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Chicago

2 day itinerary for Chicago

Personalized with:

Best local coffee spots in the morning

Walking and public transportation

Almond croissant

Best Pilsen Mexican food

Local beer spots in the afternoon

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Itinerary

Chicago is such a vibrant city with so much to offer, and I’m excited to help you plan your two-day adventure. Let’s dive right in!

## Day 1: Exploring the Heart of the City

Morning: Coffee and Pastries

  • Start your day at Intelligentsia Coffee in the Loop. This local favorite is known for its artisanal brews and cozy atmosphere. Grab a cup of their delicious pour-over coffee and don’t forget to ask for an almond croissant! They’re flaky, buttery, and the perfect start to your day.

  • After your caffeine fix, take a leisurely stroll through Millennium Park. Snap a photo with the iconic Cloud Gate (aka "The Bean") and enjoy the beautiful surroundings.

Mid-Morning: Art and Culture

  • Head over to the Art Institute of Chicago, just a short walk away. Spend a couple of hours exploring the impressive collection of art. Don’t miss the Impressionist paintings!

Lunch: A Taste of Chicago

  • For lunch, make your way to Lou Malnati’s Pizzeria for a classic Chicago deep-dish pizza. It’s a must-try when in the city! You can take the ‘L’ train from the Art Institute to the nearest station.

Afternoon: Local Brews

  • After lunch, hop on the ‘L’ to the Logan Square neighborhood. Here, you can visit Revolution Brewing, one of the city’s most popular breweries. Enjoy a flight of their craft beers and soak in the local vibe.

Evening: Dinner in Pilsen

  • Now, let’s head to Pilsen for some authentic Mexican food! Stop by Carnitas Uruapan for some of the best carnitas in the city. The atmosphere is casual, and the food is absolutely delicious.

  • After dinner, take a stroll around the neighborhood to admire the vibrant murals and street art that Pilsen is famous for.

Nightcap: Local Bars

  • End your day at Thalia Hall, a historic venue that often has live music. They also have a great bar where you can enjoy a local beer or a cocktail.

## Day 2: Neighborhood Adventures

Morning: Coffee and Croissants

  • Start your day at Cafe Integral in the historic Merchandise Mart. They serve fantastic coffee and have a lovely almond croissant that you won’t want to miss!

Mid-Morning: Riverwalk Stroll

  • After breakfast, take a walk along the Chicago Riverwalk. It’s a beautiful area to explore, with stunning views of the city’s architecture. You can even hop on a boat tour if you’re feeling adventurous!

Lunch: More Local Flavors

  • For lunch, head to Portillo’s for a Chicago-style hot dog or Italian beef sandwich. It’s a fun spot with a lively atmosphere.

Afternoon: Beer Tasting

  • After lunch, make your way to the West Loop and visit Goose Island Beer Co. for a brewery tour and tasting. It’s a great way to learn about the brewing process and sample some local favorites.

Evening: Dinner and More Brews

  • For dinner, check out Birrieria Zaragoza in the Little Village neighborhood for some incredible birria tacos. It’s a bit of a trek, but totally worth it for the authentic flavors!

  • After dinner, if you’re up for it, head back to the West Loop and visit The Aviary for a unique cocktail experience. It’s a bit upscale, but the drinks are creative and delicious.

Night: Wind Down

  • Finally, if you’re not too tired, you can end your night at The Empty Bottle in Ukrainian Village, a local music venue with a great selection of beers. It’s a fun spot to catch some live music and mingle with locals.

And there you have it! A fun-filled two-day itinerary in Chicago that hits all your requests. Enjoy your trip, and don’t forget to take lots of pictures! If you have any other questions or need more recommendations, feel free to ask. Safe travels!

Places of interest

Intelligentsia Coffee Chicago

Intelligentsia Coffee

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Millennium Park Chicago

Millennium Park

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Cloud Gate (The Bean) Chicago

Cloud Gate (The Bean)

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Art Institute of Chicago Chicago

Art Institute of Chicago

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Lou Malnati’s Pizzeria Chicago

Lou Malnati’s Pizzeria

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Revolution Brewing Chicago

Revolution Brewing

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Carnitas Uruapan Chicago

Carnitas Uruapan

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Thalia Hall Chicago

Thalia Hall

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Cafe Integral Chicago

Cafe Integral

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Chicago Riverwalk Chicago

Chicago Riverwalk

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Portillo’s Chicago

Portillo’s

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Goose Island Beer Co. Chicago

Goose Island Beer Co.

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Birrieria Zaragoza Chicago

Birrieria Zaragoza

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The Aviary Chicago

The Aviary

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The Empty Bottle Chicago

The Empty Bottle

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