A photo of downtown Chicago. A skyscraper has a large, red vertical sign that says "Chicago" attached to the side of it.

The Ultimate Chicago, Illinois Travel Guide

Welcome to the city that stands tall and proud, where history meets urban elegance, and deep-dish pizza reigns supreme. Chicago, Illinois, is a vibrant metropolis that beckons travelers from around the globe.

Our one-stop guide shares everything you need to know about visiting the vibrant city of Chicago! Our comprehensive travel guide is packed full of insider tips, money-saving tricks, and the best of what the Windy City has to offer. Whether you’re a foodie looking to taste Chicago’s world-renowned deep-dish pizza and Italian beef, an architecture aficionado eager to gaze upon the city’s pioneering skyscrapers, or a culture enthusiast ready to immerse yourself in the city’s rich history and thriving arts scene, we’ve got you covered.

Dive in and start exploring the city that has something for everyone, where every neighborhood holds a new adventure, every restaurant a culinary delight, and every vista a breathtaking view. Welcome to Chicago!

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Top 5 things to do in chicago

Full view of The Bean, otherwise known as Cloud Gate located in Millennium Park during the fall. Colorful trees frame the photo.

1. Millennium Park: Where Art, Music, and Reflection Meet

Welcome to the heart of Chicago, where a captivating blend of art, music, and nature awaits at Millennium Park. Get ready to be mesmerized by “The Bean” (officially known as Cloud Gate), a reflective sculpture that distorts reality and offers the perfect selfie backdrop. Take a leisurely stroll through Lurie Garden, a tranquil oasis bursting with vibrant flowers and serene paths. And if you’re lucky, you might catch a free outdoor concert at the Jay Pritzker Pavilion, where music fills the air and memories are made. Millennium Park is where Chicagoans come to celebrate, reflect, and bask in the beauty of their city.

A picture of the outside of The Art Institute of Chicago.

2. The Art Institute of Chicago: A Masterpiece of Creative Wonder

Prepare to embark on an artistic journey through time and space at the renowned Art Institute of Chicago. As you step through the grand entrance, you’ll be greeted by an extraordinary collection that spans centuries and continents. Lose yourself in the brushstrokes of Monet, marvel at the grandeur of ancient Egyptian artifacts, and immerse yourself in the world of modern and contemporary art. And don’t forget to make a stop at the Thorne Miniature Rooms, where you can step into tiny, intricately detailed worlds. The Art Institute of Chicago is a haven for art enthusiasts and curious minds alike, where inspiration knows no bounds.

A view of Navy Pier in Chicago. The Centennial Ferris Wheel is visible in the image.

3. Navy Pier: A Playground of Fun, Thrills, and Unforgettable Views

Hold onto your hats and get ready for an adventure at Navy Pier! This iconic lakeside destination offers a little something for everyone. Take a ride on the Ferris wheel and witness breathtaking views of Lake Michigan and the city skyline. Indulge your inner child at the Chicago Children’s Museum, where imaginations run wild. And if you’re seeking entertainment, catch a live performance at the Shakespeare Theater or laugh your socks off at the Navy Pier IMAX Theater. With a vibrant carnival atmosphere, delightful eateries, and plenty of Instagram-worthy moments, Navy Pier is the place where laughter, excitement, and lasting memories collide.

A drone photo of the Chicago skyline at night. Willis Tower can be seen on the right side of the image.

4. Willis Tower Skydeck: Touch the Sky and Conquer Your Fear of Heights

Step into the elevator and prepare for a thrilling ascent to the 103rd floor of the Willis Tower. As the doors open, brace yourself for jaw-dropping views from the Skydeck. Stepping out onto “The Ledge,” a glass balcony that extends four feet from the building’s edge, you’ll feel a rush of adrenaline as the city spreads out beneath you. Snap a selfie against the breathtaking backdrop of Chicago’s skyscrapers and Lake Michigan. The Willis Tower Skydeck is not only a testament to human engineering marvels but also a place where you can conquer your fear of heights and feel like you’re on top of the world. The Willis tower is on the left in the photo above. 

