4-Day Chicago and Milwaukee Adventure Itinerary

Begin your day with a visit to Skydeck Chicago at Willis Tower (Sears Tower). Take an elevator ride up to the 103rd floor for breathtaking views of the city from The Ledge's glass boxes that extend out 4.3 feet from the Skydeck.

Next, explore Field Museum, where you can discover fascinating exhibits on natural history. Don't miss Sue, the largest and most complete T. rex ever found! For lunch, stop by Portillo's Hot Dogs for a taste of classic Chicago-style hot dogs.

Spend your evening at Navy Pier, which offers entertainment options including rides, shops, and restaurants. End your day with dinner at Lou Malnati's Pizzeria, famous for its deep-dish pizza.

Start your morning with a visit to Chicago Riverwalk. Enjoy a scenic walk along this pedestrian waterfront while taking in views of some of Chicago’s most iconic architecture.

Head over to Museum of Science and Industry in Hyde Park. This museum offers interactive exhibits that are fun for all ages. For lunch, dine at Frontera Grill, known for its delicious Mexican cuisine by celebrity chef Rick Bayless.

In the evening, experience live music at House of Blues. This legendary venue hosts performances by top artists across various genres. For dinner afterward, enjoy steaks or seafood at Joe's Seafood, Prime Steak & Stone Crab.

Begin your day with a visit to Lincoln Park & Zoo. This free zoo is home to various animals from around the world and is located within Lincoln Park which also offers beautiful walking trails.

Next up is a trip to Adler Planetarium, where you can explore fascinating exhibits about space science and astronomy. Have lunch nearby at Smoque BBQ, renowned for its mouthwatering barbecue dishes.

Conclude your day with an evening show at The Second City comedy club where many famous comedians got their start (Second City). Afterward, head over to dine at one of Chicago’s finest steakhouses:  Gibsons Bar & Steakhouse.

Start your day with a visit to the Milwaukee Art Museum. This architectural marvel houses over 25,000 works of art and offers stunning views of Lake Michigan. The museum's Quadracci Pavilion, designed by Santiago Calatrava, is a must-see.

Head to the Historic Third Ward for lunch at one of its many trendy eateries. Afterward, explore the neighborhood's boutique shops, galleries, and the Milwaukee Public Market. This area is known for its vibrant arts scene and charming streets.

In the evening, enjoy a relaxing stroll along the Milwaukee RiverWalk. This scenic path offers beautiful views of the city and plenty of spots to sit and unwind. For dinner, head to one of Milwaukee's renowned restaurants such as Sanford or Lakefront Brewery for a taste of local cuisine.