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  • Writer's pictureSamantha Diaz

The Ultimate Travel Guide to Chicago, Illinois

Updated: Sep 7, 2023

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Chicago, known by various names like the Windy City or Chi-Town, has become a top choice for tourists seeking an unforgettable experience. This vibrant city exudes a sense of freshness and allure, boasting magnificent skyscrapers that mirror the heavens above, along with impeccable urban planning. With its thriving culinary scene, artistic flair, and inclusive atmosphere, Chicago warmly embraces visitors from all walks of life. Offering a plethora of activities, it's no surprise that people continuously flock back to this captivating destination. Whether you revel in exploring architectural wonders, indulging in retail therapy, savoring delectable meals, or immersing yourself in popular attractions, Chicago caters to every taste. To assist you in planning your adventure, I have meticulously crafted this travel guide, brimming with valuable tips on budget-friendly options and must-see landmarks. Prepare to embark on an unforgettable journey through the perfect itinerary for an idyllic getaway in the beautiful city of Chicago.

Things to Do in Chicago, Illinois

Chicago River

The Chicago River offers a splendid opportunity for leisurely walks or captivating boat tours, providing unparalleled views of the city. Flowing through the bustling downtown area, this iconic river allows visitors to stroll along its picturesque banks, embark on guided tours, and revel in the vibrant atmosphere created by the numerous bars and restaurants that grace its shores. Whether you seek a day of sightseeing or simply wish to unwind and soak in the city's charm, the Chicago River presents an ideal setting for exploration and relaxation alike.

Millennium Park

Located in the heart of downtown Chicago, Millennium Park is a must-visit destination. Admire the iconic Cloud Gate sculpture, also known as "The Bean," which reflects the city's skyline. Enjoy free outdoor concerts, art installations, and beautiful gardens.

Art Institute of Chicago

Indulge in the captivating world of art at the renowned Art Institute of Chicago, where you can marvel at an exquisite collection of masterpieces by esteemed artists such as Monet, Van Gogh, and Picasso. Be sure not to overlook Grant Wood's iconic painting, "American Gothic," a symbol of American culture. With its extensive array of artwork and architectural wonders, the Art Institute of Chicago is a must-visit destination that promises a memorable experience during your stay in the city.

Chicago Water Tower

This is a Chicago icon that offers spectacular views of the city. It is a great place to take pictures or enjoy some ice cream. It is also a great place to learn about the history of Chicago. The Chicago Water Tower is one of the most recognizable symbols of Chicago. This is a must-see for any Chicago tourist.

Skydeck Chicago at Willis Tower (Sears Tower)

Make your way to the Skydeck located on the 103rd floor of the magnificent Willis Tower in Chicago, and prepare to be awestruck by the breathtaking bird's-eye view of the city. This elevated floor provides panoramic vistas that stretch as far as the eye can see. A favorite spot for photographers and tourists alike, the Skydeck at the Willis Tower stands as a popular attraction, beckoning visitors to capture the awe-inspiring beauty of Chicago from new heights.

Museum Of Contemporary Art Chicago (MCA Chicago)

Situated in the vibrant downtown area, the Museum of Contemporary Art stands as a prominent highlight among Chicago's top attractions. Drawing visitors from around the globe, this modern art museum has secured its place as a must-visit destination. Boasting a diverse collection comprising paintings, sculptures, installations, and photographs sourced from various corners of the world, the museum offers an immersive experience for art enthusiasts. Additionally, the museum hosts regular exhibitions that delve into the realm of modern art, showcasing its global influence and significance. Embark on a journey of artistic exploration at the Museum of Contemporary Art, where creativity knows no bounds and cultural perspectives converge.

Magnificent Mile

Chicago's Magnificent Mile is known as the city's premier shopping district, with upscale shops like Hermes, Louis Vuitton, and Burberry. The area also boasts some of Chicago’s most famous landmarks, including the historic Chicago Water Tower, the neo-Gothic Tribune Tower, and the terracotta Wrigley Building skyscraper that has a restaurant on its rooftop. Nearby are other attractions, such as the John Hancock Center observation deck at 100 stories high, which offers fine dining in addition to views from above of the north side of downtown Chicago.