A photo overlooking Wrigley Field. The Chicago Skyline can be seen in the background.

5. Wrigley Field: Home of Baseball Legends and Unforgettable Moments

Welcome to the Friendly Confines of Wrigley Field, where the crack of the bat, the roar of the crowd, and the smell of fresh-cut grass create an electric atmosphere. This historic baseball stadium is where legends have played and epic moments have unfolded. Cheer on the Chicago Cubs, one of the most beloved teams in Major League Baseball, as you join a sea of passionate fans. Experience the thrill of a home run, sing “Take Me Out to the Ball Game” during the seventh-inning stretch, and savor the timeless traditions of America’s favorite pastime. Wrigley Field is not just a stadium; it’s a hallowed ground where dreams come true and memories are etched in history.

Top 3 Luxury Hotels in Chicago

1. The Langham Chicago

Indulge in the lap of luxury at The Langham, Chicago. This prestigious hotel is the epitome of elegance and sophistication. With its sweeping views of the Chicago River and impeccable service, you’ll feel like royalty from the moment you step foot in the door. Unwind in the luxurious spa, sip on exquisite cocktails at the elegant bar, and let the plush bedding lull you into a dreamy slumber. The Langham, Chicago is where luxury meets blissful perfection.

2. The Peninsula Chicago

Step into a world of opulence and sophistication at The Peninsula Chicago. This legendary hotel exudes timeless glamour and offers a seamless fusion of modern amenities and classic charm. From the stunning rooftop pool to the award-winning dining options, every moment spent at The Peninsula is a celebration of refined taste. And don’t miss their legendary afternoon tea, where you can nibble on delicate treats fit for royalty. Prepare to be pampered, dazzled, and utterly enchanted at The Peninsula Chicago.

3. Four Seasons Hotel Chicago

Welcome to the pinnacle of luxury at the Four Seasons Hotel Chicago. This iconic hotel offers breathtaking views of Lake Michigan and impeccable service that will make you feel like a VIP. With its sleek and stylish design, lavish suites, and world-class dining, the Four Seasons creates an atmosphere of unparalleled indulgence. Relax in the opulent spa, sip on craft cocktails at the chic lounge, and let the expert concierge curate a truly unforgettable experience. When it comes to luxury, the Four Seasons Hotel Chicago sets the bar sky-high.

Top 3 budget Hotels in Chicago

1. Freehand Chicago

Welcome to the hip and vibrant world of Freehand Chicago! This budget-friendly gem offers a creative and playful atmosphere that will make you feel like you’ve stepped into an art gallery. With its stylish shared rooms and communal spaces, you’ll have the chance to meet fellow travelers and swap stories over a game of pool. Plus, their on-site bar is the perfect spot to sip on craft cocktails and mingle with fellow adventurers. Freehand Chicago proves that budget travel doesn’t mean compromising on style or fun!

2. Acme Hotel Company Chicago

Experience the heart of Chicago at the Acme Hotel Company. Rated 4.5 out of 5 with thousands of excellent reviews, this hotel lands within the top 15% of Chicago hotels. Indulge in the city’s vibrant nightlife, explore the diverse food scene, or just unwind in the comfort of your room. At the Acme Hotel Company, the city’s best is just outside your door.

3. The Sono Chicago

Experience a unique blend of warmth, comfort, and hospitality at The Sono Chicago. Nestled in the heart of the historic Old Town District, this boutique bed and breakfast is your home away from home. Enjoy the cozy, intimate accommodations, perfectly situated on a tree-lined neighborhood street, designed to offer a sense of community that is truly unparalleled. Start your day with a continental breakfast served from our top of the line kitchen, and end it with a breathtaking view of the Chicago skyline from our rooftop deck, complete with a firepit for those cooler nights.

A man in a Cubs jersey stands in front of a mural that says Chicago. Within the letters there are depictions of important pieces of Chicago's history, culture, and traditions.

