5 Days in Chicago Adventure Itinerary

Begin your day with a visit to the Field Museum. This natural history museum is home to Sue, the largest and most complete T. rex ever discovered. Afterward, have breakfast at Lou Malnati's Pizzeria for some classic deep-dish pizza.

Next, explore the wonders of marine life at Shedd Aquarium. Spend your afternoon marveling at aquatic creatures from around the world. For lunch, head over to Portillo's Hot Dogs for some classic Chicago-style hot dogs.

Conclude your day with an evening visit to Adler Planetarium, where you can gaze at the stars and learn about space exploration. For dinner, dine at RPM Italian, which offers delicious Italian cuisine.

Start your morning with an architectural tour on the famous Chicago Architectural River Cruise. This tour provides fascinating insights into Chicago's architectural history while cruising along the river. Have breakfast beforehand at The Publican, known for its hearty brunch options.

Afterward, head over to explore more architecture by visiting the historic Rookery Building. Then take some time for lunch at Girl & The Goat, offering innovative small plates that are perfect for sharing.

In the evening, visit the observation deck at 360 Chicago Observation Deck (Formerly John Hancock Observatory) for stunning panoramic views of the city. End your day with dinner at Joe's Seafood Prime Steak & Stone Crab.

Spend your morning exploring nature by visiting  Lincoln Park & Zoo. This free zoo offers a great variety of animals and beautiful park scenery. Have breakfast nearby at  Smoque BBQ for some hearty barbecue dishes.

Afterward head over to  Navy Pier, where you can enjoy various attractions including rides and shops. Grab lunch there from one of many eateries available such as  Pequod's Pizza for their famous caramelized crust pizza.

Conclude this exciting day by catching live music or entertainment show at  House of Blues . Finish off with dinner reservations made earlier on  Alinea , which is renowned globally as one best dining experiences.

Begin your last day in Chicago with a visit to 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 Frontera Grill, known for its delicious Mexican cuisine.

Afterward, explore the vibrant Chicago Loop, which is filled with shops, theaters, and historic landmarks. Take a break for lunch at The Publican, offering hearty and flavorful dishes.

End your trip with a relaxing evening at Chicago Theatre. Catch a show or simply admire the beautiful architecture. For your final dinner in Chicago, dine at Gibsons Bar & Steakhouse, renowned for its prime steaks and classic American fare.