Chicago Riverwalk

The Chicago Riverwalk is a particularly popular walkway. You can walk along the river, passing through many different city parks, and enjoy the views. You can also take a tour of the city using a hop-on hop-off bus tour. Chicago architectural landmarks - There are many walkways in the city, making it an ideal place to take a stroll.

Where to Eat in Chicago, Illinois

When it comes to dining in Chicago, Illinois, the city's culinary scene is nothing short of extraordinary. From Michelin-starred restaurants to beloved local eateries, there's something to please every palate. Here are a few noteworthy dining establishments that you won't want to miss during your visit:


Prepare for a gastronomic adventure at Alinea, a three-Michelin-star restaurant that consistently pushes the boundaries of fine dining. Chef Grant Achatz's innovative and artistic approach to cuisine will take you on a culinary journey like no other.

Girl & the Goat

Helmed by award-winning chef Stephanie Izard, Girl & the Goat offers a menu bursting with bold flavors and creative dishes. This popular West Loop restaurant showcases Izard's expertise in blending global influences with locally sourced ingredients.

Lou Malnati's Pizzeria

No trip to Chicago is complete without indulging in the city's famous deep-dish pizza. Head to Lou Malnati's Pizzeria for a true Chicago-style pizza experience. With its buttery crust, generous cheese, and flavorful toppings, it's a must-try for pizza lovers.

The Purple Pig

Located on the bustling Magnificent Mile, The Purple Pig celebrates Mediterranean flavors with a focus on charcuterie, cheeses, and small plates. Sample a variety of dishes, from crispy pig's ears to house-cured ham, while enjoying a vibrant atmosphere.


For a taste of Chicago's classic comfort food, make your way to Portillo's. This iconic chain is renowned for its mouthwatering Chicago-style hot dogs and Italian beef sandwiches. Don't forget to try their famous chocolate cake shake for a sweet treat.


With its rustic-chic ambiance and Mediterranean-inspired menu, Avec is a popular spot in the West Loop. Share small plates like chorizo-stuffed dates and roasted pork shoulder while sipping on carefully crafted cocktails.

Little Goat Diner

Another culinary gem from Stephanie Izard, Little Goat Diner is a whimsical and inviting spot that serves up creative comfort food with a twist. Indulge in indulgent brunch dishes, burgers, and decadent milkshakes.

Coffee Shops in Chicago, Illinois

Intelligentsia Coffee

With multiple locations across the city, Intelligentsia Coffee is a local favorite known for its meticulously sourced and expertly brewed coffee. Step into their sleek and stylish spaces to savor a perfectly crafted pour-over or a velvety cappuccino.

Ipsento Coffee

Ipsento Coffee, located in Chicago's Bucktown neighborhood, is a cozy and inviting spot that offers a range of carefully crafted drinks. Try their famous Ipsento Latte, infused with a hint of house-made chai, or indulge in one of their delicious pastries.

Gaslight Coffee Roasters

For a true artisanal coffee experience, head to Gaslight Coffee Roasters in Logan Square. This intimate coffee shop not only serves exceptional espresso drinks and pour-overs but also roasts their own beans in-house, ensuring freshness and quality in every sip.

Metric Coffee

Situated in Chicago's Fulton Market District, Metric Coffee is a sleek and contemporary coffee shop that takes its craft seriously. Sip on their meticulously brewed coffees while enjoying the minimalist aesthetic and friendly atmosphere.

Whether you're in need of a morning pick-me-up, a cozy spot to work, or a place to catch up with friends, these coffee shops in Chicago provide the perfect setting to enjoy a delightful cup of coffee and immerse yourself in the city's vibrant café culture.