Chicago Culture & Traditions

Culture, customs, and traditions in Chicago are as diverse and vibrant as the city itself! From its deep-rooted history to its thriving arts scene, Chicago offers a melting pot of cultures that intertwine to create a unique tapestry. 

Whether you’re diving into the city’s deep-dish pizza obsession or cheering alongside passionate sports fans, you’ll find that Chicagoans take their customs and traditions seriously, with a side of lightheartedness.

The city’s love for live music is infectious, with jazz clubs and blues bars serving up soul-stirring melodies that will make you want to dance the night away. 

And let’s not forget the pride Chicagoans have for their beloved sports teams; whether you’re wearing Cubs blue or Bulls red, you’ll instantly be welcomed into a community bonded by unwavering loyalty. 

Chicago’s culture is a delightful blend of historical significance, artistic expression, and a dash of Midwestern charm. So, embrace the Windy City’s customs, join the local festivities, and prepare to be swept up in the energy that makes Chicago truly one of a kind!

Money Saving Tips for Visiting Chicago

Embrace Public Transportation:

Hop on the “L” train, and let it take you on a money-saving adventure through the city! Not only will you save on expensive parking fees and traffic-induced headaches, but you’ll also get a front-row seat to Chicago’s colorful characters and lively energy. Plus, who doesn’t love a little people-watching while commuting?

Snack & Dine Like a Local:

While deep-dish pizza and gourmet eats may tempt your taste buds, don’t forget to explore Chicago’s street food scene! From delicious hot dogs to mouthwatering tacos, the city’s food carts and neighborhood joints offer tasty treats at pocket-friendly prices. Also, seek out the hidden culinary gems that locals rave about. From hole-in-the-wall ethnic eateries to mom-and-pop diners, you’ll savor authentic flavors at a fraction of the cost. Trust us, the locals know where the good eats are!

Seek Out Free Attractions:

Who says the best things in life aren’t free? Discover Chicago’s wealth of free attractions, from strolling along the scenic Lakefront Trail to admiring the masterpieces at the Art Institute of Chicago during their free admission hours. Embrace your inner culture vulture without breaking the bank.

Take Advantage of City Passes:

Unlock the city’s treasures while saving a bundle with Chicago’s city passes. These convenient passes offer discounted access to multiple attractions, museums, and even tours. So, go ahead and splurge on that city pass. Your wallet will thank you as you immerse yourself in the best of Chicago without emptying your pockets.

Time Your Visit Strategically:

Timing is everything, even when it comes to saving money on travel. Consider visiting Chicago during its shoulder seasons, like spring or fall, when hotel rates tend to be lower, and crowds are thinner. Plus, you’ll get to enjoy mild weather while exploring the city’s parks and lakeshores without the summer heatwaves.

security Tips for Visiting Chicago

While certain neighborhoods may experience higher crime rates, the majority of areas frequented by tourists are generally safe. The Chicago Police Department works diligently to maintain safety and reduce crime in the city. It’s advisable to stay informed about any potential safety concerns or areas to avoid during your visit. Checking the latest travel advisories and consulting local resources, such as tourism websites or hotel staff, can provide valuable insights into the current safety situation. In the meantime, here are some essential tips to stay safe and healthy during your visit to the Windy City:

  1. Stay Aware of Your Surroundings: Like any bustling city, it’s important to remain vigilant and aware of your surroundings. Stay alert, especially in crowded areas, and keep an eye on your belongings to deter pickpockets. Stick to well-lit and populated areas, and if you’re unsure about a particular neighborhood, do some research beforehand or seek local advice.

  2. Use Reliable Transportation: Opt for reputable transportation options, such as licensed taxis, ride-sharing services, or public transportation. If using public transport, be mindful of your belongings and keep valuables secure. Avoid traveling alone late at night, and if you’re unsure about directions or which stops to take, don’t hesitate to ask fellow travelers or transportation staff.

  3. Dress Appropriately for the Weather: Chicago experiences distinct seasons, so dress accordingly to stay comfortable and healthy. In cold weather, layer up and wear a warm coat, hat, gloves, and sturdy footwear. In hot weather, dress in lightweight, breathable fabrics, wear sunscreen, and stay hydrated. Being prepared for the elements will help you avoid weather-related health issues.

