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5 Days in Chicago Illinois Itinerary

Last updated: 2024 Jun 14

Exploring Downtown Chicago

Morning

Start your day with a visit to the iconic Skydeck Chicago at Willis Tower (Sears Tower). Enjoy breathtaking views of the city from one of the tallest buildings in the world. For breakfast, head to The Bongo Room, known for its decadent pancakes and creative brunch dishes.

Afternoon

In the afternoon, take a stroll along the Chicago Riverwalk, a scenic promenade along the Chicago River. Stop for lunch at Green Street Smoked Meats, where you can enjoy some of the best BBQ in town. After lunch, explore Millennium Park, home to the famous Cloud Gate sculpture (The Bean).

Evening

End your day with an evening visit to House of Blues for some live music and dinner at their restaurant. The vibrant atmosphere and great music make it a perfect spot to unwind.

Bedtime

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Cultural Gems and Historic Sites

Morning

Begin your day with a visit to the renowned Art Institute of Chicago, home to an extensive collection of art from around the world. Enjoy breakfast at Lou Mitchell's, a classic diner known for its hearty breakfasts.

Afternoon

After exploring the museum, head over to Grant Park for a leisurely walk and then visit The Magnificent Mile for some shopping. For lunch, dine at The Purple Pig, which offers delicious Mediterranean-inspired small plates.

Evening

In the evening, catch a show at the historic Chicago Theatre. Beforehand, have dinner at Girl & The Goat, one of Chicago's most celebrated restaurants offering innovative dishes.

Bedtime

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Science and Nature Day

Morning

Start your day with a trip to the fascinating Museum of Science and Industry. This museum offers interactive exhibits that are fun for all ages. Grab breakfast at Valois Restaurant, known for its affordable and tasty meals.

Afternoon

Afterward, head over to Shedd Aquarium to explore marine life from around the world. For lunch, stop by Shaw's Crab House for some fresh seafood delights.

Evening

Spend your evening at Navy Pier enjoying rides and attractions including dining options like Riva Crabhouse or Harry Caray's Tavern.

Bedtime

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Architectural Wonders

Morning

Begin with an architectural tour starting with visiting Marina City complex followed by breakfast at Wildberry Pancakes & Cafe.

Afternoon

Visit iconic buildings such as Tribune Tower Wrigley Building finishing off afternoon exploring Adler Planetarium having lunch nearby Lou Malnati’s Pizzeria.

Evening

Evening takes you through Second City comedy club experiencing laughter-filled night dining beforehand Pequod’s Pizza famous deep-dish pizza.

Bedtime

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