Chicago Travel Guide 2025

A thrilling and vibrant metropolis located in the heart of the United States, Chicago has become one of the country’s most beloved travel destinations. Known around the world for its rich history, iconic architecture and one of the most captivating culinary scenes in the region, the “Windy City” offers unique and inspiring experiences for every type of traveler. 

Whether you’re hoping to explore some of the world’s very best museums, meander through some of the city’s magnificent waterfront parks, or snap a few shots of Chicago’s jaw-dropping cityscape views, this phenomenal city has wonderful world-class opportunities around every corner. Located along the banks of Lake Michigan, Chicago is the embodiment of the Midwest, beautifully blending exhilarating fun activities with warm and welcoming hospitality to make every dream vacation come to life. 

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Planning your sensational Chicago getaway will begin with choosing the way to get there that works best for you. Luckily, as the country’s third-largest city and the Midwest’s key metropolis, transportation in and out of the Windy City is incredibly straightforward from nearly every direction 

Chicago’s central location has helped it become a focal point for several major highways making it one of the nation’s most accessible destinations for drivers to navigate. The I-90 and I-94 are two of the most popular options for travelers making their way North or South while the I-55, I-290 and I-294 are options for travelers coming in from the west. 

However, it’s important to keep in mind that Chicago is one of the region's busiest areas and congestion during peak travel times such as rush hour can become a bit heavy. 

For travelers making their way to Chicago from farther distances, flying in may very well be the best option. Chicago is home to the 7th largest international airport in the US. 

O’Hare International Airport has won multiple industry awards and has been recognized as one of the best in the business. Being one of the country’s largest airports, it’s often preferred with travelers loving the ease with which they’re able to make their way through the airport's numerous terminals and safety checks. 

Midway International Airport is located just 11 miles from Downtown Chicago and is a favorite for travelers looking for faster and more efficient service. Perfect for business professionals on the go, this airport has direct flights to over 60 international and domestic destinations. 

If you’re looking for a more nostalgic start to your Chicago adventure, then there’s nothing better than traveling by train. The city’s iconic Union Station is located in the city’s West Loop and is known as Chicago’s primary train station. Servicing the city’s Metra Rail, South Shore Line as well and Amtrak, this is a great place to quickly make your way either around the city or to any of the beautiful cities across the United States. 

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Getting out and seeing the numerous sights spread throughout this illustrious city will is a priority of many visitors. Chicago boasts numerous transportation options to help you make your way around its many travel destinations. 

If you’re looking to travel around Chicago with ease, then the CTA will be helpful. As the nation’s second-largest public transportation system, the Chicago Transit Authority (CTA) operates eight Chicago “L” train lines which can take travelers downtown as well as several of the city’s most beloved neighborhoods in addition to 129 bus routes that travel to and from numerous points within Chicago city limits.

Travelers have the option to purchase single-ride tickets or unlimited passes at any of the CTA’s easy-to-find stations. Or, if you’d prefer contactless payment options for your travels, the Ventra Card is a great way to go. By downloading the app, you’ll be able to quickly reload your balance as well as keep an eye on all arrival and departure times for any of the CTA trains and bus lines, ensuring you have safe and easy travel throughout the city during the entirety of your stay. 

Chicago is a very pedestrian-friendly city, often regarded as one of the best places to explore on foot or with a bike. Many of the city’s main attractions are within easy walking distance and Chicago has an ever-expanding network of bike lanes ensuring you’re able to quickly make your way through all its unbelievable and scenic neighborhoods all with their own unique experiences. 

While driving around Chicago can get a bit hectic, particularly during rush hour, it’s still a great way to see the plethora of rich experiences, particularly if you’re planning on adventuring a bit outside of some of the area’s more popular destinations. The city is filled with a variety of parking options, with numerous public parking lots around every corner. Several local parking tools can help travelers find available parking spots at any point in time, guaranteeing you have a safe and secure place to leave your vehicle throughout your stay. 

