5 day itinerary for Chicago

Itinerary

Chicago is such a vibrant city with a rich tapestry of culture, food, and stunning architecture. I’m excited to help you plan a relaxed 5-day itinerary that lets you soak in the sights without feeling rushed. Let’s dive in!

## Day 1: Arrival and Exploring the Loop

Morning:

• Arrive in Chicago and check into your hotel. If you’re staying in the Loop, you’ll be right in the heart of the city!
• Grab a leisurely breakfast at Wildberry Pancakes and Cafe. Their berry bliss pancakes are a must-try!

Afternoon:

• Stroll through Millennium Park. Don’t miss the iconic Cloud Gate (aka "The Bean") and the beautiful Crown Fountain.
• Head over to the Art Institute of Chicago. Spend a couple of hours exploring its impressive collection. The Impressionist paintings are a highlight!

Evening:

• Enjoy dinner at Lou Malnati’s for some classic Chicago deep-dish pizza. It’s a local favorite!
• If you’re up for it, take a leisurely walk along the Chicago Riverwalk to see the city lights reflecting on the water.

## Day 2: Museums and Lakefront

Morning:

• Start your day with breakfast at The Bongo Room. Their French toast is heavenly!
• Visit the Field Museum. Spend a few hours exploring the exhibits, especially the dinosaur fossils!

Afternoon:

• Grab lunch at The Museum Café inside the Field Museum or head to Portillo’s for a Chicago-style hot dog.
• After lunch, take a stroll through Grant Park and enjoy the gardens and fountains.

Evening:

• Head to Navy Pier. You can take a ride on the Ferris wheel for stunning views of the skyline.
• Have dinner at Riva Crab House on the pier for a lovely lakeside dining experience.

## Day 3: Neighborhood Exploration

Morning:

• Enjoy breakfast at Beatrix in River North. Their coffee is fantastic!
• Spend the morning exploring the Magnificent Mile. Check out the shops and maybe pop into the Chicago Water Tower.

Afternoon:

• Head to Lincoln Park. Visit the Lincoln Park Zoo (free admission!) and take a leisurely walk through the park.
• Have lunch at The Chicago Diner, famous for its vegetarian options and delicious milkshakes.

Evening:

• Explore the charming streets of Old Town. You can check out the historic architecture and maybe catch a comedy show at The Second City.
• Dinner at Café Ba-Ba-Reeba! for some tapas and sangria to end your day on a high note.

## Day 4: Architecture and Culture

Morning:

• Start with breakfast at Egg Harbor Café. Their omelets are delightful!
• Take an architecture boat tour on the Chicago River. It’s a relaxing way to see the city’s stunning skyline and learn about its history.

Afternoon:

• After the tour, grab lunch at The Purple Pig. Their Mediterranean-inspired dishes are delicious!
• Spend the afternoon at the Museum of Contemporary Art. It’s a great spot to see modern art and often has interesting exhibitions.

Evening:

• Head to Wicker Park for a more laid-back vibe. Explore the boutiques and coffee shops.
• Dinner at Big Star for some tasty tacos and a fun atmosphere.

## Day 5: Relax and Reflect

Morning:

• Enjoy a leisurely breakfast at M. Henry in Andersonville, known for its creative brunch options.
• Spend your morning at The Chicago Botanic Garden (a bit of a drive, but worth it for the tranquility).

Afternoon:

• Have lunch at The Harvest at the Botanic Garden or head back to the city for a bite at Al’s Beef for an Italian beef sandwich.
• Spend your afternoon at Shedd Aquarium. It’s a great way to unwind and enjoy the aquatic exhibits.

Evening:

• For your last dinner, treat yourself at The Signature Room at the 95th floor of the John Hancock Center. The views are breathtaking, especially at sunset!
• If you have the energy, consider catching a show at the Chicago Symphony Orchestra or a local theater.

Tips for Your Trip:

• Don’t forget to wear comfortable shoes; you’ll be doing a fair bit of walking!
• Consider getting a Chicago CityPASS if you plan to visit multiple attractions; it can save you some money.
• Check the weather before you go, as it can be quite variable!

I hope this itinerary helps you have a wonderful and relaxed time in Chicago! Enjoy every moment! 🌆✨