4-Day Itinerary in Chicago

Chicago is a vibrant city with a rich culture, breathtaking architecture, and mouthwatering deep-dish pizza. If you’re planning a trip to the Windy City and have four days to explore, you’re in for a treat. In this comprehensive guide, we’ll provide you with a detailed 4-day itinerary to help you make the most of your time in Chicago.

From iconic attractions to hidden gems, this itinerary covers all the must-see sights and experiences that Chicago has to offer. Whether you’re a history buff, a foodie, or an architecture enthusiast, there’s something for everyone in this incredible city.

4-Day Itinerary in Chicago

Key Takeaways:

  • Explore top attractions and must-see sights in Chicago during your 4-day trip.
  • Discover the best places to visit and things to do in Chicago in just four days.
  • Plan your itinerary based on your interests and preferences.
  • Make use of a Chicago travel guide or itinerary planner to optimize your trip.
  • Don’t miss out on exploring the vibrant culture, stunning architecture, and delicious food of Chicago.

Tips for Creating a 4-Day Itinerary in Chicago

Planning a trip to Chicago? With so much to see and do, it’s important to optimize your 4-day itinerary to make the most of your time in the Windy City. Here are some helpful tips to ensure you have an unforgettable experience:

1. Buy a Transit Pass

Getting around Chicago is easy with a transit pass. Invest in a multi-day pass that allows unlimited rides on buses and trains. This not only saves you money on transportation but also ensures seamless travel between attractions.

2. Consider Walking or Renting Divvy Bikes

Chicago’s compact downtown area and beautiful neighborhoods are perfect for exploring on foot or by bike. Consider renting Divvy Bikes, Chicago’s bike-sharing system, and enjoy the city’s numerous bike lanes and scenic lakefront trails.

3. Look for Discount Cards and Passes

To save money on Chicago’s top attractions, look for discount cards and passes. The Go Chicago Card and the Chicago CityPASS offer discounted admission to popular sights like the Art Institute of Chicago, SkyDeck at Willis Tower, and more.

4. Pack Layers for Unpredictable Weather

Chicago’s weather can be unpredictable, so it’s wise to pack layers. In the summer, temperatures can vary greatly from day to night. Even during other seasons, sudden weather changes can occur, so be prepared with a light jacket and versatile clothing options.

5. Don’t Forget Travel Insurance

When planning any trip, it’s important to have peace of mind. Consider purchasing travel insurance to protect yourself against unforeseen circumstances such as trip cancellations, medical emergencies, or lost luggage. It’s a small investment that can provide significant benefits.

By following these tips, you can optimize your 4-day itinerary in Chicago, ensuring that you make the most of your time exploring this vibrant city. Now that you have the tools and knowledge, it’s time to start planning your unforgettable trip to Chicago!

Best Hotels to Stay During Your 4-Day Chicago Itinerary

When planning your 4-day Chicago itinerary, choosing the right accommodation is essential for a comfortable and enjoyable stay. The city offers a wide range of hotels in various neighborhoods, each with its own unique charm. Here are some top recommendations for where to stay in Chicago:

The Loop/Downtown Chicago

The Loop/Downtown Chicago is the city’s vibrant central business district, known for its iconic skyscrapers, shopping, and cultural attractions. Staying in this area will put you in the heart of the action. Here are some of the best hotels in the Loop/Downtown Chicago:

Hotel Rating
The Langham Chicago 5 stars
Hyatt Regency Chicago 4.5 stars
LondonHouse Chicago 4.5 stars
Swissotel Chicago 4 stars
Hotel Julian Chicago 4 stars

River North

River North is a trendy neighborhood known for its art galleries, upscale dining, and vibrant nightlife. It’s a great choice for those looking for a lively atmosphere. Here are some top hotels in River North:

Hotel Rating
Chicago Marriott Downtown Magnificent Mile 4.5 stars
Kimpton Hotel Palomar Chicago 4.5 stars
The Westin Chicago River North 4 stars
Four Seasons Chicago 5 stars


Streeterville is home to many popular attractions, including Navy Pier and the Magnificent Mile shopping district. It’s a bustling area with a mix of hotels, restaurants, and entertainment options. Here are some top choices in Streeterville:

Hotel Rating
InterContinental Chicago Magnificent Mile 4.5 stars
Embassy Suites Chicago Downtown Magnificent Mile 4 stars
The Drake 4 stars
The Ritz-Carlton, Chicago 5 stars

Gold Coast

Gold Coast is a historic neighborhood known for its beautiful homes, upscale boutiques, and charming tree-lined streets. It offers a more relaxed atmosphere while still being close to the city’s attractions. Here are some recommended hotels in Gold Coast:

Hotel Rating
Thompson Chicago 4.5 stars
Viceroy Chicago 4.5 stars
The Talbott Hotel 4 stars
Waldorf Astoria Chicago 5 stars

Choosing the right hotel in one of these fantastic neighborhoods will enhance your overall experience during your 4-day Chicago itinerary. Whether you prefer luxury or boutique accommodations, there’s something for every traveler in the Windy City.