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Chicago is a beautiful city to visit at any time of year. However, the city does experience dramatic seasonal weather and the month you choose to book your stay will certainly have an impact on your overall experience. 

Generally considered the very best time to visit this captivating city, April and May offer travelers some of Chicago’s most comfortable temperatures, limited crowds and some of the city’s most striking scenery. Travelers can venture to any of Chicago’s picturesque parks to enjoy springtime in full bloom or take advantage of some of the city’s most highly anticipated annual events such as the Garfield Park Conservatory Spring Flower Show, Manifest Chicago, or the Chicagoland Spring Marathon. Keep in mind that while temperatures usually stay between the high 50s and low 70s this time of year, it can be a bit rainy. Make sure you bring a light waterproof jacket so that you can still take advantage of the city’s comfortable walking conditions during your stay. 

June, July and August are, without a doubt, one of the most popular times of year to visit the Windy City. With a wide range of fairs and festivals found throughout the city’s numerous neighborhoods and some of the area’s very best weather, it’s no wonder travelers come from around the world to explore Chicago’s summertime opportunities. However, if you plan on visiting during any of these months, make sure you remember to book reservations weeks in advance. Not only do many of the city’s beautiful and historic hotels fill up fast, but some of the most popular attractions and events as well. 

Another great time of year, especially for those travelers looking to enjoy the city without the crowds, is Fall. September, October and even the beginning of November offer significantly lower temperatures while still allowing guests to make their way around on foot comfortably. Fewer crowds also help ensure you’re able to see all of the city’s beautiful sights at your leisure. However, it’s important to remember that several of the city’s outdoor attractions begin limiting their hours this time of year, so you will need to plan your days out accordingly. 

If you can stand Chicago’s biting winds and below-freezing temperatures, then booking your stay between November and March will be perfect for you. Many travelers avoid the city’s extreme winter weather, meaning many local hotels, world-class restaurants and exclusive attractions will have more than enough space to accommodate you. You may even be able to find a few reduced rates along the way. However, while this is a great time of year to take advantage of the city’s magnificent range of museums, make sure you bundle up in your warmest layers if you plan on exploring any of its stunning outdoor attractions. 

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Considered one of the very best big cities in the United States, Chicago features exciting adventures around every corner. Never short on outdoor and indoor things to do in Chicago, rest assured there is an attraction or experience for every type of visitor.

One of the oldest and largest art museums in the entire country, the Art Institute of Chicago is one of the most beloved and respected galleries in the city. Home to over 300,000 works spanning from awe-inspiring ancient pieces to magnificent modern masterpieces, this is a must-see for art enthusiasts and history buffs alike. 

An engaging and innovative natural history museum, the Field Museum offers visitors the opportunity to explore a range of interactive exhibitions and creative displays. Home to over 20 million artifacts, including the world’s largest T-Rex skeleton, a visit to this museum will transport you back in time as you wander through the numerous fascinating periods already seen on this planet. 

While Chicago’s Shedd Aquarium may no longer be the world’s largest museum, it is still one of the city’s most impressive sights. Located in the city’s renowned Museum Campus, this beautiful aquarium is home to over 1,500 species of marine life and showcases not only stunning internationally beloved species but also the beauty found along the enchanting shores of Lake Michigan. 

Sitting atop what was once the world’s tallest building, the Willis Tower Skydeck will leave you speechless. Visitors can take an elevator to the 103rd floor where they will walk out to panoramic views of not only the incredible Chicago skyline but even as far as Indiana and Wisconsin. For those travelers looking for a heart-pumping experience, The Ledge is a beautifully enclosed glass-bottomed balcony offering breathtaking views of the city streets right below. 

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While Chicago winters may be brutal, the city is still home to several outstanding outdoor opportunities for travelers once the sun comes out. Take advantage of the plethora of exciting experiences spread throughout the city just waiting to be explored. 

