Planning a comprehensive Chicago itinerary is crucial to getting the most out of your trip to the Windy City. With Chicago being the third-largest city in the U.S., there’s a lot of ground to cover. From world-class museums to famous attractions, shopping, dining, and exceptional entertainment, there is no shortage of stuff to do in Chicago during your 5 days in the city. In this itinerary, you will discover the best places to visit and things to do during your 5-day trip to Chicago.
Key Takeaways:
- Discover the best places to visit and things to do in Chicago during a 5-day trip
- Explore world-class museums, famous attractions, and vibrant neighborhoods
- Experience the breathtaking Chicago skyline and enjoy a variety of entertainment options
- Plan your Chicago itinerary in advance to make the most of your time in the city
- Consider purchasing a Chicago CityPASS for discounted admission to multiple attractions
Day 1 – Get to Know Chicago
On your first day in Chicago, get ready to immerse yourself in the vibrant city and discover its iconic attractions. Start your day by visiting the legendary John Hancock building in Streeterville, known for its impressive architecture and breathtaking views of the city.
For an unforgettable experience, make your way up to the 94th floor and step onto the 360 Chicago Observation Deck. From here, you’ll be treated to panoramic views of the stunning Chicago skyline. Take your time to admire the city from above and capture some memorable photos.
After taking in the magnificent views, it’s time to explore one of Chicago’s most famous shopping destinations—the Magnificent Mile. This bustling district is home to a plethora of luxury boutiques, department stores, and designer brands. Whether you’re looking for the latest fashion trends or unique souvenirs, the Magnificent Mile has it all.
While exploring the Magnificent Mile, you’ll find yourself surrounded by numerous dining options. Take a break and recharge at the Starbucks Reserve, where you can indulge in a cup of expertly crafted coffee. Sit back, relax, and soak in the bustling atmosphere of this popular coffee spot.
For those seeking an adrenaline rush, make sure to experience the Tilt ride. Located on the 94th floor of the John Hancock building, this thrilling attraction tilts you 1,000 feet above the Magnificent Mile, offering a heart-pumping and exhilarating experience.
“The view from the 360 Chicago Observation Deck is absolutely breathtaking. It’s a must-visit attraction for anyone visiting Chicago.”
Highlights of Day 1
- Visit the John Hancock building
- Experience the 360 Chicago Observation Deck
- Explore the Magnificent Mile
- Grab a cup of coffee at the Starbucks Reserve
- Take a ride on the thrilling Tilt attraction
| Attraction | Description |
|---|---|
| John Hancock building | An architectural icon offering magnificent views of the city |
| 360 Chicago Observation Deck | A panoramic viewpoint on the 94th floor of the John Hancock building |
| Magnificent Mile | A famous shopping district with a wide range of luxury boutiques and stores |
| Starbucks Reserve | A coffee destination to savor expertly crafted beverages |
| Tilt ride | A thrilling attraction that tilts you 1,000 feet above the Magnificent Mile |
Day 2 – Wander Museums or Head to Wrigley Field
On your second day in Chicago, you have the option to explore the city’s world-class museums or head to the iconic Wrigley Field. Whether you’re a lover of arts and culture or a sports enthusiast, Chicago has something for everyone.
If you appreciate art and want to immerse yourself in the vibrant cultural scene, a visit to the Art Institute of Chicago is a must. Located in Grant Park, the Art Institute houses an impressive collection of nearly 300,000 works of art, ranging from ancient artifacts to modern masterpieces. Take your time to admire famous paintings, sculptures, and architectural marvels from around the world.
If you’re more inclined towards natural history and science, spending the day at Museum Campus is a fantastic choice. This expansive complex is home to three renowned institutions: the Field Museum, the Shedd Aquarium, and the Adler Planetarium. Explore the fascinating world of dinosaurs, ancient civilizations, and mesmerizing aquatic creatures. At the Adler Planetarium, you can embark on a journey through space and learn about the wonders of the universe.