Best Restaurants in Chicago

If you’re looking for an unforgettable dining experience in the Windy City, Chicago boasts a vibrant food scene with something to satisfy every palate. From mouthwatering deep-dish pizza to delectable desserts, here are some of the best restaurants to add to your Chicago food itinerary:

1. Giordano’s Pizza and Lou Malnati’s Pizzeria

If you’re craving authentic Chicago deep-dish pizza, Giordano’s Pizza and Lou Malnati’s Pizzeria are must-visit spots. Indulge in their famous, ooey-gooey pizzas with a perfectly crispy crust and generous toppings. These iconic establishments have been serving up delicious pizza for decades.

2. Lou Mitchell’s

Start your day off right with a classic breakfast at Lou Mitchell’s. This beloved diner has been a Chicago institution since 1923 and is known for its friendly service and hearty breakfast options. Savor their fluffy pancakes, crispy bacon, and perfectly brewed coffee.

3. The Village

Step into history at The Village, the oldest Italian restaurant in Chicago. This charming eatery has been serving traditional Italian dishes since 1927. From homemade pastas to delectable seafood dishes, prepare to be transported to the flavors of Italy.

4. The Purple Pig

If you’re looking for a restaurant with a variety of dishes, The Purple Pig is a must-visit. Located on Chicago’s Magnificent Mile, this lively eatery offers a menu showcasing Mediterranean-inspired small plates. Indulge in their delicious charcuterie, flavorful grilled meats, and mouthwatering desserts.

5. BomboBar

No meal is complete without dessert, and BomboBar is the perfect place to satisfy your sweet tooth. Known for their incredible desserts and indulgent hot chocolate, this popular spot offers a variety of treats including bomboloni (Italian doughnuts), gelato, and milkshakes.

Whether you’re a pizza lover, a fan of Italian cuisine, or simply looking for an unforgettable dining experience, these Chicago restaurants will leave you craving for more. Don’t miss the chance to savor the flavors of the city during your visit.

Top Restaurants in Chicago

Restaurant Cuisine Location
Giordano’s Pizza Deep-dish pizza Multiple locations
Lou Malnati’s Pizzeria Deep-dish pizza Multiple locations
Lou Mitchell’s American breakfast West Loop
The Village Italian Old Town
The Purple Pig Mediterranean-inspired Magnificent Mile
BomboBar Desserts West Loop

Day 1 in Chicago

On your first day in Chicago, immerse yourself in the city’s vibrant atmosphere by visiting some of its iconic attractions and exploring its renowned shopping and dining districts.

1. Visit the Magnificent Mile

Start your day by heading to the Magnificent Mile, a bustling stretch of Michigan Avenue known for its luxury shopping, world-class dining, and beautiful architecture. Stroll along the avenue, indulge in some retail therapy at designer boutiques and department stores, and grab a bite to eat at one of the many restaurants and cafes.

2. Explore the 360 Chicago Observation Deck

For breathtaking panoramic views of Chicago, make your way to the 360 Chicago Observation Deck. Located in the iconic John Hancock Center, this observation deck offers stunning vistas of the city’s skyline, Lake Michigan, and beyond. Capture some Instagram-worthy photos and take in the beauty of Chicago from above.

3. End the day with a show at the Chicago Theater

Complete your first day in Chicago with a memorable performance at the historic Chicago Theater. Known for its iconic marquee and stunning interior, this venue hosts a variety of shows including concerts, Broadway productions, and comedy performances. Immerse yourself in Chicago’s vibrant arts scene and enjoy a captivating evening of entertainment.

Day 2 in Chicago

On your second day in Chicago, explore some of the city’s iconic attractions and immerse yourself in its vibrant culture. Here are the must-see sights and activities for day 2 of your Chicago itinerary:

1. Millennium Park and Cloud Gate

Start your day at Millennium Park, a green oasis in the heart of downtown Chicago. Visit the famous Cloud Gate sculpture, also known as “The Bean,” and marvel at its unique reflective surface. Take memorable photos and enjoy the interactive experience of walking around and beneath the sculpture.

2. Art Institute of Chicago

Next, head to the Art Institute of Chicago, one of the oldest and largest art museums in the country. Explore its impressive collection, which spans thousands of years and includes artworks from diverse cultures and periods. Admire masterpieces like Grant Wood’s “American Gothic” and Vincent van Gogh’s “The Bedroom.”