One of Chicago’s most renowned and adored public spaces, Millennium Park is one of the city’s most popular destinations. Home to several architectural wonders and world-class art installations such as the beloved Cloud Gate sculpture better known as “The Bean”, this iconic park is a peaceful playground for visitors looking for a bit of an escape right in the heart of the city. 

A bustling hub of all things entertainment and culture, the 3,300-foot Navy Pier is one of Chicago’s not-to-be-missed locations. Featuring an array of attractions including the Centennial Wheel and the Chicago Children’s Museum, this is one of the city’s best places to enjoy a stroll while looking out onto some of the best Lake Michigan scenery. 

With over 385 acres of picturesque green space, the Chicago Botanic Garden is a natural urban space like no other. With 27 distinct gardens ranging from beautiful bonsai havens to exquisite rose gardens, travelers can lose themselves in this unique and treasured space. 

Connecting the beauty of Lake Michigan with the hustle and bustle of Downtown, the Chicago Riverwalk is one of the best places to get a true sense of the spirit of the city. A pedestrian-friendly walkway running right alongside the Chicago River, this world-class destination is the heart of the city’s entertainment, dining and shopping scenes. 

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When it comes to planning out the perfect Chicago getaway, choosing where to stay will play an integral role. Luckily, Chicago has an abundance of beautiful hotels catering to the needs of every type of guest, ensuring you’ll be able to find the perfect accommodations for you and your loved ones. Luckily, our picks below are all AAA Diamonds, a designation that lauds cleanliness and amenities that will meet traveler needs and experiences at every level. 

 A luxurious and contemporary respite from the busy streets of Chicago, the Kinzie Hotel offers guests an unbeatable downtown location, world-class service and local amenities to pull together your dream Chicago experience. This exquisite hotel helps guests unwind after days of exploring Chicago’s unbelievable adventures. 

 If you’re looking for the epitome of Chicago luxury, then The Langham is the right place. One of the city’s most iconic hotels, the Langham offers guests palatial accommodations, lavish amenities and an elegance that can’t be beat. 

 A chic and modern destination filled with a beautiful blend of style and comfort, the voco Chicago Downtown is a great place for families as well as business professionals. The hotel’s sleek guestrooms, unbeatable location and iconic views of the Chicago skyline are just a few of the major reasons why travelers love staying in this beautiful destination. 

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Known as one of the Midwest’s culinary meccas, the Chicago dining scene is one of the most innovative. Influenced by the city’s diversity and access to some of the country’s freshest local ingredients, this is a foodie’s dream come true. While globally known for its iconic deep-dish pizza and all-beef hotdogs, Chicago is also home to some of the world’s very best chefs and innovative restaurants, putting on every epicurean’s must-visit list. Visit a AAA Diamond restaurant for the best experience.  

This restaurant’s classy and elegant atmosphere, paired with chef Carrie Nahabedian’s iconic menu, has put Brindille on the map. Paying homage to the chef's favorite Paris restaurants, dishes change with the seasons, taking advantage of local and imported ingredients. 

A Chicago staple since 1977, Carson's Prime Steaks and Famous Barbecue - Chicago is an absolute must for anyone looking for a casual, laid-back dining experience that’s filled with flavor. Located just one block away from Navy Pier, this is a great place to unwind and enjoy a hearty meal after a day of wandering through Chicago’s numerous neighborhoods. 

It’s impossible to discuss Chicago’s culinary scene without talking about Alinea. Hailed as one of the world’s very best restaurants, Chef Grant Achatz’s masterful approach to modern gastronomy has captured the attention of epicureans, chefs and artists alike. Service is engaging, with staff accompanying guests through three dining levels, where guests can enjoy a 9-to-12-course experience or “The Kitchen Table,” the restaurant's most exclusive. More of an experience than a meal, an evening at Alinea is guaranteed to engage and inspire you, leaving your tastebuds wanting more and more.

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Widely considered one of the most beautiful cities in America, Chicago is truly a photographer's dream come true. Whether you’re looking for that idyllic one-of-a-kind shot or a great place to capture a few family memories, this unique city is filled with iconic photo spots that can’t be beaten. 