For sports enthusiasts, the Wrigley Field experience is not to be missed. As the historic home of the Chicago Cubs, Wrigley Field has been a staple of Chicago sports culture for over a century. Catch a game and soak in the electric atmosphere of one of baseball’s most beloved stadiums. Feel the energy of the crowd as you cheer on the Cubs and enjoy the thrilling sport that captivates millions.
Whether you choose to explore Chicago’s museums or head to Wrigley Field, you’ll be immersed in the rich history, culture, and entertainment that the city has to offer.
Day 3 – Explore Lincoln Park and Old Town
On your third day in Chicago, venture into the charming neighborhoods of Lincoln Park and Old Town. Begin your morning by taking a leisurely stroll along the scenic Lakefront Trail, soaking in the stunning views of Lake Michigan. Make a stop at North Avenue Beach, where you can relax on the sandy shores or take a dip in the refreshing water.
Next, immerse yourself in the natural beauty of Lincoln Park, one of Chicago’s most beloved green spaces. Within the park, you’ll find the renowned Lincoln Park Zoo, a free attraction known for its impressive collection of animals from around the world. Be sure to visit the Lincoln Park Conservatory, a beautiful glasshouse housing a variety of exotic plants and flowers. As you explore the park, don’t forget to make a visit to the Chicago History Museum, where you’ll discover the fascinating stories and heritage of the city.
In the evening, make your way to Old Town, a historic neighborhood filled with charm and character. Experience the vibrant arts scene by catching a comedy show at The Second City comedy club, known for launching the careers of many famous comedians. Prepare to laugh your evening away as you enjoy top-notch improvisational performances and hilarious sketches.
Day 4 – Take a Leisurely Walk and Then Catch a Show
On day four of your 5-day Chicago itinerary, take the opportunity to explore the city at a leisurely pace. Start your day with a delightful walk along the Chicago Riverwalk or the scenic Lakefront Trail. These popular waterfront pathways offer stunning views of the city’s skyline and provide a relaxing atmosphere.
An iconic attraction not to be missed is the Willis Tower Skydeck, where you can elevate your Chicago experience to new heights. Take an elevator ride to the top of this magnificent skyscraper and enjoy breathtaking panoramic views of the city and beyond.
Continue your exploration along the Lakefront Trail, which offers a scenic path along the shores of Lake Michigan. Make a stop at the Buckingham Fountain, one of Chicago’s most famous landmarks. This beautiful fountain features impressive water displays and is surrounded by manicured gardens, making it a perfect spot for a photo opportunity.
In the afternoon, treat yourself to a Chicago River cruise and immerse yourself in the architectural beauty of the city. Sail along the Chicago River and admire the stunning skyscrapers, historic landmarks, and distinctive bridges that showcase the city’s rich history and architectural diversity.
As evening approaches, it’s time to enjoy the vibrant entertainment scene that Chicago has to offer. Catch a Broadway show at one of the renowned theaters in the city or indulge in live music at one of the many jazz clubs. Chicago’s theater district is known for its world-class productions, ensuring a memorable night out.
Complete your fourth day in Chicago by immersing yourself in the cultural and artistic experiences that the city has to offer. From leisurely walks to architectural marvels and captivating performances, this day is sure to leave you with lasting memories.
Day 5 – Day Trip to Oak Park or Indiana Dunes National Park
On your final day in Chicago, why not embark on a memorable day trip to either Oak Park or Indiana Dunes National Park? These two destinations offer unique experiences that are worth exploring.
Oak Park: Discover Frank Lloyd Wright’s Architectural Legacy
If architecture and history intrigue you, Oak Park is the perfect place to visit. This picturesque suburb is renowned for its association with the legendary architect, Frank Lloyd Wright. Explore the Frank Lloyd Wright architecture in Oak Park and be captivated by the exceptional design elements and innovative concepts.
A must-see attraction in Oak Park is the Robie House, a masterpiece of Wright’s Prairie School architectural style. Admire its distinctive horizontal lines, expansive windows, and integration with nature, which exemplify Wright’s vision of organic architecture.
