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Roam Around

2 Days of Fun in Chicago Itinerary

Last updated: 2024 Jun 14

Exploring the Heart of Chicago

Morning

Start your day with a visit to Millennium Park. This iconic park is home to the famous Cloud Gate sculpture (also known as 'The Bean'), which is perfect for some morning photos. Stroll through the Lurie Garden and enjoy the serene atmosphere. For breakfast, head over to Lou Malnati's Pizzeria to try their renowned deep-dish pizza.

Afternoon

In the afternoon, make your way to Wrigley Field for a Cubs game. This historic ballpark offers an authentic Chicago experience and is a must-visit for any sports fan. Grab lunch at Portillo's Hot Dogs, known for its classic Chicago-style hot dogs and Italian beef sandwiches.

Evening

After the game, unwind with a walk along Chicago Riverwalk. The scenic views of the city skyline and river are stunning in the evening. For dinner, dine at Girl & the Goat, one of Chicago's most celebrated restaurants offering innovative small plates.

Bedtime

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Cultural and Culinary Delights

Morning

Begin your second day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Enjoy breathtaking views of the city from one of its tallest buildings. Afterward, have breakfast at Au Cheval, famous for its decadent burgers.

Afternoon

Head over to Art Institute of Chicago in the afternoon. This world-class museum houses an impressive collection of art from various periods and regions. For lunch, stop by The Purple Pig for some Mediterranean-inspired dishes.

Evening

Conclude your trip with an evening at House of Blues, where you can enjoy live music in a vibrant setting. Before heading there, have dinner at RPM Italian, known for its modern take on classic Italian cuisine.

Bedtime

Find amazing hotels in Chicago, Illinois.