Located in the heart of Grant Park, the Buckingham Fountain is an exquisite landmark and one of the largest fountains in the world. Snap some truly stunning photos of you and your loved ones with this sensational aquatic backdrop before wandering through the rest of the park’s enchanting scenery and pristine gardens. 

If you’re looking for a beautiful natural landscape, then Jackson Park will be the ideal setting. This 543-acre park is filled with whimsical walkways, a glorious golf course as well as the Museum of Science and Industry. The park’s numerous nature trails also make it a fantastic place to enjoy a bit of hiking or biking while you take in some of the city’s beautiful natural scenery. 

An iconic destination dating back to 1921, the Chicago Theatre is a wonderful place to capture a bit of the city’s unique architecture and rich history. Between the theater’s stunning marquee, French baroque design and the lobby beautifully inspired by a Versailles chapel, there are so many fabulous photo spots just in this one destination alone. 

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While Chicago itself is bursting with a bounty of exciting opportunities, there are also several exceptional experiences outside the city limits just waiting to be explored. Take your vacation to the next level and enjoy a day trip out to any of these unbelievable destinations ranging from beautiful nature retreats to enchanting historic towns. 

Located just 90 miles outside of Chicago, Milwaukee is a beautiful Midwest city filled with picturesque cityscapes, year-round festivals and one of the country’s best local brewery scenes. Take a Milwaukee tour, or wander solo through any of the city’s stunning nature parks before grabbing a pint at one of its world-class dining destinations to toast to a day trip you’ll never forget. 

Just an hour outside of the city, Indiana Dunes National Park is one of the region’s most beloved reserves. With over 15,000 acres of protected land, this one-of-a-kind park offers visitors the opportunity to see this alluring landscape as it’s always been and is a great escape for anyone in need of some peace and relaxation. 

While Galena may be a three-hour ride from Chicago, the journey will be more than worth it. Once the largest port along the Mississippi River, this beautiful historic town will transport you back to the 19th century. Its charming boutiques and striking period architecture make it an ideal break from the buzzing metropolis of Chicago. 

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Visiting a bustling city like Chicago can often come with a fairly hefty price tag. However, there are so many ways to enjoy the Windy City’s vibrant culture and diverse range of attractions without breaking the bank. Here are a few budget-friendly tips that can help you enjoy a dream vacation without worrying about overspending. 

If you’re a AAA member, you’ll already be well on your way to enjoying a beautiful and budget-friendly vacation. Not only do AAA members have access to numerous exclusive travel benefits including lower-price attraction tickets and discounts on rental cars but they can also use their membership to find significant savings on accommodations.

Believe it or not, the vast array of libraries found throughout Chicago is one of the very best ways to enjoy some of the city’s renowned entertainment. Many of the city’s libraries, including the Harold Washington Library Center and the Chicago Cultural Center, often host continuous free events throughout the year and are a great place to relax and enjoy some of the city’s best art, music and culture. 

While Chicago may be a culinary wonderland, making sure you’re able to stay full and satisfied throughout the day without having to pay for a full meal is a great way to stay within budget. Avoid hungry impulse purchases and carry snacks like protein bars, dried fruits, or chips with you to keep you energized during your Chicago adventures. 

When it comes to traveling to an iconic destination like Chicago, it is crucial that you carefully consider everything you pack before you leave. From fun-filled days exploring the city’s world-class museums to outdoor adventures in any of Chicago’s breathtaking parks, there are a few must-have things every Chicago traveler should come with. 

Of course, making sure you take the city’s ever-changing climate into account is a must as well. Here are a few weather-appropriate items you may need to consider for your stay.  

Book your Chicago trip with a AAA Travel Agent today. Our travel agents make planning a trip easy, with access to vacation packages and a la carte planning options for every budget. Use your AAA membership to access exclusive travel benefits and use Trip Canvas for travel inspiration.