Additionally, Oak Park is historically significant as it was once the home of esteemed author Ernest Hemingway. Take the opportunity to visit the Ernest Hemingway Birthplace Home and learn more about the Nobel Prize-winning writer’s life and works.
Indiana Dunes National Park: Nature’s Paradise
For those seeking outdoor adventure and natural beauty, a visit to Indiana Dunes National Park is highly recommended. This national park is located along the southern shore of Lake Michigan and offers breathtaking views of sandy beaches, lush dunes, and diverse ecosystems.
Immerse yourself in the tranquility of Indiana Dunes National Park and indulge in activities such as hiking, picnicking, birdwatching, and swimming along the pristine shores of Lake Michigan.
Be sure to explore the various hiking trails that wind through the park, providing opportunities to discover stunning vistas, unique plant life, and even remnants of shipwrecks.
Comparison Table: Oak Park vs. Indiana Dunes National Park
| Oak Park | Indiana Dunes National Park |
|---|---|
| Frank Lloyd Wright architecture | Nature and outdoor activities |
| Robie House | Sandy beaches and dunes |
| Ernest Hemingway history | Scenic hiking trails |
| Proximity to Chicago | Opportunity for birdwatching |
Whether you choose to explore the architectural wonders of Oak Park or indulge in the natural splendor of Indiana Dunes National Park, both options guarantee a memorable and fulfilling day trip from Chicago.
Where to Stay in Chicago
When planning your trip to Chicago, choosing the right neighborhood to stay in is essential for a convenient and enjoyable experience. With numerous accommodations available, you can find the perfect place to suit your preferences, whether you’re looking for proximity to attractions or a relaxed atmosphere. Here are some of the best neighborhoods in Chicago for accommodations:
The Loop and River North
For those seeking convenience and easy access to major attractions, The Loop and River North neighborhoods are excellent options. Located in the heart of the city, you’ll find a wide range of hotels, from luxurious options to more budget-friendly choices. These neighborhoods are ideal for travelers who want to be within walking distance of iconic sites like Millennium Park, the Art Institute of Chicago, and Grant Park.
The Magnificent Mile
If shopping and dining are high on your list, consider staying in The Magnificent Mile. This renowned area offers a mix of upscale hotels, boutique accommodations, and renowned chain hotels. You’ll be surrounded by world-class shopping along Michigan Avenue, including flagship stores and designer boutiques. The Magnificent Mile is also home to top-notch restaurants and vibrant nightlife.
Lincoln Park and Old Town
For a more relaxed and charming atmosphere, Lincoln Park and Old Town are popular choices. These neighborhoods boast tree-lined streets, historic architecture, and a plethora of dining options. You’ll find a range of accommodations, from trendy boutique hotels to cozy bed and breakfasts. Lincoln Park is also home to the Lincoln Park Zoo and lush green spaces, while Old Town offers a vibrant entertainment scene, including the famous Second City comedy club.
When choosing your accommodation in Chicago, consider factors such as location, budget, and amenities to ensure a comfortable stay. Whether you prefer the hustle and bustle of downtown or a more laid-back vibe, Chicago has accommodations to suit every traveler’s needs.
| Neighborhood | Accommodation Options | Key Features |
|---|---|---|
| The Loop and River North | Luxury hotels, budget-friendly options | Convenience, proximity to major attractions |
| The Magnificent Mile | Upscale hotels, boutique accommodations, renowned chains | World-class shopping, dining, vibrant nightlife |
| Lincoln Park and Old Town | Trendy boutiques, cozy bed and breakfasts | Relaxed atmosphere, historic architecture, entertainment options |
Getting Around Chicago
Getting around Chicago is a breeze, thanks to the city’s efficient and extensive public transportation system. Whether you’re visiting popular attractions or exploring different neighborhoods, there are various transportation options to suit your needs.
Chicago Transit Authority (CTA)
The Chicago Transit Authority (CTA) operates the city’s public transportation network, which includes the iconic “L” trains and buses. The “L” train system is a convenient and affordable way to travel around Chicago, with multiple lines connecting different parts of the city. Buses cover areas not serviced by the “L” trains, ensuring easy access to most major attractions and neighborhoods.
