5 Days Exploring Chicago Itinerary

Begin your day with breakfast at Little Goat Diner, offering creative twists on classic diner fare. Then visit the Field Museum, where you can explore natural history exhibits including Sue, the largest T. rex ever discovered.

After lunch, take a trip to Skydeck Chicago at Willis Tower (Sears Tower). Experience breathtaking views of the city from one of its tallest buildings.

Dine at The Publican, which offers a menu inspired by simple farmhouse fare and international cuisine. End your evening with some live music at the famous House of Blues.

Start your morning with coffee and pastries at Dove's Luncheonette. Then head over to explore the architectural marvel that is the Rookery Building. Its stunning lobby designed by Frank Lloyd Wright is a sight to behold.

Have lunch at Eataly Chicago - La Pizza & La Pasta Restaurant before visiting the fascinating exhibits at the Museum of Science and Industry. This museum offers interactive displays that are fun for all ages.

For dinner, enjoy some fine dining at Smyth and The Loyalist. Conclude your day with a visit to the historic Chicago Theatre, where you can catch a show or simply admire its beautiful architecture.

Kick off your day with breakfast at Café Ba-Ba-Reeba! before heading out for an adventurous bike ride with Chicago Bike Adventures Custom Neighborhood Bike Rides. Explore different neighborhoods while getting some exercise.

After working up an appetite, have lunch at Parson's Chicken & Fish, known for its fried chicken and laid-back atmosphere. Spend your afternoon shopping along The Magnificent Mile, one of Chicago's most famous shopping districts.

Enjoy dinner at RPM Italian, offering delicious Italian cuisine in a chic setting. Finish off your evening with a visit to the iconic observation deck at 360 Chicago (formerly John Hancock Observatory) for stunning nighttime views.

Begin your last day in Chicago with breakfast at Big Star Taco Bar, famous for its tacos and vibrant atmosphere. Visit the serene surroundings of Lincoln Park & Zoo (free entry), perfect for families or anyone looking to enjoy nature within city limits.

For lunch head over to Green Street Smoked Meats known for their BBQ dishes before exploring Navy Pier which offers attractions rides shops restaurants gardens exhibitions parks concert venues cruises boat tours fireworks displays seasonal events festivals more making it ideal place spend afternoon enjoying everything has offer

End trip memorable dinner Roister renowned innovative dishes lively ambiance reflecting spirit culinary creativity concludes journey perfectly