5 day itinerary for Chicago

Itinerary

Chicago is a fantastic city for a romantic getaway, and with your fast-paced travel style, we can pack in a lot of exciting experiences. Here’s a delightful 5-day itinerary that balances adventure, romance, and a bit of relaxation. Let’s dive in!

## Day 1: Arrival and Riverwalk Romance

Morning:

• Arrive in Chicago and check into a cozy hotel. Consider a place with a view, like the Waldorf Astoria or The Langham.
• Grab a quick breakfast at Wildberry Pancakes and Cafe. Their berry pancakes are a must-try!

Afternoon:

• Stroll along the Chicago Riverwalk. It’s a beautiful place to take in the architecture and enjoy the water views. Stop for a quick coffee at Intelligentsia Coffee.

Evening:

• Enjoy a romantic dinner at The Signature Room on the 95th floor of the John Hancock Center. The views of the city skyline at sunset are breathtaking!
• After dinner, take a leisurely walk through Lincoln Park. If you’re up for it, find a cozy spot to sit and enjoy the stars.

## Day 2: Art and Culture

Morning:

• Start your day with breakfast at Lou Mitchell’s, a Chicago classic.
• Head to the Art Institute of Chicago. Spend a couple of hours exploring the stunning collection, including the famous “American Gothic” and Monet’s water lilies.

Afternoon:

• Grab lunch at The Art Institute’s café or nearby at The Gage for some hearty fare.
• After lunch, take a stroll through Millennium Park. Don’t forget to snap a selfie at the iconic Cloud Gate (The Bean)!

Evening:

• For dinner, indulge in a romantic meal at RPM Italian. The ambiance is perfect for couples!
• Catch a show at The Chicago Theatre or a jazz performance at The Green Mill Cocktail Lounge for a taste of Chicago’s vibrant nightlife.

## Day 3: Architecture and Lakefront Bliss

Morning:

• Have breakfast at Beatrix in River North, known for its fresh and healthy options.
• Take an architecture boat tour on the Chicago River. It’s a fantastic way to see the city’s stunning skyline and learn about its history.

Afternoon:

• After the tour, enjoy lunch at Portillo’s for a classic Chicago-style hot dog.
• Spend the afternoon at Navy Pier. You can ride the Ferris wheel for stunning views or just wander around the shops and gardens.

Evening:

• Dine at Geja’s Café, a romantic fondue restaurant. It’s perfect for a cozy, intimate dinner.
• End the night with a stroll along the Lakefront Trail. The views of the lake at night are simply magical!

## Day 4: Neighborhood Exploration

Morning:

• Start with breakfast at The Bongo Room in Wicker Park, famous for its creative pancakes.
• Explore the Wicker Park and Bucktown neighborhoods. Check out the local boutiques and art galleries.

Afternoon:

• Have lunch at Big Star, a fun taco joint with a great outdoor patio.
• Head to Lincoln Park Zoo for a leisurely afternoon. It’s free and a lovely place to walk hand-in-hand.

Evening:

• For dinner, try Alinea (if you can snag a reservation) for a unique and unforgettable dining experience.
• If you’re up for it, catch a comedy show at The Second City for some laughs!

## Day 5: Shopping and Departure

Morning:

• Enjoy a leisurely breakfast at Egg Harbor Café.
• Spend your last morning shopping along Michigan Avenue. Don’t miss the Magnificent Mile for some high-end retail therapy.

Afternoon:

• Grab a quick lunch at Eataly for a taste of Italy before you head out.
• If time allows, visit the Museum of Science and Industry or take a quick trip to The Field Museum to see Sue the T-Rex!

Evening:

• Depending on your departure time, enjoy a final romantic dinner at The Purple Pig for Mediterranean-inspired dishes.
• Head to the airport with a heart full of memories and a camera full of photos!

There you have it! A whirlwind romantic adventure in Chicago that’s sure to leave you both enchanted. Enjoy your trip, and don’t forget to take lots of pictures! 🌆❤️