  4. Stay Hydrated and Practice Good Hygiene: Chicago’s bustling streets can be tiring, so remember to drink plenty of water to stay hydrated. Carry a reusable water bottle and refill it throughout the day. Additionally, practice good hygiene by washing your hands frequently, especially before eating or touching your face. Carry hand sanitizer for situations when handwashing facilities are not readily available.

  5. Be Mindful of Traffic and Pedestrian Safety: Chicago’s traffic can be busy and fast-paced, so exercise caution when crossing the streets. Always use designated crosswalks, obey traffic signals, and make eye contact with drivers before stepping off the curb. Look both ways before crossing, even on one-way streets, as cyclists and scooters may be approaching from unexpected directions.

  6. Stay Informed and Follow Health Guidelines: Stay updated on local health guidelines, especially during your visit. Pay attention to any advisories or recommendations regarding COVID-19 or other health concerns. Follow the guidance provided by health authorities, such as wearing masks in indoor public spaces and maintaining physical distancing.

By staying aware, prepared, and informed, you can have a safe and healthy experience while exploring the wonders of Chicago. Enjoy the city’s vibrant culture, savor its culinary delights, and create unforgettable memories while prioritizing your well-being.

Chicago's Food Scene

A picture of a slice of deep dish pizza being pulled away from the rest of the pie. Cheese pulls on both sides of the slice.

deep-dish pizza

Get ready to embark on a cheesy, saucy, and deep-dish adventure! Chicago’s iconic pizza is a marvel of culinary engineering, with its buttery, flaky crust, a layer of gooey cheese that stretches for days, and toppings that reach the heavens. Whether you’re a carnivore craving sausage or a veggie lover piling on the mushrooms, one bite of this legendary pie will have you saying, “That’s amore!”

A classic Chicago Style Hot dog with french fries on a cutting board

chicago-style hot dog

Brace yourself for a flavor explosion in a bun! A Chicago-style hot dog is no ordinary frankfurter. It’s a culinary masterpiece with a strict code of condiment conduct: yellow mustard, neon-green relish, chopped onions, tomato slices, a pickle spear, sport peppers, and a sprinkle of celery salt, all lovingly nestled in a perfectly steamed poppy seed bun. It’s a hot dog experience that will make your taste buds do a joyful dance.

A picture of an Italian Beef Sandwich with fries resting on a wood board.

italian beef sandwich

Prepare for a messy, meaty, and oh-so-satisfying delight! The Italian beef sandwich is a Chicago institution that will leave you licking your fingers and craving seconds. Thinly sliced roast beef, slow-cooked to tender perfection, is piled high on an Italian roll and soaked in flavorful jus. Top it off with sweet or hot peppers, and you have a sandwich that’s as hearty as it is delicious. Just be ready to unleash your inner napkin ninja to tackle the juicy goodness!

Top 3 Fine Dining Restaurants in Chicago

1. Alinea

Alinea is a Chicago gem that has been universally acclaimed for its unique and innovative approach to modernist cuisine. It has been honored with multiple prestigious titles, such as the Best Restaurant in the World by Elite Traveler, the Best Restaurant in North America by The World’s 50 Best Restaurants, and the Best Restaurant in the U.S. by Gourmet and Business Insider. In addition to these accolades, Alinea is one of only 14 restaurants in the U.S. to have earned the coveted Michelin 3-Star rating, and it has also won James Beard Awards for Outstanding Restaurant, Outstanding Service, and Outstanding Chef in the U.S.

2. Oriole

Oriole is a two Michelin-starred contemporary-American restaurant located in Chicago’s West Loop neighborhood. Under the guidance of Executive Chef and Owner Noah Sandoval, Oriole offers an award-winning, constantly evolving tasting menu. Since its opening in 2016, it has received the Jean Banchet Award for Restaurant of the Year. Chef Sandoval, a James Beard-nominated chef, was named one of Food & Wine’s Best New Chefs in 2017, further solidifying the restaurant’s reputation for excellence​.

