether you’re strolling along the Magnificent Mile, taking in the breathtaking views of the skyline, or exploring the local neighborhoods, Chicago never fails to leave a lasting impression.


From the bustling downtown area to the charming neighborhoods, Chicago embraces its diverse population, making it a welcoming and inclusive city. Practice cultural etiquette, respect local customs, and enjoy the richness of the city’s multiculturalism.


Remember to prioritize your safety by staying aware of your surroundings, choosing reliable transportation options, and taking necessary precautions. With a bit of vigilance, you can navigate the city confidently and enjoy all that it has to offer.


Whether you’re a first-time visitor or a repeat traveler, Chicago’s ever-evolving attractions, dining scene, shopping experiences, and vibrant culture promise to keep you coming back for more.


So pack your bags, set out on an adventure, and get ready to create unforgettable memories in the vibrant city of Chicago – a metropolis filled with endless possibilities and boundless charm.