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Chicago

3 day itinerary for Chicago

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For a couple

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Itinerary

Chicago is such a vibrant city with a mix of culture, food, and stunning architecture. Here’s a fun and romantic 3-day itinerary for you and your partner to explore the Windy City!

## Day 1: Downtown Delights & River Views

Morning:

  • Breakfast at Wildberry Pancakes and Cafe: Start your day with a delicious breakfast. Their berry bliss pancakes are a must-try!
  • Millennium Park: After breakfast, take a stroll through Millennium Park. Don’t forget to snap a selfie with the iconic Cloud Gate (aka "The Bean"). The park is beautiful, and you can enjoy the art installations and gardens.

Afternoon:

  • Lunch at The Purple Pig: Head over to The Purple Pig for a Mediterranean-inspired lunch. Their charcuterie and cheese boards are perfect for sharing!
  • Architecture River Cruise: Post-lunch, hop on an architecture river cruise. It’s a fantastic way to see the city’s stunning skyline and learn about its history. Plus, it’s super romantic!

Evening:

  • Dinner at The Signature Room: For dinner, make a reservation at The Signature Room on the 95th floor of the John Hancock Center. The views are breathtaking, especially at sunset!
  • Nightcap at a Rooftop Bar: After dinner, head to a nearby rooftop bar like Cindy’s Rooftop for a nightcap. The views of Lake Michigan and the city lights are magical.

## Day 2: Culture & Neighborhood Exploration

Morning:

  • Breakfast at Lou Mitchell’s: Start your day with a hearty breakfast at this Chicago institution. Their homemade donuts and fluffy omelets are a great way to fuel up!
  • Art Institute of Chicago: Spend your morning exploring the Art Institute. From Impressionist paintings to modern art, there’s something for everyone. Don’t miss the iconic “American Gothic”!

Afternoon:

  • Lunch in the West Loop: Head to the West Loop for lunch at Au Cheval, known for its amazing burgers. It’s a bit of a wait, but totally worth it!
  • Explore the West Loop: After lunch, take a stroll through the West Loop. Check out the street art and maybe pop into a few boutiques or galleries.

Evening:

  • Dinner at Girl & The Goat: For dinner, make a reservation at this famous restaurant by Chef Stephanie Izard. The small plates are perfect for sharing, and the flavors are out of this world!
  • Live Music at a Jazz Club: End your night with some live jazz at a club like The Green Mill Cocktail Lounge. It’s a historic venue with a great atmosphere.

## Day 3: Lakeside Leisure & Local Favorites

Morning:

  • Brunch at The Bongo Room: Treat yourselves to a leisurely brunch at The Bongo Room. Their decadent French toast and creative brunch cocktails are a great way to start the day!
  • Lakefront Walk: After brunch, take a romantic walk along the Lakefront Trail. The views of Lake Michigan are stunning, and it’s a lovely way to enjoy the outdoors.

Afternoon:

Evening:

  • Dinner at RPM Italian: For your final dinner, indulge in a meal at RPM Italian. The ambiance is chic, and the food is fantastic. Don’t forget to try their famous burrata!
  • Chicago Riverwalk: After dinner, take a romantic stroll along the Chicago Riverwalk. The city lights reflecting on the water create a perfect ending to your trip.

Tips:

  • Transportation: Consider getting a Ventra card for easy access to public transportation. The “L” train is a great way to get around.
  • Reservations: Make dinner reservations in advance, especially for popular spots!
  • Weather: Check the weather before your trip and pack accordingly, as Chicago can be quite windy!

I hope you have an amazing time in Chicago! Enjoy every moment together! 🌆❤️

Places of interest

Wildberry Pancakes and Cafe Chicago

Wildberry Pancakes and Cafe

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Millennium Park Chicago

Millennium Park

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The Purple Pig Chicago

The Purple Pig

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Architecture River Cruise Chicago

Architecture River Cruise

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The Signature Room Chicago

The Signature Room

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Cindy’s Rooftop Chicago

Cindy’s Rooftop

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Lou Mitchell’s Chicago

Lou Mitchell’s

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Art Institute of Chicago Chicago

Art Institute of Chicago

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Au Cheval Chicago

Au Cheval

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West Loop Chicago

West Loop

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Girl & The Goat Chicago

Girl & The Goat

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The Green Mill Cocktail Lounge Chicago

The Green Mill Cocktail Lounge

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The Bongo Room Chicago

The Bongo Room

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Lakefront Trail Chicago

Lakefront Trail

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Lincoln Park Zoo Chicago

Lincoln Park Zoo

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Lincoln Park Conservatory Café Chicago

Lincoln Park Conservatory Café

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RPM Italian Chicago

RPM Italian

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Chicago Riverwalk Chicago

Chicago Riverwalk

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