Consider purchasing a Ventra card, the reloadable payment card for the CTA system. It provides a convenient and cost-effective way to pay for your rides, eliminating the need for cash or individual tickets.
Chicago Taxis
If you prefer a more direct and personalized mode of transportation, taxis are readily available throughout the city. Flagging down a taxi on the street or using ride-hailing apps like Uber and Lyft are popular choices for getting around Chicago. Taxis offer a convenient option, especially when traveling with luggage or in groups.
Walkability
Chicago is known for its walkability, with many attractions, neighborhoods, and scenic spots within comfortable walking distance of each other. Exploring the city on foot allows you to soak in the vibrant atmosphere, discover hidden gems, and stumble upon unique experiences along the way. Put on a comfortable pair of shoes and explore Chicago by foot.
Tips for Visiting Chicago
When planning your trip to Chicago, it’s important to be prepared for the weather, as it can vary greatly throughout the year. Here are some helpful tips to ensure you have a fantastic time exploring the Windy City:
1. Know the Weather
Chicago experiences four distinct seasons, each with its own unique charm. Summer is the peak tourist season, with warm temperatures and plenty of festivals and events. Spring and fall offer milder weather and fewer crowds, making it a great time to visit. Winter can be cold and snowy, but it’s also a fantastic time to enjoy indoor attractions and cozy restaurants.
2. Dress Appropriately
Regardless of the season, it’s wise to dress in layers when visiting Chicago. This way, you can adapt to the changing temperatures throughout the day. Don’t forget to pack a warm jacket, comfortable walking shoes, and accessories like scarves and gloves during the colder months.
3. Consider a Chicago CityPASS
If you’re planning to visit multiple attractions in Chicago, purchasing a Chicago CityPASS can save you time and money. With the CityPASS, you’ll get discounted admission to some of the city’s top attractions, including museums, architectural tours, and observation decks. It’s a convenient and cost-effective way to explore Chicago’s best sights.
4. Pack a Chicago Travel Essentials List
Regardless of the season, there are a few items that you should consider packing for your trip to Chicago. Here’s a list of essentials that will come in handy:
| Essentials | Reason |
|---|---|
| Comfortable walking shoes | Chicago is a walkable city, so be prepared to explore on foot. |
| Umbrella or raincoat | Chicago is known for its unpredictable weather, so it’s always wise to be prepared for rain. |
| Reusable water bottle | Stay hydrated while you’re out and about exploring the city. |
| Sunscreen | Protect your skin from the sun, especially during the summer months. |
| Camera or smartphone | Capture the memories and beautiful sights that Chicago has to offer. |
5. Plan for Public Transportation
Getting around Chicago is easy thanks to the city’s efficient public transportation system. The Chicago Transit Authority (CTA) operates buses and trains that can take you to most major attractions and neighborhoods. Consider purchasing a Ventra card for easy access to the CTA system. Taxis and ride-sharing services like Uber and Lyft are also widely available if you prefer a more convenient way of getting around.
By following these tips and being prepared for the weather, you’ll be able to make the most of your visit to Chicago. Enjoy exploring the city’s vibrant culture, iconic landmarks, and world-class attractions!
“Chicago is a city of neighborhoods, each with its own unique character and charm. Take the time to explore beyond the tourist hotspots and discover the hidden gems that make Chicago truly special.”
Conclusion
A 5-Day Itinerary in Chicago offers an incredible opportunity to explore the city’s famous attractions, indulge in its vibrant neighborhoods, and experience its diverse cultural offerings. With world-class museums, beautiful parks, and a food scene that will tantalize your taste buds, Chicago is a destination that appeals to all. By following this itinerary, you can maximize your time in the Windy City and create unforgettable memories.
Start your adventure by visiting iconic Chicago attractions such as the John Hancock Building with its breathtaking 360 Chicago Observation Deck, where you can enjoy panoramic views of the city. Explore the famous Magnificent Mile for shopping bliss and make sure to stop at the Starbucks Reserve for a cup of joe. For an adrenaline rush, don’t miss the Tilt ride, Chicago’s highest thrill ride, which will take you soaring over the Magnificent Mile.