3. Goosefoot

Goosefoot, located in Chicago’s Lincoln Square, is a fine dining BYOB restaurant that is a true culinary gem. Helmed by chef/owners Chris and Nina Nugent, the restaurant showcases an artful blend of French technique with a modern vision. The cuisine is created from small artisan farm products, ensuring that each dish is as fresh as it is flavorful​. The restaurant currently has one Michelin Star. 

Top 3 Restaurants to Get Chicago's Famous Dishes

1. Giordano's Pizza

With a rich history spanning over 200 years, Giordano’s is renowned for its stuffed pizza, an evolved recipe from a small town near Torino, Italy. First introduced to Chicago by Italian immigrants Efren and Joseph Boglio in 1974, Giordano’s quickly became a city favorite and has since been acclaimed as Chicago’s Best Pizza by numerous media outlets. Along with their famous stuffed pizza, they also serve great starters, fresh salads, outstanding pastas, and unique sandwiches​

2. Superdawg

Founded in 1948 by World War II veteran Maurie and his wife Flaurie, Superdawg is a beloved institution in the heart of Chicago. Known for their pleasant drive-in experience, the restaurant offers delicious hot dogs and a dedication to service that will make you want to return again and again. Located on N. Milwaukee Avenue, Superdawg provides a taste of authentic Chicago cuisine every day of the week

3. Al's Beef

Starting as a humble street peddler’s business at the end of World War I, Al’s Beef has grown into a Chicago culinary landmark. The creation of the Italian Beef Sandwich is attributed to Anthony Ferreri, whose thin beef cuts cooked in juices with secret spices became a hit in the city. In 1938, his son Albert and his relatives opened Al’s Beef in the Little Italy neighborhood, cementing their legacy in the city’s food scene. With numerous awards under its belt, including being named the #1 Italian Beef Sandwich in Chicago, Al’s Beef continues to serve its passionately crafted sandwiches to locals and tourists alike, over 80 years after its inception

Chicago Transportation

The "L" Train:

All aboard the excitement express! Hop on Chicago’s famous “L” train system and let it whisk you away to every corner of the city. From the Loop to the hipster havens of Wicker Park, this elevated adventure is a great way to get around. You can learn more about how to ride the “L” Train by visiting the Chicago Transit Authority.

Divvy Bikes:

Pedal power to the rescue! Grab a Divvy bike and channel your inner Tour de Chicago. With the wind in your hair and the city at your fingertips, you’ll feel like a two-wheeled superhero, cruising past skyscrapers and leaving traffic jams in the dust. Plus, bonus points for burning off those deep-dish pizza calories!

Water Taxis:

Why walk when you can sail? Hop aboard a water taxi and float your way through the Chicago River and Lake Michigan. Nothing is quite like commuting on the water with a view! Marvel at the breathtaking skyline as you cruise from one waterfront hotspot to another, feeling like a modern-day explorer on a nautical adventure.

Chicago Riverwalk:

Who needs wheels when you’ve got the Riverwalk? Lace up your sneakers and stroll along this picturesque promenade that winds its way through the heart of the city. With scenic views, charming cafes, and plenty of Instagram-worthy spots, you’ll feel like you’re walking on sunshine (and maybe a little bit of river magic).

Hop-On, Hop-Off Bus:

Feeling like a tourist? Embrace it! Jump on a hop-on, hop-off bus tour and let the city’s sights come to you. It’s like a mobile sightseeing extravaganza, complete with a knowledgeable guide and the freedom to explore at your own pace. Just remember to wave at the pedestrians—after all, you’re riding high on a moving attraction!

Taxi and Ride-Sharing:

When all else fails, embrace the power of the yellow cab or summon a ride-sharing superhero. Whether it’s a classic taxi or a four-wheeled chariot summoned via app, these trusty vehicles will whisk you away to your destination in style. Just sit back, relax, and enjoy the ride while pretending you’re in your very own Chicago-themed action movie.

