10 Days Exploring Chicago Itinerary

Begin your day with a visit to the towering Skydeck Chicago at Willis Tower (Sears Tower) for breathtaking views of the city. Grab breakfast at Lou Mitchell's, a classic diner known for its hearty breakfasts.

Explore the historic Chicago Board of Trade Building and take a guided tour to learn about its significance. Have lunch at The Dearborn, which offers modern American fare in a chic setting.

Visit the famous Chicago Theatre for an evening show or tour. Enjoy dinner at Girl & The Goat, one of Chicago's most popular restaurants offering innovative small plates.

Start your day with a trip to the fascinating Field Museum, home to Sue, the largest T-Rex skeleton ever discovered. Breakfast can be enjoyed at Yolk South Loop, known for its creative breakfast dishes.

Head over to the nearby Shedd Aquarium and explore its vast collection of marine life. For lunch, dine at Giordano's Pizza, famous for its deep-dish pizza.

Conclude your day with a visit to the serene Grant Park where you can relax and enjoy nature. Have dinner at Park Grill, located within Millennium Park offering great views and delicious food.

Begin your morning with an architectural tour of the stunning Rookery Building. Enjoy breakfast nearby at Café Bonhomme which offers European-inspired dishes.

Visit Marina City, an iconic part of Chicago’s skyline known as 'the corn cob towers.' Have lunch at nearby restaurant 312 Chicago which serves Italian cuisine in an elegant setting.

Spend your evening exploring The Magnificent Mile where you can shop till you drop. End your day with dinner at RPM Italian which offers modern Italian dishes in a stylish setting.

'Field' Day Out: Begin your morning by visiting Soldier Field, home of NFL’s Chicago Bears followed by breakfast from Wildberry Pancakes & Cafe renowned for their pancakes.

'Field' Day Out: Visit Adler Planetarium located on Northerly Island providing amazing space exhibits followed by lunch from Riva Crabhouse on Navy Pier serving fresh seafood dishes while enjoying lakefront views.

'Field' Day Out: Spend evening catching live music performance House Blues located Marina City complex then have dinner Smith Wollensky steakhouse offering prime steaks seafood options.

'Wrigleyville Adventure': Start off visiting historic Wrigley Field home MLB’s Cubs followed by breakfast Ann Sather Swedish cuisine cinnamon rolls specialty.

'Wrigleyville Adventure': Explore Lincoln Park Zoo free admission zoo featuring wide variety animals then have lunch RJ Grunts classic American fare.

'Wrigleyville Adventure': Catch comedy show Second City renowned improv theater group followed by dinner Pequod’s Pizza famous caramelized crust deep dish pizza.

'Cultural Immersion': Begin day exploring exhibits Chicago Cultural Center free admission cultural center followed by breakfast Goddess Baker artisanal bakery cafe.

'Cultural Immersion': Visit Museum Science Industry interactive science museum housed within beautiful building then have lunch Medici Kitchen Bar eclectic menu options.

'Cultural Immersion': Attend performance Biograph Theater historic theater venue known hosting live performances then enjoy dinner Alinea Michelin-starred restaurant offering innovative tasting menus.

'Riverfront Relaxation': Start off relaxing walk along scenic Chicago River enjoy architecture followed by brunch Beatnik On River bohemian-inspired restaurant.

'Riverfront Relaxation': Take boat tour explore more sights from water perspective then have light snack Nutella Cafe unique cafe dedicated hazelnut spread.

'Riverfront Relaxation': End day dining Gibsons Bar Steakhouse classic steakhouse experience located Rush Street area known nightlife entertainment options.

'Artistic Exploration': Begin morning visiting Art Institute world-renowned art museum extensive collection artworks followed brunch Cindy’s Rooftop overlooking Millennium Park.

'Artistic Exploration': Explore more public art installations throughout city including Picasso Daley Plaza Flamingo Federal Center Plaza snack Stan’s Donuts coffee donuts specialty items.

'Artistic Exploration': Attend live jazz performance Green Mill Cocktail Lounge historic jazz club once frequented Al Capone enjoy dinner Bavette’s Bar Boeuf French-inspired steakhouse vintage decor ambiance.

'Farewell Windy City ': Spend final morning shopping Water Tower Place multi-story mall featuring variety stores boutiques followed brunch NoMI Kitchen upscale restaurant located within Park Hyatt Hotel overlooking Michigan Avenue.

'Farewell Windy City ': Visit Navy Pier iconic landmark featuring rides attractions entertainment venues light snack Garrett Popcorn Shops famous caramel popcorn cheese popcorn mix flavors .

'Farewell Windy City ': Conclude trip attending sunset cruise Lake Michigan breathtaking views skyline reflection water enjoy farewell dinner Signature Room John Hancock Center offering panoramic cityscape vistas .