Delve into the city’s rich culture and history by exploring world-class museums like the Art Institute of Chicago and the Museum Campus, where you’ll find the Field Museum, Shedd Aquarium, and Adler Planetarium. Sports enthusiasts can catch a game at Wrigley Field, home of the Chicago Cubs. Take a leisurely walk along the Chicago Riverwalk or the Lakefront Trail and soak in the city’s architectural beauty, or catch a Broadway show or enjoy live music at one of the city’s jazz clubs.
End your Chicago adventure with a day trip to Oak Park to marvel at the Frank Lloyd Wright architecture or visit the Indiana Dunes National Park for sandy beaches and scenic hiking trails. With so much to see and do, planning a visit to Chicago is an exciting and rewarding endeavor. So pack your bags, follow this itinerary, and get ready to immerse yourself in the wonders of the Windy City. Chicago awaits!
FAQ
What should I do on my first day in Chicago?
On your first day in Chicago, you should visit the John Hancock building and experience the 360 Chicago Observation Deck for panoramic city views. Afterward, explore the famous Magnificent Mile and grab a coffee at the Starbucks Reserve. For an adrenaline rush, take a ride on Tilt, Chicago’s highest thrill ride.
What can I do on the second day of my Chicago itinerary?
On your second day, you have the option to explore Chicago’s world-class museums or head to Wrigley Field. Visit the Art Institute of Chicago for arts and culture, or spend the day at Museum Campus, home to the Field Museum, Shedd Aquarium, and Adler Planetarium. Sports lovers can enjoy a game at Wrigley Field, home of the Chicago Cubs.
What should I explore on the third day in Chicago?
On the third day, explore the charming neighborhoods of Lincoln Park and Old Town. Start by walking along the Lakefront Trail and visit North Avenue Beach. Then, explore Lincoln Park, including the Lincoln Park Zoo, Lincoln Park Conservatory, and Chicago History Museum. In the evening, enjoy a comedy show at The Second City comedy club in Old Town.
What are some must-see attractions on the fourth day of my Chicago trip?
On the fourth day, take a leisurely walk along the Chicago Riverwalk or the Lakefront Trail. Visit the famous Willis Tower Skydeck for panoramic views, explore the Lakefront Trail, and make a stop at Buckingham Fountain. In the afternoon, enjoy a Chicago River cruise and experience the architectural beauty of the city. In the evening, catch a Broadway show or listen to live music at a jazz club.
What are some day trip options for the last day in Chicago?
Consider taking a day trip to Oak Park to explore Frank Lloyd Wright’s architecture and visit the Robie House. Alternatively, you can visit the Museum of Science & Industry and explore various scientific exhibits. If you’re craving nature, head to Indiana Dunes National Park and enjoy sandy beaches and hiking trails.
Where are the best neighborhoods to stay in Chicago?
Some great neighborhoods to consider for accommodation in Chicago are the Loop and River North for convenience and proximity to major attractions. The Magnificent Mile is popular for shopping and dining. Lincoln Park and Old Town offer a charming and relaxed atmosphere. Consider factors such as location, budget, and amenities when choosing your accommodation in Chicago.
How can I get around Chicago?
Getting around Chicago is relatively easy with the city’s public transportation system, known as the CTA. The “L” train and buses can take you to most major attractions and neighborhoods. Taxis and ride-sharing services like Uber and Lyft are also widely available. Consider purchasing a Ventra card for easy access to the CTA system. Additionally, Chicago is a walkable city, so don’t hesitate to explore on foot.
What tips should I know before visiting Chicago?
When visiting Chicago, be prepared for the weather as it can vary greatly throughout the year. Summer is the peak tourist season with warm temperatures and numerous events. Spring and fall offer milder weather and fewer crowds. Winter can be cold, but it’s a great time to enjoy indoor attractions and cozy restaurants. Pack comfortable walking shoes and dress in layers. Consider purchasing a Chicago CityPASS for discounted admission to multiple attractions.