Where to Stay in Chicago, Illinois

Finding the perfect place to stay in Chicago, Illinois, can elevate your experience and serve as a comfortable base for exploring the city. From luxurious hotels to charming boutique accommodations, Chicago offers a diverse range of options to suit every traveler's needs. Here are a few noteworthy places to consider for your stay:

The Langham, Chicago

Nestled along the Chicago River, The Langham exudes elegance and sophistication. This luxurious hotel features spacious rooms with stunning city views, a world-class spa, and impeccable service. Its prime location near Millennium Park and the Magnificent Mile ensures easy access to top attractions.

The Peninsula Chicago

Situated on the iconic Magnificent Mile, The Peninsula is synonymous with opulence and impeccable hospitality. From its stylish rooms to its award-winning restaurants and rooftop terrace with panoramic city views, this five-star hotel offers a truly indulgent experience.

The Gwen, a Luxury Collection Hotel

Located in the historic McGraw-Hill Building, The Gwen seamlessly blends modern luxury with Art Deco influences. Its chic rooms, rooftop terrace with a terrace bar, and proximity to renowned shopping and dining destinations make it a desirable choice.

The Robey

Housed in a converted 1920s Art Deco building, The Robey is a trendy boutique hotel located in the vibrant Wicker Park neighborhood. Its stylish rooms, rooftop lounge with breathtaking skyline views, and proximity to trendy shops, bars, and restaurants make it a popular choice among the hip crowd.

Best Time to Visit Chicago, Illinois

The best time to visit Chicago, Illinois, largely depends on your preferences for weather, events, and crowd levels. Here's a breakdown of the seasons to help you plan your trip:

  1. Spring (April to May): Spring in Chicago brings milder temperatures, budding trees, and blooming flowers. This season is ideal for exploring outdoor attractions, such as Millennium Park and the Chicago Botanic Garden. However, keep in mind that spring can be unpredictable, with occasional rain showers and fluctuating temperatures.

  2. Summer (June to August): Chicago summers are vibrant and bustling with activity. The city comes alive with numerous festivals, outdoor concerts, and events like the Taste of Chicago and Lollapalooza. The weather is generally warm and sunny, making it a great time to enjoy the city's beaches, Navy Pier, and boat tours along the Chicago River.

  3. Fall (September to October): Fall in Chicago is characterized by pleasant temperatures and beautiful foliage. The city takes on a cozy ambiance, and you can enjoy events like the Chicago Jazz Festival and Chicago Gourmet. It's also a great time to explore the city's neighborhoods, visit museums, and take architectural tours.

  4. Winter (November to March): Chicago winters can be quite cold, with temperatures dropping below freezing. However, if you're prepared for the chill, you can experience the magic of the city adorned in holiday lights, ice skating at Millennium Park, and festive events like the Christkindlmarket and Winter Wonderfest. Plus, you can enjoy indoor attractions like the Art Institute of Chicago and Museum of Science and Industry without the large crowds.

It's important to note that Chicago's weather can be unpredictable, so be prepared for sudden changes in temperature and pack layers accordingly. Additionally, summer months tend to be the busiest in terms of tourist activity, while spring and fall offer a pleasant balance of favorable weather and fewer crowds. Ultimately, the best time to visit Chicago depends on your interests and priorities. Consider the weather, events, and activities that align with your preferences to ensure a memorable and enjoyable visit to the Windy City.

Chicago is an absolute gem when it comes to tourism. It's no surprise that people keep flocking to this vibrant city with its endless array of activities and attractions. Whether you're into marveling at stunning architecture, indulging in retail therapy, savoring delicious meals, or embarking on thrilling adventures, Chicago has got you covered. The city is massive, and it's bursting at the seams with things to see, do, and eat. In this section, we've put together some fantastic tips on exploring Chicago without breaking the bank. Trust me, there's something for everyone here!


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I'm Samantha! A photographer and I believe that every picture has a story. As a blogger, I share my travel stories with everyone. I think it's important to document my travels and share my experiences with others. I've been to some amazing places and I've seen some incredible things. I want to share my stories and photos with the world.

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