3. Shedd Aquarium

Conclude your day by visiting the Shedd Aquarium, where you can discover a fascinating world beneath the waves. Explore vibrant exhibits showcasing diverse aquatic life, from colorful fish to majestic sea turtles and playful dolphins. Don’t miss the opportunity to witness captivating animal presentations and learn about conservation efforts.

Day 2 in Chicago offers a perfect blend of art, culture, and marine exploration. With visits to Millennium Park, the Art Institute of Chicago, and the Shedd Aquarium, you’ll have an unforgettable day filled with captivating experiences.

Day 3 in Chicago

As you continue your Chicago adventure on day 3, be prepared to experience the city’s architectural marvels, picturesque riverwalk, and iconic observation decks. Here are the top attractions and must-see sights to explore:

1. Chicago Architecture River Cruise

Embark on a Chicago Architecture River Cruise to immerse yourself in the city’s rich architectural history. Sail along the Chicago River as knowledgeable guides share fascinating stories about the renowned buildings that line its banks. From the iconic Wrigley Building to the modern marvels of the Trump Tower, this cruise offers a unique perspective on Chicago’s skyline.

2. Chicago Riverwalk and Navy Pier

After your river cruise, take a leisurely walk along the scenic Chicago Riverwalk. Admire the beautiful bridges, charming cafes, and stunning views of the city. Continue your journey to the famous Navy Pier, a bustling entertainment hub that offers a ferris wheel, restaurants, shops, and exciting attractions for all ages. Don’t miss the mesmerizing fireworks display if you’re visiting during the summer!

3. SkyDeck at Willis Tower

End your day by taking in breathtaking views of Chicago from the SkyDeck at Willis Tower. Step onto the glass ledge, hovering 1,353 feet above the ground, and feel the thrill as you gaze out over the city’s skyline. Capture stunning photos and create memories that will last a lifetime.

Day 3 of your Chicago itinerary promises a perfect blend of architectural wonders, scenic walks, and panoramic city views. Get ready for an unforgettable day in the Windy City!

Attraction Opening Hours Address
Chicago Architecture River Cruise Varies by season 112 E Wacker Dr, Chicago, IL 60601
Chicago Riverwalk Open 24/7 Chicago Riverwalk, Chicago, IL 60601
Navy Pier Varies by season 600 E Grand Ave, Chicago, IL 60611
SkyDeck at Willis Tower 9:00 AM – 10:00 PM (last entry at 9:30 PM) 233 S Wacker Dr, Chicago, IL 60606

Day 4 in Chicago

On the final day of your Chicago adventure, make sure to explore some of the city’s most exciting attractions. Start your day by visiting Lincoln Park, a beautiful outdoor space that stretches along Lake Michigan. Take a leisurely stroll through the park and enjoy the stunning views of the city skyline.

While you’re in Lincoln Park, don’t miss the chance to visit the Lincoln Park Zoo. This historic zoo is home to a wide variety of animals and offers a unique opportunity to get up close and personal with nature. Explore the exhibits, learn about conservation efforts, and enjoy the beauty of the zoo’s lush surroundings.

“The Lincoln Park Zoo is an incredible place to learn about wildlife and support conservation efforts. It’s a must-visit attraction for animal lovers.”

In the evening, immerse yourself in the soulful sounds of jazz at Winter’s Jazz Club. This intimate venue offers live performances by talented musicians, creating a cozy and vibrant atmosphere. Sit back, relax, and let the music transport you to another era.

Before concluding your day, make sure to visit the iconic Art Institute of Chicago. This world-renowned museum houses an extensive collection of artworks from around the globe. Marvel at famous masterpieces, discover new artists, and appreciate the beauty of human creativity. Afterward, take a leisurely stroll through Millennium Park and enjoy the iconic Cloud Gate sculpture, affectionately known as “The Bean”.

Day 4 Highlights:

  • Explore Lincoln Park
  • Visit the Lincoln Park Zoo
  • Catch a live jazz performance at Winter’s Jazz Club
  • Visit the Art Institute of Chicago
  • Stroll through Millennium Park

Transportation Tip:

If you prefer not to walk long distances, consider using public transportation or ride-sharing services to navigate between attractions on day 4.

Attraction Address Opening Hours
Lincoln Park Chicago, IL 60614 Open 24 hours
Lincoln Park Zoo 2001 N Clark St, Chicago, IL 60614 10am – 5pm
Winter’s Jazz Club 465 N McClurg Ct, Chicago, IL 60611 7pm – 11pm
Art Institute of Chicago 111 S Michigan Ave, Chicago, IL 60603 10:30am – 5pm
Millennium Park 201 E Randolph St, Chicago, IL 60602 Open 24 hours

Explore More of Chicago

While following the 4-day itinerary will allow you to experience the best of Chicago, there are many additional activities and hidden gems in the city that are worth exploring. Here are some off-the-beaten-path Chicago attractions to consider:

  1. Explore Wrigleyville and catch a Chicago Cubs game

    Immerse yourself in the lively atmosphere of Wrigleyville, the vibrant neighborhood surrounding Wrigley Field. Watch a baseball game and cheer for the Chicago Cubs while indulging in classic ballpark snacks.