Chicago Weather & Climate

26ºF

winter

During winter, Chicago transforms into a glittering winter wonderland. Average temperatures range from 18°F (-8°C) to 35°F (2°C), with snowfall covering the cityscape in a cozy blanket. Brace yourself for chilly winds that lend the city its nickname. Brace yourself for chilly winds that lend the city its nickname. Bundle up in layers, sip on hot chocolate, and marvel at the beauty of Millennium Park adorned in a frosty white veil.

50ºF

spring

As spring arrives, Chicago experiences a burst of color and renewed energy. Average temperatures range from 39°F (4°C) to 61°F (16°C), with nature awakening from its slumber. Cherry blossoms and tulips grace the city’s parks, while residents shed their winter coats for lighter attire. Spring is the season of renewal, where Chicagoans eagerly embrace the longer days and enjoy outdoor activities.

78ºF

summer

When summer arrives, Chicago radiates with warmth and excitement. Average temperatures soar between 71°F (22°C) and 84°F (29°C), inviting residents and visitors to explore the city’s abundant outdoor offerings. Stroll along the picturesque Lakefront Trail, soak up the sun at one of the many beaches, or immerse yourself in the lively festivals and concerts that fill the city’s calendar.

54ºF

Fall

As summer bids farewell, Chicago unveils its captivating autumn splendor. Average temperatures range from 41°F (5°C) to 67°F (19°C), providing a comfortable backdrop for leaf-peeping and outdoor pursuits. The city’s parks and tree-lined streets transform into a kaleidoscope of vibrant reds, oranges, and golds, inviting residents to savor cozy moments and indulge in pumpkin-spiced delights.

chicago fun facts

Chicago holds a special place in architectural history as the birthplace of the modern skyscraper. The city was the site of the first skyscraper in the United States, the Home Insurance Building, which was completed in 1885. This iconic building, designed by William Le Baron Jenney, stood at a then-impressive ten stories high and introduced the structural use of steel, setting the precedent for future high-rise constructions. Though it was demolished in 1931, the legacy of the Home Insurance Building continues to influence the cityscape of Chicago and the design of skyscrapers worldwide.

The iconic Ferris wheel, a staple of amusement parks worldwide, made its debut in none other than Chicago. Designed by George Washington Gale Ferris Jr., the Ferris wheel was unveiled at the 1893 World’s Columbian Exposition held in Chicago. It forever changed the landscape of amusement rides and continues to be a beloved attraction today.

Chicago is often referred to as the “Blues Capital of the World.” The city’s rich musical heritage includes the birth of electric blues in the 1950s, with legendary artists like Muddy Waters and Howlin’ Wolf making their mark on the genre. To this day, Chicago remains a vibrant hub for blues music, with numerous clubs and festivals dedicated to the genre.

In the Loop area of downtown Chicago, there is an extensive underground network of pedestrian tunnels known as the Pedway. Stretching over five miles, this hidden labyrinth connects various buildings, train stations, and shops, offering a convenient way to navigate the city during harsh weather conditions.

Every year on St. Patrick’s Day, the Chicago River transforms into a brilliant shade of emerald green. This vibrant tradition dates back to 1962 when the river was dyed green for the first time using a special eco-friendly dye. It’s now an annual spectacle that attracts crowds of enthusiastic spectators.

In Daley Plaza, you’ll find a towering and abstract sculpture known simply as “The Picasso.” Created by renowned artist Pablo Picasso, this 50-foot-tall artwork was a gift to the city of Chicago in 1967. Its unconventional design sparked controversy initially, but it has since become a beloved symbol of the city’s commitment to public art.

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A photo of downtown Chicago. A skyscraper has a large, red vertical sign that says "Chicago" attached to the side of it.

The Ultimate Chicago, Illinois Travel Guide

Your ultimate guide to exploring Chicago! Discover top attractions, dining experiences, hotel recommendations, money-saving tips, and more in our comprehensive Windy City travel guide. Uncover the city that pioneered skyscrapers and delights foodies worldwide.

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