  2. Visit the Chicago Riverwalk for a leisurely walk or kayak rental

    Take a stroll along the picturesque Chicago Riverwalk, a scenic promenade lined with restaurants, bars, and stunning architecture. Enjoy a leisurely walk or rent a kayak to explore the city from a different perspective.

  3. Head to the Magnificent Mile for shopping and dining

    Shop ’til you drop along the Magnificent Mile, Chicago’s premier shopping district. Browse through upscale boutiques, department stores, and luxury brands. Treat yourself to a delicious meal at one of the many restaurants offering diverse cuisines.

  4. Explore other museums in Chicago such as the Field Museum

    Expand your cultural horizons by visiting other museums in Chicago. The Field Museum showcases fascinating exhibits on natural history, including the famous T-Rex skeleton named Sue. Immerse yourself in the wonders of science, history, and art at these hidden gems.

No matter how you choose to spend your time, these additional activities will enhance your Chicago experience and make your trip even more memorable.


Chicago is a vibrant city that offers a variety of attractions, restaurants, and experiences for visitors to enjoy during a 4-day itinerary. From exploring iconic landmarks to indulging in delicious deep-dish pizza, there is something for everyone in the Windy City.

To make the most of your trip, it’s important to plan your itinerary based on your interests and preferences. This guide provides a detailed 4-day Chicago itinerary, highlighting the top attractions and must-see sights.

Whether you choose to stroll down the Magnificent Mile, admire the stunning views from the SkyDeck at Willis Tower, or immerse yourself in art at the Art Institute of Chicago, Chicago has it all.

So, pack your bags, follow this guide, and get ready to make unforgettable memories during your 4 days in the Windy City.


What are the top attractions in Chicago?

The top attractions in Chicago include the Magnificent Mile, Millennium Park, the Art Institute of Chicago, the Shedd Aquarium, and the Chicago Architecture River Cruise.

How can I save money on transportation in Chicago?

To save money on transportation in Chicago, you can buy a transit pass or consider walking or renting Divvy Bikes to explore the city.

Are there any recommended neighborhoods to stay in Chicago?

Yes, recommended neighborhoods to stay in Chicago are the Loop/Downtown Chicago, River North, Streeterville, and Gold Coast.

Where can I find the best deep-dish pizza in Chicago?

Iconic spots for delicious deep-dish pizza in Chicago include Giordano’s Pizza and Lou Malnati’s Pizzeria.

What are some of the best hotels in Chicago?

Some of the best hotels in Chicago include The Langham Chicago, Chicago Marriott Downtown Magnificent Mile, InterContinental Chicago Magnificent Mile, and Thompson Chicago.

What are the must-see sights in Chicago on day 1?

On day 1 in Chicago, you should visit the Magnificent Mile for shopping and dining, explore the 360 Chicago Observation Deck for stunning views, and end the day with a show at the Chicago Theater.

What are the must-see sights in Chicago on day 2?

On day 2 in Chicago, you should explore Millennium Park and see the iconic Cloud Gate statue, visit the Art Institute of Chicago, and discover marine life at the Shedd Aquarium.

What are the must-see sights in Chicago on day 3?

On day 3 in Chicago, you should take a Chicago Architecture River Cruise to learn about the city’s architecture, enjoy a walk along the Chicago Riverwalk, and visit the Navy Pier.

What are the must-see sights in Chicago on day 4?

On day 4 in Chicago, you should take in the views from the SkyDeck at Willis Tower, explore Lincoln Park and visit the Lincoln Park Zoo, and catch a live jazz performance at Winter’s Jazz Club.

What other attractions are there to explore in Chicago?

In addition to the main attractions, you can also explore other museums in Chicago such as the Field Museum, visit Wrigleyville and catch a Chicago Cubs game, and take a leisurely walk or kayak rental along the Chicago Riverwalk.

How can I optimize my 4-day Chicago itinerary?

To optimize your 4-day Chicago itinerary, make sure to plan your itinerary based on your interests and preferences and follow this guide to explore the top attractions and must-see sights in Chicago.

What are some hidden gems in Chicago that are off-the-beaten-path?

Some hidden gems in Chicago that are off-the-beaten-path include Garfield Park Conservatory, Chicago Pedway, and the Chicago Riverwalk at night.

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